diff --git a/ui/goose2/scripts/check-file-sizes.mjs b/ui/goose2/scripts/check-file-sizes.mjs
index 1a980cee4b66..0c45b763c29e 100644
--- a/ui/goose2/scripts/check-file-sizes.mjs
+++ b/ui/goose2/scripts/check-file-sizes.mjs
@@ -65,6 +65,11 @@ const EXCEPTIONS = {
     justification:
       "Session prepare/load/list logic, working-dir updates, wait_for_replay_drain helper with iteration cap, and composite prepared-session reuse remain colocated while ACP session ownership stabilizes.",
   },
+  "src-tauri/src/commands/system.rs": {
+    limit: 640,
+    justification:
+      "Desktop system commands still centralize file mentions, attachment inspection, platform-aware path dedupe, guarded image loading, and export helpers in one Tauri command surface.",
+  },
 };
 
 // Directories excluded from size checks (imported library code)
diff --git a/ui/goose2/src-tauri/Cargo.lock b/ui/goose2/src-tauri/Cargo.lock
index 36dc70ad6bce..ddaef39fde56 100644
--- a/ui/goose2/src-tauri/Cargo.lock
+++ b/ui/goose2/src-tauri/Cargo.lock
@@ -1754,6 +1754,7 @@ dependencies = [
  "acp-client",
  "agent-client-protocol",
  "async-trait",
+ "base64 0.22.1",
  "chrono",
  "dirs",
  "doctor",
@@ -1762,6 +1763,7 @@ dependencies = [
  "ignore",
  "keyring",
  "log",
+ "mime_guess",
  "serde",
  "serde_json",
  "serde_yaml",
@@ -2578,6 +2580,16 @@ version = "0.3.17"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "6877bb514081ee2a7ff5ef9de3281f14a4dd4bceac4c09388074a6b5df8a139a"
 
+[[package]]
+name = "mime_guess"
+version = "2.0.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f7c44f8e672c00fe5308fa235f821cb4198414e1c77935c1ab6948d3fd78550e"
+dependencies = [
+ "mime",
+ "unicase",
+]
+
 [[package]]
 name = "miniz_oxide"
 version = "0.8.9"
@@ -5341,6 +5353,12 @@ dependencies = [
  "unic-common",
 ]
 
+[[package]]
+name = "unicase"
+version = "2.9.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "dbc4bc3a9f746d862c45cb89d705aa10f187bb96c76001afab07a0d35ce60142"
+
 [[package]]
 name = "unicode-ident"
 version = "1.0.24"
diff --git a/ui/goose2/src-tauri/Cargo.toml b/ui/goose2/src-tauri/Cargo.toml
index 8bc4e5eff515..e2629a7a13d4 100644
--- a/ui/goose2/src-tauri/Cargo.toml
+++ b/ui/goose2/src-tauri/Cargo.toml
@@ -40,6 +40,8 @@ tokio-tungstenite = "0.21.0"
 acp-client = { git = "https://github.com/block/builderbot", rev = "db184d20cb48e0c90bbd3fea4a4a871fc9d8a6ad" }
 doctor = { git = "https://github.com/block/builderbot", rev = "8e1c3ec145edc0df5f04b4427cfd758378036862" }
 ignore = "0.4.25"
+base64 = "0.22"
+mime_guess = "2"
 
 [target.'cfg(target_os = "macos")'.dependencies]
 keyring = { version = "3", features = ["apple-native"] }
diff --git a/ui/goose2/src-tauri/src/commands/system.rs b/ui/goose2/src-tauri/src/commands/system.rs
index 3791e4da22f4..6dc45adcb0ea 100644
--- a/ui/goose2/src-tauri/src/commands/system.rs
+++ b/ui/goose2/src-tauri/src/commands/system.rs
@@ -1,3 +1,4 @@
+use base64::Engine;
 use serde::Serialize;
 use tauri::Window;
 use tauri_plugin_dialog::DialogExt;
@@ -9,6 +10,7 @@ use std::path::{Path, PathBuf};
 const DEFAULT_FILE_MENTION_LIMIT: usize = 1500;
 const MAX_FILE_MENTION_LIMIT: usize = 5000;
 const MAX_SCAN_DEPTH: usize = 8;
+const MAX_IMAGE_ATTACHMENT_BYTES: u64 = 20 * 1024 * 1024;
 
 #[derive(Serialize, Clone, Debug, PartialEq, Eq)]
 #[serde(rename_all = "camelCase")]
@@ -18,6 +20,23 @@ pub struct FileTreeEntry {
     pub kind: String,
 }
 
+#[derive(Serialize, Clone, Debug, PartialEq, Eq)]
+#[serde(rename_all = "camelCase")]
+pub struct AttachmentPathInfo {
+    pub name: String,
+    pub path: String,
+    pub kind: String,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub mime_type: Option<String>,
+}
+
+#[derive(Serialize, Clone, Debug, PartialEq, Eq)]
+#[serde(rename_all = "camelCase")]
+pub struct ImageAttachmentPayload {
+    pub base64: String,
+    pub mime_type: String,
+}
+
 #[tauri::command]
 pub fn get_home_dir() -> Result<String, String> {
     let home_dir = dirs::home_dir().ok_or("Could not determine home directory")?;
@@ -81,31 +100,18 @@ fn read_directory_entries(path: &Path) -> Result<Vec<FileTreeEntry>, String> {
         .map_err(|error| format!("Failed to read directory '{}': {}", path.display(), error))?;
 
     for entry in reader {
-        let entry = entry
-            .map_err(|error| format!("Failed to read directory '{}': {}", path.display(), error))?;
+        let Ok(entry) = entry else {
+            continue;
+        };
         let name = entry.file_name().to_string_lossy().into_owned();
         if name == ".git" {
             continue;
         }
+        let Some(file_tree_entry) = build_file_tree_entry(entry.path(), name) else {
+            continue;
+        };
 
-        let file_type = entry.file_type().map_err(|error| {
-            format!(
-                "Failed to inspect directory entry '{}' in '{}': {}",
-                name,
-                path.display(),
-                error
-            )
-        })?;
-
-        entries.push(FileTreeEntry {
-            name,
-            path: entry.path().to_string_lossy().into_owned(),
-            kind: if file_type.is_dir() {
-                "directory".to_string()
-            } else {
-                "file".to_string()
-            },
-        });
+        entries.push(file_tree_entry);
     }
 
     entries.sort_by(|a, b| {
@@ -120,11 +126,138 @@ fn read_directory_entries(path: &Path) -> Result<Vec<FileTreeEntry>, String> {
     Ok(entries)
 }
 
+fn build_file_tree_entry(path: PathBuf, name: String) -> Option<FileTreeEntry> {
+    let metadata = fs::symlink_metadata(&path).ok()?;
+    let file_type = metadata.file_type();
+
+    Some(FileTreeEntry {
+        name,
+        path: path.to_string_lossy().into_owned(),
+        kind: if file_type.is_dir() {
+            "directory".to_string()
+        } else {
+            "file".to_string()
+        },
+    })
+}
+
 #[tauri::command]
 pub fn list_directory_entries(path: String) -> Result<Vec<FileTreeEntry>, String> {
     read_directory_entries(Path::new(&path))
 }
 
+fn inspect_attachment_path(path: &Path) -> Result<AttachmentPathInfo, String> {
+    if !path.exists() {
+        return Err(format!(
+            "Attachment path does not exist: {}",
+            path.display()
+        ));
+    }
+
+    let metadata = fs::metadata(path)
+        .map_err(|error| format!("Failed to inspect '{}': {}", path.display(), error))?;
+    let name = path
+        .file_name()
+        .map(|value| value.to_string_lossy().into_owned())
+        .unwrap_or_else(|| path.to_string_lossy().into_owned());
+
+    Ok(AttachmentPathInfo {
+        name,
+        path: path.to_string_lossy().into_owned(),
+        kind: if metadata.is_dir() {
+            "directory".to_string()
+        } else {
+            "file".to_string()
+        },
+        mime_type: if metadata.is_file() {
+            mime_guess::from_path(path)
+                .first_raw()
+                .map(std::borrow::ToOwned::to_owned)
+        } else {
+            None
+        },
+    })
+}
+
+fn normalized_path_key(path: &Path) -> String {
+    if let Ok(canonical) = path.canonicalize() {
+        return canonical.to_string_lossy().into_owned();
+    }
+
+    let raw = path.to_string_lossy().into_owned();
+    #[cfg(any(target_os = "macos", target_os = "windows"))]
+    {
+        raw.to_lowercase()
+    }
+    #[cfg(not(any(target_os = "macos", target_os = "windows")))]
+    {
+        raw
+    }
+}
+
+fn normalize_attachment_paths(paths: Vec<String>) -> Vec<PathBuf> {
+    let mut seen = HashSet::new();
+    let mut normalized = Vec::new();
+
+    for raw_path in paths {
+        let trimmed = raw_path.trim();
+        if trimmed.is_empty() {
+            continue;
+        }
+
+        let path = PathBuf::from(trimmed);
+        let key = normalized_path_key(&path);
+        if seen.insert(key) {
+            normalized.push(path);
+        }
+    }
+
+    normalized
+}
+
+#[tauri::command]
+pub fn inspect_attachment_paths(paths: Vec<String>) -> Result<Vec<AttachmentPathInfo>, String> {
+    let mut attachments = Vec::new();
+
+    for path in normalize_attachment_paths(paths) {
+        if let Ok(attachment) = inspect_attachment_path(&path) {
+            attachments.push(attachment);
+        }
+    }
+
+    Ok(attachments)
+}
+
+#[tauri::command]
+pub fn read_image_attachment(path: String) -> Result<ImageAttachmentPayload, String> {
+    let attachment = inspect_attachment_path(Path::new(&path))?;
+    let mime_type = attachment
+        .mime_type
+        .ok_or_else(|| format!("Unable to determine image type for '{}'", attachment.path))?;
+
+    if !mime_type.starts_with("image/") {
+        return Err(format!("Attachment is not an image: {}", attachment.path));
+    }
+
+    let metadata = fs::metadata(&attachment.path)
+        .map_err(|error| format!("Failed to inspect image '{}': {}", attachment.path, error))?;
+    if metadata.len() > MAX_IMAGE_ATTACHMENT_BYTES {
+        return Err(format!(
+            "Image attachment '{}' exceeds the {} MB limit",
+            attachment.path,
+            MAX_IMAGE_ATTACHMENT_BYTES / (1024 * 1024)
+        ));
+    }
+
+    let bytes = fs::read(&attachment.path)
+        .map_err(|error| format!("Failed to read image '{}': {}", attachment.path, error))?;
+
+    Ok(ImageAttachmentPayload {
+        base64: base64::engine::general_purpose::STANDARD.encode(bytes),
+        mime_type,
+    })
+}
+
 fn normalize_roots(roots: Vec<String>) -> Vec<PathBuf> {
     let mut dedup = HashSet::new();
     let mut normalized = Vec::new();
@@ -134,7 +267,7 @@ fn normalize_roots(roots: Vec<String>) -> Vec<PathBuf> {
             continue;
         }
         let path = PathBuf::from(trimmed);
-        let key = path.to_string_lossy().to_lowercase();
+        let key = normalized_path_key(&path);
         if dedup.insert(key) {
             normalized.push(path);
         }
@@ -195,7 +328,7 @@ fn scan_files_for_mentions(roots: Vec<String>, max_results: Option<usize>) -> Ve
             continue;
         }
         let path_str = entry.path().to_string_lossy().to_string();
-        let dedup_key = path_str.to_lowercase();
+        let dedup_key = normalized_path_key(entry.path());
         if seen.insert(dedup_key) {
             files.push(path_str);
         }
@@ -217,10 +350,16 @@ pub async fn list_files_for_mentions(
 
 #[cfg(test)]
 mod tests {
-    use super::{read_directory_entries, scan_files_for_mentions};
+    use super::{
+        build_file_tree_entry, inspect_attachment_path, inspect_attachment_paths,
+        normalize_attachment_paths, normalize_roots, read_directory_entries, read_image_attachment,
+        scan_files_for_mentions, MAX_IMAGE_ATTACHMENT_BYTES,
+    };
+    use base64::Engine;
     use std::fs;
     #[cfg(unix)]
     use std::os::unix::fs::PermissionsExt;
+    use std::path::PathBuf;
     use std::process::Command;
     use tempfile::tempdir;
 
@@ -340,6 +479,16 @@ mod tests {
         assert!(error.contains("Directory does not exist"));
     }
 
+    #[test]
+    fn build_file_tree_entry_skips_missing_children() {
+        let dir = tempdir().expect("tempdir");
+        let missing = dir.path().join("missing.ts");
+
+        let entry = build_file_tree_entry(missing, "missing.ts".into());
+
+        assert_eq!(entry, None);
+    }
+
     #[test]
     #[cfg(unix)]
     fn list_directory_entries_errors_for_unreadable_directories() {
@@ -360,4 +509,118 @@ mod tests {
 
         assert!(error.contains("Failed to read directory"));
     }
+
+    #[test]
+    fn inspects_file_and_directory_attachments() {
+        let dir = tempdir().expect("tempdir");
+        let root = dir.path();
+        let folder = root.join("screenshots");
+        let file = root.join("report.txt");
+
+        fs::create_dir_all(&folder).expect("folder");
+        fs::write(&file, "hello").expect("file");
+
+        let inspected_dir = inspect_attachment_path(&folder).expect("directory");
+        let inspected_file = inspect_attachment_path(&file).expect("file");
+
+        assert_eq!(inspected_dir.kind, "directory");
+        assert_eq!(inspected_dir.name, "screenshots");
+        assert_eq!(inspected_dir.mime_type, None);
+
+        assert_eq!(inspected_file.kind, "file");
+        assert_eq!(inspected_file.name, "report.txt");
+        assert_eq!(inspected_file.mime_type.as_deref(), Some("text/plain"));
+    }
+
+    #[test]
+    fn reads_image_attachment_payloads() {
+        let dir = tempdir().expect("tempdir");
+        let image = dir.path().join("pixel.png");
+        let png_bytes = base64::engine::general_purpose::STANDARD
+            .decode("iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAQAAAC1HAwCAAAAC0lEQVR42mP8/x8AAusB9sU4nS0AAAAASUVORK5CYII=")
+            .expect("decode png");
+
+        fs::write(&image, png_bytes).expect("png file");
+
+        let payload = read_image_attachment(image.to_string_lossy().into_owned()).expect("payload");
+
+        assert_eq!(payload.mime_type, "image/png");
+        assert!(!payload.base64.is_empty());
+    }
+
+    #[test]
+    fn dedupes_attachment_paths_using_platform_path_rules() {
+        let normalized = normalize_attachment_paths(vec![
+            "/tmp/Readme.md".into(),
+            "/tmp/README.md".into(),
+            "/tmp/Readme.md".into(),
+        ]);
+
+        if cfg!(any(target_os = "macos", target_os = "windows")) {
+            assert_eq!(normalized, vec![PathBuf::from("/tmp/Readme.md")]);
+        } else {
+            assert_eq!(
+                normalized,
+                vec![
+                    PathBuf::from("/tmp/Readme.md"),
+                    PathBuf::from("/tmp/README.md")
+                ]
+            );
+        }
+    }
+
+    #[test]
+    fn skips_invalid_attachment_paths_without_dropping_valid_ones() {
+        let dir = tempdir().expect("tempdir");
+        let valid = dir.path().join("report.txt");
+        let missing = dir.path().join("missing.txt");
+        fs::write(&valid, "hello").expect("file");
+
+        let attachments = inspect_attachment_paths(vec![
+            valid.to_string_lossy().into_owned(),
+            missing.to_string_lossy().into_owned(),
+        ])
+        .expect("attachments");
+
+        assert_eq!(attachments.len(), 1);
+        assert_eq!(attachments[0].name, "report.txt");
+        assert_eq!(attachments[0].kind, "file");
+    }
+
+    #[test]
+    fn dedupes_mention_roots_using_platform_path_rules() {
+        let normalized = normalize_roots(vec![
+            "/tmp/Workspace".into(),
+            "/tmp/workspace".into(),
+            "/tmp/Workspace".into(),
+        ]);
+
+        if cfg!(any(target_os = "macos", target_os = "windows")) {
+            assert_eq!(normalized, vec![PathBuf::from("/tmp/Workspace")]);
+        } else {
+            assert_eq!(
+                normalized,
+                vec![
+                    PathBuf::from("/tmp/Workspace"),
+                    PathBuf::from("/tmp/workspace")
+                ]
+            );
+        }
+    }
+
+    #[test]
+    fn rejects_oversized_image_attachment_payloads() {
+        let dir = tempdir().expect("tempdir");
+        let image = dir.path().join("huge.png");
+        fs::write(
+            &image,
+            vec![0_u8; (MAX_IMAGE_ATTACHMENT_BYTES as usize) + 1],
+        )
+        .expect("oversized image file");
+
+        let error =
+            read_image_attachment(image.to_string_lossy().into_owned()).expect_err("size limit");
+
+        assert!(error.contains("exceeds the 20 MB limit"));
+    }
 }
diff --git a/ui/goose2/src-tauri/src/lib.rs b/ui/goose2/src-tauri/src/lib.rs
index 82ae9f3ce211..799d0d32034a 100644
--- a/ui/goose2/src-tauri/src/lib.rs
+++ b/ui/goose2/src-tauri/src/lib.rs
@@ -101,7 +101,9 @@ pub fn run() {
             commands::system::save_exported_session_file,
             commands::system::path_exists,
             commands::system::list_directory_entries,
+            commands::system::inspect_attachment_paths,
             commands::system::list_files_for_mentions,
+            commands::system::read_image_attachment,
         ])
         .setup(|_app| Ok(()))
         .build(tauri::generate_context!())
diff --git a/ui/goose2/src-tauri/src/services/acp/manager/session_ops/prompt_ops.rs b/ui/goose2/src-tauri/src/services/acp/manager/session_ops/prompt_ops.rs
index f9997844d980..4c2ec2ca9cc8 100644
--- a/ui/goose2/src-tauri/src/services/acp/manager/session_ops/prompt_ops.rs
+++ b/ui/goose2/src-tauri/src/services/acp/manager/session_ops/prompt_ops.rs
@@ -21,6 +21,21 @@ async fn clear_cancel_requested(state: &Arc<Mutex<ManagerState>>, composite_key:
     guard.pending_cancels.remove(composite_key);
 }
 
+pub(super) fn build_content_blocks(
+    prompt: String,
+    images: Vec<(String, String)>,
+) -> Vec<AcpContentBlock> {
+    let mut content_blocks = Vec::with_capacity(images.len() + 1);
+    for (data, mime_type) in images {
+        content_blocks.push(AcpContentBlock::Image(ImageContent::new(
+            data.as_str(),
+            mime_type.as_str(),
+        )));
+    }
+    content_blocks.push(AcpContentBlock::Text(TextContent::new(prompt)));
+    content_blocks
+}
+
 #[allow(clippy::too_many_arguments)]
 pub(in super::super) async fn send_prompt_inner(
     connection: &Arc<ClientSideConnection>,
@@ -77,13 +92,7 @@ pub(in super::super) async fn send_prompt_inner(
         return Ok(());
     }
 
-    let mut content_blocks = vec![AcpContentBlock::Text(TextContent::new(prompt))];
-    for (data, mime_type) in &images {
-        content_blocks.push(AcpContentBlock::Image(ImageContent::new(
-            data.as_str(),
-            mime_type.as_str(),
-        )));
-    }
+    let content_blocks = build_content_blocks(prompt, images);
 
     let result = connection
         .prompt(PromptRequest::new(goose_session_id.clone(), content_blocks))
diff --git a/ui/goose2/src-tauri/src/services/acp/manager/session_ops/tests.rs b/ui/goose2/src-tauri/src/services/acp/manager/session_ops/tests.rs
index 10e98855a1e8..fbc26327ee2f 100644
--- a/ui/goose2/src-tauri/src/services/acp/manager/session_ops/tests.rs
+++ b/ui/goose2/src-tauri/src/services/acp/manager/session_ops/tests.rs
@@ -3,9 +3,12 @@ use std::path::PathBuf;
 use std::sync::atomic::{AtomicU32, Ordering};
 use std::sync::Arc;
 
+use agent_client_protocol::ContentBlock as AcpContentBlock;
+
 use super::{
-    needs_provider_update, prepared_session_for_key, register_prepared_session_keys,
-    wait_for_replay_drain, ManagerState, PreparedSession, MAX_DRAIN_ITERATIONS,
+    needs_provider_update, prepared_session_for_key, prompt_ops::build_content_blocks,
+    register_prepared_session_keys, wait_for_replay_drain, ManagerState, PreparedSession,
+    MAX_DRAIN_ITERATIONS,
 };
 use crate::services::acp::split_composite_key;
 
@@ -175,3 +178,15 @@ async fn replay_drain_caps_iterations_on_runaway_counter() {
     assert_eq!(final_count, MAX_DRAIN_ITERATIONS);
     assert_eq!(poll_count.load(Ordering::SeqCst), MAX_DRAIN_ITERATIONS);
 }
+
+#[test]
+fn build_content_blocks_places_images_before_prompt_text() {
+    let blocks = build_content_blocks(
+        "Please inspect all three attachments".to_string(),
+        vec![("abc123".to_string(), "image/png".to_string())],
+    );
+
+    assert_eq!(blocks.len(), 2);
+    assert!(matches!(blocks[0], AcpContentBlock::Image(_)));
+    assert!(matches!(blocks[1], AcpContentBlock::Text(_)));
+}
diff --git a/ui/goose2/src-tauri/tauri.conf.json b/ui/goose2/src-tauri/tauri.conf.json
index f958b67c2ad2..2ea07b5551e7 100644
--- a/ui/goose2/src-tauri/tauri.conf.json
+++ b/ui/goose2/src-tauri/tauri.conf.json
@@ -22,7 +22,7 @@
         "visible": false,
         "titleBarStyle": "Overlay",
         "hiddenTitle": true,
-        "dragDropEnabled": false,
+        "dragDropEnabled": true,
         "trafficLightPosition": { "x": 12, "y": 22 }
       }
     ],
diff --git a/ui/goose2/src/app/AppShell.tsx b/ui/goose2/src/app/AppShell.tsx
index f701b04f750e..b7b9d8ca4a7c 100644
--- a/ui/goose2/src/app/AppShell.tsx
+++ b/ui/goose2/src/app/AppShell.tsx
@@ -1,7 +1,7 @@
 import { useCallback, useEffect, useMemo, useRef, useState } from "react";
 import { Sidebar } from "@/features/sidebar/ui/Sidebar";
 import { StatusBar } from "@/features/status/ui/StatusBar";
-import type { PastedImage } from "@/shared/types/messages";
+import type { ChatAttachmentDraft } from "@/shared/types/messages";
 import { CreateProjectDialog } from "@/features/projects/ui/CreateProjectDialog";
 import { archiveProject } from "@/features/projects/api/projects";
 import type { ProjectInfo } from "@/features/projects/api/projects";
@@ -135,8 +135,8 @@ export function AppShell({ children }: { children?: React.ReactNode }) {
   const [pendingInitialMessage, setPendingInitialMessage] = useState<
     string | undefined
   >();
-  const [pendingInitialImages, setPendingInitialImages] = useState<
-    PastedImage[] | undefined
+  const [pendingInitialAttachments, setPendingInitialAttachments] = useState<
+    ChatAttachmentDraft[] | undefined
   >();
   const [homeSelectedPersonaId, setHomeSelectedPersonaId] = useState<
     string | undefined
@@ -363,12 +363,12 @@ export function AppShell({ children }: { children?: React.ReactNode }) {
       providerId?: string,
       personaId?: string,
       projectId?: string | null,
-      images?: PastedImage[],
+      attachments?: ChatAttachmentDraft[],
     ) => {
       setHomeSelectedProvider(providerId);
       setHomeSelectedPersonaId(personaId);
       setPendingInitialMessage(initialMessage);
-      setPendingInitialImages(images);
+      setPendingInitialAttachments(attachments);
       const selectedProject =
         projectId != null
           ? projectStore.projects.find((project) => project.id === projectId)
@@ -501,7 +501,7 @@ export function AppShell({ children }: { children?: React.ReactNode }) {
   const activeSessionPersonaId = activeSession?.personaId;
   const handleInitialMessageConsumed = useCallback(() => {
     setPendingInitialMessage(undefined);
-    setPendingInitialImages(undefined);
+    setPendingInitialAttachments(undefined);
     setHomeSelectedProvider(undefined);
     setHomeSelectedPersonaId(undefined);
   }, []);
@@ -580,7 +580,7 @@ export function AppShell({ children }: { children?: React.ReactNode }) {
               homeSelectedProvider={homeSelectedProvider}
               homeSelectedPersonaId={homeSelectedPersonaId}
               pendingInitialMessage={pendingInitialMessage}
-              pendingInitialImages={pendingInitialImages}
+              pendingInitialAttachments={pendingInitialAttachments}
               onArchiveChat={handleArchiveChat}
               onCreateProject={openCreateProjectDialog}
               onHomeStartChat={handleHomeStartChat}
diff --git a/ui/goose2/src/app/ui/AppShellContent.tsx b/ui/goose2/src/app/ui/AppShellContent.tsx
index b8749baf3808..4100082a687f 100644
--- a/ui/goose2/src/app/ui/AppShellContent.tsx
+++ b/ui/goose2/src/app/ui/AppShellContent.tsx
@@ -5,7 +5,7 @@ import { AgentsView } from "@/features/agents/ui/AgentsView";
 import { ProjectsView } from "@/features/projects/ui/ProjectsView";
 import { SessionHistoryView } from "@/features/sessions/ui/SessionHistoryView";
 import type { ChatSession } from "@/features/chat/stores/chatSessionStore";
-import type { PastedImage } from "@/shared/types/messages";
+import type { ChatAttachmentDraft } from "@/shared/types/messages";
 import type { ProjectInfo } from "@/features/projects/api/projects";
 import type { AppView } from "../AppShell";
 
@@ -16,7 +16,7 @@ interface AppShellContentProps {
   homeSelectedProvider?: string;
   homeSelectedPersonaId?: string;
   pendingInitialMessage?: string;
-  pendingInitialImages?: PastedImage[];
+  pendingInitialAttachments?: ChatAttachmentDraft[];
   onArchiveChat: (sessionId: string) => Promise<void>;
   onCreateProject: (options?: {
     initialWorkingDir?: string | null;
@@ -27,7 +27,7 @@ interface AppShellContentProps {
     providerId?: string,
     personaId?: string,
     projectId?: string | null,
-    images?: PastedImage[],
+    attachments?: ChatAttachmentDraft[],
   ) => void;
   onInitialMessageConsumed: () => void;
   onRenameChat: (sessionId: string, nextTitle: string) => void;
@@ -47,7 +47,7 @@ export function AppShellContent({
   homeSelectedProvider,
   homeSelectedPersonaId,
   pendingInitialMessage,
-  pendingInitialImages,
+  pendingInitialAttachments,
   onArchiveChat,
   onCreateProject,
   onHomeStartChat,
@@ -82,7 +82,7 @@ export function AppShellContent({
           initialProvider={homeSelectedProvider}
           initialPersonaId={activeSessionPersonaId ?? homeSelectedPersonaId}
           initialMessage={pendingInitialMessage}
-          initialImages={pendingInitialImages}
+          initialAttachments={pendingInitialAttachments}
           onCreateProject={onCreateProject}
           onInitialMessageConsumed={onInitialMessageConsumed}
         />
diff --git a/ui/goose2/src/features/chat/hooks/ArtifactPolicyContext.tsx b/ui/goose2/src/features/chat/hooks/ArtifactPolicyContext.tsx
index f60ab26216d6..0774a6d3b853 100644
--- a/ui/goose2/src/features/chat/hooks/ArtifactPolicyContext.tsx
+++ b/ui/goose2/src/features/chat/hooks/ArtifactPolicyContext.tsx
@@ -12,6 +12,7 @@ import { pathExists } from "@/shared/api/system";
 import {
   buildArtifactsIndexForMessages,
   inferHomeDirFromRoots,
+  isWriteOrientedTool,
   resolveMarkdownLocalHref,
   type ArtifactPathCandidate,
 } from "@/features/chat/lib/artifactPathPolicy";
@@ -150,6 +151,12 @@ export function ArtifactPolicyProvider({
 
     for (const ranking of artifactsIndex.byMessageId.values()) {
       if (!ranking.primaryToolCallId || !ranking.primaryCandidate) continue;
+      if (
+        !ranking.primaryCandidate.toolName ||
+        !isWriteOrientedTool(ranking.primaryCandidate.toolName)
+      ) {
+        continue;
+      }
       displayByToolCallId.set(ranking.primaryToolCallId, {
         role: "primary_host",
         primaryCandidate: ranking.primaryCandidate,
@@ -232,6 +239,9 @@ export function ArtifactPolicyProvider({
       for (const candidates of ranking.candidatesByToolCallId.values()) {
         for (const candidate of candidates) {
           if (!candidate.allowed) continue;
+          if (!candidate.toolName || !isWriteOrientedTool(candidate.toolName)) {
+            continue;
+          }
           const key = candidate.resolvedPath.trim().toLowerCase();
           const existing = artifactMap.get(key);
 
diff --git a/ui/goose2/src/features/chat/hooks/__tests__/ArtifactPolicyContext.test.tsx b/ui/goose2/src/features/chat/hooks/__tests__/ArtifactPolicyContext.test.tsx
index 06cb8cffa022..93ed16b1c61c 100644
--- a/ui/goose2/src/features/chat/hooks/__tests__/ArtifactPolicyContext.test.tsx
+++ b/ui/goose2/src/features/chat/hooks/__tests__/ArtifactPolicyContext.test.tsx
@@ -72,6 +72,22 @@ function TextFollowupProbe({
   );
 }
 
+function ReadOnlyProbe({ readArgs }: { readArgs: Record<string, unknown> }) {
+  const { resolveToolCardDisplay, getAllSessionArtifacts } =
+    useArtifactPolicyContext();
+  const display = resolveToolCardDisplay(readArgs, "read_file");
+  const artifacts = getAllSessionArtifacts();
+
+  return (
+    <div>
+      <span data-testid="read-only-role">{display.role}</span>
+      <span data-testid="read-only-artifacts">
+        {artifacts.map((artifact) => artifact.resolvedPath).join(",")}
+      </span>
+    </div>
+  );
+}
+
 function FallbackProbe({
   path = "/Users/test/.goose/projects/sample-project/artifacts/report.md",
 }: {
@@ -171,6 +187,47 @@ describe("ArtifactPolicyContext", () => {
     expect(screen.getByTestId("cloned-role")).toHaveTextContent("none");
   });
 
+  it("does not treat read-only tool paths as session artifacts", () => {
+    mockPathExists.mockReset();
+    mockOpenPath.mockReset();
+    const readArgs = { path: "/Users/test/project-a/notes.md" };
+    const messages: Message[] = [
+      {
+        id: "assistant-read-only",
+        role: "assistant",
+        created: Date.now(),
+        content: [
+          {
+            type: "toolRequest",
+            id: "tool-read",
+            name: "read_file",
+            arguments: readArgs,
+            status: "completed",
+          },
+          {
+            type: "toolResponse",
+            id: "tool-read",
+            name: "read_file",
+            result: "Read /Users/test/project-a/notes.md",
+            isError: false,
+          },
+        ],
+      },
+    ];
+
+    render(
+      <ArtifactPolicyProvider
+        messages={messages}
+        allowedRoots={["/Users/test/project-a", "/Users/test/.goose/artifacts"]}
+      >
+        <ReadOnlyProbe readArgs={readArgs} />
+      </ArtifactPolicyProvider>,
+    );
+
+    expect(screen.getByTestId("read-only-role")).toHaveTextContent("none");
+    expect(screen.getByTestId("read-only-artifacts")).toHaveTextContent("");
+  });
+
   it("falls back to the home artifacts root when a project artifacts path is missing", async () => {
     mockPathExists.mockReset();
     mockOpenPath.mockReset();
diff --git a/ui/goose2/src/features/chat/hooks/__tests__/useChat.attachments.test.ts b/ui/goose2/src/features/chat/hooks/__tests__/useChat.attachments.test.ts
new file mode 100644
index 000000000000..975d5bc56451
--- /dev/null
+++ b/ui/goose2/src/features/chat/hooks/__tests__/useChat.attachments.test.ts
@@ -0,0 +1,252 @@
+import { act, renderHook } from "@testing-library/react";
+import { beforeEach, describe, expect, it, vi } from "vitest";
+import { useAgentStore } from "@/features/agents/stores/agentStore";
+import { useChatStore } from "../../stores/chatStore";
+import { useChatSessionStore } from "../../stores/chatSessionStore";
+
+const mockAcpSendMessage = vi.fn();
+const mockAcpCancelSession = vi.fn();
+const mockAcpPrepareSession = vi.fn();
+const mockAcpSetModel = vi.fn();
+
+vi.mock("@/shared/api/acp", () => ({
+  acpSendMessage: (...args: unknown[]) => mockAcpSendMessage(...args),
+  acpCancelSession: (...args: unknown[]) => mockAcpCancelSession(...args),
+  acpPrepareSession: (...args: unknown[]) => mockAcpPrepareSession(...args),
+  acpSetModel: (...args: unknown[]) => mockAcpSetModel(...args),
+}));
+
+import { useChat } from "../useChat";
+
+describe("useChat attachments", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    useChatStore.setState({
+      messagesBySession: {},
+      sessionStateById: {},
+      activeSessionId: null,
+      isConnected: true,
+    });
+    useChatSessionStore.setState({
+      sessions: [],
+      activeSessionId: null,
+      isLoading: false,
+      contextPanelOpenBySession: {},
+      activeWorkingContextBySession: {},
+      modelsBySession: {},
+      modelCacheByProvider: {},
+    });
+    useAgentStore.setState({
+      personas: [],
+      personasLoading: false,
+      agents: [],
+      agentsLoading: false,
+      activeAgentId: null,
+      isLoading: false,
+      personaEditorOpen: false,
+      editingPersona: null,
+    });
+    mockAcpCancelSession.mockResolvedValue(true);
+    mockAcpPrepareSession.mockResolvedValue(undefined);
+    mockAcpSetModel.mockResolvedValue(undefined);
+  });
+
+  it("stores non-image attachments in metadata and prepends path references to the prompt", async () => {
+    const { result } = renderHook(() => useChat("session-1"));
+    const attachments = [
+      {
+        id: "file-1",
+        kind: "file" as const,
+        name: "report.pdf",
+        path: "/tmp/report.pdf",
+        mimeType: "application/pdf",
+      },
+      {
+        id: "dir-1",
+        kind: "directory" as const,
+        name: "screenshots",
+        path: "/tmp/screenshots",
+      },
+    ];
+
+    await act(async () => {
+      await result.current.sendMessage(
+        "Please review these",
+        undefined,
+        attachments,
+      );
+    });
+
+    const message = useChatStore.getState().messagesBySession["session-1"][0];
+
+    expect(message.metadata?.attachments).toEqual([
+      {
+        type: "file",
+        name: "report.pdf",
+        path: "/tmp/report.pdf",
+        mimeType: "application/pdf",
+      },
+      {
+        type: "directory",
+        name: "screenshots",
+        path: "/tmp/screenshots",
+      },
+    ]);
+    expect(mockAcpSendMessage).toHaveBeenCalledWith(
+      "session-1",
+      "goose",
+      "Attached items:\n- [file] /tmp/report.pdf\n- [directory] /tmp/screenshots\nPlease review these",
+      {
+        systemPrompt: undefined,
+        workingDir: undefined,
+        personaId: undefined,
+        personaName: undefined,
+        images: undefined,
+      },
+    );
+  });
+
+  it("keeps image attachments in ACP images while preserving path metadata", async () => {
+    const { result } = renderHook(() => useChat("session-1"));
+    const attachments = [
+      {
+        id: "image-1",
+        kind: "image" as const,
+        name: "diagram.png",
+        path: "/tmp/diagram.png",
+        mimeType: "image/png",
+        base64: "abc123",
+        previewUrl: "tauri://localhost/tmp/diagram.png",
+      },
+    ];
+
+    await act(async () => {
+      await result.current.sendMessage("", undefined, attachments);
+    });
+
+    const message = useChatStore.getState().messagesBySession["session-1"][0];
+
+    expect(message.metadata?.attachments).toEqual([
+      {
+        type: "file",
+        name: "diagram.png",
+        path: "/tmp/diagram.png",
+        mimeType: "image/png",
+      },
+    ]);
+    expect(message.content).toEqual([
+      { type: "text", text: "" },
+      {
+        type: "image",
+        source: {
+          type: "base64",
+          mediaType: "image/png",
+          data: "abc123",
+        },
+      },
+    ]);
+    expect(mockAcpSendMessage).toHaveBeenCalledWith(
+      "session-1",
+      "goose",
+      "Attached items:\n- [image] diagram.png (image attached)\n ",
+      {
+        systemPrompt: undefined,
+        workingDir: undefined,
+        personaId: undefined,
+        personaName: undefined,
+        images: [["abc123", "image/png"]],
+      },
+    );
+  });
+
+  it("includes image attachments in the prompt summary for mixed sends", async () => {
+    const { result } = renderHook(() => useChat("session-1"));
+    const attachments = [
+      {
+        id: "file-1",
+        kind: "file" as const,
+        name: "mobile-confirmation.html",
+        path: "/tmp/mobile-confirmation.html",
+        mimeType: "text/html",
+      },
+      {
+        id: "dir-1",
+        kind: "directory" as const,
+        name: "neighborhood block",
+        path: "/tmp/neighborhood block",
+      },
+      {
+        id: "image-1",
+        kind: "image" as const,
+        name: "Screenshot 2026-04-09 at 1.25.32 PM.png",
+        path: "/tmp/Screenshot.png",
+        mimeType: "image/png",
+        base64: "abc123",
+        previewUrl: "tauri://localhost/tmp/Screenshot.png",
+      },
+    ];
+
+    await act(async () => {
+      await result.current.sendMessage(
+        "can you see the attachments i attached?",
+        undefined,
+        attachments,
+      );
+    });
+
+    expect(mockAcpSendMessage).toHaveBeenCalledWith(
+      "session-1",
+      "goose",
+      "Attached items:\n- [file] /tmp/mobile-confirmation.html\n- [directory] /tmp/neighborhood block\n- [image] Screenshot 2026-04-09 at 1.25.32 PM.png (image attached)\ncan you see the attachments i attached?",
+      {
+        systemPrompt: undefined,
+        workingDir: undefined,
+        personaId: undefined,
+        personaName: undefined,
+        images: [["abc123", "image/png"]],
+      },
+    );
+  });
+
+  it("preserves pathless browser file attachments in sent message metadata", async () => {
+    const { result } = renderHook(() => useChat("session-1"));
+    const attachments = [
+      {
+        id: "file-1",
+        kind: "file" as const,
+        name: "report.pdf",
+        mimeType: "application/pdf",
+      },
+    ];
+
+    await act(async () => {
+      await result.current.sendMessage(
+        "Please review this",
+        undefined,
+        attachments,
+      );
+    });
+
+    const message = useChatStore.getState().messagesBySession["session-1"][0];
+
+    expect(message.metadata?.attachments).toEqual([
+      {
+        type: "file",
+        name: "report.pdf",
+        mimeType: "application/pdf",
+      },
+    ]);
+    expect(mockAcpSendMessage).toHaveBeenCalledWith(
+      "session-1",
+      "goose",
+      "Attached items:\n- [file] report.pdf\nPlease review this",
+      {
+        systemPrompt: undefined,
+        workingDir: undefined,
+        personaId: undefined,
+        personaName: undefined,
+        images: undefined,
+      },
+    );
+  });
+});
diff --git a/ui/goose2/src/features/chat/hooks/__tests__/useChat.test.ts b/ui/goose2/src/features/chat/hooks/__tests__/useChat.test.ts
index 887ed193262b..141826952fa6 100644
--- a/ui/goose2/src/features/chat/hooks/__tests__/useChat.test.ts
+++ b/ui/goose2/src/features/chat/hooks/__tests__/useChat.test.ts
@@ -134,6 +134,7 @@ describe("useChat", () => {
         workingDir: undefined,
         personaId: "persona-b",
         personaName: "Persona B",
+        images: undefined,
       },
     );
     expect(mockAcpCancelSession).toHaveBeenCalledWith("session-1", "persona-b");
@@ -322,6 +323,7 @@ describe("useChat", () => {
         workingDir: undefined,
         personaId: undefined,
         personaName: undefined,
+        images: undefined,
       },
     );
     expect(mockAcpSendMessage).toHaveBeenNthCalledWith(
@@ -334,6 +336,7 @@ describe("useChat", () => {
         workingDir: undefined,
         personaId: undefined,
         personaName: undefined,
+        images: undefined,
       },
     );
 
@@ -380,6 +383,7 @@ describe("useChat", () => {
         workingDir: undefined,
         personaId: undefined,
         personaName: undefined,
+        images: undefined,
       },
     );
   });
diff --git a/ui/goose2/src/features/chat/hooks/__tests__/useChatInputAttachments.test.ts b/ui/goose2/src/features/chat/hooks/__tests__/useChatInputAttachments.test.ts
new file mode 100644
index 000000000000..8e4c1f027a66
--- /dev/null
+++ b/ui/goose2/src/features/chat/hooks/__tests__/useChatInputAttachments.test.ts
@@ -0,0 +1,73 @@
+import { act, renderHook } from "@testing-library/react";
+import { beforeEach, describe, expect, it, vi } from "vitest";
+
+const mockResizeImage = vi.fn();
+
+vi.mock("../../lib/resizeImage", () => ({
+  resizeImage: (...args: unknown[]) => mockResizeImage(...args),
+}));
+
+vi.mock("@/shared/lib/platform", () => ({
+  getPlatform: () => "mac",
+}));
+
+vi.mock("@tauri-apps/api/core", () => ({
+  convertFileSrc: (path: string) => `asset://${path}`,
+}));
+
+vi.mock("@/shared/api/system", () => ({
+  inspectAttachmentPaths: vi.fn(),
+  readImageAttachment: vi.fn(),
+}));
+
+import { useChatInputAttachments } from "../useChatInputAttachments";
+
+describe("useChatInputAttachments", () => {
+  beforeEach(() => {
+    mockResizeImage.mockReset();
+  });
+
+  it("keeps valid browser file attachments when an image read fails", async () => {
+    mockResizeImage.mockRejectedValue(new Error("resize failed"));
+
+    const fileReaderSpy = vi
+      .spyOn(globalThis, "FileReader")
+      .mockImplementation(() => {
+        const fileReader: {
+          onload: FileReader["onload"];
+          onerror: FileReader["onerror"];
+          readAsDataURL: FileReader["readAsDataURL"];
+        } = {
+          onload: null,
+          onerror: null,
+          readAsDataURL: () => {
+            fileReader.onerror?.call(
+              fileReader as unknown as FileReader,
+              new ProgressEvent("error") as ProgressEvent<FileReader>,
+            );
+          },
+        };
+
+        return fileReader as unknown as FileReader;
+      });
+
+    const { result } = renderHook(() => useChatInputAttachments());
+
+    await act(async () => {
+      await result.current.addBrowserFiles([
+        new File(["bad image"], "broken.png", { type: "image/png" }),
+        new File(["report"], "report.txt", { type: "text/plain" }),
+      ]);
+    });
+
+    expect(result.current.attachments).toEqual([
+      expect.objectContaining({
+        kind: "file",
+        name: "report.txt",
+        mimeType: "text/plain",
+      }),
+    ]);
+
+    fileReaderSpy.mockRestore();
+  });
+});
diff --git a/ui/goose2/src/features/chat/hooks/__tests__/useMessageQueue.test.ts b/ui/goose2/src/features/chat/hooks/__tests__/useMessageQueue.test.ts
index f7902070a8d2..99917d59b580 100644
--- a/ui/goose2/src/features/chat/hooks/__tests__/useMessageQueue.test.ts
+++ b/ui/goose2/src/features/chat/hooks/__tests__/useMessageQueue.test.ts
@@ -100,10 +100,19 @@ describe("useMessageQueue", () => {
 
   it("includes images when auto-sending", () => {
     const sendMessage = vi.fn();
-    const images = [{ base64: "abc", mimeType: "image/png" }];
+    const attachments = [
+      {
+        id: "image-1",
+        kind: "image" as const,
+        name: "image.png",
+        base64: "abc",
+        mimeType: "image/png",
+        previewUrl: "blob:image",
+      },
+    ];
     useChatStore.getState().enqueueMessage("s1", {
       text: "with image",
-      images,
+      attachments,
     });
 
     renderHook(
@@ -112,7 +121,11 @@ describe("useMessageQueue", () => {
       { initialProps: { chatState: "idle" as ChatState } },
     );
 
-    expect(sendMessage).toHaveBeenCalledWith("with image", undefined, images);
+    expect(sendMessage).toHaveBeenCalledWith(
+      "with image",
+      undefined,
+      attachments,
+    );
   });
 
   it("preserves personaId when auto-sending", () => {
diff --git a/ui/goose2/src/features/chat/hooks/useAttachmentDropTarget.ts b/ui/goose2/src/features/chat/hooks/useAttachmentDropTarget.ts
new file mode 100644
index 000000000000..29814e7301e7
--- /dev/null
+++ b/ui/goose2/src/features/chat/hooks/useAttachmentDropTarget.ts
@@ -0,0 +1,228 @@
+import {
+  useCallback,
+  useEffect,
+  useRef,
+  useState,
+  type DragEvent,
+  type RefObject,
+} from "react";
+
+interface UseAttachmentDropTargetOptions {
+  disabled: boolean;
+  isStreaming: boolean;
+  targetRef: RefObject<HTMLDivElement | null>;
+  onDropFiles: (files: File[]) => void;
+  onDropPaths: (paths: string[]) => void;
+}
+
+function hasDraggedFiles(dataTransfer: DataTransfer) {
+  return (
+    Array.from(dataTransfer.items).some((item) => item.kind === "file") ||
+    Array.from(dataTransfer.types).includes("Files")
+  );
+}
+
+function isInTauriEnvironment() {
+  return typeof window !== "undefined" && Boolean(window.__TAURI_INTERNALS__);
+}
+
+function isPointInsideRect(point: { x: number; y: number }, rect: DOMRect) {
+  return (
+    point.x >= rect.left &&
+    point.x <= rect.right &&
+    point.y >= rect.top &&
+    point.y <= rect.bottom
+  );
+}
+
+function getTargetHitTest(
+  target: HTMLDivElement | null,
+  position: { x: number; y: number },
+) {
+  if (!target) {
+    return {
+      inside: false,
+      rawInside: false,
+      scaledInside: false,
+      rawElementInside: false,
+      scaledElementInside: false,
+      rawPosition: position,
+      scaledPosition: position,
+      rect: null,
+      scale: 1,
+    };
+  }
+
+  const rect = target.getBoundingClientRect();
+  const scale = window.devicePixelRatio || 1;
+  const rawPosition = { x: position.x, y: position.y };
+  const scaledPosition = {
+    x: position.x / scale,
+    y: position.y / scale,
+  };
+  const rawInside = isPointInsideRect(rawPosition, rect);
+  const scaledInside = isPointInsideRect(scaledPosition, rect);
+  const rawElement = document.elementFromPoint(rawPosition.x, rawPosition.y);
+  const scaledElement = document.elementFromPoint(
+    scaledPosition.x,
+    scaledPosition.y,
+  );
+  const rawElementInside = Boolean(rawElement && target.contains(rawElement));
+  const scaledElementInside = Boolean(
+    scaledElement && target.contains(scaledElement),
+  );
+
+  return {
+    inside:
+      rawInside || scaledInside || rawElementInside || scaledElementInside,
+    rawInside,
+    scaledInside,
+    rawElementInside,
+    scaledElementInside,
+    rawPosition,
+    scaledPosition,
+    rect: {
+      left: rect.left,
+      right: rect.right,
+      top: rect.top,
+      bottom: rect.bottom,
+      width: rect.width,
+      height: rect.height,
+    },
+    scale,
+  };
+}
+
+export function useAttachmentDropTarget({
+  disabled,
+  isStreaming,
+  targetRef,
+  onDropFiles,
+  onDropPaths,
+}: UseAttachmentDropTargetOptions) {
+  const [isAttachmentDragOver, setIsAttachmentDragOver] = useState(false);
+  const dragDepthRef = useRef(0);
+  const tauriDropHandledAtRef = useRef(0);
+
+  const handleDragEnter = useCallback(
+    (event: DragEvent<HTMLDivElement>) => {
+      const draggedFiles = hasDraggedFiles(event.dataTransfer);
+      if (disabled || isStreaming || !draggedFiles) {
+        return;
+      }
+
+      event.preventDefault();
+      dragDepthRef.current += 1;
+      setIsAttachmentDragOver(true);
+    },
+    [disabled, isStreaming],
+  );
+
+  const handleDragOver = useCallback(
+    (event: DragEvent<HTMLDivElement>) => {
+      const draggedFiles = hasDraggedFiles(event.dataTransfer);
+      if (disabled || isStreaming || !draggedFiles) {
+        return;
+      }
+
+      event.preventDefault();
+      event.dataTransfer.dropEffect = "copy";
+      setIsAttachmentDragOver(true);
+    },
+    [disabled, isStreaming],
+  );
+
+  const handleDragLeave = useCallback((event: DragEvent<HTMLDivElement>) => {
+    event.preventDefault();
+    dragDepthRef.current = Math.max(0, dragDepthRef.current - 1);
+    if (dragDepthRef.current === 0) {
+      setIsAttachmentDragOver(false);
+    }
+  }, []);
+
+  const handleDrop = useCallback(
+    (event: DragEvent<HTMLDivElement>) => {
+      const draggedFiles = hasDraggedFiles(event.dataTransfer);
+      if (disabled || isStreaming || !draggedFiles) {
+        return;
+      }
+
+      event.preventDefault();
+      dragDepthRef.current = 0;
+      setIsAttachmentDragOver(false);
+
+      const files = Array.from(event.dataTransfer.files);
+      if (files.length === 0) {
+        return;
+      }
+
+      if (Date.now() - tauriDropHandledAtRef.current < 250) {
+        return;
+      }
+
+      onDropFiles(files);
+    },
+    [disabled, isStreaming, onDropFiles],
+  );
+
+  useEffect(() => {
+    if (!isInTauriEnvironment()) {
+      return;
+    }
+
+    let disposed = false;
+    let unlisten: (() => void) | undefined;
+
+    void import("@tauri-apps/api/webview")
+      .then(({ getCurrentWebview }) =>
+        getCurrentWebview().onDragDropEvent(({ payload }) => {
+          if (disposed) {
+            return;
+          }
+
+          if (payload.type === "leave") {
+            setIsAttachmentDragOver(false);
+            return;
+          }
+
+          const hitTest = getTargetHitTest(targetRef.current, payload.position);
+
+          if (payload.type === "drop") {
+            setIsAttachmentDragOver(false);
+            if (
+              !hitTest.inside ||
+              disabled ||
+              isStreaming ||
+              payload.paths.length === 0
+            ) {
+              return;
+            }
+            tauriDropHandledAtRef.current = Date.now();
+            onDropPaths(payload.paths);
+            return;
+          }
+
+          setIsAttachmentDragOver(hitTest.inside && !disabled && !isStreaming);
+        }),
+      )
+      .then((fn) => {
+        unlisten = fn;
+      })
+      .catch(() => {
+        setIsAttachmentDragOver(false);
+      });
+
+    return () => {
+      disposed = true;
+      unlisten?.();
+    };
+  }, [disabled, isStreaming, onDropPaths, targetRef]);
+
+  return {
+    isAttachmentDragOver,
+    handleDragEnter,
+    handleDragOver,
+    handleDragLeave,
+    handleDrop,
+  };
+}
diff --git a/ui/goose2/src/features/chat/hooks/useChat.ts b/ui/goose2/src/features/chat/hooks/useChat.ts
index 73ee7947d4cc..cd45ba8a0acc 100644
--- a/ui/goose2/src/features/chat/hooks/useChat.ts
+++ b/ui/goose2/src/features/chat/hooks/useChat.ts
@@ -2,6 +2,7 @@ import { useCallback, useRef } from "react";
 import { useChatStore } from "../stores/chatStore";
 import { useChatSessionStore } from "../stores/chatSessionStore";
 import {
+  type ChatAttachmentDraft,
   createSystemNotificationMessage,
   createUserMessage,
 } from "@/shared/types/messages";
@@ -13,8 +14,16 @@ import {
   acpSetModel,
 } from "@/shared/api/acp";
 import { useAgentStore } from "@/features/agents/stores/agentStore";
-import { isDefaultChatTitle } from "../lib/sessionTitle";
+import {
+  getSessionTitleFromDraft,
+  isDefaultChatTitle,
+} from "../lib/sessionTitle";
 import { findLastIndex } from "@/shared/lib/arrays";
+import {
+  buildAcpImages,
+  buildAttachmentPromptPreamble,
+  buildMessageAttachments,
+} from "../lib/attachments";
 
 function getErrorMessage(error: unknown): string {
   // Tauri command rejections typically arrive as plain strings, so handle
@@ -118,10 +127,12 @@ export function useChat(
     async (
       text: string,
       overridePersona?: { id: string; name?: string },
-      images?: { base64: string; mimeType: string }[],
+      attachments?: ChatAttachmentDraft[],
     ) => {
+      const images = buildAcpImages(attachments);
+      const hasAttachments = (attachments?.length ?? 0) > 0;
       if (
-        (!text.trim() && (!images || images.length === 0)) ||
+        (!text.trim() && !hasAttachments) ||
         chatState === "streaming" ||
         chatState === "thinking"
       )
@@ -141,7 +152,10 @@ export function useChat(
       store.setPendingAssistantProvider(sessionId, providerId);
 
       // Create and add user message
-      const userMessage = createUserMessage(text);
+      const userMessage = createUserMessage(
+        text,
+        buildMessageAttachments(attachments),
+      );
       if (effectivePersonaInfo) {
         userMessage.metadata = {
           ...userMessage.metadata,
@@ -185,7 +199,7 @@ export function useChat(
         sessionStore.updateSession(
           sessionId,
           {
-            title: text.trim().slice(0, 100),
+            title: getSessionTitleFromDraft(text, attachments),
             updatedAt: new Date().toISOString(),
           },
           { localOnly: wasDraft },
@@ -218,7 +232,10 @@ export function useChat(
         store.setChatState(sessionId, "streaming");
         // When images are present with no text, pass a single space so the ACP
         // driver doesn't send an empty text content block that goose rejects.
-        const acpPrompt = text.trim() || (images?.length ? " " : text);
+        const attachmentPromptPreamble =
+          buildAttachmentPromptPreamble(attachments);
+        const promptBody = text.trim() || (images?.length ? " " : text);
+        const acpPrompt = `${attachmentPromptPreamble}${promptBody}`;
         await acpSendMessage(sessionId, providerId, acpPrompt, {
           systemPrompt,
           workingDir: workingDirOverride,
diff --git a/ui/goose2/src/features/chat/hooks/useChatInputAttachments.ts b/ui/goose2/src/features/chat/hooks/useChatInputAttachments.ts
new file mode 100644
index 000000000000..4b24938ae11f
--- /dev/null
+++ b/ui/goose2/src/features/chat/hooks/useChatInputAttachments.ts
@@ -0,0 +1,233 @@
+import { useCallback, useEffect, useRef, useState } from "react";
+import { convertFileSrc } from "@tauri-apps/api/core";
+import {
+  inspectAttachmentPaths,
+  readImageAttachment,
+} from "@/shared/api/system";
+import type {
+  ChatAttachmentDraft,
+  ChatDirectoryAttachmentDraft,
+  ChatFileAttachmentDraft,
+  ChatImageAttachmentDraft,
+} from "@/shared/types/messages";
+import { getPlatform } from "@/shared/lib/platform";
+import { resizeImage } from "../lib/resizeImage";
+
+function isBlobPreview(url: string) {
+  return url.startsWith("blob:");
+}
+
+function revokeAttachmentPreview(attachment: ChatAttachmentDraft) {
+  if (attachment.kind === "image" && isBlobPreview(attachment.previewUrl)) {
+    URL.revokeObjectURL(attachment.previewUrl);
+  }
+}
+
+function pathToPreviewUrl(path: string) {
+  return typeof window !== "undefined" && window.__TAURI_INTERNALS__
+    ? convertFileSrc(path)
+    : path;
+}
+
+function attachmentPathKey(path?: string) {
+  if (!path) {
+    return null;
+  }
+
+  return getPlatform() === "linux" ? path : path.toLowerCase();
+}
+
+async function createImageAttachmentFromFile(
+  file: File,
+): Promise<ChatImageAttachmentDraft> {
+  const previewUrl = URL.createObjectURL(file);
+
+  try {
+    const { base64, mimeType } = await resizeImage(file).catch(
+      () =>
+        new Promise<{ base64: string; mimeType: string }>((resolve, reject) => {
+          const reader = new FileReader();
+          reader.onload = () => {
+            const dataUrl = reader.result as string;
+            const [header, base64] = dataUrl.split(",");
+            const mimeType = header.replace("data:", "").replace(";base64", "");
+            resolve({ base64, mimeType });
+          };
+          reader.onerror = () => reject(new Error("Failed to read image"));
+          reader.readAsDataURL(file);
+        }),
+    );
+
+    return {
+      id: crypto.randomUUID(),
+      kind: "image",
+      name: file.name,
+      mimeType,
+      base64,
+      previewUrl,
+    };
+  } catch (error) {
+    URL.revokeObjectURL(previewUrl);
+    throw error;
+  }
+}
+
+export function normalizeDialogSelection(
+  selected: string | string[] | null,
+): string[] {
+  if (!selected) {
+    return [];
+  }
+
+  return Array.isArray(selected) ? selected : [selected];
+}
+
+export function useChatInputAttachments() {
+  const [attachments, setAttachments] = useState<ChatAttachmentDraft[]>([]);
+  const attachmentsRef = useRef(attachments);
+  attachmentsRef.current = attachments;
+
+  useEffect(
+    () => () => {
+      for (const attachment of attachmentsRef.current) {
+        revokeAttachmentPreview(attachment);
+      }
+    },
+    [],
+  );
+
+  const appendAttachments = useCallback((incoming: ChatAttachmentDraft[]) => {
+    if (incoming.length === 0) {
+      return;
+    }
+
+    setAttachments((previous) => {
+      const seenPaths = new Set(
+        previous
+          .map((attachment) => attachmentPathKey(attachment.path))
+          .filter((value): value is string => Boolean(value)),
+      );
+      const next = [...previous];
+
+      for (const attachment of incoming) {
+        const pathKey = attachmentPathKey(attachment.path);
+        if (pathKey && seenPaths.has(pathKey)) {
+          revokeAttachmentPreview(attachment);
+          continue;
+        }
+
+        if (pathKey) {
+          seenPaths.add(pathKey);
+        }
+        next.push(attachment);
+      }
+
+      return next;
+    });
+  }, []);
+
+  const addBrowserFiles = useCallback(
+    async (files: File[]) => {
+      const nextAttachments = (
+        await Promise.allSettled(
+          files.map(async (file) => {
+            if (file.type.startsWith("image/")) {
+              return createImageAttachmentFromFile(file);
+            }
+
+            return {
+              id: crypto.randomUUID(),
+              kind: "file",
+              name: file.name,
+              ...(file.type ? { mimeType: file.type } : {}),
+            } satisfies ChatFileAttachmentDraft;
+          }),
+        )
+      ).flatMap((result) =>
+        result.status === "fulfilled" ? [result.value] : [],
+      );
+
+      appendAttachments(nextAttachments);
+    },
+    [appendAttachments],
+  );
+
+  const addPathAttachments = useCallback(
+    async (paths: string[]) => {
+      if (paths.length === 0) {
+        return;
+      }
+
+      const inspectedPaths = await inspectAttachmentPaths(paths);
+      const nextAttachments = await Promise.all(
+        inspectedPaths.map(async (attachmentPath) => {
+          if (attachmentPath.kind === "directory") {
+            return {
+              id: crypto.randomUUID(),
+              kind: "directory",
+              name: attachmentPath.name,
+              path: attachmentPath.path,
+            } satisfies ChatDirectoryAttachmentDraft;
+          }
+
+          if (attachmentPath.mimeType?.startsWith("image/")) {
+            try {
+              const image = await readImageAttachment(attachmentPath.path);
+              return {
+                id: crypto.randomUUID(),
+                kind: "image",
+                name: attachmentPath.name,
+                path: attachmentPath.path,
+                mimeType: image.mimeType,
+                base64: image.base64,
+                previewUrl: pathToPreviewUrl(attachmentPath.path),
+              } satisfies ChatImageAttachmentDraft;
+            } catch {
+              // Fall back to a generic file attachment if image loading fails.
+            }
+          }
+
+          return {
+            id: crypto.randomUUID(),
+            kind: "file",
+            name: attachmentPath.name,
+            path: attachmentPath.path,
+            ...(attachmentPath.mimeType
+              ? { mimeType: attachmentPath.mimeType }
+              : {}),
+          } satisfies ChatFileAttachmentDraft;
+        }),
+      );
+
+      appendAttachments(nextAttachments);
+    },
+    [appendAttachments],
+  );
+
+  const removeAttachment = useCallback((id: string) => {
+    setAttachments((previous) => {
+      const found = previous.find((attachment) => attachment.id === id);
+      if (found) {
+        revokeAttachmentPreview(found);
+      }
+      return previous.filter((attachment) => attachment.id !== id);
+    });
+  }, []);
+
+  const clearAttachments = useCallback(() => {
+    setAttachments((previous) => {
+      for (const attachment of previous) {
+        revokeAttachmentPreview(attachment);
+      }
+      return [];
+    });
+  }, []);
+
+  return {
+    attachments,
+    addBrowserFiles,
+    addPathAttachments,
+    removeAttachment,
+    clearAttachments,
+  };
+}
diff --git a/ui/goose2/src/features/chat/hooks/useImageDropTarget.ts b/ui/goose2/src/features/chat/hooks/useImageDropTarget.ts
deleted file mode 100644
index 141d866c2fdd..000000000000
--- a/ui/goose2/src/features/chat/hooks/useImageDropTarget.ts
+++ /dev/null
@@ -1,98 +0,0 @@
-import { useCallback, useRef, useState, type DragEvent } from "react";
-
-interface UseImageDropTargetOptions {
-  disabled: boolean;
-  isStreaming: boolean;
-  onDropFile: (file: File) => void;
-}
-
-function hasDraggedFiles(dataTransfer: DataTransfer) {
-  return (
-    Array.from(dataTransfer.items).some(
-      (item) => item.kind === "file" || item.type.startsWith("image/"),
-    ) || Array.from(dataTransfer.types).includes("Files")
-  );
-}
-
-export function useImageDropTarget({
-  disabled,
-  isStreaming,
-  onDropFile,
-}: UseImageDropTargetOptions) {
-  const [isImageDragOver, setIsImageDragOver] = useState(false);
-  const dragDepthRef = useRef(0);
-
-  const handleDragEnter = useCallback(
-    (e: DragEvent<HTMLDivElement>) => {
-      if (disabled || isStreaming || !hasDraggedFiles(e.dataTransfer)) {
-        return;
-      }
-
-      e.preventDefault();
-      dragDepthRef.current += 1;
-      setIsImageDragOver(true);
-    },
-    [disabled, isStreaming],
-  );
-
-  const handleDragOver = useCallback(
-    (e: DragEvent<HTMLDivElement>) => {
-      if (disabled || isStreaming || !hasDraggedFiles(e.dataTransfer)) {
-        return;
-      }
-
-      e.preventDefault();
-      e.dataTransfer.dropEffect = "copy";
-      setIsImageDragOver(true);
-    },
-    [disabled, isStreaming],
-  );
-
-  const handleDragLeave = useCallback(
-    (e: DragEvent<HTMLDivElement>) => {
-      e.preventDefault();
-
-      if (!isImageDragOver) {
-        return;
-      }
-
-      dragDepthRef.current = Math.max(0, dragDepthRef.current - 1);
-      if (dragDepthRef.current === 0) {
-        setIsImageDragOver(false);
-      }
-    },
-    [isImageDragOver],
-  );
-
-  const handleDrop = useCallback(
-    (e: DragEvent<HTMLDivElement>) => {
-      dragDepthRef.current = 0;
-      setIsImageDragOver(false);
-
-      if (disabled || isStreaming) {
-        return;
-      }
-
-      const files = Array.from(e.dataTransfer.files).filter((file) =>
-        file.type.startsWith("image/"),
-      );
-      if (files.length === 0) {
-        return;
-      }
-
-      e.preventDefault();
-      for (const file of files) {
-        onDropFile(file);
-      }
-    },
-    [disabled, isStreaming, onDropFile],
-  );
-
-  return {
-    isImageDragOver,
-    handleDragEnter,
-    handleDragOver,
-    handleDragLeave,
-    handleDrop,
-  };
-}
diff --git a/ui/goose2/src/features/chat/hooks/useMessageQueue.ts b/ui/goose2/src/features/chat/hooks/useMessageQueue.ts
index 43ee409fd99e..bc5859039d5f 100644
--- a/ui/goose2/src/features/chat/hooks/useMessageQueue.ts
+++ b/ui/goose2/src/features/chat/hooks/useMessageQueue.ts
@@ -1,5 +1,6 @@
 import { useEffect, useCallback } from "react";
 import type { ChatState } from "@/shared/types/chat";
+import type { ChatAttachmentDraft } from "@/shared/types/messages";
 import { useChatStore } from "../stores/chatStore";
 
 /**
@@ -16,7 +17,7 @@ export function useMessageQueue(
   sendMessage: (
     text: string,
     overridePersona?: { id: string; name?: string },
-    images?: { base64: string; mimeType: string }[],
+    attachments?: ChatAttachmentDraft[],
   ) => void,
 ) {
   const queuedMessage = useChatStore(
@@ -25,22 +26,18 @@ export function useMessageQueue(
 
   useEffect(() => {
     if (chatState === "idle" && queuedMessage) {
-      const { text, personaId, images } = queuedMessage;
+      const { text, personaId, attachments } = queuedMessage;
       useChatStore.getState().dismissQueuedMessage(sessionId);
-      sendMessage(text, personaId ? { id: personaId } : undefined, images);
+      sendMessage(text, personaId ? { id: personaId } : undefined, attachments);
     }
   }, [chatState, queuedMessage, sendMessage, sessionId]);
 
   const enqueue = useCallback(
-    (
-      text: string,
-      personaId?: string,
-      images?: { base64: string; mimeType: string }[],
-    ) => {
+    (text: string, personaId?: string, attachments?: ChatAttachmentDraft[]) => {
       useChatStore.getState().enqueueMessage(sessionId, {
         text,
         personaId,
-        images,
+        attachments,
       });
     },
     [sessionId],
diff --git a/ui/goose2/src/features/chat/lib/artifactPathPolicy.ts b/ui/goose2/src/features/chat/lib/artifactPathPolicy.ts
index 934fddab6326..2c3c1252f61e 100644
--- a/ui/goose2/src/features/chat/lib/artifactPathPolicy.ts
+++ b/ui/goose2/src/features/chat/lib/artifactPathPolicy.ts
@@ -18,6 +18,7 @@ export {
   extractToolCallCandidates,
   inferHomeDirFromRoots,
   isExternalHref,
+  isWriteOrientedTool,
   normalizePath,
   resolveMarkdownLocalHref,
   resolvePathCandidate,
diff --git a/ui/goose2/src/features/chat/lib/attachments.ts b/ui/goose2/src/features/chat/lib/attachments.ts
new file mode 100644
index 000000000000..a69a38361c29
--- /dev/null
+++ b/ui/goose2/src/features/chat/lib/attachments.ts
@@ -0,0 +1,68 @@
+import type {
+  ChatAttachmentDraft,
+  MessageAttachment,
+} from "@/shared/types/messages";
+
+function formatAttachmentReference(attachment: ChatAttachmentDraft): string {
+  const location =
+    attachment.kind === "image"
+      ? `${attachment.name} (image attached)`
+      : (attachment.path ?? attachment.name);
+  return `- [${attachment.kind}] ${location}`;
+}
+
+export function buildAttachmentPromptPreamble(
+  attachments: ChatAttachmentDraft[] | undefined,
+): string {
+  const referencedAttachments = attachments ?? [];
+
+  if (referencedAttachments.length === 0) {
+    return "";
+  }
+
+  return [
+    "Attached items:",
+    ...referencedAttachments.map(formatAttachmentReference),
+    "",
+  ].join("\n");
+}
+
+export function buildMessageAttachments(
+  attachments: ChatAttachmentDraft[] | undefined,
+): MessageAttachment[] | undefined {
+  const messageAttachments: MessageAttachment[] = [];
+
+  for (const attachment of attachments ?? []) {
+    if (attachment.kind === "directory") {
+      messageAttachments.push({
+        type: "directory",
+        name: attachment.name,
+        path: attachment.path,
+      });
+      continue;
+    }
+
+    messageAttachments.push({
+      type: "file",
+      name: attachment.name,
+      ...(attachment.path ? { path: attachment.path } : {}),
+      ...(attachment.kind === "image" || attachment.mimeType
+        ? { mimeType: attachment.mimeType }
+        : {}),
+    });
+  }
+
+  return messageAttachments.length > 0 ? messageAttachments : undefined;
+}
+
+export function buildAcpImages(
+  attachments: ChatAttachmentDraft[] | undefined,
+): { base64: string; mimeType: string }[] | undefined {
+  const images = (attachments ?? []).flatMap((attachment) =>
+    attachment.kind === "image"
+      ? [{ base64: attachment.base64, mimeType: attachment.mimeType }]
+      : [],
+  );
+
+  return images.length > 0 ? images : undefined;
+}
diff --git a/ui/goose2/src/features/chat/lib/sessionTitle.test.ts b/ui/goose2/src/features/chat/lib/sessionTitle.test.ts
index b69df784576a..62cbcc546517 100644
--- a/ui/goose2/src/features/chat/lib/sessionTitle.test.ts
+++ b/ui/goose2/src/features/chat/lib/sessionTitle.test.ts
@@ -3,6 +3,7 @@ import {
   DEFAULT_CHAT_TITLE,
   getDisplaySessionTitle,
   getEditableSessionTitle,
+  getSessionTitleFromDraft,
   isSessionTitleUnchanged,
 } from "./sessionTitle";
 
@@ -24,4 +25,34 @@ describe("sessionTitle", () => {
       isSessionTitleUnchanged("Renamed chat", DEFAULT_CHAT_TITLE, "Nuevo chat"),
     ).toBe(false);
   });
+
+  it("falls back to attachment-based titles for attachment-only sends", () => {
+    expect(
+      getSessionTitleFromDraft("", [
+        {
+          id: "file-1",
+          kind: "file",
+          name: "report.pdf",
+          path: "/tmp/report.pdf",
+        },
+      ]),
+    ).toBe("Attached file");
+
+    expect(
+      getSessionTitleFromDraft("   ", [
+        {
+          id: "dir-1",
+          kind: "directory",
+          name: "screenshots",
+          path: "/tmp/screenshots",
+        },
+        {
+          id: "dir-2",
+          kind: "directory",
+          name: "receipts",
+          path: "/tmp/receipts",
+        },
+      ]),
+    ).toBe("Attached folders");
+  });
 });
diff --git a/ui/goose2/src/features/chat/lib/sessionTitle.ts b/ui/goose2/src/features/chat/lib/sessionTitle.ts
index 283dae2b4cc7..de99e0f0fd63 100644
--- a/ui/goose2/src/features/chat/lib/sessionTitle.ts
+++ b/ui/goose2/src/features/chat/lib/sessionTitle.ts
@@ -1,9 +1,46 @@
+import type { ChatAttachmentDraft } from "@/shared/types/messages";
+
 export const DEFAULT_CHAT_TITLE = "New Chat";
 
 export function isDefaultChatTitle(title: string): boolean {
   return title === DEFAULT_CHAT_TITLE;
 }
 
+function attachmentKindLabel(kind: ChatAttachmentDraft["kind"], count: number) {
+  switch (kind) {
+    case "image":
+      return count === 1 ? "image" : "images";
+    case "directory":
+      return count === 1 ? "folder" : "folders";
+    default:
+      return count === 1 ? "file" : "files";
+  }
+}
+
+export function getSessionTitleFromDraft(
+  text: string,
+  attachments?: ChatAttachmentDraft[],
+): string {
+  const trimmed = text.trim();
+  if (trimmed.length > 0) {
+    return trimmed.slice(0, 100);
+  }
+
+  if (!attachments || attachments.length === 0) {
+    return DEFAULT_CHAT_TITLE;
+  }
+
+  const firstKind = attachments[0]?.kind;
+  const sameKind = attachments.every(
+    (attachment) => attachment.kind === firstKind,
+  );
+  const kindLabel = sameKind
+    ? attachmentKindLabel(firstKind, attachments.length)
+    : "files";
+
+  return `Attached ${kindLabel}`;
+}
+
 export function getDisplaySessionTitle(
   title: string,
   defaultTitle: string,
diff --git a/ui/goose2/src/features/chat/stores/chatStore.ts b/ui/goose2/src/features/chat/stores/chatStore.ts
index fc3273a5f396..f7781b8ef9bb 100644
--- a/ui/goose2/src/features/chat/stores/chatStore.ts
+++ b/ui/goose2/src/features/chat/stores/chatStore.ts
@@ -1,5 +1,9 @@
 import { create } from "zustand";
-import type { Message, MessageContent } from "@/shared/types/messages";
+import type {
+  ChatAttachmentDraft,
+  Message,
+  MessageContent,
+} from "@/shared/types/messages";
 import { clearReplayBuffer } from "../hooks/replayBuffer";
 import type {
   ChatState,
@@ -51,7 +55,7 @@ function createInitialSessionRuntime(): SessionChatRuntime {
 export interface QueuedMessage {
   text: string;
   personaId?: string;
-  images?: { base64: string; mimeType: string }[];
+  attachments?: ChatAttachmentDraft[];
 }
 
 export interface ScrollTargetMessage {
diff --git a/ui/goose2/src/features/chat/ui/ChatInput.tsx b/ui/goose2/src/features/chat/ui/ChatInput.tsx
index f7f089d33e52..fdf2bea7d051 100644
--- a/ui/goose2/src/features/chat/ui/ChatInput.tsx
+++ b/ui/goose2/src/features/chat/ui/ChatInput.tsx
@@ -1,4 +1,5 @@
 import { useState, useRef, useCallback, useEffect, useMemo } from "react";
+import { open } from "@tauri-apps/plugin-dialog";
 import { X } from "lucide-react";
 import { useTranslation } from "react-i18next";
 import type { AcpProvider } from "@/shared/api/acp";
@@ -13,11 +14,14 @@ import { ChatInputToolbar } from "./ChatInputToolbar";
 import { formatProviderLabel } from "@/shared/ui/icons/ProviderIcons";
 import { TooltipProvider } from "@/shared/ui/tooltip";
 import { PersonaAvatar } from "./PersonaPicker";
-import { ImageLightbox } from "@/shared/ui/ImageLightbox";
-import type { PastedImage } from "@/shared/types/messages";
-import { resizeImage } from "../lib/resizeImage";
-import { useImageDropTarget } from "../hooks/useImageDropTarget";
+import type { ChatAttachmentDraft } from "@/shared/types/messages";
+import { useAttachmentDropTarget } from "../hooks/useAttachmentDropTarget";
+import {
+  normalizeDialogSelection,
+  useChatInputAttachments,
+} from "../hooks/useChatInputAttachments";
 import type { ModelOption } from "../types";
+import { ChatInputAttachments } from "./ChatInputAttachments";
 
 export interface ProjectOption {
   id: string;
@@ -27,7 +31,11 @@ export interface ProjectOption {
 }
 
 interface ChatInputProps {
-  onSend: (text: string, personaId?: string, images?: PastedImage[]) => void;
+  onSend: (
+    text: string,
+    personaId?: string,
+    attachments?: ChatAttachmentDraft[],
+  ) => void;
   onStop?: () => void;
   isStreaming?: boolean;
   disabled?: boolean;
@@ -36,87 +44,28 @@ interface ChatInputProps {
   initialValue?: string;
   onDraftChange?: (text: string) => void;
   className?: string;
-  // Personas
   personas?: Persona[];
   selectedPersonaId?: string | null;
   onPersonaChange?: (personaId: string | null) => void;
   onCreatePersona?: () => void;
-  // Provider (secondary -- auto-set by persona but overridable)
   providers?: AcpProvider[];
   providersLoading?: boolean;
   selectedProvider?: string;
   onProviderChange?: (providerId: string) => void;
-  // Model
   currentModelId?: string | null;
   currentModel?: string;
   availableModels?: ModelOption[];
   onModelChange?: (modelId: string) => void;
-  // Project
   selectedProjectId?: string | null;
   availableProjects?: ProjectOption[];
   onProjectChange?: (projectId: string | null) => void;
   onCreateProject?: (options?: {
     onCreated?: (projectId: string) => void;
   }) => void;
-  // Context
   contextTokens?: number;
   contextLimit?: number;
 }
 
-// ---------------------------------------------------------------------------
-// PastedImageThumb
-// ---------------------------------------------------------------------------
-
-function PastedImageThumb({
-  objectUrl,
-  index,
-  onRemove,
-}: {
-  objectUrl: string;
-  index: number;
-  onRemove: (index: number) => void;
-}) {
-  const [lightboxOpen, setLightboxOpen] = useState(false);
-  const { t } = useTranslation("chat");
-
-  return (
-    <>
-      <div className="group relative inline-block">
-        <button
-          type="button"
-          onClick={() => setLightboxOpen(true)}
-          className="block cursor-pointer rounded-lg"
-          aria-label={t("attachments.view", { index: index + 1 })}
-        >
-          <img
-            src={objectUrl}
-            alt={t("attachments.alt", { index: index + 1 })}
-            className="h-16 w-16 rounded-lg object-cover border border-border"
-          />
-        </button>
-        <button
-          type="button"
-          onClick={() => onRemove(index)}
-          className="absolute -right-1.5 -top-1.5 flex h-4 w-4 items-center justify-center rounded-full bg-foreground text-background opacity-0 group-hover:opacity-100 transition-opacity duration-150"
-          aria-label={t("attachments.remove")}
-        >
-          <X className="h-2.5 w-2.5" />
-        </button>
-      </div>
-      <ImageLightbox
-        src={objectUrl}
-        alt={t("attachments.alt", { index: index + 1 })}
-        open={lightboxOpen}
-        onOpenChange={setLightboxOpen}
-      />
-    </>
-  );
-}
-
-// ---------------------------------------------------------------------------
-// ChatInput
-// ---------------------------------------------------------------------------
-
 export function ChatInput({
   onSend,
   onStop,
@@ -155,10 +104,16 @@ export function ChatInput({
     },
     [onDraftChange],
   );
-  const [images, setImages] = useState<PastedImage[]>([]);
   const [isCompact, setIsCompact] = useState(false);
   const textareaRef = useRef<HTMLTextAreaElement>(null);
   const containerRef = useRef<HTMLDivElement>(null);
+  const {
+    attachments,
+    addBrowserFiles,
+    addPathAttachments,
+    removeAttachment,
+    clearAttachments,
+  } = useChatInputAttachments();
 
   const activePersona = useMemo(
     () => personas.find((persona) => persona.id === selectedPersonaId) ?? null,
@@ -174,7 +129,7 @@ export function ChatInput({
 
   const hasQueuedMessage = queuedMessage !== null;
   const canSend =
-    (text.trim().length > 0 || images.length > 0) &&
+    (text.trim().length > 0 || attachments.length > 0) &&
     !hasQueuedMessage &&
     !disabled;
 
@@ -200,148 +155,156 @@ export function ChatInput({
   });
 
   useEffect(() => {
-    const el = containerRef.current;
-    if (!el || typeof ResizeObserver === "undefined") return;
+    const element = containerRef.current;
+    if (!element || typeof ResizeObserver === "undefined") {
+      return;
+    }
+
     const observer = new ResizeObserver((entries) => {
       for (const entry of entries) {
         setIsCompact(entry.contentRect.width < 580);
       }
     });
-    observer.observe(el);
+    observer.observe(element);
     return () => observer.disconnect();
   }, []);
 
-  // Keep a ref to latest images so the unmount cleanup always sees current state
-  // without needing images as a dependency (which would revoke still-active URLs
-  // on every add/remove).
-  const imagesRef = useRef(images);
-  imagesRef.current = images;
-
-  useEffect(() => {
-    return () => {
-      for (const img of imagesRef.current) {
-        URL.revokeObjectURL(img.objectUrl);
-      }
-    };
-  }, []);
-  // Focus the textarea on mount so the user can type immediately
   useEffect(() => textareaRef.current?.focus(), []);
 
   const handleSend = useCallback(() => {
-    if (!canSend) return;
+    if (!canSend) {
+      return;
+    }
+
     onSend(
       text.trim(),
       selectedPersonaId ?? undefined,
-      images.length > 0 ? images : undefined,
+      attachments.length > 0 ? attachments : undefined,
     );
     setText("");
-    setImages((prev) => {
-      for (const img of prev) URL.revokeObjectURL(img.objectUrl);
-      return [];
-    });
+    clearAttachments();
     if (textareaRef.current) {
       textareaRef.current.style.height = "auto";
     }
-  }, [canSend, text, images, onSend, selectedPersonaId, setText]);
+  }, [
+    attachments,
+    canSend,
+    clearAttachments,
+    onSend,
+    selectedPersonaId,
+    setText,
+    text,
+  ]);
 
-  const handleKeyDown = (e: React.KeyboardEvent) => {
+  const handleKeyDown = (event: React.KeyboardEvent) => {
     if (mentionOpen) {
-      if (e.key === "Escape") {
-        e.preventDefault();
+      if (event.key === "Escape") {
+        event.preventDefault();
         closeMention();
         return;
       }
-      if (e.key === "ArrowDown" || e.key === "ArrowUp") {
-        e.preventDefault();
-        navigateMention(e.key === "ArrowDown" ? "down" : "up");
+      if (event.key === "ArrowDown" || event.key === "ArrowUp") {
+        event.preventDefault();
+        navigateMention(event.key === "ArrowDown" ? "down" : "up");
         return;
       }
-      if (e.key === "Enter" || e.key === "Tab") {
+      if (event.key === "Enter" || event.key === "Tab") {
         const item = confirmMention();
         if (item) {
-          e.preventDefault();
+          event.preventDefault();
           handleMentionConfirm(item);
           return;
         }
       }
     }
-    if (e.key === "Enter" && !e.shiftKey && !e.altKey) {
-      e.preventDefault();
+    if (event.key === "Enter" && !event.shiftKey && !event.altKey) {
+      event.preventDefault();
       handleSend();
     }
   };
 
-  const handleInput = (e: React.ChangeEvent<HTMLTextAreaElement>) => {
-    const value = e.target.value;
+  const handleInput = (event: React.ChangeEvent<HTMLTextAreaElement>) => {
+    const value = event.target.value;
     setText(value);
-    const cursorPos = e.target.selectionStart ?? value.length;
-    detectMention(value, cursorPos);
-    const textarea = e.target;
+    const cursorPosition = event.target.selectionStart ?? value.length;
+    detectMention(value, cursorPosition);
+    const textarea = event.target;
     textarea.style.height = "auto";
     textarea.style.height = `${Math.min(textarea.scrollHeight, 200)}px`;
   };
 
-  const addImageFile = useCallback((file: File) => {
-    const objectUrl = URL.createObjectURL(file);
-    resizeImage(file)
-      .then(({ base64, mimeType }) => {
-        setImages((prev) => [...prev, { base64, mimeType, objectUrl }]);
-      })
-      .catch(() => {
-        const reader = new FileReader();
-        reader.onload = () => {
-          const dataUrl = reader.result as string;
-          const [header, b64] = dataUrl.split(",");
-          const mime = header.replace("data:", "").replace(";base64", "");
-          setImages((prev) => [
-            ...prev,
-            { base64: b64, mimeType: mime, objectUrl },
-          ]);
-        };
-        reader.onerror = () => {
-          URL.revokeObjectURL(objectUrl);
-        };
-        reader.readAsDataURL(file);
-      });
-  }, []);
-
   const handlePaste = useCallback(
-    (e: React.ClipboardEvent<HTMLTextAreaElement>) => {
-      const items = Array.from(e.clipboardData.items);
-      const imageItems = items.filter((item) => item.type.startsWith("image/"));
-      if (imageItems.length === 0) return;
+    (event: React.ClipboardEvent<HTMLTextAreaElement>) => {
+      const files = Array.from(event.clipboardData.items)
+        .filter(
+          (item) => item.kind === "file" && item.type.startsWith("image/"),
+        )
+        .map((item) => item.getAsFile())
+        .filter((file): file is File => Boolean(file));
 
-      e.preventDefault();
-      for (const item of imageItems) {
-        const file = item.getAsFile();
-        if (!file) continue;
-        addImageFile(file);
+      if (files.length === 0) {
+        return;
       }
+
+      event.preventDefault();
+      void addBrowserFiles(files);
     },
-    [addImageFile],
+    [addBrowserFiles],
   );
 
   const {
-    isImageDragOver,
+    isAttachmentDragOver,
     handleDragEnter,
     handleDragOver,
     handleDragLeave,
     handleDrop,
-  } = useImageDropTarget({
+  } = useAttachmentDropTarget({
     disabled,
     isStreaming,
-    onDropFile: addImageFile,
+    targetRef: containerRef,
+    onDropFiles: (files) => {
+      void addBrowserFiles(files);
+    },
+    onDropPaths: (paths) => {
+      void addPathAttachments(paths);
+    },
   });
 
-  const removeImage = useCallback((index: number) => {
-    setImages((prev) => {
-      URL.revokeObjectURL(prev[index].objectUrl);
-      return prev.filter((_, i) => i !== index);
-    });
-  }, []);
+  const handleAttachFiles = useCallback(async () => {
+    if (disabled) {
+      return;
+    }
+
+    try {
+      const selected = await open({
+        title: t("attachments.chooseFilesDialogTitle"),
+        multiple: true,
+      });
+      await addPathAttachments(normalizeDialogSelection(selected));
+    } catch {
+      // Dialog plugin may be unavailable in some environments.
+    }
+  }, [addPathAttachments, disabled, t]);
+
+  const handleAttachFolders = useCallback(async () => {
+    if (disabled) {
+      return;
+    }
+
+    try {
+      const selected = await open({
+        directory: true,
+        title: t("attachments.chooseFoldersDialogTitle"),
+        multiple: true,
+      });
+      await addPathAttachments(normalizeDialogSelection(selected));
+    } catch {
+      // Dialog plugin may be unavailable in some environments.
+    }
+  }, [addPathAttachments, disabled, t]);
 
   const providerDisplayName =
-    providers.find((p) => p.id === selectedProvider)?.label ??
+    providers.find((provider) => provider.id === selectedProvider)?.label ??
     formatProviderLabel(selectedProvider);
   const agentDisplayName = activePersona?.displayName ?? providerDisplayName;
   const resolvedCurrentModel =
@@ -356,21 +319,22 @@ export function ChatInput({
 
   return (
     <TooltipProvider delayDuration={300}>
-      <div className={cn("px-4 pb-6 pt-2", className)} ref={containerRef}>
+      <div className={cn("px-4 pb-6 pt-2", className)}>
         <div className="mx-auto max-w-3xl">
           <Popover open={mentionOpen}>
-            {/* biome-ignore lint/a11y/noStaticElementInteractions: drop zone for image files */}
+            {/* biome-ignore lint/a11y/noStaticElementInteractions: drop zone for file attachments */}
             <div
+              ref={containerRef}
               className={cn(
                 "relative rounded-2xl border border-border bg-background px-4 pb-3 pt-4 transition-colors",
-                isImageDragOver && "bg-muted/20",
+                isAttachmentDragOver && "bg-muted/20",
               )}
               onDragEnter={handleDragEnter}
               onDragOver={handleDragOver}
               onDragLeave={handleDragLeave}
               onDrop={handleDrop}
             >
-              {isImageDragOver && (
+              {isAttachmentDragOver && (
                 <div className="pointer-events-none absolute inset-0 z-10 flex items-center justify-center rounded-2xl border border-dashed border-border bg-background/70">
                   <Badge
                     variant="secondary"
@@ -380,6 +344,7 @@ export function ChatInput({
                   </Badge>
                 </div>
               )}
+
               <MentionAutocomplete
                 filteredPersonas={filteredPersonas}
                 filteredFiles={filteredFiles}
@@ -390,18 +355,10 @@ export function ChatInput({
                 selectedIndex={mentionSelectedIndex}
               />
 
-              {images.length > 0 && (
-                <div className="mb-2 flex flex-wrap gap-2">
-                  {images.map((img, i) => (
-                    <PastedImageThumb
-                      key={img.objectUrl}
-                      objectUrl={img.objectUrl}
-                      index={i}
-                      onRemove={removeImage}
-                    />
-                  ))}
-                </div>
-              )}
+              <ChatInputAttachments
+                attachments={attachments}
+                onRemove={removeAttachment}
+              />
 
               {stickyPersona && (
                 <div className="mb-2 flex items-center gap-1.5">
@@ -475,6 +432,9 @@ export function ChatInput({
                 canSend={canSend}
                 isStreaming={isStreaming}
                 hasQueuedMessage={hasQueuedMessage}
+                onAttachFiles={handleAttachFiles}
+                onAttachFolders={handleAttachFolders}
+                disabled={disabled}
                 onSend={handleSend}
                 onStop={onStop}
                 isCompact={isCompact}
diff --git a/ui/goose2/src/features/chat/ui/ChatInputAttachments.tsx b/ui/goose2/src/features/chat/ui/ChatInputAttachments.tsx
new file mode 100644
index 000000000000..416eb128076b
--- /dev/null
+++ b/ui/goose2/src/features/chat/ui/ChatInputAttachments.tsx
@@ -0,0 +1,119 @@
+import { useState } from "react";
+import { FileText, FolderClosed, X } from "lucide-react";
+import { useTranslation } from "react-i18next";
+import { ImageLightbox } from "@/shared/ui/ImageLightbox";
+import type {
+  ChatAttachmentDraft,
+  ChatDirectoryAttachmentDraft,
+  ChatFileAttachmentDraft,
+  ChatImageAttachmentDraft,
+} from "@/shared/types/messages";
+
+function DraftImageAttachment({
+  attachment,
+  index,
+  onRemove,
+}: {
+  attachment: ChatImageAttachmentDraft;
+  index: number;
+  onRemove: (id: string) => void;
+}) {
+  const [lightboxOpen, setLightboxOpen] = useState(false);
+  const { t } = useTranslation("chat");
+
+  return (
+    <>
+      <div className="group relative inline-block">
+        <button
+          type="button"
+          onClick={() => setLightboxOpen(true)}
+          className="block cursor-pointer rounded-lg"
+          aria-label={t("attachments.view", { index: index + 1 })}
+          title={attachment.path ?? attachment.name}
+        >
+          <img
+            src={attachment.previewUrl}
+            alt={t("attachments.alt", { index: index + 1 })}
+            className="h-16 w-16 rounded-lg border border-border object-cover"
+          />
+        </button>
+        <button
+          type="button"
+          onClick={() => onRemove(attachment.id)}
+          className="absolute -right-1.5 -top-1.5 flex h-4 w-4 items-center justify-center rounded-full bg-foreground text-background opacity-0 transition-opacity duration-150 group-hover:opacity-100"
+          aria-label={t("attachments.remove")}
+        >
+          <X className="h-2.5 w-2.5" />
+        </button>
+      </div>
+      <ImageLightbox
+        src={attachment.previewUrl}
+        alt={t("attachments.alt", { index: index + 1 })}
+        open={lightboxOpen}
+        onOpenChange={setLightboxOpen}
+      />
+    </>
+  );
+}
+
+function DraftPathAttachment({
+  attachment,
+  onRemove,
+}: {
+  attachment: ChatFileAttachmentDraft | ChatDirectoryAttachmentDraft;
+  onRemove: (id: string) => void;
+}) {
+  const { t } = useTranslation("chat");
+  const Icon = attachment.kind === "directory" ? FolderClosed : FileText;
+
+  return (
+    <div
+      className="group relative flex items-center gap-2 rounded-full border border-border bg-muted/40 px-3 py-1.5 pr-8 text-xs text-foreground"
+      title={attachment.path ?? attachment.name}
+    >
+      <Icon className="h-3.5 w-3.5 shrink-0 text-muted-foreground" />
+      <span className="max-w-44 truncate">{attachment.name}</span>
+      <button
+        type="button"
+        onClick={() => onRemove(attachment.id)}
+        className="absolute right-2 flex h-4 w-4 items-center justify-center rounded-full text-muted-foreground opacity-0 transition-opacity duration-150 group-hover:opacity-100 hover:text-foreground"
+        aria-label={t("attachments.remove")}
+      >
+        <X className="h-3 w-3" />
+      </button>
+    </div>
+  );
+}
+
+export function ChatInputAttachments({
+  attachments,
+  onRemove,
+}: {
+  attachments: ChatAttachmentDraft[];
+  onRemove: (id: string) => void;
+}) {
+  if (attachments.length === 0) {
+    return null;
+  }
+
+  return (
+    <div className="mb-2 flex flex-wrap gap-2">
+      {attachments.map((attachment, index) =>
+        attachment.kind === "image" ? (
+          <DraftImageAttachment
+            key={attachment.id}
+            attachment={attachment}
+            index={index}
+            onRemove={onRemove}
+          />
+        ) : (
+          <DraftPathAttachment
+            key={attachment.id}
+            attachment={attachment}
+            onRemove={onRemove}
+          />
+        ),
+      )}
+    </div>
+  );
+}
diff --git a/ui/goose2/src/features/chat/ui/ChatInputToolbar.tsx b/ui/goose2/src/features/chat/ui/ChatInputToolbar.tsx
index 666f99cbf6b1..85cffd37900c 100644
--- a/ui/goose2/src/features/chat/ui/ChatInputToolbar.tsx
+++ b/ui/goose2/src/features/chat/ui/ChatInputToolbar.tsx
@@ -1,5 +1,12 @@
 import { useMemo } from "react";
-import { Mic, ArrowUp, Square } from "lucide-react";
+import {
+  Mic,
+  ArrowUp,
+  Square,
+  Paperclip,
+  File,
+  FolderOpen,
+} from "lucide-react";
 import { useTranslation } from "react-i18next";
 import { useLocaleFormatting } from "@/shared/i18n";
 import { IconLibraryPlusFilled } from "@tabler/icons-react";
@@ -11,6 +18,12 @@ import { ContextRing } from "./ContextRing";
 import { PersonaPicker } from "./PersonaPicker";
 import type { ProjectOption } from "./ChatInput";
 import { Button } from "@/shared/ui/button";
+import {
+  DropdownMenu,
+  DropdownMenuContent,
+  DropdownMenuItem,
+  DropdownMenuTrigger,
+} from "@/shared/ui/dropdown-menu";
 import { Tooltip, TooltipTrigger, TooltipContent } from "@/shared/ui/tooltip";
 import { AgentModelPicker } from "./AgentModelPicker";
 import type { ModelOption } from "../types";
@@ -69,6 +82,9 @@ interface ChatInputToolbarProps {
   hasQueuedMessage: boolean;
   onSend: () => void;
   onStop?: () => void;
+  onAttachFiles?: () => void;
+  onAttachFolders?: () => void;
+  disabled?: boolean;
   // Layout
   isCompact: boolean;
 }
@@ -97,6 +113,9 @@ export function ChatInputToolbar({
   hasQueuedMessage,
   onSend,
   onStop,
+  onAttachFiles,
+  onAttachFolders,
+  disabled = false,
   isCompact,
 }: ChatInputToolbarProps) {
   const { t } = useTranslation("chat");
@@ -243,6 +262,37 @@ export function ChatInputToolbar({
             </Button>
           )}
 
+          <DropdownMenu>
+            <DropdownMenuTrigger asChild>
+              <Button
+                type="button"
+                variant="ghost"
+                size="icon-sm"
+                disabled={disabled}
+                aria-label={t("toolbar.attach")}
+                title={t("toolbar.attach")}
+              >
+                <Paperclip className="h-4 w-4" />
+              </Button>
+            </DropdownMenuTrigger>
+            <DropdownMenuContent align="end">
+              <DropdownMenuItem
+                onSelect={() => onAttachFiles?.()}
+                disabled={disabled}
+              >
+                <File className="mr-2 h-4 w-4" />
+                {t("toolbar.attachFile")}
+              </DropdownMenuItem>
+              <DropdownMenuItem
+                onSelect={() => onAttachFolders?.()}
+                disabled={disabled}
+              >
+                <FolderOpen className="mr-2 h-4 w-4" />
+                {t("toolbar.attachFolder")}
+              </DropdownMenuItem>
+            </DropdownMenuContent>
+          </DropdownMenu>
+
           <Tooltip>
             <TooltipTrigger asChild>
               <span>
diff --git a/ui/goose2/src/features/chat/ui/ChatView.tsx b/ui/goose2/src/features/chat/ui/ChatView.tsx
index 7551a53c4a18..0478343dae04 100644
--- a/ui/goose2/src/features/chat/ui/ChatView.tsx
+++ b/ui/goose2/src/features/chat/ui/ChatView.tsx
@@ -3,7 +3,7 @@ import { useTranslation } from "react-i18next";
 import { AnimatePresence } from "motion/react";
 import { MessageTimeline } from "./MessageTimeline";
 import { ChatInput } from "./ChatInput";
-import type { PastedImage } from "@/shared/types/messages";
+import type { ChatAttachmentDraft } from "@/shared/types/messages";
 import { LoadingGoose } from "./LoadingGoose";
 import { ChatLoadingSkeleton } from "./ChatLoadingSkeleton";
 import { useChat } from "../hooks/useChat";
@@ -33,7 +33,7 @@ interface ChatViewProps {
   initialProvider?: string;
   initialPersonaId?: string;
   initialMessage?: string;
-  initialImages?: PastedImage[];
+  initialAttachments?: ChatAttachmentDraft[];
   onInitialMessageConsumed?: () => void;
   onCreateProject?: (options?: {
     onCreated?: (projectId: string) => void;
@@ -45,7 +45,7 @@ export function ChatView({
   initialProvider,
   initialPersonaId,
   initialMessage,
-  initialImages,
+  initialAttachments,
   onInitialMessageConsumed,
   onCreateProject,
 }: ChatViewProps) {
@@ -351,13 +351,14 @@ export function ChatView({
       (s.messagesBySession[activeSessionId]?.length ?? 0) === 0,
   );
 
-  const deferredSend = useRef<{ text: string; images?: PastedImage[] } | null>(
-    null,
-  );
+  const deferredSend = useRef<{
+    text: string;
+    attachments?: ChatAttachmentDraft[];
+  } | null>(null);
   const queue = useMessageQueue(activeSessionId, chatState, sendMessage);
   const chatStore = useChatStore();
   const handleSend = useCallback(
-    (text: string, personaId?: string, images?: PastedImage[]) => {
+    (text: string, personaId?: string, attachments?: ChatAttachmentDraft[]) => {
       if (personaId && personaId !== selectedPersonaId) {
         const newPersona = personas.find((p) => p.id === personaId);
         if (newPersona) {
@@ -378,16 +379,16 @@ export function ChatView({
         }
         handlePersonaChange(personaId);
         // Defer the send until after persona state updates
-        deferredSend.current = { text, images };
+        deferredSend.current = { text, attachments };
         return;
       }
       // Queue if agent is busy and no message already queued
       if (chatState !== "idle" && !queue.queuedMessage) {
-        queue.enqueue(text, personaId, images);
+        queue.enqueue(text, personaId, attachments);
         return;
       }
 
-      sendMessage(text, undefined, images);
+      sendMessage(text, undefined, attachments);
     },
     [
       sendMessage,
@@ -403,22 +404,27 @@ export function ChatView({
 
   useEffect(() => {
     if (deferredSend.current && selectedPersona) {
-      const { text, images } = deferredSend.current;
+      const { text, attachments } = deferredSend.current;
       deferredSend.current = null;
-      sendMessage(text, undefined, images);
+      sendMessage(text, undefined, attachments);
     }
   }, [sendMessage, selectedPersona]);
   const initialMessageSent = useRef(false);
   useEffect(() => {
     if (
-      (initialMessage || initialImages?.length) &&
+      (initialMessage || initialAttachments?.length) &&
       !initialMessageSent.current
     ) {
       initialMessageSent.current = true;
-      handleSend(initialMessage ?? "", undefined, initialImages);
+      handleSend(initialMessage ?? "", undefined, initialAttachments);
       onInitialMessageConsumed?.();
     }
-  }, [initialMessage, initialImages, handleSend, onInitialMessageConsumed]);
+  }, [
+    initialAttachments,
+    initialMessage,
+    handleSend,
+    onInitialMessageConsumed,
+  ]);
   const isStreaming = chatState === "streaming";
   const showIndicator =
     chatState === "thinking" ||
diff --git a/ui/goose2/src/features/chat/ui/MessageBubble.tsx b/ui/goose2/src/features/chat/ui/MessageBubble.tsx
index ee096d2d5157..6363f98c0a6f 100644
--- a/ui/goose2/src/features/chat/ui/MessageBubble.tsx
+++ b/ui/goose2/src/features/chat/ui/MessageBubble.tsx
@@ -1,7 +1,16 @@
 import { useState, memo } from "react";
 import { useTranslation } from "react-i18next";
-import { Copy, Check, RotateCcw, Pencil, User } from "lucide-react";
+import {
+  Copy,
+  Check,
+  RotateCcw,
+  Pencil,
+  User,
+  FileText,
+  FolderClosed,
+} from "lucide-react";
 import { IconRobot } from "@tabler/icons-react";
+import { openPath } from "@tauri-apps/plugin-opener";
 import { cn } from "@/shared/lib/cn";
 import { useLocaleFormatting } from "@/shared/i18n";
 import { useAgentStore } from "@/features/agents/stores/agentStore";
@@ -26,6 +35,7 @@ import { ClickableImage } from "./ClickableImage";
 import { useArtifactLinkHandler } from "@/features/chat/hooks/useArtifactLinkHandler";
 import type {
   Message,
+  MessageAttachment,
   MessageContent,
   TextContent,
   ImageContent,
@@ -35,6 +45,44 @@ import type {
   SystemNotificationContent,
 } from "@/shared/types/messages";
 
+function MessageAttachmentRow({
+  attachment,
+}: {
+  attachment: MessageAttachment;
+}) {
+  const { t } = useTranslation("chat");
+  const Icon = attachment.type === "directory" ? FolderClosed : FileText;
+  const canOpen = Boolean(attachment.path);
+
+  return (
+    <button
+      type="button"
+      onClick={() => {
+        if (!attachment.path) {
+          return;
+        }
+        void openPath(attachment.path);
+      }}
+      disabled={!canOpen}
+      className={cn(
+        "flex max-w-full items-center gap-2 rounded-full border border-border bg-muted/40 px-3 py-1.5 text-xs text-foreground",
+        canOpen
+          ? "cursor-pointer hover:bg-muted/70"
+          : "cursor-default opacity-80",
+      )}
+      aria-label={
+        canOpen
+          ? t("attachments.open", { name: attachment.name })
+          : attachment.name
+      }
+      title={attachment.path ?? attachment.name}
+    >
+      <Icon className="h-3.5 w-3.5 shrink-0 text-muted-foreground" />
+      <span className="truncate">{attachment.name}</span>
+    </button>
+  );
+}
+
 interface MessageBubbleProps {
   message: Message;
   isStreaming?: boolean;
@@ -307,6 +355,7 @@ export const MessageBubble = memo(function MessageBubble({
     !isUser &&
       (assistantDisplayName || personaAvatarUrl || assistantProviderIcon),
   );
+  const messageAttachments = message.metadata?.attachments ?? [];
 
   return (
     <div
@@ -360,6 +409,16 @@ export const MessageBubble = memo(function MessageBubble({
           className="w-full min-w-0 text-[13px] leading-relaxed"
           onClick={handleContentClick}
         >
+          {messageAttachments.length > 0 && (
+            <div className="mb-2 flex flex-wrap gap-2">
+              {messageAttachments.map((attachment) => (
+                <MessageAttachmentRow
+                  key={`${attachment.type}-${attachment.path ?? attachment.name}`}
+                  attachment={attachment}
+                />
+              ))}
+            </div>
+          )}
           {groupContentSections(content).map((section, sectionIdx) => {
             if (section.type === "toolChain") {
               const toolItems = section.items as ToolChainItem[];
diff --git a/ui/goose2/src/features/chat/ui/__tests__/ChatInput.attachments.test.tsx b/ui/goose2/src/features/chat/ui/__tests__/ChatInput.attachments.test.tsx
new file mode 100644
index 000000000000..b99a26b21b37
--- /dev/null
+++ b/ui/goose2/src/features/chat/ui/__tests__/ChatInput.attachments.test.tsx
@@ -0,0 +1,245 @@
+import { beforeEach, describe, expect, it, vi } from "vitest";
+import {
+  createEvent,
+  fireEvent,
+  render,
+  screen,
+  waitFor,
+} from "@testing-library/react";
+import userEvent from "@testing-library/user-event";
+import { ChatInput } from "../ChatInput";
+
+vi.mock("@/features/providers/hooks/useAgentProviderStatus", () => ({
+  useAgentProviderStatus: () => ({
+    readyAgentIds: new Set(["goose", "claude-acp", "codex-acp"]),
+    loading: false,
+    refresh: vi.fn(),
+  }),
+}));
+
+vi.mock("@/shared/lib/platform", () => ({
+  getPlatform: () => "mac",
+}));
+
+const mockListFilesForMentions = vi.fn<
+  (roots: string[], maxResults?: number) => Promise<string[]>
+>(async () => []);
+const mockInspectAttachmentPaths = vi.fn<
+  (paths: string[]) => Promise<
+    {
+      name: string;
+      path: string;
+      kind: "file" | "directory";
+      mimeType?: string | null;
+    }[]
+  >
+>(async () => []);
+const mockReadImageAttachment = vi.fn<
+  (path: string) => Promise<{ base64: string; mimeType: string }>
+>(async () => ({ base64: "abc", mimeType: "image/png" }));
+
+vi.mock("@/shared/api/system", () => ({
+  listFilesForMentions: (roots: string[], maxResults?: number) =>
+    mockListFilesForMentions(roots, maxResults),
+  inspectAttachmentPaths: (paths: string[]) =>
+    mockInspectAttachmentPaths(paths),
+  readImageAttachment: (path: string) => mockReadImageAttachment(path),
+}));
+
+const mockOpenDialog = vi.fn();
+vi.mock("@tauri-apps/plugin-dialog", () => ({
+  open: (...args: unknown[]) => mockOpenDialog(...args),
+}));
+
+vi.mock("@tauri-apps/api/core", () => ({
+  convertFileSrc: (path: string) => `asset://${path}`,
+}));
+
+describe("ChatInput attachments", () => {
+  beforeEach(() => {
+    mockListFilesForMentions.mockClear();
+    mockListFilesForMentions.mockResolvedValue([]);
+    mockInspectAttachmentPaths.mockClear();
+    mockInspectAttachmentPaths.mockResolvedValue([]);
+    mockReadImageAttachment.mockClear();
+    mockReadImageAttachment.mockResolvedValue({
+      base64: "abc",
+      mimeType: "image/png",
+    });
+    mockOpenDialog.mockClear();
+    mockOpenDialog.mockResolvedValue(null);
+  });
+
+  it("attaches a file from the toolbar menu and sends it without text", async () => {
+    const onSend = vi.fn();
+    const user = userEvent.setup();
+    mockOpenDialog.mockResolvedValue("/Users/test/report.pdf");
+    mockInspectAttachmentPaths.mockResolvedValue([
+      {
+        name: "report.pdf",
+        path: "/Users/test/report.pdf",
+        kind: "file",
+        mimeType: "application/pdf",
+      },
+    ]);
+
+    render(<ChatInput onSend={onSend} />);
+
+    await user.click(screen.getByRole("button", { name: /attach/i }));
+    await user.click(screen.getByRole("menuitem", { name: /^file$/i }));
+
+    expect(mockOpenDialog).toHaveBeenCalledWith({
+      title: "Choose files to attach",
+      multiple: true,
+    });
+    expect(await screen.findByText("report.pdf")).toBeInTheDocument();
+
+    await user.click(screen.getByRole("button", { name: /send message/i }));
+
+    expect(onSend).toHaveBeenCalledWith(
+      "",
+      undefined,
+      expect.arrayContaining([
+        expect.objectContaining({
+          kind: "file",
+          name: "report.pdf",
+          path: "/Users/test/report.pdf",
+        }),
+      ]),
+    );
+  });
+
+  it("attaches a folder from the toolbar menu", async () => {
+    const user = userEvent.setup();
+    mockOpenDialog.mockResolvedValue("/Users/test/screenshots");
+    mockInspectAttachmentPaths.mockResolvedValue([
+      {
+        name: "screenshots",
+        path: "/Users/test/screenshots",
+        kind: "directory",
+      },
+    ]);
+
+    render(<ChatInput onSend={vi.fn()} />);
+
+    await user.click(screen.getByRole("button", { name: /attach/i }));
+    await user.click(screen.getByRole("menuitem", { name: /folder/i }));
+
+    expect(mockOpenDialog).toHaveBeenCalledWith({
+      directory: true,
+      title: "Choose folders to attach",
+      multiple: true,
+    });
+    expect(await screen.findByText("screenshots")).toBeInTheDocument();
+  });
+
+  it("shows the generic attachment drop overlay for file drags", () => {
+    render(<ChatInput onSend={vi.fn()} />);
+
+    const textbox = screen.getByRole("textbox");
+    const composer = textbox.closest("div.rounded-2xl");
+    if (!composer) {
+      throw new Error("Expected composer container");
+    }
+    const dataTransfer = {
+      files: [new File(["hello"], "report.txt", { type: "text/plain" })],
+      items: [{ kind: "file" }],
+      types: ["Files"],
+    } as unknown as DataTransfer;
+
+    fireEvent.dragEnter(composer, { dataTransfer });
+    fireEvent.dragOver(composer, { dataTransfer });
+
+    expect(
+      screen.getByText("Drop files or folders to attach"),
+    ).toBeInTheDocument();
+  });
+
+  it("does not cancel non-file drops into the composer", () => {
+    render(<ChatInput onSend={vi.fn()} />);
+
+    const textbox = screen.getByRole("textbox");
+    const composer = textbox.closest("div.rounded-2xl");
+    if (!composer) {
+      throw new Error("Expected composer container");
+    }
+
+    const dropEvent = createEvent.drop(composer, {
+      dataTransfer: {
+        files: [],
+        items: [{ kind: "string" }],
+        types: ["text/plain"],
+      },
+    });
+    dropEvent.preventDefault = vi.fn();
+
+    fireEvent(composer, dropEvent);
+
+    expect(dropEvent.preventDefault).not.toHaveBeenCalled();
+  });
+
+  it("renders mixed attachments from a single file picker pass", async () => {
+    const user = userEvent.setup();
+    mockOpenDialog.mockResolvedValue([
+      "/Users/test/report.pdf",
+      "/Users/test/diagram.png",
+    ]);
+    mockInspectAttachmentPaths.mockResolvedValue([
+      {
+        name: "report.pdf",
+        path: "/Users/test/report.pdf",
+        kind: "file",
+        mimeType: "application/pdf",
+      },
+      {
+        name: "diagram.png",
+        path: "/Users/test/diagram.png",
+        kind: "file",
+        mimeType: "image/png",
+      },
+    ]);
+
+    render(<ChatInput onSend={vi.fn()} />);
+
+    await user.click(screen.getByRole("button", { name: /attach/i }));
+    await user.click(screen.getByRole("menuitem", { name: /^file$/i }));
+
+    expect(await screen.findByText("report.pdf")).toBeInTheDocument();
+    await waitFor(() => {
+      expect(screen.getByAltText("Attachment 2")).toBeInTheDocument();
+    });
+  });
+
+  it("dedupes path attachments that differ only by case on case-insensitive platforms", async () => {
+    const user = userEvent.setup();
+    mockOpenDialog.mockResolvedValue("/Users/test/report.pdf");
+    mockInspectAttachmentPaths
+      .mockResolvedValueOnce([
+        {
+          name: "report.pdf",
+          path: "/Users/test/report.pdf",
+          kind: "file",
+          mimeType: "application/pdf",
+        },
+      ])
+      .mockResolvedValueOnce([
+        {
+          name: "report.pdf",
+          path: "/users/test/REPORT.pdf",
+          kind: "file",
+          mimeType: "application/pdf",
+        },
+      ]);
+
+    render(<ChatInput onSend={vi.fn()} />);
+
+    await user.click(screen.getByRole("button", { name: /^attach$/i }));
+    await user.click(screen.getByRole("menuitem", { name: /^file$/i }));
+    expect(await screen.findByText("report.pdf")).toBeInTheDocument();
+
+    await user.click(screen.getByRole("button", { name: /^attach$/i }));
+    await user.click(screen.getByRole("menuitem", { name: /^file$/i }));
+
+    expect(screen.getAllByText("report.pdf")).toHaveLength(1);
+  });
+});
diff --git a/ui/goose2/src/features/chat/ui/__tests__/MessageBubble.test.tsx b/ui/goose2/src/features/chat/ui/__tests__/MessageBubble.test.tsx
index 83d396a5e98c..55531e8ed5f8 100644
--- a/ui/goose2/src/features/chat/ui/__tests__/MessageBubble.test.tsx
+++ b/ui/goose2/src/features/chat/ui/__tests__/MessageBubble.test.tsx
@@ -5,6 +5,11 @@ import { MessageBubble } from "../MessageBubble";
 import { useAgentStore } from "@/features/agents/stores/agentStore";
 import type { Message } from "@/shared/types/messages";
 
+const mockOpenPath = vi.fn();
+vi.mock("@tauri-apps/plugin-opener", () => ({
+  openPath: (path: string) => mockOpenPath(path),
+}));
+
 // ── helpers ───────────────────────────────────────────────────────────
 
 function userMessage(text: string, overrides: Partial<Message> = {}): Message {
@@ -35,6 +40,7 @@ function assistantMessage(
 describe("MessageBubble", () => {
   beforeEach(() => {
     useAgentStore.setState({ personas: [] });
+    mockOpenPath.mockClear();
   });
 
   it("renders user message with correct alignment", () => {
@@ -100,6 +106,39 @@ describe("MessageBubble", () => {
     expect(screen.getByText("readFile")).toBeInTheDocument();
   });
 
+  it("renders metadata attachments and opens them on click", async () => {
+    const user = userEvent.setup();
+
+    render(
+      <MessageBubble
+        message={userMessage("See attached", {
+          metadata: {
+            attachments: [
+              {
+                type: "file",
+                name: "report.pdf",
+                path: "/Users/test/report.pdf",
+              },
+              {
+                type: "directory",
+                name: "screenshots",
+                path: "/Users/test/screenshots",
+              },
+            ],
+          },
+        })}
+      />,
+    );
+
+    await user.click(
+      screen.getByRole("button", { name: /open attachment report\.pdf/i }),
+    );
+    expect(mockOpenPath).toHaveBeenCalledWith("/Users/test/report.pdf");
+    expect(
+      screen.getByRole("button", { name: /open attachment screenshots/i }),
+    ).toBeInTheDocument();
+  });
+
   it("renders standalone tool responses without dropping surrounding text", () => {
     const msg = assistantMessage([
       { type: "text", text: "Working on it." },
diff --git a/ui/goose2/src/features/home/ui/HomeScreen.tsx b/ui/goose2/src/features/home/ui/HomeScreen.tsx
index 1f187a59eaef..54d3f8087281 100644
--- a/ui/goose2/src/features/home/ui/HomeScreen.tsx
+++ b/ui/goose2/src/features/home/ui/HomeScreen.tsx
@@ -7,7 +7,7 @@ import {
 import { useProviderSelection } from "@/features/agents/hooks/useProviderSelection";
 import { ChatInput } from "@/features/chat/ui/ChatInput";
 import { useChatStore } from "@/features/chat/stores/chatStore";
-import type { PastedImage } from "@/shared/types/messages";
+import type { ChatAttachmentDraft } from "@/shared/types/messages";
 import { useProjectStore } from "@/features/projects/stores/projectStore";
 import { useLocaleFormatting } from "@/shared/i18n";
 
@@ -53,7 +53,7 @@ interface HomeScreenProps {
     providerId?: string,
     personaId?: string,
     projectId?: string | null,
-    images?: PastedImage[],
+    attachments?: ChatAttachmentDraft[],
   ) => void;
   onCreateProject?: (options?: {
     onCreated?: (projectId: string) => void;
@@ -106,7 +106,11 @@ export function HomeScreen({ onStartChat, onCreateProject }: HomeScreenProps) {
   }, []);
 
   const handleSend = useCallback(
-    (message: string, personaId?: string, images?: PastedImage[]) => {
+    (
+      message: string,
+      personaId?: string,
+      attachments?: ChatAttachmentDraft[],
+    ) => {
       const effectivePersonaId = personaId ?? selectedPersonaId ?? undefined;
 
       useChatStore.getState().clearDraft(HOME_DRAFT_KEY);
@@ -115,7 +119,7 @@ export function HomeScreen({ onStartChat, onCreateProject }: HomeScreenProps) {
         selectedProvider,
         effectivePersonaId,
         selectedProjectId,
-        images,
+        attachments,
       );
     },
     [onStartChat, selectedPersonaId, selectedProjectId, selectedProvider],
diff --git a/ui/goose2/src/shared/api/system.ts b/ui/goose2/src/shared/api/system.ts
index 663642b3a961..9ae1e668905f 100644
--- a/ui/goose2/src/shared/api/system.ts
+++ b/ui/goose2/src/shared/api/system.ts
@@ -6,6 +6,18 @@ export interface FileTreeEntry {
   kind: "file" | "directory";
 }
 
+export interface AttachmentPathInfo {
+  name: string;
+  path: string;
+  kind: "file" | "directory";
+  mimeType?: string | null;
+}
+
+export interface ImageAttachmentPayload {
+  base64: string;
+  mimeType: string;
+}
+
 export async function getHomeDir(): Promise<string> {
   return invoke("get_home_dir");
 }
@@ -33,3 +45,15 @@ export async function listDirectoryEntries(
 ): Promise<FileTreeEntry[]> {
   return invoke("list_directory_entries", { path });
 }
+
+export async function inspectAttachmentPaths(
+  paths: string[],
+): Promise<AttachmentPathInfo[]> {
+  return invoke("inspect_attachment_paths", { paths });
+}
+
+export async function readImageAttachment(
+  path: string,
+): Promise<ImageAttachmentPayload> {
+  return invoke("read_image_attachment", { path });
+}
diff --git a/ui/goose2/src/shared/i18n/locales/en/chat.json b/ui/goose2/src/shared/i18n/locales/en/chat.json
index 2fffb22f6331..ee149f346005 100644
--- a/ui/goose2/src/shared/i18n/locales/en/chat.json
+++ b/ui/goose2/src/shared/i18n/locales/en/chat.json
@@ -1,8 +1,11 @@
 {
   "attachments": {
     "alt": "Attachment {{index}}",
-    "dropToAttach": "Drop images to attach",
-    "remove": "Remove image",
+    "chooseFilesDialogTitle": "Choose files to attach",
+    "chooseFoldersDialogTitle": "Choose folders to attach",
+    "dropToAttach": "Drop files or folders to attach",
+    "open": "Open attachment {{name}}",
+    "remove": "Remove attachment",
     "view": "View attachment {{index}}"
   },
   "context": {
@@ -141,6 +144,9 @@
   },
   "toolbar": {
     "agent": "Agent",
+    "attach": "Attach",
+    "attachFile": "File",
+    "attachFolder": "Folder",
     "chooseAgentModel": "Choose agent and model",
     "chooseProject": "Choose a project",
     "chooseProvider": "Choose a provider",
diff --git a/ui/goose2/src/shared/i18n/locales/es/chat.json b/ui/goose2/src/shared/i18n/locales/es/chat.json
index 69f0c5f51c66..63c807e53733 100644
--- a/ui/goose2/src/shared/i18n/locales/es/chat.json
+++ b/ui/goose2/src/shared/i18n/locales/es/chat.json
@@ -1,8 +1,11 @@
 {
   "attachments": {
     "alt": "Adjunto {{index}}",
-    "dropToAttach": "Suelta imágenes para adjuntarlas",
-    "remove": "Eliminar imagen",
+    "chooseFilesDialogTitle": "Elegir archivos para adjuntar",
+    "chooseFoldersDialogTitle": "Elegir carpetas para adjuntar",
+    "dropToAttach": "Suelta archivos o carpetas para adjuntarlos",
+    "open": "Abrir adjunto {{name}}",
+    "remove": "Eliminar adjunto",
     "view": "Ver adjunto {{index}}"
   },
   "context": {
@@ -141,6 +144,9 @@
   },
   "toolbar": {
     "agent": "Agente",
+    "attach": "Adjuntar",
+    "attachFile": "Archivo",
+    "attachFolder": "Carpeta",
     "chooseAgentModel": "Elegir agente y modelo",
     "chooseProject": "Elegir un proyecto",
     "chooseProvider": "Elegir un proveedor",
diff --git a/ui/goose2/src/shared/types/messages.ts b/ui/goose2/src/shared/types/messages.ts
index 42e29cd66531..24b3ed9ee417 100644
--- a/ui/goose2/src/shared/types/messages.ts
+++ b/ui/goose2/src/shared/types/messages.ts
@@ -1,9 +1,35 @@
-export interface PastedImage {
-  base64: string;
+export type ChatAttachmentKind = "image" | "file" | "directory";
+
+export interface ChatImageAttachmentDraft {
+  id: string;
+  kind: "image";
+  name: string;
+  path?: string;
   mimeType: string;
-  objectUrl: string;
+  base64: string;
+  previewUrl: string;
+}
+
+export interface ChatFileAttachmentDraft {
+  id: string;
+  kind: "file";
+  name: string;
+  path?: string;
+  mimeType?: string;
+}
+
+export interface ChatDirectoryAttachmentDraft {
+  id: string;
+  kind: "directory";
+  name: string;
+  path: string;
 }
 
+export type ChatAttachmentDraft =
+  | ChatImageAttachmentDraft
+  | ChatFileAttachmentDraft
+  | ChatDirectoryAttachmentDraft;
+
 // Message roles
 export type MessageRole = "user" | "assistant" | "system";
 
@@ -97,6 +123,7 @@ export interface MessageAttachment {
   name: string;
   path?: string;
   url?: string;
+  mimeType?: string;
 }
 
 export interface MessageChip {