diff --git a/package-lock.json b/package-lock.json
index e38bb0445ac..5ca83e43c01 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -14,6 +14,7 @@
 				"@iconify-json/bi": "^1.1.21",
 				"@resvg/resvg-js": "^2.6.2",
 				"autoprefixer": "^10.4.14",
+				"bits-ui": "^2.14.2",
 				"date-fns": "^2.29.3",
 				"dotenv": "^16.5.0",
 				"file-type": "^21.0.0",
@@ -954,6 +955,31 @@
 				"npm": ">=6.14.13"
 			}
 		},
+		"node_modules/@floating-ui/core": {
+			"version": "1.7.3",
+			"resolved": "https://registry.npmjs.org/@floating-ui/core/-/core-1.7.3.tgz",
+			"integrity": "sha512-sGnvb5dmrJaKEZ+LDIpguvdX3bDlEllmv4/ClQ9awcmCZrlx5jQyyMWFM5kBI+EyNOCDDiKk8il0zeuX3Zlg/w==",
+			"license": "MIT",
+			"dependencies": {
+				"@floating-ui/utils": "^0.2.10"
+			}
+		},
+		"node_modules/@floating-ui/dom": {
+			"version": "1.7.4",
+			"resolved": "https://registry.npmjs.org/@floating-ui/dom/-/dom-1.7.4.tgz",
+			"integrity": "sha512-OOchDgh4F2CchOX94cRVqhvy7b3AFb+/rQXyswmzmGakRfkMgoWVjfnLWkRirfLEfuD4ysVW16eXzwt3jHIzKA==",
+			"license": "MIT",
+			"dependencies": {
+				"@floating-ui/core": "^1.7.3",
+				"@floating-ui/utils": "^0.2.10"
+			}
+		},
+		"node_modules/@floating-ui/utils": {
+			"version": "0.2.10",
+			"resolved": "https://registry.npmjs.org/@floating-ui/utils/-/utils-0.2.10.tgz",
+			"integrity": "sha512-aGTxbpbg8/b5JfU1HXSrbH3wXZuLPJcNEcZQFMxLs3oSzgtVu6nFPkbbGGUvBcUjKV2YyB9Wxxabo+HEH9tcRQ==",
+			"license": "MIT"
+		},
 		"node_modules/@huggingface/hub": {
 			"version": "2.2.0",
 			"resolved": "https://registry.npmjs.org/@huggingface/hub/-/hub-2.2.0.tgz",
@@ -1560,6 +1586,16 @@
 				"url": "https://opencollective.com/libvips"
 			}
 		},
+		"node_modules/@internationalized/date": {
+			"version": "3.10.0",
+			"resolved": "https://registry.npmjs.org/@internationalized/date/-/date-3.10.0.tgz",
+			"integrity": "sha512-oxDR/NTEJ1k+UFVQElaNIk65E/Z83HK1z1WI3lQyhTtnNg4R5oVXaPzK3jcpKG8UHKDVuDQHzn+wsxSz8RP3aw==",
+			"license": "Apache-2.0",
+			"peer": true,
+			"dependencies": {
+				"@swc/helpers": "^0.5.0"
+			}
+		},
 		"node_modules/@isaacs/cliui": {
 			"version": "8.0.2",
 			"resolved": "https://registry.npmjs.org/@isaacs/cliui/-/cliui-8.0.2.tgz",
@@ -2477,7 +2513,7 @@
 			"version": "2.21.2",
 			"resolved": "https://registry.npmjs.org/@sveltejs/kit/-/kit-2.21.2.tgz",
 			"integrity": "sha512-EMYTY4+rNa7TaRZYzCqhQslEkACEZzWc363jOYuc90oJrgvlWTcgqTxcGSIJim48hPaXwYlHyatRnnMmTFf5tA==",
-			"dev": true,
+			"devOptional": true,
 			"license": "MIT",
 			"dependencies": {
 				"@sveltejs/acorn-typescript": "^1.0.5",
@@ -2509,7 +2545,7 @@
 			"version": "5.1.0",
 			"resolved": "https://registry.npmjs.org/@sveltejs/vite-plugin-svelte/-/vite-plugin-svelte-5.1.0.tgz",
 			"integrity": "sha512-wojIS/7GYnJDYIg1higWj2ROA6sSRWvcR1PO/bqEyFr/5UZah26c8Cz4u0NaqjPeVltzsVpt2Tm8d2io0V+4Tw==",
-			"dev": true,
+			"devOptional": true,
 			"license": "MIT",
 			"dependencies": {
 				"@sveltejs/vite-plugin-svelte-inspector": "^4.0.1",
@@ -2531,7 +2567,7 @@
 			"version": "4.0.1",
 			"resolved": "https://registry.npmjs.org/@sveltejs/vite-plugin-svelte-inspector/-/vite-plugin-svelte-inspector-4.0.1.tgz",
 			"integrity": "sha512-J/Nmb2Q2y7mck2hyCX4ckVHcR5tu2J+MtBEQqpDrrgELZ2uvraQcK/ioCV61AqkdXFgriksOKIceDcQmqnGhVw==",
-			"dev": true,
+			"devOptional": true,
 			"license": "MIT",
 			"dependencies": {
 				"debug": "^4.3.7"
@@ -2545,6 +2581,16 @@
 				"vite": "^6.0.0"
 			}
 		},
+		"node_modules/@swc/helpers": {
+			"version": "0.5.17",
+			"resolved": "https://registry.npmjs.org/@swc/helpers/-/helpers-0.5.17.tgz",
+			"integrity": "sha512-5IKx/Y13RsYd+sauPb2x+U/xZikHjolzfuDgTAl/Tdf3Q8rslRvC19NKDLgAJQ6wsqADk10ntlv08nPFw/gO/A==",
+			"license": "Apache-2.0",
+			"peer": true,
+			"dependencies": {
+				"tslib": "^2.8.0"
+			}
+		},
 		"node_modules/@tailwindcss/typography": {
 			"version": "0.5.16",
 			"resolved": "https://registry.npmjs.org/@tailwindcss/typography/-/typography-0.5.16.tgz",
@@ -2648,7 +2694,7 @@
 			"version": "0.6.0",
 			"resolved": "https://registry.npmjs.org/@types/cookie/-/cookie-0.6.0.tgz",
 			"integrity": "sha512-4Kh9a6B2bQciAhf7FSuMRRkUWecJgJu9nPnx3yzpsfXX/c50REIqpHY4C82bXP90qrLtXtkDxTZosYO3UpOwlA==",
-			"dev": true,
+			"devOptional": true,
 			"license": "MIT"
 		},
 		"node_modules/@types/deep-eql": {
@@ -3531,6 +3577,30 @@
 			"integrity": "sha512-VOMgTMwjAaUG580SXn3LacVgjurrbMme7ZZNYGSSV7mmtY6QQRh0Eg3pwIcntQ77DErK1L0NxkbetjcoXzVwKw==",
 			"license": "MIT"
 		},
+		"node_modules/bits-ui": {
+			"version": "2.14.2",
+			"resolved": "https://registry.npmjs.org/bits-ui/-/bits-ui-2.14.2.tgz",
+			"integrity": "sha512-YqpAJj/nRTZjf7IlgUC3QlepVZ7YFiAQWpZaYUOAZFW5Py+g5DYkhEDTdNFI5SReo7l1rct/nRpMK4pfL9Xffw==",
+			"license": "MIT",
+			"dependencies": {
+				"@floating-ui/core": "^1.7.1",
+				"@floating-ui/dom": "^1.7.1",
+				"esm-env": "^1.1.2",
+				"runed": "^0.35.1",
+				"svelte-toolbelt": "^0.10.6",
+				"tabbable": "^6.2.0"
+			},
+			"engines": {
+				"node": ">=20"
+			},
+			"funding": {
+				"url": "https://github.com/sponsors/huntabyte"
+			},
+			"peerDependencies": {
+				"@internationalized/date": "^3.8.1",
+				"svelte": "^5.33.0"
+			}
+		},
 		"node_modules/brace-expansion": {
 			"version": "2.0.2",
 			"resolved": "https://registry.npmjs.org/brace-expansion/-/brace-expansion-2.0.2.tgz",
@@ -3916,7 +3986,7 @@
 			"version": "0.6.0",
 			"resolved": "https://registry.npmjs.org/cookie/-/cookie-0.6.0.tgz",
 			"integrity": "sha512-U71cyTamuh1CRNCfpGY6to28lxvNwPG4Guz/EVjgf3Jmzv0vlDp1atT9eS5dDjMYHucpHbWns6Lwf3BKz6svdw==",
-			"dev": true,
+			"devOptional": true,
 			"license": "MIT",
 			"engines": {
 				"node": ">= 0.6"
@@ -4090,7 +4160,7 @@
 			"version": "4.3.1",
 			"resolved": "https://registry.npmjs.org/deepmerge/-/deepmerge-4.3.1.tgz",
 			"integrity": "sha512-3sUqbMEc77XqpdNO7FRyRog+eW3ph+GYCbj+rK+uYyRMuwsVy0rMiVtPn+QJlKFvWP/1PYpapqYn0Me2knFn+A==",
-			"dev": true,
+			"devOptional": true,
 			"license": "MIT",
 			"engines": {
 				"node": ">=0.10.0"
@@ -4110,7 +4180,6 @@
 			"resolved": "https://registry.npmjs.org/dequal/-/dequal-2.0.3.tgz",
 			"integrity": "sha512-0je+qPKHEMohvfRTCEo3CrPG6cAzAYgmzKyxRiYSSDkS6eGJdyVJm7WaYA5ECaAD9wLB2T4EEeymA5aFVcYXCA==",
 			"license": "MIT",
-			"peer": true,
 			"engines": {
 				"node": ">=6"
 			}
@@ -4128,7 +4197,7 @@
 			"version": "5.1.1",
 			"resolved": "https://registry.npmjs.org/devalue/-/devalue-5.1.1.tgz",
 			"integrity": "sha512-maua5KUiapvEwiEAe+XnlZ3Rh0GD+qI1J/nb9vrJc3muPXvcF/8gXYTWF76+5DAqHyDUtOIImEuo0YKE9mshVw==",
-			"dev": true,
+			"devOptional": true,
 			"license": "MIT"
 		},
 		"node_modules/didyoumean": {
@@ -5567,6 +5636,12 @@
 			"dev": true,
 			"license": "ISC"
 		},
+		"node_modules/inline-style-parser": {
+			"version": "0.2.6",
+			"resolved": "https://registry.npmjs.org/inline-style-parser/-/inline-style-parser-0.2.6.tgz",
+			"integrity": "sha512-gtGXVaBdl5mAes3rPcMedEBm12ibjt1kDMFfheul1wUAOVEJW60voNdMVzVkfLN06O7ZaD/rxhfKgtlgtTbMjg==",
+			"license": "MIT"
+		},
 		"node_modules/int53": {
 			"version": "0.2.4",
 			"resolved": "https://registry.npmjs.org/int53/-/int53-0.2.4.tgz",
@@ -6113,7 +6188,7 @@
 			"version": "4.1.5",
 			"resolved": "https://registry.npmjs.org/kleur/-/kleur-4.1.5.tgz",
 			"integrity": "sha512-o+NO+8WrRiQEE4/7nwRJhN1HWpVmJm511pBHUxPLtp0BUISzlBplORYSmTclCnJvQq2tKu/sgl3xVpkc7ZWuQQ==",
-			"dev": true,
+			"devOptional": true,
 			"license": "MIT",
 			"engines": {
 				"node": ">=6"
@@ -6417,7 +6492,6 @@
 			"resolved": "https://registry.npmjs.org/lz-string/-/lz-string-1.5.0.tgz",
 			"integrity": "sha512-h5bgJWpxJNswbU7qCrV0tIKQCaS3blPDrqKWx+QxzuzL1zGUzij9XCWLrSLsJPu5t+eWA/ycetzYAO5IOMcWAQ==",
 			"license": "MIT",
-			"peer": true,
 			"bin": {
 				"lz-string": "bin/bin.js"
 			}
@@ -6859,7 +6933,7 @@
 			"version": "1.2.0",
 			"resolved": "https://registry.npmjs.org/mri/-/mri-1.2.0.tgz",
 			"integrity": "sha512-tzzskb3bG8LvYGFF/mDTpq3jpI6Q9wc3LEmBaghu+DdCssd1FakN7Bc0hVNmEyGq1bq3RgfkCb3cmQLpNPOroA==",
-			"dev": true,
+			"devOptional": true,
 			"license": "MIT",
 			"engines": {
 				"node": ">=4"
@@ -8415,11 +8489,35 @@
 				"queue-microtask": "^1.2.2"
 			}
 		},
+		"node_modules/runed": {
+			"version": "0.35.1",
+			"resolved": "https://registry.npmjs.org/runed/-/runed-0.35.1.tgz",
+			"integrity": "sha512-2F4Q/FZzbeJTFdIS/PuOoPRSm92sA2LhzTnv6FXhCoENb3huf5+fDuNOg1LNvGOouy3u/225qxmuJvcV3IZK5Q==",
+			"funding": [
+				"https://github.com/sponsors/huntabyte",
+				"https://github.com/sponsors/tglide"
+			],
+			"license": "MIT",
+			"dependencies": {
+				"dequal": "^2.0.3",
+				"esm-env": "^1.0.0",
+				"lz-string": "^1.5.0"
+			},
+			"peerDependencies": {
+				"@sveltejs/kit": "^2.21.0",
+				"svelte": "^5.7.0"
+			},
+			"peerDependenciesMeta": {
+				"@sveltejs/kit": {
+					"optional": true
+				}
+			}
+		},
 		"node_modules/sade": {
 			"version": "1.8.1",
 			"resolved": "https://registry.npmjs.org/sade/-/sade-1.8.1.tgz",
 			"integrity": "sha512-xal3CZX1Xlo/k4ApwCFrHVACi9fBqJ7V+mwhBsuf/1IOKbBy098Fex+Wa/5QMubw09pSZ/u8EY8PWgevJsXp1A==",
-			"dev": true,
+			"devOptional": true,
 			"license": "MIT",
 			"dependencies": {
 				"mri": "^1.1.0"
@@ -8527,7 +8625,7 @@
 			"version": "2.7.1",
 			"resolved": "https://registry.npmjs.org/set-cookie-parser/-/set-cookie-parser-2.7.1.tgz",
 			"integrity": "sha512-IOc8uWeOZgnb3ptbCURJWNjWUPcO3ZnTTdzsurqERrP6nPyv+paC55vJM0LpOlT2ne+Ix+9+CRG1MNLlyZ4GjQ==",
-			"dev": true,
+			"devOptional": true,
 			"license": "MIT"
 		},
 		"node_modules/sharp": {
@@ -8941,6 +9039,15 @@
 				"url": "https://github.com/sponsors/Borewit"
 			}
 		},
+		"node_modules/style-to-object": {
+			"version": "1.0.12",
+			"resolved": "https://registry.npmjs.org/style-to-object/-/style-to-object-1.0.12.tgz",
+			"integrity": "sha512-ddJqYnoT4t97QvN2C95bCgt+m7AAgXjVnkk/jxAfmp7EAB8nnqqZYEbMd3em7/vEomDb2LAQKAy1RFfv41mdNw==",
+			"license": "MIT",
+			"dependencies": {
+				"inline-style-parser": "0.2.6"
+			}
+		},
 		"node_modules/sucrase": {
 			"version": "3.35.0",
 			"resolved": "https://registry.npmjs.org/sucrase/-/sucrase-3.35.0.tgz",
@@ -9130,6 +9237,26 @@
 				}
 			}
 		},
+		"node_modules/svelte-toolbelt": {
+			"version": "0.10.6",
+			"resolved": "https://registry.npmjs.org/svelte-toolbelt/-/svelte-toolbelt-0.10.6.tgz",
+			"integrity": "sha512-YWuX+RE+CnWYx09yseAe4ZVMM7e7GRFZM6OYWpBKOb++s+SQ8RBIMMe+Bs/CznBMc0QPLjr+vDBxTAkozXsFXQ==",
+			"funding": [
+				"https://github.com/sponsors/huntabyte"
+			],
+			"dependencies": {
+				"clsx": "^2.1.1",
+				"runed": "^0.35.1",
+				"style-to-object": "^1.0.8"
+			},
+			"engines": {
+				"node": ">=18",
+				"pnpm": ">=8.7.0"
+			},
+			"peerDependencies": {
+				"svelte": "^5.30.2"
+			}
+		},
 		"node_modules/svelte/node_modules/aria-query": {
 			"version": "5.3.2",
 			"resolved": "https://registry.npmjs.org/aria-query/-/aria-query-5.3.2.tgz",
@@ -9154,6 +9281,12 @@
 			"integrity": "sha512-9QNk5KwDF+Bvz+PyObkmSYjI5ksVUYtjW7AU22r2NKcfLJcXp96hkDWU3+XndOsUb+AQ9QhfzfCT2O+CNWT5Tw==",
 			"license": "MIT"
 		},
+		"node_modules/tabbable": {
+			"version": "6.3.0",
+			"resolved": "https://registry.npmjs.org/tabbable/-/tabbable-6.3.0.tgz",
+			"integrity": "sha512-EIHvdY5bPLuWForiR/AN2Bxngzpuwn1is4asboytXtpTgsArc+WmSJKVLlhdh71u7jFcryDqB2A8lQvj78MkyQ==",
+			"license": "MIT"
+		},
 		"node_modules/tailwind-scrollbar": {
 			"version": "3.1.0",
 			"resolved": "https://registry.npmjs.org/tailwind-scrollbar/-/tailwind-scrollbar-3.1.0.tgz",
@@ -9551,7 +9684,6 @@
 			"version": "2.8.1",
 			"resolved": "https://registry.npmjs.org/tslib/-/tslib-2.8.1.tgz",
 			"integrity": "sha512-oJFu94HQb+KVduSUQL7wnpmqnfmLsOA/nAh6b6EH0wCEoK0/mPeXU6c3wKDV83MkOuHPRHtSXKKU99IBazS/2w==",
-			"devOptional": true,
 			"license": "0BSD"
 		},
 		"node_modules/type-check": {
@@ -9908,7 +10040,7 @@
 			"version": "1.0.6",
 			"resolved": "https://registry.npmjs.org/vitefu/-/vitefu-1.0.6.tgz",
 			"integrity": "sha512-+Rex1GlappUyNN6UfwbVZne/9cYC4+R2XDk9xkNXBKMw6HQagdX9PgZ8V2v1WUSK1wfBLp7qbI1+XSNIlB1xmA==",
-			"dev": true,
+			"devOptional": true,
 			"license": "MIT",
 			"workspaces": [
 				"tests/deps/*",
diff --git a/package.json b/package.json
index 3e7e01069d6..377de0e6a3d 100644
--- a/package.json
+++ b/package.json
@@ -72,6 +72,7 @@
 		"@iconify-json/bi": "^1.1.21",
 		"@resvg/resvg-js": "^2.6.2",
 		"autoprefixer": "^10.4.14",
+		"bits-ui": "^2.14.2",
 		"date-fns": "^2.29.3",
 		"dotenv": "^16.5.0",
 		"file-type": "^21.0.0",
diff --git a/src/lib/components/chat/ChatInput.svelte b/src/lib/components/chat/ChatInput.svelte
index 62dcf84bd1b..d9916ced20f 100644
--- a/src/lib/components/chat/ChatInput.svelte
+++ b/src/lib/components/chat/ChatInput.svelte
@@ -3,8 +3,15 @@
 
 	import { afterNavigate } from "$app/navigation";
 
-	import HoverTooltip from "$lib/components/HoverTooltip.svelte";
-	import IconPaperclip from "$lib/components/icons/IconPaperclip.svelte";
+	import { DropdownMenu } from "bits-ui";
+	import CarbonAdd from "~icons/carbon/add";
+	import CarbonImage from "~icons/carbon/image";
+	import CarbonDocument from "~icons/carbon/document";
+	import CarbonUpload from "~icons/carbon/upload";
+	import CarbonLink from "~icons/carbon/link";
+	import CarbonChevronRight from "~icons/carbon/chevron-right";
+	import UrlFetchModal from "./UrlFetchModal.svelte";
+	import { TEXT_MIME_ALLOWLIST, IMAGE_MIME_ALLOWLIST_DEFAULT } from "$lib/constants/mime";
 
 	import { isVirtualKeyboard } from "$lib/utils/isVirtualKeyboard";
 	import { requireAuthUser } from "$lib/utils/auth";
@@ -42,13 +49,42 @@
 	const onFileChange = async (e: Event) => {
 		if (!e.target) return;
 		const target = e.target as HTMLInputElement;
-		files = [...files, ...(target.files ?? [])];
+		const selected = Array.from(target.files ?? []);
+		if (selected.length === 0) return;
+		files = [...files, ...selected];
+		await tick();
+		void focusTextarea();
 	};
 
 	let textareaElement: HTMLTextAreaElement | undefined = $state();
 	let isCompositionOn = $state(false);
 	let blurTimeout: ReturnType<typeof setTimeout> | null = $state(null);
 
+	let fileInputEl: HTMLInputElement | undefined = $state();
+	let isUrlModalOpen = $state(false);
+
+	function openPickerWithAccept(accept: string) {
+		if (!fileInputEl) return;
+		const allAccept = mimeTypes.join(",");
+		fileInputEl.setAttribute("accept", accept);
+		fileInputEl.click();
+		queueMicrotask(() => fileInputEl?.setAttribute("accept", allAccept));
+	}
+
+	function openFilePickerText() {
+		const textAccept =
+			mimeTypes.filter((m) => !(m === "image/*" || m.startsWith("image/"))).join(",") ||
+			TEXT_MIME_ALLOWLIST.join(",");
+		openPickerWithAccept(textAccept);
+	}
+
+	function openFilePickerImage() {
+		const imageAccept =
+			mimeTypes.filter((m) => m === "image/*" || m.startsWith("image/")).join(",") ||
+			IMAGE_MIME_ALLOWLIST_DEFAULT.join(",");
+		openPickerWithAccept(imageAccept);
+	}
+
 	const waitForAnimationFrame = () =>
 		typeof requestAnimationFrame === "function"
 			? new Promise<void>((resolve) => {
@@ -76,6 +112,15 @@
 		}
 	}
 
+	function handleFetchedFiles(newFiles: File[]) {
+		if (!newFiles?.length) return;
+		files = [...files, ...newFiles];
+		queueMicrotask(async () => {
+			await tick();
+			void focusTextarea();
+		});
+	}
+
 	onMount(() => {
 		void focusTextarea();
 	});
@@ -141,8 +186,8 @@
 		});
 	}
 
-	// Tools removed; only show file upload when applicable
-	let showFileUpload = $derived(modelIsMultimodal && mimeTypes.length > 0);
+	// Show file upload when any mime is allowed (text always; images if multimodal)
+	let showFileUpload = $derived(mimeTypes.length > 0);
 	let showNoTools = $derived(!showFileUpload);
 </script>
 
@@ -172,46 +217,93 @@
 			]}
 		>
 			{#if showFileUpload}
-				{@const mimeTypesString = mimeTypes
-					.map((m) => {
-						// if the mime type ends in *, grab the first part so image/* becomes image
-						if (m.endsWith("*")) {
-							return m.split("/")[0];
-						}
-						// otherwise, return the second part for example application/pdf becomes pdf
-						return m.split("/")[1];
-					})
-					.join(", ")}
 				<div class="flex items-center">
-					<HoverTooltip
-						label={mimeTypesString.includes("*")
-							? "Upload any file"
-							: `Upload ${mimeTypesString} files`}
-						position="top"
-						TooltipClassNames="text-xs !text-left !w-auto whitespace-nowrap !py-1 !mb-0 max-sm:hidden"
-					>
-						<label class="base-tool relative">
-							<input
-								disabled={loading}
-								class="absolute hidden size-0"
-								aria-label="Upload file"
-								type="file"
-								onchange={onFileChange}
-								onclick={(e) => {
-									if (requireAuthUser()) {
-										e.preventDefault();
-									}
-								}}
-								accept={mimeTypes.join(",")}
-							/>
-							<IconPaperclip classNames="text-xl" />
-						</label>
-					</HoverTooltip>
+					<input
+						bind:this={fileInputEl}
+						disabled={loading}
+						class="absolute hidden size-0"
+						aria-label="Upload file"
+						type="file"
+						onchange={onFileChange}
+						onclick={(e) => {
+							if (requireAuthUser()) {
+								e.preventDefault();
+							}
+						}}
+						accept={mimeTypes.join(",")}
+					/>
+
+					<DropdownMenu.Root>
+						<DropdownMenu.Trigger
+							class="btn size-7 rounded-full border bg-white text-black shadow transition-none enabled:hover:bg-white enabled:hover:shadow-inner dark:border-transparent dark:bg-gray-600/50 dark:text-white dark:hover:enabled:bg-black"
+							disabled={loading}
+							aria-label="Add attachment"
+						>
+							<CarbonAdd class="text-base" />
+						</DropdownMenu.Trigger>
+						<DropdownMenu.Portal>
+							<DropdownMenu.Content
+								class="z-50 rounded-xl border border-gray-200 bg-white/95 p-1 text-gray-800 shadow-lg backdrop-blur supports-[backdrop-filter]:bg-white/80 dark:border-gray-700/60 dark:bg-gray-800/95 dark:text-gray-100 dark:supports-[backdrop-filter]:bg-gray-800/80"
+								side="top"
+								sideOffset={8}
+								align="start"
+							>
+								{#if modelIsMultimodal}
+									<DropdownMenu.Item
+										class="flex h-8 select-none items-center gap-1 rounded-md px-2 text-sm text-gray-700 data-[highlighted]:bg-gray-100 focus-visible:outline-none dark:text-gray-200 dark:data-[highlighted]:bg-white/10"
+										onSelect={() => openFilePickerImage()}
+									>
+										<CarbonImage class="size-4 opacity-90 dark:opacity-80" />
+										Add image
+									</DropdownMenu.Item>
+								{/if}
+
+								<DropdownMenu.Sub>
+									<DropdownMenu.SubTrigger
+										class="flex h-8 select-none items-center gap-1 rounded-md px-2 text-sm text-gray-700 data-[highlighted]:bg-gray-100 data-[state=open]:bg-gray-100 focus-visible:outline-none dark:text-gray-200 dark:data-[highlighted]:bg-white/10 dark:data-[state=open]:bg-white/10"
+									>
+										<div class="flex items-center gap-1">
+											<CarbonDocument class="size-4 opacity-90 dark:opacity-80" />
+											Add text file
+										</div>
+										<div class="ml-auto flex items-center">
+											<CarbonChevronRight class="size-4 opacity-70 dark:opacity-80" />
+										</div>
+									</DropdownMenu.SubTrigger>
+									<DropdownMenu.SubContent
+										class="z-50 rounded-xl border border-gray-200 bg-white/95 p-1 text-gray-800 shadow-lg backdrop-blur supports-[backdrop-filter]:bg-white/80 dark:border-gray-700/60 dark:bg-gray-800/95 dark:text-gray-100 dark:supports-[backdrop-filter]:bg-gray-800/80"
+										sideOffset={10}
+									>
+										<DropdownMenu.Item
+											class="flex h-8 select-none items-center gap-1 rounded-md px-2 text-sm text-gray-700 data-[highlighted]:bg-gray-100 focus-visible:outline-none dark:text-gray-200 dark:data-[highlighted]:bg-white/10"
+											onSelect={() => openFilePickerText()}
+										>
+											<CarbonUpload class="size-4 opacity-90 dark:opacity-80" />
+											Upload from device
+										</DropdownMenu.Item>
+										<DropdownMenu.Item
+											class="flex h-8 select-none items-center gap-1 rounded-md px-2 text-sm text-gray-700 data-[highlighted]:bg-gray-100 focus-visible:outline-none dark:text-gray-200 dark:data-[highlighted]:bg-white/10"
+											onSelect={() => (isUrlModalOpen = true)}
+										>
+											<CarbonLink class="size-4 opacity-90 dark:opacity-80" />
+											Fetch from URL
+										</DropdownMenu.Item>
+									</DropdownMenu.SubContent>
+								</DropdownMenu.Sub>
+							</DropdownMenu.Content>
+						</DropdownMenu.Portal>
+					</DropdownMenu.Root>
 				</div>
 			{/if}
 		</div>
 	{/if}
 	{@render children?.()}
+
+	<UrlFetchModal
+		bind:open={isUrlModalOpen}
+		acceptMimeTypes={mimeTypes}
+		onfiles={handleFetchedFiles}
+	/>
 </div>
 
 <style lang="postcss">
diff --git a/src/lib/components/chat/ChatWindow.svelte b/src/lib/components/chat/ChatWindow.svelte
index f3d5d35ff7d..702842c84cc 100644
--- a/src/lib/components/chat/ChatWindow.svelte
+++ b/src/lib/components/chat/ChatWindow.svelte
@@ -230,10 +230,17 @@
 	// Respect per‑model multimodal toggle from settings (force enable)
 	let modelIsMultimodalOverride = $derived($settings.multimodalOverrides?.[currentModel.id]);
 	let modelIsMultimodal = $derived((modelIsMultimodalOverride ?? currentModel.multimodal) === true);
+
+	// Always allow common text-like files; add images only when model is multimodal
+	import { TEXT_MIME_ALLOWLIST, IMAGE_MIME_ALLOWLIST_DEFAULT } from "$lib/constants/mime";
+
 	let activeMimeTypes = $derived(
 		Array.from(
 			new Set([
-				...(modelIsMultimodal ? (currentModel.multimodalAcceptedMimetypes ?? ["image/*"]) : []),
+				...TEXT_MIME_ALLOWLIST,
+				...(modelIsMultimodal
+					? (currentModel.multimodalAcceptedMimetypes ?? [...IMAGE_MIME_ALLOWLIST_DEFAULT])
+					: []),
 			])
 		)
 	);
diff --git a/src/lib/components/chat/UploadedFile.svelte b/src/lib/components/chat/UploadedFile.svelte
index 5153ff3b65b..8dcca28369d 100644
--- a/src/lib/components/chat/UploadedFile.svelte
+++ b/src/lib/components/chat/UploadedFile.svelte
@@ -9,6 +9,7 @@
 	import AudioPlayer from "../players/AudioPlayer.svelte";
 	import EosIconsLoading from "~icons/eos-icons/loading";
 	import { base } from "$app/paths";
+	import { TEXT_MIME_ALLOWLIST } from "$lib/constants/mime";
 
 	interface Props {
 		file: MessageFile;
@@ -43,20 +44,28 @@
 	const isVideo = (mime: string) =>
 		mime.startsWith("video/") || mime === "mp4" || mime === "x-mpeg";
 
+	function matchesAllowed(contentType: string, allowed: readonly string[]): boolean {
+		const ct = contentType.split(";")[0]?.trim().toLowerCase();
+		if (!ct) return false;
+		const [ctType, ctSubtype] = ct.split("/");
+		for (const a of allowed) {
+			const [aType, aSubtype] = a.toLowerCase().split("/");
+			const typeOk = aType === "*" || aType === ctType;
+			const subOk = aSubtype === "*" || aSubtype === ctSubtype;
+			if (typeOk && subOk) return true;
+		}
+		return false;
+	}
+
 	const isPlainText = (mime: string) =>
-		mime === "text/plain" ||
-		mime === "text/csv" ||
-		mime === "text/markdown" ||
-		mime === "application/json" ||
-		mime === "application/xml" ||
-		mime === "application/vnd.chatui.clipboard";
+		mime === "application/vnd.chatui.clipboard" || matchesAllowed(mime, TEXT_MIME_ALLOWLIST);
 
 	let isClickable = $derived(isImage(file.mime) || isPlainText(file.mime));
 </script>
 
 {#if showModal && isClickable}
 	<!-- show the image file full screen, click outside to exit -->
-	<Modal width="sm:max-w-[800px]" onclose={() => (showModal = false)}>
+	<Modal width="xl:max-w-[75dvw]" onclose={() => (showModal = false)}>
 		{#if isImage(file.mime)}
 			{#if file.type === "hash"}
 				<img
@@ -182,7 +191,7 @@
 					{/if}
 				</dl>
 			</div>
-		{:else if file.mime === "octet-stream"}
+		{:else if file.mime === "application/octet-stream"}
 			<div
 				class="flex h-14 w-72 items-center gap-2 overflow-hidden rounded-xl border border-gray-200 bg-white p-2 dark:border-gray-800 dark:bg-gray-900"
 				class:file-hoverable={isClickable}
diff --git a/src/lib/components/chat/UrlFetchModal.svelte b/src/lib/components/chat/UrlFetchModal.svelte
new file mode 100644
index 00000000000..3dd4ca6c059
--- /dev/null
+++ b/src/lib/components/chat/UrlFetchModal.svelte
@@ -0,0 +1,190 @@
+<script lang="ts">
+	import Modal from "../Modal.svelte";
+	import { base } from "$app/paths";
+	import { tick } from "svelte";
+
+	interface Props {
+		open?: boolean;
+		acceptMimeTypes?: string[]; // optional client-side validation
+		onclose?: () => void;
+		onfiles?: (files: File[]) => void;
+	}
+
+	let { open = $bindable(false), acceptMimeTypes = [], onclose, onfiles }: Props = $props();
+
+	let urlValue = $state("");
+	let loading = $state(false);
+	let errorMsg = $state("");
+	let inputEl: HTMLInputElement | undefined = $state();
+
+	async function focusInputSoon() {
+		// Wait for modal and content to mount, then focus and select
+		await tick();
+		await tick();
+		setTimeout(() => {
+			inputEl?.focus();
+			inputEl?.select();
+		}, 0);
+	}
+
+	$effect(() => {
+		if (open) {
+			// reset state when opening
+			urlValue = "";
+			errorMsg = "";
+			void focusInputSoon();
+		}
+	});
+
+	function isHttpsUrl(url: string) {
+		try {
+			const u = new URL(url);
+			return u.protocol === "https:";
+		} catch {
+			return false;
+		}
+	}
+
+	function matchesAllowed(contentType: string, allowed: string[]): boolean {
+		const ct = contentType.split(";")[0]?.trim().toLowerCase();
+		if (!ct) return false;
+		const [ctType, ctSubtype] = ct.split("/");
+		for (const a of allowed) {
+			const [aType, aSubtype] = a.toLowerCase().split("/");
+			const typeOk = aType === "*" || aType === ctType;
+			const subOk = aSubtype === "*" || aSubtype === ctSubtype;
+			if (typeOk && subOk) return true;
+		}
+		return false;
+	}
+
+	function close() {
+		open = false;
+		onclose?.();
+	}
+
+	async function handleSubmit() {
+		errorMsg = "";
+		const trimmed = urlValue.trim();
+		if (!isHttpsUrl(trimmed)) {
+			errorMsg = "Enter a valid HTTPS URL.";
+			return;
+		}
+		loading = true;
+		try {
+			// Use server proxy directly for one URL to validate size/types before creating File
+			const params = new URLSearchParams({ url: trimmed });
+			if (acceptMimeTypes.length > 0) params.set("accept", acceptMimeTypes.join(","));
+			const proxyUrl = `${base}/api/fetch-url?${params}`;
+			const res = await fetch(proxyUrl);
+			if (!res.ok) {
+				const txt = await res.text();
+				throw new Error(txt || `Failed to fetch (${res.status})`);
+			}
+			const blob = await res.blob();
+			// Optional client-side mime filter (same wildcard semantics as dropzone)
+			if (acceptMimeTypes.length > 0 && blob.type && !matchesAllowed(blob.type, acceptMimeTypes)) {
+				throw new Error("File type not allowed.");
+			}
+			const disp = res.headers.get("content-disposition");
+			let filename = "attachment";
+			const match = disp?.match(/filename[^;=\n]*=((['"]).*?\2|[^;\n]*)/);
+			if (match && match[1]) filename = match[1].replace(/['"]/g, "");
+			else {
+				try {
+					const u = new URL(trimmed);
+					const last = u.pathname.split("/").pop() || "attachment";
+					filename = decodeURIComponent(last);
+				} catch {}
+			}
+			const file = new File([blob], filename, { type: blob.type || "application/octet-stream" });
+			onfiles?.([file]);
+			close();
+		} catch (e) {
+			errorMsg = e instanceof Error ? e.message : "Failed to fetch URL";
+		} finally {
+			loading = false;
+		}
+	}
+</script>
+
+{#if open}
+	<Modal onclose={close} width="w-[90dvh] md:w-[480px]">
+		{#snippet children()}
+			<form
+				class="flex w-full flex-col gap-5 p-6"
+				onsubmit={(e) => {
+					e.preventDefault();
+					handleSubmit();
+				}}
+			>
+				<div class="flex items-start justify-between">
+					<h2 class="text-xl font-semibold text-gray-800 dark:text-gray-200">Add from URL</h2>
+					<button type="button" class="group" onclick={close} aria-label="Close">
+						<svg
+							xmlns="http://www.w3.org/2000/svg"
+							viewBox="0 0 32 32"
+							class="size-5 text-gray-700 group-hover:text-gray-500 dark:text-gray-300 dark:group-hover:text-gray-400"
+						>
+							<path
+								d="M24 9.41 22.59 8 16 14.59 9.41 8 8 9.41 14.59 16 8 22.59 9.41 24 16 17.41 22.59 24 24 22.59 17.41 16 24 9.41z"
+								fill="currentColor"
+							/>
+						</svg>
+					</button>
+				</div>
+
+				<div class="flex flex-col gap-2">
+					<label class="text-sm text-gray-600 dark:text-gray-400" for="fetch-url-input"
+						>Enter URL</label
+					>
+					<input
+						id="fetch-url-input"
+						bind:this={inputEl}
+						bind:value={urlValue}
+						type="url"
+						placeholder="https://example.com/file.txt"
+						class="w-full rounded-xl border border-gray-200 bg-white px-3 py-2 text-[15px] text-gray-800 outline-none placeholder:text-gray-400 focus:ring-2 focus:ring-gray-200 dark:border-gray-700 dark:bg-gray-800 dark:text-gray-100 dark:placeholder:text-gray-500 dark:focus:ring-gray-700"
+						aria-invalid={errorMsg ? "true" : "false"}
+						onkeydown={(e) => {
+							if (e.key === "Enter") {
+								e.preventDefault();
+								handleSubmit();
+							}
+						}}
+					/>
+				</div>
+
+				{#if errorMsg}
+					<p class="-mt-1 text-sm text-red-600 dark:text-red-400">{errorMsg}</p>
+				{/if}
+				<p class="-mt-2 text-xs text-gray-500 dark:text-gray-400">Only HTTPS. Max 10MB.</p>
+
+				<div class="flex items-center justify-end gap-2">
+					<button
+						type="button"
+						class="inline-flex items-center rounded-xl border border-gray-300 bg-white px-3 py-1.5 text-sm font-medium text-gray-900 shadow hover:bg-gray-50 dark:border-gray-700 dark:bg-gray-700 dark:text-gray-100 dark:hover:bg-gray-600"
+						onclick={close}
+					>
+						Cancel
+					</button>
+					<button
+						type="submit"
+						class="inline-flex items-center rounded-xl border border-gray-900 bg-gray-900 px-3 py-1.5 text-sm font-semibold text-white hover:bg-black disabled:cursor-not-allowed disabled:opacity-50 dark:border-gray-100 dark:bg-gray-100 dark:text-gray-900 dark:hover:bg-white"
+						disabled={loading || urlValue.trim() === ""}
+					>
+						{#if loading}Fetching…{:else}Add{/if}
+					</button>
+				</div>
+			</form>
+		{/snippet}
+	</Modal>
+{/if}
+
+<style lang="postcss">
+	:global(input) {
+		font-family: inherit;
+	}
+	/* Uses app-level colors and rounded/blur styles via utility classes */
+	/* The Modal itself provides consistent container + scrollbar-custom styling */
+</style>
diff --git a/src/lib/constants/mime.ts b/src/lib/constants/mime.ts
new file mode 100644
index 00000000000..77608d20d81
--- /dev/null
+++ b/src/lib/constants/mime.ts
@@ -0,0 +1,11 @@
+// Centralized MIME allowlists used across client and server
+// Keep these lists minimal and consistent with server processing.
+
+export const TEXT_MIME_ALLOWLIST = [
+	"text/*",
+	"application/json",
+	"application/xml",
+	"application/csv",
+] as const;
+
+export const IMAGE_MIME_ALLOWLIST_DEFAULT = ["image/jpeg", "image/png"] as const;
diff --git a/src/lib/server/conversation.ts b/src/lib/server/conversation.ts
index 5aa1fb9ada1..cbe46f3ca04 100644
--- a/src/lib/server/conversation.ts
+++ b/src/lib/server/conversation.ts
@@ -47,6 +47,35 @@ export async function createConversationFromShare(
 		meta: { fromShareId },
 	});
 
+	// Copy files from shared conversation bucket entries to the new conversation
+	// Shared files are stored with filenames "${sharedId}-${sha}" and metadata.conversation = sharedId
+	// New conversation expects files to be stored under its own id prefix
+	const newConvId = res.insertedId.toString();
+	const sharedId = fromShareId;
+	const files = await collections.bucket.find({ filename: { $regex: `^${sharedId}-` } }).toArray();
+
+	await Promise.all(
+		files.map(
+			(file) =>
+				new Promise<void>((resolve, reject) => {
+					try {
+						const newFilename = file.filename.replace(`${sharedId}-`, `${newConvId}-`);
+						const downloadStream = collections.bucket.openDownloadStream(file._id);
+						const uploadStream = collections.bucket.openUploadStream(newFilename, {
+							metadata: { ...file.metadata, conversation: newConvId },
+						});
+						downloadStream
+							.on("error", reject)
+							.pipe(uploadStream)
+							.on("error", reject)
+							.on("finish", () => resolve());
+					} catch (e) {
+						reject(e);
+					}
+				})
+		)
+	);
+
 	if (MetricsServer.isEnabled()) {
 		MetricsServer.getMetrics().model.conversationsTotal.inc({ model: conversation.model });
 	}
diff --git a/src/lib/server/endpoints/openai/endpointOai.ts b/src/lib/server/endpoints/openai/endpointOai.ts
index 5b0d4b13dd0..1490bc6da75 100644
--- a/src/lib/server/endpoints/openai/endpointOai.ts
+++ b/src/lib/server/endpoints/openai/endpointOai.ts
@@ -14,6 +14,7 @@ import { config } from "$lib/server/config";
 import type { Endpoint } from "../endpoints";
 import type OpenAI from "openai";
 import { createImageProcessorOptionsValidator, makeImageProcessor } from "../images";
+import { TEXT_MIME_ALLOWLIST } from "$lib/constants/mime";
 import type { MessageFile } from "$lib/types/Message";
 import type { EndpointMessage } from "../endpoints";
 // uuid import removed (no tool call ids)
@@ -283,13 +284,16 @@ async function prepareFiles(
 }> {
 	// Separate image and text files
 	const imageFiles = files.filter((file) => file.mime.startsWith("image/"));
-	const textFiles = files.filter(
-		(file) =>
-			file.mime.startsWith("text/") ||
-			file.mime === "application/json" ||
-			file.mime === "application/xml" ||
-			file.mime === "application/csv"
-	);
+	const textFiles = files.filter((file) => {
+		const mime = (file.mime || "").toLowerCase();
+		const [fileType, fileSubtype] = mime.split("/");
+		return TEXT_MIME_ALLOWLIST.some((allowed) => {
+			const [type, subtype] = allowed.toLowerCase().split("/");
+			const typeOk = type === "*" || type === fileType;
+			const subOk = subtype === "*" || subtype === fileSubtype;
+			return typeOk && subOk;
+		});
+	});
 
 	// Process images if multimodal is enabled
 	let imageParts: OpenAI.Chat.Completions.ChatCompletionContentPartImage[] = [];