diff --git a/src-tauri/src/actions.rs b/src-tauri/src/actions.rs
index 8232dedcd..98973faea 100644
--- a/src-tauri/src/actions.rs
+++ b/src-tauri/src/actions.rs
@@ -436,6 +436,56 @@ impl ShortcutAction for CancelAction {
     }
 }
 
+struct RetypeLastAction;
+
+impl ShortcutAction for RetypeLastAction {
+    fn start(&self, app: &AppHandle, _binding_id: &str, _shortcut_str: &str) {
+        debug!("RetypeLastAction::start called");
+
+        let app_handle = app.clone();
+        tauri::async_runtime::spawn(async move {
+            let hm = app_handle.state::<Arc<HistoryManager>>();
+
+            match hm.get_latest_entry().await {
+                Ok(Some(entry)) => {
+                    let text = entry
+                        .post_processed_text
+                        .filter(|t| !t.is_empty())
+                        .unwrap_or(entry.transcription_text);
+
+                    if text.is_empty() {
+                        debug!("RetypeLastAction: Latest entry has empty text");
+                        return;
+                    }
+
+                    debug!("RetypeLastAction: Retyping text: '{}'", text);
+
+                    let app_for_paste = app_handle.clone();
+                    app_handle
+                        .run_on_main_thread(move || {
+                            if let Err(e) = utils::paste(text, app_for_paste) {
+                                error!("RetypeLastAction: Failed to paste text: {}", e);
+                            }
+                        })
+                        .unwrap_or_else(|e| {
+                            error!("RetypeLastAction: Failed to run on main thread: {:?}", e);
+                        });
+                }
+                Ok(None) => {
+                    debug!("RetypeLastAction: No history entries found");
+                }
+                Err(e) => {
+                    error!("RetypeLastAction: Failed to get latest entry: {}", e);
+                }
+            }
+        });
+    }
+
+    fn stop(&self, _app: &AppHandle, _binding_id: &str, _shortcut_str: &str) {
+        // Nothing to do on stop for retype
+    }
+}
+
 // Test Action
 struct TestAction;
 
@@ -470,6 +520,10 @@ pub static ACTION_MAP: Lazy<HashMap<String, Arc<dyn ShortcutAction>>> = Lazy::ne
         "cancel".to_string(),
         Arc::new(CancelAction) as Arc<dyn ShortcutAction>,
     );
+    map.insert(
+        "retype_last".to_string(),
+        Arc::new(RetypeLastAction) as Arc<dyn ShortcutAction>,
+    );
     map.insert(
         "test".to_string(),
         Arc::new(TestAction) as Arc<dyn ShortcutAction>,
diff --git a/src-tauri/src/managers/history.rs b/src-tauri/src/managers/history.rs
index 0a8c7f07b..eff459cb5 100644
--- a/src-tauri/src/managers/history.rs
+++ b/src-tauri/src/managers/history.rs
@@ -379,6 +379,32 @@ impl HistoryManager {
         Ok(entries)
     }
 
+    pub async fn get_latest_entry(&self) -> Result<Option<HistoryEntry>> {
+        let conn = self.get_connection()?;
+        let mut stmt = conn.prepare(
+            "SELECT id, file_name, timestamp, saved, title, transcription_text, post_processed_text, post_process_prompt FROM transcription_history ORDER BY timestamp DESC LIMIT 1"
+        )?;
+
+        let result = stmt.query_row([], |row| {
+            Ok(HistoryEntry {
+                id: row.get("id")?,
+                file_name: row.get("file_name")?,
+                timestamp: row.get("timestamp")?,
+                saved: row.get("saved")?,
+                title: row.get("title")?,
+                transcription_text: row.get("transcription_text")?,
+                post_processed_text: row.get("post_processed_text")?,
+                post_process_prompt: row.get("post_process_prompt")?,
+            })
+        });
+
+        match result {
+            Ok(entry) => Ok(Some(entry)),
+            Err(rusqlite::Error::QueryReturnedNoRows) => Ok(None),
+            Err(e) => Err(e.into()),
+        }
+    }
+
     pub async fn toggle_saved_status(&self, id: i64) -> Result<()> {
         let conn = self.get_connection()?;
 
diff --git a/src-tauri/src/settings.rs b/src-tauri/src/settings.rs
index 1bd0d718e..2772eaad9 100644
--- a/src-tauri/src/settings.rs
+++ b/src-tauri/src/settings.rs
@@ -544,6 +544,16 @@ pub fn get_default_settings() -> AppSettings {
             current_binding: "escape".to_string(),
         },
     );
+    bindings.insert(
+        "retype_last".to_string(),
+        ShortcutBinding {
+            id: "retype_last".to_string(),
+            name: "Retype Last".to_string(),
+            description: "Retypes the last transcription.".to_string(),
+            default_binding: "".to_string(),
+            current_binding: "".to_string(),
+        },
+    );
 
     AppSettings {
         bindings,
diff --git a/src-tauri/src/shortcut.rs b/src-tauri/src/shortcut.rs
index a827ad838..1169f0d52 100644
--- a/src-tauri/src/shortcut.rs
+++ b/src-tauri/src/shortcut.rs
@@ -81,6 +81,25 @@ pub fn change_binding(
         }
     }
 
+    // If the new binding is empty, unregister the existing one and save
+    if binding.trim().is_empty() {
+        if !binding_to_modify.current_binding.trim().is_empty() {
+            if let Err(e) = unregister_shortcut(&app, binding_to_modify.clone()) {
+                warn!("Failed to unregister shortcut when clearing: {}", e);
+            }
+        }
+        if let Some(mut b) = settings.bindings.get(&id).cloned() {
+            b.current_binding = binding;
+            settings.bindings.insert(id.clone(), b.clone());
+            settings::write_settings(&app, settings);
+            return Ok(BindingResponse {
+                success: true,
+                binding: Some(b.clone()),
+                error: None,
+            });
+        }
+    }
+
     // Unregister the existing binding
     if let Err(e) = unregister_shortcut(&app, binding_to_modify.clone()) {
         let error_msg = format!("Failed to unregister shortcut: {}", e);
diff --git a/src/components/settings/HandyShortcut.tsx b/src/components/settings/HandyShortcut.tsx
index bc595f004..7fda4c76c 100644
--- a/src/components/settings/HandyShortcut.tsx
+++ b/src/components/settings/HandyShortcut.tsx
@@ -331,10 +331,14 @@ export const HandyShortcut: React.FC<HandyShortcutProps> = ({
           </div>
         ) : (
           <div
-            className="px-2 py-1 text-sm font-semibold bg-mid-gray/10 border border-mid-gray/80 hover:bg-logo-primary/10 rounded cursor-pointer hover:border-logo-primary"
+            className={`px-2 py-1 text-sm bg-mid-gray/10 border border-mid-gray/80 hover:bg-logo-primary/10 rounded cursor-pointer hover:border-logo-primary ${
+              binding.current_binding ? "font-semibold" : "text-mid-gray italic"
+            }`}
             onClick={() => startRecording(shortcutId)}
           >
-            {formatKeyCombination(binding.current_binding, osType)}
+            {binding.current_binding
+              ? formatKeyCombination(binding.current_binding, osType)
+              : t("settings.general.shortcut.notSet", "Not set")}
           </div>
         )}
         <ResetButton
diff --git a/src/components/settings/general/GeneralSettings.tsx b/src/components/settings/general/GeneralSettings.tsx
index b3a0ad678..5a3db7f32 100644
--- a/src/components/settings/general/GeneralSettings.tsx
+++ b/src/components/settings/general/GeneralSettings.tsx
@@ -17,6 +17,7 @@ export const GeneralSettings: React.FC = () => {
     <div className="max-w-3xl w-full mx-auto space-y-6">
       <SettingsGroup title={t("settings.general.title")}>
         <HandyShortcut shortcutId="transcribe" grouped={true} />
+        <HandyShortcut shortcutId="retype_last" grouped={true} />
         <LanguageSelector descriptionMode="tooltip" grouped={true} />
         <PushToTalk descriptionMode="tooltip" grouped={true} />
       </SettingsGroup>
diff --git a/src/i18n/locales/en/translation.json b/src/i18n/locales/en/translation.json
index 3e1fd3267..bb70a68af 100644
--- a/src/i18n/locales/en/translation.json
+++ b/src/i18n/locales/en/translation.json
@@ -89,6 +89,7 @@
         "loading": "Loading shortcuts...",
         "none": "No shortcuts configured",
         "notFound": "Shortcut not found",
+        "notSet": "Not set",
         "pressKeys": "Press keys...",
         "bindings": {
           "transcribe": {
@@ -98,6 +99,10 @@
           "cancel": {
             "name": "Cancel",
             "description": "Cancels the current recording."
+          },
+          "retype_last": {
+            "name": "Retype Last",
+            "description": "Retypes the last transcription."
           }
         },
         "errors": {