diff --git a/apps/desktop/src/components/claude-chat/chat-composer.tsx b/apps/desktop/src/components/claude-chat/chat-composer.tsx
index 97a923c..e5bf297 100644
--- a/apps/desktop/src/components/claude-chat/chat-composer.tsx
+++ b/apps/desktop/src/components/claude-chat/chat-composer.tsx
@@ -32,7 +32,7 @@ import {
   ListEndIcon,
 } from "lucide-react";
 import { getCurrentWebview } from "@tauri-apps/api/webview";
-import { writeFile, mkdir, exists } from "@tauri-apps/plugin-fs";
+import { writeFile, mkdir, exists, remove } from "@tauri-apps/plugin-fs";
 import { join, tempDir } from "@tauri-apps/api/path";
 import { invoke } from "@tauri-apps/api/core";
 import {
@@ -87,6 +87,7 @@ interface PinnedContext {
   filePath: string;
   selectedText: string;
   imageDataUrl?: string; // thumbnail for captured images
+  isTemporary?: boolean;
 }
 
 function pastedFileExtension(file: File) {
@@ -113,6 +114,33 @@ function readFileAsDataUrl(file: File) {
   });
 }
 
+function temporaryFilePaths(contexts: PinnedContext[]) {
+  return contexts
+    .filter((context) => context.isTemporary)
+    .map((context) => context.filePath);
+}
+
+async function cleanupTemporaryFilePaths(paths: string[] | undefined) {
+  if (!paths?.length) return;
+  await Promise.all(
+    paths.map(async (path) => {
+      try {
+        await remove(path);
+      } catch (err) {
+        log.warn("Failed to remove temporary pasted file", {
+          path,
+          error: String(err),
+        });
+      }
+    }),
+  );
+}
+
+function cleanupTemporaryPinnedContext(context: PinnedContext) {
+  if (!context.isTemporary) return;
+  void cleanupTemporaryFilePaths([context.filePath]);
+}
+
 function getFileIcon(file: ProjectFile) {
   if (file.type === "image")
     return <ImageIcon className="size-3.5 shrink-0 text-muted-foreground" />;
@@ -813,6 +841,7 @@ export const ChatComposer: FC<{ isOpen?: boolean }> = ({ isOpen }) => {
                 "Use this image file as visual context for the user's message.",
               ].join("\n"),
               imageDataUrl: await readFileAsDataUrl(file),
+              isTemporary: true,
             });
           } catch (err) {
             log.error("Failed to save pasted image", {
@@ -946,6 +975,7 @@ export const ChatComposer: FC<{ isOpen?: boolean }> = ({ isOpen }) => {
         label: combinedLabel,
         filePath: pinnedContexts[0].filePath,
         selectedText: combinedText,
+        temporaryFilePaths: temporaryFilePaths(pinnedContexts),
       };
     }
 
@@ -960,7 +990,8 @@ export const ChatComposer: FC<{ isOpen?: boolean }> = ({ isOpen }) => {
     if (textareaRef.current) {
       textareaRef.current.style.height = "auto";
     }
-    // Clear pinned contexts after send
+    // Clear pinned contexts after send. Temporary files are removed by the
+    // completion event once the provider has finished with them.
     setPinnedContexts([]);
   }, [
     activeTabId,
@@ -1655,9 +1686,12 @@ export const ChatComposer: FC<{ isOpen?: boolean }> = ({ isOpen }) => {
                     type="button"
                     aria-label="Remove queued guidance"
                     className="flex size-6 shrink-0 items-center justify-center rounded-md text-muted-foreground transition-colors hover:bg-red-500/10 hover:text-red-600 dark:hover:bg-red-500/15 dark:hover:text-red-400"
-                    onClick={() =>
-                      removeQueuedGuidance(activeTabId, guidance.id)
-                    }
+                    onClick={() => {
+                      void cleanupTemporaryFilePaths(
+                        guidance.contextOverride?.temporaryFilePaths,
+                      );
+                      removeQueuedGuidance(activeTabId, guidance.id);
+                    }}
                   >
                     <Trash2Icon className="size-3" />
                   </button>
@@ -1683,11 +1717,12 @@ export const ChatComposer: FC<{ isOpen?: boolean }> = ({ isOpen }) => {
                   />
                   <button
                     aria-label="Remove attachment"
-                    onClick={() =>
+                    onClick={() => {
+                      void cleanupTemporaryPinnedContext(ctx);
                       setPinnedContexts((prev) =>
                         prev.filter((_, idx) => idx !== i),
-                      )
-                    }
+                      );
+                    }}
                     className="absolute top-0.5 right-0.5 rounded-full bg-background/80 p-0.5 opacity-0 transition-opacity group-hover:opacity-100"
                   >
                     <XIcon className="size-3" />
@@ -1701,11 +1736,12 @@ export const ChatComposer: FC<{ isOpen?: boolean }> = ({ isOpen }) => {
                   {ctx.label}
                   <button
                     aria-label="Remove context"
-                    onClick={() =>
+                    onClick={() => {
+                      void cleanupTemporaryPinnedContext(ctx);
                       setPinnedContexts((prev) =>
                         prev.filter((_, idx) => idx !== i),
-                      )
-                    }
+                      );
+                    }}
                     className="ml-0.5 rounded-sm p-0.5 transition-colors hover:bg-muted-foreground/20"
                   >
                     <XIcon className="size-3" />
diff --git a/apps/desktop/src/hooks/use-claude-events.ts b/apps/desktop/src/hooks/use-claude-events.ts
index 25a5853..d706a55 100644
--- a/apps/desktop/src/hooks/use-claude-events.ts
+++ b/apps/desktop/src/hooks/use-claude-events.ts
@@ -1,6 +1,7 @@
 import { useEffect, useRef } from "react";
 import { listen, type UnlistenFn } from "@tauri-apps/api/event";
 import { invoke } from "@tauri-apps/api/core";
+import { remove } from "@tauri-apps/plugin-fs";
 import {
   CLAUDE_CODE_PROVIDER_ID,
   useClaudeChatStore,
@@ -20,6 +21,21 @@ import { createLogger } from "@/lib/debug/logger";
 
 const log = createLogger("claude-event");
 
+async function cleanupTemporaryFiles(paths: string[]) {
+  await Promise.all(
+    paths.map(async (path) => {
+      try {
+        await remove(path);
+      } catch (err) {
+        log.warn("failed to remove temporary chat file", {
+          path,
+          error: String(err),
+        });
+      }
+    }),
+  );
+}
+
 /** Backend event payload shapes (include tab_id for routing) */
 interface ClaudeOutputPayload {
   tab_id: string;
@@ -388,6 +404,7 @@ export function useClaudeEvents() {
 
       const completedSessionId = tab.sessionId;
       chatStore._setStreaming(tabId, false);
+      void cleanupTemporaryFiles(chatStore.consumeTemporaryFilePaths(tabId));
 
       const forceQueuedGuidance = tab.forceQueuedGuidanceOnComplete === true;
       if (forceQueuedGuidance) {
diff --git a/apps/desktop/src/stores/claude-chat-store.ts b/apps/desktop/src/stores/claude-chat-store.ts
index 6a92fb7..80df88f 100644
--- a/apps/desktop/src/stores/claude-chat-store.ts
+++ b/apps/desktop/src/stores/claude-chat-store.ts
@@ -97,6 +97,7 @@ export interface TabDraft {
     filePath: string;
     selectedText: string;
     imageDataUrl?: string;
+    isTemporary?: boolean;
   }[];
 }
 
@@ -104,6 +105,7 @@ export interface PromptContextOverride {
   label: string;
   filePath: string;
   selectedText: string;
+  temporaryFilePaths?: string[];
 }
 
 export interface QueuedGuidance {
@@ -128,6 +130,7 @@ export interface TabState {
   queuedGuidance?: QueuedGuidance[];
   forceQueuedGuidanceOnComplete?: boolean;
   forcedQueuedGuidanceId?: string | null;
+  pendingTemporaryFilePaths?: string[];
 }
 
 /** Fields that are projected from the active tab to top-level state */
@@ -155,6 +158,7 @@ function makeDefaultTab(id: string): TabState {
     queuedGuidance: [],
     forceQueuedGuidanceOnComplete: false,
     forcedQueuedGuidanceId: null,
+    pendingTemporaryFilePaths: [],
   };
 }
 
@@ -530,6 +534,7 @@ interface ClaudeChatState {
   ) => string | null;
   removeQueuedGuidance: (tabId: string, guidanceId: string) => void;
   clearQueuedGuidance: (tabId: string) => void;
+  consumeTemporaryFilePaths: (tabId: string) => string[];
   forceQueuedGuidanceNow: (tabId: string, guidanceId?: string) => Promise<void>;
   cancelExecution: () => Promise<void>;
   clearMessages: () => void;
@@ -717,15 +722,20 @@ export const useClaudeChatStore = create<ClaudeChatState>()((set, get) => ({
       : undefined;
 
     set((s) => {
+      const currentTab = s.tabs.find((t) => t.id === activeTabId);
+      const temporaryFilePaths = Array.from(
+        new Set([
+          ...(currentTab?.pendingTemporaryFilePaths ?? []),
+          ...(contextOverride?.temporaryFilePaths ?? []),
+        ]),
+      );
       const tabUpdates: Partial<TabState> = {
-        messages: [
-          ...(s.tabs.find((t) => t.id === activeTabId)?.messages ?? []),
-          userMessage,
-        ],
+        messages: [...(currentTab?.messages ?? []), userMessage],
         sessionId: resumeSessionId,
         providerKey: requestProviderKey,
         isStreaming: true,
         error: null,
+        pendingTemporaryFilePaths: temporaryFilePaths,
       };
       if (tabTitle) tabUpdates.title = tabTitle;
       return {
@@ -936,6 +946,18 @@ export const useClaudeChatStore = create<ClaudeChatState>()((set, get) => ({
     );
   },
 
+  consumeTemporaryFilePaths: (tabId) => {
+    const paths =
+      get().tabs.find((tab) => tab.id === tabId)?.pendingTemporaryFilePaths ??
+      [];
+    if (paths.length > 0) {
+      set((state) =>
+        applyTabUpdate(state, tabId, { pendingTemporaryFilePaths: [] }),
+      );
+    }
+    return paths;
+  },
+
   forceQueuedGuidanceNow: async (tabId, guidanceId) => {
     const tab = get().tabs.find((t) => t.id === tabId);
     if (!tab?.isStreaming || !(tab.queuedGuidance?.length ?? 0)) return;