diff --git a/packages/extension/src/chat_bridge.ts b/packages/extension/src/chat_bridge.ts
index 48f52283..f829e057 100644
--- a/packages/extension/src/chat_bridge.ts
+++ b/packages/extension/src/chat_bridge.ts
@@ -149,6 +149,30 @@ export function handleAmicodeBridgeMessage(msg: unknown, io: BridgeIo): boolean
     return true;
   }
 
+  // Clipboard image bridge: the outer webview's navigator.clipboard.read()
+  // requires user activation (a keystroke on that document), but the user typed
+  // inside the sandboxed iframe — so the async Clipboard API throws in newer
+  // Chromium/Electron. Route through the extension host instead: we spawn a
+  // platform-native tool to read the clipboard image as PNG and reply with a
+  // base64 data URL. Same visibility gate as text reads.
+  if (msg.kind === "clipboard-image-read") {
+    if (!io.visible()) return true;
+    const nonce = (msg as { nonce?: string }).nonce;
+    const tab = (msg as { tab?: string }).tab;
+    void readClipboardImageNative().then((result) => {
+      io.postToWebview({
+        source: "amicode",
+        kind: "clipboard-image",
+        nonce,
+        tab,
+        dataUrl: result?.dataUrl ?? null,
+        mime: result?.mime ?? null,
+        filename: result?.filename ?? null,
+      });
+    });
+    return true;
+  }
+
   // Save bridge (run-card PNG + session markdown export): downloads are dead
   // inside the framed app — the extension shows a save dialog and writes the
   // file. Bounded size, basename-only: the payload is untrusted.
@@ -852,3 +876,235 @@ export function handleAmicodeBridgeMessage(msg: unknown, io: BridgeIo): boolean
 
   return false;
 }
+
+// ---------------------------------------------------------------------------
+// Native clipboard image reader
+// ---------------------------------------------------------------------------
+// Reads the system clipboard image using platform-native tools. Returns a
+// base64 data URL on success, null if the clipboard holds no image or the
+// platform isn't supported. This sidesteps the Chromium user-activation
+// requirement that blocks navigator.clipboard.read() in the webview.
+
+interface ClipboardImageResult {
+  dataUrl: string;
+  mime: string;
+  filename: string;
+}
+
+async function readClipboardImageNative(): Promise<ClipboardImageResult | null> {
+  const platform = process.platform;
+  try {
+    if (platform === "darwin") {
+      return await readClipboardImageMac();
+    } else if (platform === "linux") {
+      return await readClipboardImageLinux();
+    } else if (platform === "win32") {
+      return await readClipboardImageWindows();
+    }
+  } catch {
+    // Any failure → no image
+  }
+  return null;
+}
+
+function execPromise(
+  cmd: string,
+  args: string[],
+  options?: { encoding?: "buffer" | BufferEncoding; timeout?: number },
+): Promise<Buffer> {
+  return new Promise((resolve, reject) => {
+    import("node:child_process").then(({ execFile }) => {
+      execFile(cmd, args, { timeout: options?.timeout ?? 3000, maxBuffer: 20 * 1024 * 1024, encoding: "buffer" }, (err, stdout) => {
+        if (err) reject(err);
+        else resolve(stdout as unknown as Buffer);
+      });
+    });
+  });
+}
+
+async function readClipboardImageMac(): Promise<ClipboardImageResult | null> {
+  // Priority 1: If the clipboard has a file URL pointing to an image, read the
+  // file directly. Finder file copies put the file icon as image data and the
+  // file path as public.file-url — we want the actual file contents.
+  try {
+    const fileUrlScript = [
+      'use framework "AppKit"',
+      "set pb to current application's NSPasteboard's generalPasteboard()",
+      'set furlType to "public.file-url"',
+      "set urlStr to (pb's stringForType:furlType) as text",
+      "if urlStr is missing value or urlStr is \"\" then",
+      '  error "no file url"',
+      "end if",
+      "return urlStr",
+    ].join("\n");
+    const urlOut = await execPromise("osascript", ["-l", "AppleScript", "-e", fileUrlScript]);
+    const fileUrl = urlOut.toString("utf8").trim();
+    if (fileUrl) {
+      const { readFileSync, existsSync } = await import("node:fs");
+      const { basename } = await import("node:path");
+      const { fileURLToPath } = await import("node:url");
+      // Resolve macOS .file ID URLs via osascript
+      let filePath: string;
+      if (fileUrl.startsWith("file:///.file/id=")) {
+        const resolveScript = `POSIX path of ("${fileUrl}" as POSIX file)`;
+        const resolved = await execPromise("osascript", ["-e", resolveScript]);
+        filePath = resolved.toString("utf8").trim();
+      } else {
+        filePath = fileURLToPath(fileUrl);
+      }
+      const imageExts = /\.(png|jpe?g|gif|webp|avif|tiff?|bmp|heic|svg|ico)$/i;
+      if (filePath && imageExts.test(filePath) && existsSync(filePath)) {
+        const buf = readFileSync(filePath);
+        const ext = filePath.match(imageExts)![1].toLowerCase();
+        const mime = ext === "jpg" ? "image/jpeg" : ext === "tif" ? "image/tiff" : `image/${ext}`;
+        return {
+          dataUrl: `data:${mime};base64,${buf.toString("base64")}`,
+          mime,
+          filename: basename(filePath),
+        };
+      }
+    }
+  } catch {
+    // No file URL or not an image file — fall through to pasteboard image
+  }
+
+  // Priority 2: Read clipboard image via osascript + NSPasteboard. Try PNG first
+  // (covers screenshots, browser copies), then fall back to TIFF (some apps only
+  // put TIFF on the pasteboard). The TIFF path writes to a temp file and uses
+  // `sips` to convert rather than fighting AppleScript-ObjC's syntax for
+  // NSBitmapImageRep.
+  const pngScript = [
+    'use framework "AppKit"',
+    "set pb to current application's NSPasteboard's generalPasteboard()",
+    "set pngType to current application's NSPasteboardTypePNG",
+    "set imgData to pb's dataForType:pngType",
+    "if imgData is missing value then",
+    '  error "no image"',
+    "end if",
+    "set rawBytes to (imgData's base64EncodedStringWithOptions:0) as text",
+    "return rawBytes",
+  ].join("\n");
+
+  try {
+    const stdout = await execPromise("osascript", ["-l", "AppleScript", "-e", pngScript]);
+    const base64 = stdout.toString("utf8").trim();
+    if (base64) {
+      return { dataUrl: `data:image/png;base64,${base64}`, mime: "image/png", filename: "pasted-image.png" };
+    }
+  } catch {
+    // PNG not on clipboard — try TIFF path
+  }
+
+  // TIFF fallback: write raw TIFF to a temp file, convert with sips
+  const tiffScript = [
+    'use framework "AppKit"',
+    'use framework "Foundation"',
+    "set pb to current application's NSPasteboard's generalPasteboard()",
+    "set tiffType to current application's NSPasteboardTypeTIFF",
+    "set imgData to pb's dataForType:tiffType",
+    "if imgData is missing value then",
+    '  error "no image"',
+    "end if",
+    "set rawBytes to (imgData's base64EncodedStringWithOptions:0) as text",
+    "return rawBytes",
+  ].join("\n");
+
+  try {
+    const { writeFileSync, readFileSync, unlinkSync } = await import("node:fs");
+    const { tmpdir } = await import("node:os");
+    const { join } = await import("node:path");
+
+    const stdout = await execPromise("osascript", ["-l", "AppleScript", "-e", tiffScript]);
+    const tiffBase64 = stdout.toString("utf8").trim();
+    if (!tiffBase64) return null;
+
+    // Write TIFF, convert to PNG with sips
+    const tiffPath = join(tmpdir(), `amicode-paste-${Date.now()}.tiff`);
+    const pngPath = tiffPath.replace(".tiff", ".png");
+    writeFileSync(tiffPath, Buffer.from(tiffBase64, "base64"));
+    await execPromise("sips", ["-s", "format", "png", tiffPath, "--out", pngPath]);
+    const pngBuf = readFileSync(pngPath);
+    unlinkSync(tiffPath);
+    unlinkSync(pngPath);
+
+    return { dataUrl: `data:image/png;base64,${pngBuf.toString("base64")}`, mime: "image/png", filename: "pasted-image.png" };
+  } catch {
+    return null;
+  }
+}
+
+async function readClipboardImageLinux(): Promise<ClipboardImageResult | null> {
+  const { readFileSync, existsSync } = await import("node:fs");
+  const { basename } = await import("node:path");
+
+  // Priority 1: file URI list (Nautilus/Dolphin file copy)
+  try {
+    const uriOut = await execPromise("xclip", ["-selection", "clipboard", "-t", "text/uri-list", "-o"]);
+    const uri = uriOut.toString("utf8").trim().split("\n")[0];
+    if (uri && uri.startsWith("file://")) {
+      const filePath = decodeURIComponent(uri.replace("file://", ""));
+      const imageExts = /\.(png|jpe?g|gif|webp|avif|tiff?|bmp|heic|svg|ico)$/i;
+      if (imageExts.test(filePath) && existsSync(filePath)) {
+        const buf = readFileSync(filePath);
+        const ext = filePath.match(imageExts)![1].toLowerCase();
+        const mime = ext === "jpg" ? "image/jpeg" : ext === "tif" ? "image/tiff" : `image/${ext}`;
+        return { dataUrl: `data:${mime};base64,${buf.toString("base64")}`, mime, filename: basename(filePath) };
+      }
+    }
+  } catch {
+    // No URI list — fall through to image data
+  }
+
+  // Priority 2: raw image data
+  const stdout = await execPromise("xclip", ["-selection", "clipboard", "-t", "image/png", "-o"]);
+  if (!stdout.length) return null;
+  const base64 = stdout.toString("base64");
+  return {
+    dataUrl: `data:image/png;base64,${base64}`,
+    mime: "image/png",
+    filename: "pasted-image.png",
+  };
+}
+
+async function readClipboardImageWindows(): Promise<ClipboardImageResult | null> {
+  const { readFileSync, existsSync } = await import("node:fs");
+  const { basename } = await import("node:path");
+
+  // Priority 1: file drop list (Explorer file copy)
+  try {
+    const fileScript = `
+Add-Type -AssemblyName System.Windows.Forms
+$files = [System.Windows.Forms.Clipboard]::GetFileDropList()
+if ($files.Count -gt 0) { $files[0] } else { exit 1 }
+`;
+    const fileOut = await execPromise("powershell", ["-NoProfile", "-Command", fileScript]);
+    const filePath = fileOut.toString("utf8").trim();
+    const imageExts = /\.(png|jpe?g|gif|webp|avif|tiff?|bmp|heic|svg|ico)$/i;
+    if (filePath && imageExts.test(filePath) && existsSync(filePath)) {
+      const buf = readFileSync(filePath);
+      const ext = filePath.match(imageExts)![1].toLowerCase();
+      const mime = ext === "jpg" ? "image/jpeg" : ext === "tif" ? "image/tiff" : `image/${ext}`;
+      return { dataUrl: `data:${mime};base64,${buf.toString("base64")}`, mime, filename: basename(filePath) };
+    }
+  } catch {
+    // No file drop list — fall through to image data
+  }
+
+  // Priority 2: clipboard image data
+  const script = `
+Add-Type -AssemblyName System.Windows.Forms
+$img = [System.Windows.Forms.Clipboard]::GetImage()
+if ($img -eq $null) { exit 1 }
+$ms = New-Object System.IO.MemoryStream
+$img.Save($ms, [System.Drawing.Imaging.ImageFormat]::Png)
+[Convert]::ToBase64String($ms.ToArray())
+`;
+  const stdout = await execPromise("powershell", ["-NoProfile", "-Command", script]);
+  const base64 = stdout.toString("utf8").trim();
+  if (!base64) return null;
+  return {
+    dataUrl: `data:image/png;base64,${base64}`,
+    mime: "image/png",
+    filename: "pasted-image.png",
+  };
+}
diff --git a/packages/extension/src/chat_panel.ts b/packages/extension/src/chat_panel.ts
index c4c41be1..a01512ab 100644
--- a/packages/extension/src/chat_panel.ts
+++ b/packages/extension/src/chat_panel.ts
@@ -370,12 +370,13 @@ export class ChatPanel {
         // Lane 1 — iframe → extension (commands): MUST come from the opencode
         // origin; the extension side additionally allowlists commands.
         if (e.origin === ${origin}) {
-          // Image paste: the outer webview CAN read clipboard images
-          // (navigator.clipboard.read is granted here); the sandboxed iframe
-          // can't, and vscode.env.clipboard is text-only. So we answer this one
-          // client-side instead of forwarding it to the host.
+          // Image paste: forward to the extension host which reads the clipboard
+          // image natively (osascript/xclip/powershell). The browser Clipboard API
+          // in the outer webview requires user activation from a keystroke on THIS
+          // document, but the keystroke fires inside the iframe — so the async API
+          // throws. The extension host has no such constraint.
           if (d && d.source === "amicode" && d.kind === "clipboard-image-request") {
-            replyClipboardImage(d.nonce);
+            vscode.postMessage({ source: "amicode", kind: "clipboard-image-read", nonce: d.nonce });
             return;
           }
           if (d && d.source === "amicode" && (d.kind === "command" || d.kind === "clipboard-request" || d.kind === "clipboard-write" || d.kind === "open-external" || d.kind === "open-file" || d.kind === "save-file" || d.kind === "set-default-model" || d.kind === "bug-filed" || d.kind === "bug-report-closed" || d.kind === "bug-report-poke" || d.kind === "dev-tools-update" || d.kind === "dev-tools-rebuild" || d.kind === "data-storage-query" || d.kind === "data-storage-update" || d.kind === "redo-onboarding" || d.kind === "device:refresh" || d.kind === "connections-credential" || d.kind === "connections-disconnect" || d.kind === "connections-revalidate" || d.kind === "connections-auth" || d.kind === "connections-choose-project" || d.kind === "connections-add-custom" || d.kind === "connections-remove" || d.kind === "app-ready")) {
@@ -392,44 +393,6 @@ export class ChatPanel {
           if (f && f.contentWindow) f.contentWindow.postMessage(d, ${origin});
         }
       });
-
-      // Answer a clipboard-image-request from the framed app: read the first
-      // image/* item off the OS clipboard (client-side; clipboard-read is
-      // granted to this webview) and post it into the frame as a data URL. On
-      // any failure we still reply with dataUrl:null so the app falls back to
-      // text paste rather than hanging on its timeout.
-      function blobToDataUrl(blob) {
-        return new Promise(function (res) {
-          var r = new FileReader();
-          r.onload = function () { res(typeof r.result === "string" ? r.result : null); };
-          r.onerror = function () { res(null); };
-          r.readAsDataURL(blob);
-        });
-      }
-      async function replyClipboardImage(nonce) {
-        var payload = { source: "amicode", kind: "clipboard-image", nonce: nonce, dataUrl: null, mime: null, filename: null };
-        try {
-          if (navigator.clipboard && navigator.clipboard.read) {
-            var items = await navigator.clipboard.read();
-            for (var i = 0; i < items.length && !payload.dataUrl; i++) {
-              var types = items[i].types || [];
-              for (var j = 0; j < types.length; j++) {
-                if (types[j].indexOf("image/") !== 0) continue;
-                var blob = await items[i].getType(types[j]);
-                var dataUrl = await blobToDataUrl(blob);
-                if (dataUrl) {
-                  payload.dataUrl = dataUrl;
-                  payload.mime = types[j];
-                  payload.filename = "pasted-image." + (types[j].split("/")[1] || "png");
-                }
-                break;
-              }
-            }
-          }
-        } catch (e) { /* reply with dataUrl:null → app falls back to text paste */ }
-        var f = document.querySelector("iframe");
-        if (f && f.contentWindow) f.contentWindow.postMessage(payload, ${origin});
-      }
     })();
   </script>
 </body>
@@ -564,7 +527,7 @@ export class ChatPanel {
             return;
           }
           if (d && d.source === "amicode" && d.kind === "clipboard-image-request") {
-            replyClipboardImage(d.nonce);
+            vscode.postMessage({ source: "amicode", kind: "clipboard-image-read", nonce: d.nonce });
             return;
           }
           if (d && d.source === "amicode" && (d.kind === "command" || d.kind === "clipboard-request" || d.kind === "clipboard-write" || d.kind === "open-external" || d.kind === "open-file" || d.kind === "save-file" || d.kind === "set-default-model" || d.kind === "bug-filed" || d.kind === "bug-report-closed" || d.kind === "bug-report-poke" || d.kind === "dev-tools-update" || d.kind === "dev-tools-rebuild" || d.kind === "data-storage-query" || d.kind === "data-storage-update" || d.kind === "redo-onboarding" || d.kind === "device:refresh" || d.kind === "connections-credential" || d.kind === "connections-disconnect" || d.kind === "connections-revalidate" || d.kind === "connections-auth" || d.kind === "connections-choose-project" || d.kind === "connections-add-custom" || d.kind === "connections-remove" || d.kind === "app-ready")) {
@@ -577,38 +540,6 @@ export class ChatPanel {
           if (f && f.contentWindow) f.contentWindow.postMessage(d, origin);
         }
       });
-      function blobToDataUrl(blob) {
-        return new Promise(function (res) {
-          var r = new FileReader();
-          r.onload = function () { res(typeof r.result === "string" ? r.result : null); };
-          r.onerror = function () { res(null); };
-          r.readAsDataURL(blob);
-        });
-      }
-      async function replyClipboardImage(nonce) {
-        var payload = { source: "amicode", kind: "clipboard-image", nonce: nonce, dataUrl: null, mime: null, filename: null };
-        try {
-          if (navigator.clipboard && navigator.clipboard.read) {
-            var items = await navigator.clipboard.read();
-            for (var i = 0; i < items.length && !payload.dataUrl; i++) {
-              var types = items[i].types || [];
-              for (var j = 0; j < types.length; j++) {
-                if (types[j].indexOf("image/") !== 0) continue;
-                var blob = await items[i].getType(types[j]);
-                var dataUrl = await blobToDataUrl(blob);
-                if (dataUrl) {
-                  payload.dataUrl = dataUrl;
-                  payload.mime = types[j];
-                  payload.filename = "pasted-image." + (types[j].split("/")[1] || "png");
-                }
-                break;
-              }
-            }
-          }
-        } catch (e) { /* reply with dataUrl:null */ }
-        var f = document.querySelector("iframe");
-        if (f && f.contentWindow) f.contentWindow.postMessage(payload, origin);
-      }
     })();
   </script>
 </body>
diff --git a/packages/extension/src/deck/shell.ts b/packages/extension/src/deck/shell.ts
index f0f79f69..83eb92ad 100644
--- a/packages/extension/src/deck/shell.ts
+++ b/packages/extension/src/deck/shell.ts
@@ -461,34 +461,13 @@ window.addEventListener("message", (e) => {
     return;
   }
 
-  // clipboard-image-request is answered shell-side (the shell webview has
-  // clipboard-read; the sandboxed iframe doesn't) — reply to the ASKING pane.
+  // clipboard-image-request: forward to the extension host which reads the
+  // clipboard image natively. The shell webview's navigator.clipboard.read()
+  // requires user activation from a keystroke on THIS document, but the
+  // keystroke fires inside the sandboxed iframe — so the async Clipboard API
+  // throws in newer Chromium. The extension host has no such constraint.
   if (d.kind === "clipboard-image-request") {
-    void (async () => {
-      const payload = { source: "amicode", kind: "clipboard-image", nonce: d.nonce, dataUrl: null as string | null, mime: null as string | null, filename: null as string | null };
-      try {
-        const items = await navigator.clipboard.read();
-        for (const item of items) {
-          const type = item.types.find((t) => t.startsWith("image/"));
-          if (!type) continue;
-          const blob = await item.getType(type);
-          payload.dataUrl = await new Promise<string | null>((res) => {
-            const r = new FileReader();
-            r.onload = () => res(typeof r.result === "string" ? r.result : null);
-            r.onerror = () => res(null);
-            r.readAsDataURL(blob);
-          });
-          if (payload.dataUrl) {
-            payload.mime = type;
-            payload.filename = `pasted-image.${type.split("/")[1] ?? "png"}`;
-          }
-          break;
-        }
-      } catch {
-        /* dataUrl:null → app falls back to text paste */
-      }
-      (e.source as Window | null)?.postMessage(payload, boot.origin);
-    })();
+    vscode.postMessage({ source: "amicode", kind: "clipboard-image-read", nonce: d.nonce, tab: tabId });
     return;
   }
 
diff --git a/packages/extension/test/chat_bridge.test.ts b/packages/extension/test/chat_bridge.test.ts
index 271dba0f..00672f37 100644
--- a/packages/extension/test/chat_bridge.test.ts
+++ b/packages/extension/test/chat_bridge.test.ts
@@ -232,3 +232,44 @@ describe("extractReportBugModel — the command's optional model payload (amicod
     expect(extractReportBugModel({ model: { providerID: "p" } })).toBeUndefined();
   });
 });
+
+describe("amicode bridge — clipboard-image-read", () => {
+  it("reads a clipboard image via native tools and replies with a data URL", async () => {
+    const host = io();
+    const handled = handleAmicodeBridgeMessage(
+      { source: "amicode", kind: "clipboard-image-read", nonce: "img-1", tab: "pane-2" },
+      host,
+    );
+    expect(handled).toBe(true);
+    // The handler is async (spawns a native process); wait for it to complete.
+    // Multiple ticks needed: dynamic import + process spawn + result processing.
+    for (let i = 0; i < 60 && host.posted.length === 0; i++) {
+      await new Promise((r) => setTimeout(r, 50));
+    }
+    expect(host.posted).toHaveLength(1);
+    const reply = host.posted[0] as Record<string, unknown>;
+    expect(reply.source).toBe("amicode");
+    expect(reply.kind).toBe("clipboard-image");
+    expect(reply.nonce).toBe("img-1");
+    expect(reply.tab).toBe("pane-2");
+    // dataUrl is either null (no image) or a valid data URL with image content
+    if (reply.dataUrl !== null) {
+      expect(typeof reply.dataUrl).toBe("string");
+      expect((reply.dataUrl as string).startsWith("data:image/")).toBe(true);
+      expect(typeof reply.mime).toBe("string");
+      expect((reply.mime as string).startsWith("image/")).toBe(true);
+      expect(typeof reply.filename).toBe("string");
+    }
+  });
+
+  it("a hidden panel never answers clipboard-image-read", async () => {
+    const host = io(false);
+    const handled = handleAmicodeBridgeMessage(
+      { source: "amicode", kind: "clipboard-image-read", nonce: "img-2" },
+      host,
+    );
+    expect(handled).toBe(true);
+    await flush();
+    expect(host.posted).toHaveLength(0);
+  });
+});
diff --git a/packages/extension/test/chat_panel.test.ts b/packages/extension/test/chat_panel.test.ts
index 91c23b5a..eeb4f149 100644
--- a/packages/extension/test/chat_panel.test.ts
+++ b/packages/extension/test/chat_panel.test.ts
@@ -328,3 +328,27 @@ describe("ChatPanel.adopt — transforms an existing panel into the chat singlet
     expect(readyFired).toHaveLength(1);
   });
 });
+
+describe("ChatPanel — clipboard-image-request routes through extension host", () => {
+  let restore: (() => void) | undefined;
+  let created: CapturedPanel[] = [];
+  afterEach(() => {
+    for (const p of created) p.dispose();
+    restore?.();
+    restore = undefined;
+    created = [];
+  });
+
+  it("the relay forwards clipboard-image-request to the extension host (not navigator.clipboard.read)", () => {
+    const cap = capturePanel();
+    restore = cap.restore;
+    created = cap.created;
+    ChatPanel.openOrReveal(fakeCtx(), new URL("http://127.0.0.1:43117/"));
+    const html = cap.created[0].webview.html;
+    // The outer webview relay should forward clipboard-image-request to the
+    // extension via vscode.postMessage — NOT handle it with navigator.clipboard.read
+    expect(html).toContain('"clipboard-image-read"');
+    // The old client-side replyClipboardImage with navigator.clipboard.read should be gone
+    expect(html).not.toContain("navigator.clipboard.read");
+  });
+});