fix: improve image paste handling with resizing and error feedback (#601)

Co-authored-by: Letta <noreply@letta.com>
2026-01-19 21:57:39 -08:00
parent 86553db606
commit acc134027b
7 changed files with 372 additions and 80 deletions
--- a/bun.lock
+++ b/bun.lock
@@ -8,6 +8,7 @@
        "glob": "^13.0.0",
        "ink-link": "^5.0.0",
        "open": "^10.2.0",
+        "sharp": "^0.34.5",
      },
      "devDependencies": {
        "@types/bun": "latest",
@@ -32,6 +33,58 @@
  "packages": {
    "@alcalzone/ansi-tokenize": ["@alcalzone/ansi-tokenize@0.1.3", "", { "dependencies": { "ansi-styles": "^6.2.1", "is-fullwidth-code-point": "^4.0.0" } }, "sha512-3yWxPTq3UQ/FY9p1ErPxIyfT64elWaMvM9lIHnaqpyft63tkxodF5aUElYHrdisWve5cETkh1+KBw1yJuW0aRw=="],

+    "@emnapi/runtime": ["@emnapi/runtime@1.8.1", "", { "dependencies": { "tslib": "^2.4.0" } }, "sha512-mehfKSMWjjNol8659Z8KxEMrdSJDDot5SXMq00dM8BN4o+CLNXQ0xH2V7EchNHV4RmbZLmmPdEaXZc5H2FXmDg=="],
+
+    "@img/colour": ["@img/colour@1.0.0", "", {}, "sha512-A5P/LfWGFSl6nsckYtjw9da+19jB8hkJ6ACTGcDfEJ0aE+l2n2El7dsVM7UVHZQ9s2lmYMWlrS21YLy2IR1LUw=="],
+
+    "@img/sharp-darwin-arm64": ["@img/sharp-darwin-arm64@0.34.5", "", { "optionalDependencies": { "@img/sharp-libvips-darwin-arm64": "1.2.4" }, "os": "darwin", "cpu": "arm64" }, "sha512-imtQ3WMJXbMY4fxb/Ndp6HBTNVtWCUI0WdobyheGf5+ad6xX8VIDO8u2xE4qc/fr08CKG/7dDseFtn6M6g/r3w=="],
+
+    "@img/sharp-darwin-x64": ["@img/sharp-darwin-x64@0.34.5", "", { "optionalDependencies": { "@img/sharp-libvips-darwin-x64": "1.2.4" }, "os": "darwin", "cpu": "x64" }, "sha512-YNEFAF/4KQ/PeW0N+r+aVVsoIY0/qxxikF2SWdp+NRkmMB7y9LBZAVqQ4yhGCm/H3H270OSykqmQMKLBhBJDEw=="],
+
+    "@img/sharp-libvips-darwin-arm64": ["@img/sharp-libvips-darwin-arm64@1.2.4", "", { "os": "darwin", "cpu": "arm64" }, "sha512-zqjjo7RatFfFoP0MkQ51jfuFZBnVE2pRiaydKJ1G/rHZvnsrHAOcQALIi9sA5co5xenQdTugCvtb1cuf78Vf4g=="],
+
+    "@img/sharp-libvips-darwin-x64": ["@img/sharp-libvips-darwin-x64@1.2.4", "", { "os": "darwin", "cpu": "x64" }, "sha512-1IOd5xfVhlGwX+zXv2N93k0yMONvUlANylbJw1eTah8K/Jtpi15KC+WSiaX/nBmbm2HxRM1gZ0nSdjSsrZbGKg=="],
+
+    "@img/sharp-libvips-linux-arm": ["@img/sharp-libvips-linux-arm@1.2.4", "", { "os": "linux", "cpu": "arm" }, "sha512-bFI7xcKFELdiNCVov8e44Ia4u2byA+l3XtsAj+Q8tfCwO6BQ8iDojYdvoPMqsKDkuoOo+X6HZA0s0q11ANMQ8A=="],
+
+    "@img/sharp-libvips-linux-arm64": ["@img/sharp-libvips-linux-arm64@1.2.4", "", { "os": "linux", "cpu": "arm64" }, "sha512-excjX8DfsIcJ10x1Kzr4RcWe1edC9PquDRRPx3YVCvQv+U5p7Yin2s32ftzikXojb1PIFc/9Mt28/y+iRklkrw=="],
+
+    "@img/sharp-libvips-linux-ppc64": ["@img/sharp-libvips-linux-ppc64@1.2.4", "", { "os": "linux", "cpu": "ppc64" }, "sha512-FMuvGijLDYG6lW+b/UvyilUWu5Ayu+3r2d1S8notiGCIyYU/76eig1UfMmkZ7vwgOrzKzlQbFSuQfgm7GYUPpA=="],
+
+    "@img/sharp-libvips-linux-riscv64": ["@img/sharp-libvips-linux-riscv64@1.2.4", "", { "os": "linux", "cpu": "none" }, "sha512-oVDbcR4zUC0ce82teubSm+x6ETixtKZBh/qbREIOcI3cULzDyb18Sr/Wcyx7NRQeQzOiHTNbZFF1UwPS2scyGA=="],
+
+    "@img/sharp-libvips-linux-s390x": ["@img/sharp-libvips-linux-s390x@1.2.4", "", { "os": "linux", "cpu": "s390x" }, "sha512-qmp9VrzgPgMoGZyPvrQHqk02uyjA0/QrTO26Tqk6l4ZV0MPWIW6LTkqOIov+J1yEu7MbFQaDpwdwJKhbJvuRxQ=="],
+
+    "@img/sharp-libvips-linux-x64": ["@img/sharp-libvips-linux-x64@1.2.4", "", { "os": "linux", "cpu": "x64" }, "sha512-tJxiiLsmHc9Ax1bz3oaOYBURTXGIRDODBqhveVHonrHJ9/+k89qbLl0bcJns+e4t4rvaNBxaEZsFtSfAdquPrw=="],
+
+    "@img/sharp-libvips-linuxmusl-arm64": ["@img/sharp-libvips-linuxmusl-arm64@1.2.4", "", { "os": "linux", "cpu": "arm64" }, "sha512-FVQHuwx1IIuNow9QAbYUzJ+En8KcVm9Lk5+uGUQJHaZmMECZmOlix9HnH7n1TRkXMS0pGxIJokIVB9SuqZGGXw=="],
+
+    "@img/sharp-libvips-linuxmusl-x64": ["@img/sharp-libvips-linuxmusl-x64@1.2.4", "", { "os": "linux", "cpu": "x64" }, "sha512-+LpyBk7L44ZIXwz/VYfglaX/okxezESc6UxDSoyo2Ks6Jxc4Y7sGjpgU9s4PMgqgjj1gZCylTieNamqA1MF7Dg=="],
+
+    "@img/sharp-linux-arm": ["@img/sharp-linux-arm@0.34.5", "", { "optionalDependencies": { "@img/sharp-libvips-linux-arm": "1.2.4" }, "os": "linux", "cpu": "arm" }, "sha512-9dLqsvwtg1uuXBGZKsxem9595+ujv0sJ6Vi8wcTANSFpwV/GONat5eCkzQo/1O6zRIkh0m/8+5BjrRr7jDUSZw=="],
+
+    "@img/sharp-linux-arm64": ["@img/sharp-linux-arm64@0.34.5", "", { "optionalDependencies": { "@img/sharp-libvips-linux-arm64": "1.2.4" }, "os": "linux", "cpu": "arm64" }, "sha512-bKQzaJRY/bkPOXyKx5EVup7qkaojECG6NLYswgktOZjaXecSAeCWiZwwiFf3/Y+O1HrauiE3FVsGxFg8c24rZg=="],
+
+    "@img/sharp-linux-ppc64": ["@img/sharp-linux-ppc64@0.34.5", "", { "optionalDependencies": { "@img/sharp-libvips-linux-ppc64": "1.2.4" }, "os": "linux", "cpu": "ppc64" }, "sha512-7zznwNaqW6YtsfrGGDA6BRkISKAAE1Jo0QdpNYXNMHu2+0dTrPflTLNkpc8l7MUP5M16ZJcUvysVWWrMefZquA=="],
+
+    "@img/sharp-linux-riscv64": ["@img/sharp-linux-riscv64@0.34.5", "", { "optionalDependencies": { "@img/sharp-libvips-linux-riscv64": "1.2.4" }, "os": "linux", "cpu": "none" }, "sha512-51gJuLPTKa7piYPaVs8GmByo7/U7/7TZOq+cnXJIHZKavIRHAP77e3N2HEl3dgiqdD/w0yUfiJnII77PuDDFdw=="],
+
+    "@img/sharp-linux-s390x": ["@img/sharp-linux-s390x@0.34.5", "", { "optionalDependencies": { "@img/sharp-libvips-linux-s390x": "1.2.4" }, "os": "linux", "cpu": "s390x" }, "sha512-nQtCk0PdKfho3eC5MrbQoigJ2gd1CgddUMkabUj+rBevs8tZ2cULOx46E7oyX+04WGfABgIwmMC0VqieTiR4jg=="],
+
+    "@img/sharp-linux-x64": ["@img/sharp-linux-x64@0.34.5", "", { "optionalDependencies": { "@img/sharp-libvips-linux-x64": "1.2.4" }, "os": "linux", "cpu": "x64" }, "sha512-MEzd8HPKxVxVenwAa+JRPwEC7QFjoPWuS5NZnBt6B3pu7EG2Ge0id1oLHZpPJdn3OQK+BQDiw9zStiHBTJQQQQ=="],
+
+    "@img/sharp-linuxmusl-arm64": ["@img/sharp-linuxmusl-arm64@0.34.5", "", { "optionalDependencies": { "@img/sharp-libvips-linuxmusl-arm64": "1.2.4" }, "os": "linux", "cpu": "arm64" }, "sha512-fprJR6GtRsMt6Kyfq44IsChVZeGN97gTD331weR1ex1c1rypDEABN6Tm2xa1wE6lYb5DdEnk03NZPqA7Id21yg=="],
+
+    "@img/sharp-linuxmusl-x64": ["@img/sharp-linuxmusl-x64@0.34.5", "", { "optionalDependencies": { "@img/sharp-libvips-linuxmusl-x64": "1.2.4" }, "os": "linux", "cpu": "x64" }, "sha512-Jg8wNT1MUzIvhBFxViqrEhWDGzqymo3sV7z7ZsaWbZNDLXRJZoRGrjulp60YYtV4wfY8VIKcWidjojlLcWrd8Q=="],
+
+    "@img/sharp-wasm32": ["@img/sharp-wasm32@0.34.5", "", { "dependencies": { "@emnapi/runtime": "^1.7.0" }, "cpu": "none" }, "sha512-OdWTEiVkY2PHwqkbBI8frFxQQFekHaSSkUIJkwzclWZe64O1X4UlUjqqqLaPbUpMOQk6FBu/HtlGXNblIs0huw=="],
+
+    "@img/sharp-win32-arm64": ["@img/sharp-win32-arm64@0.34.5", "", { "os": "win32", "cpu": "arm64" }, "sha512-WQ3AgWCWYSb2yt+IG8mnC6Jdk9Whs7O0gxphblsLvdhSpSTtmu69ZG1Gkb6NuvxsNACwiPV6cNSZNzt0KPsw7g=="],
+
+    "@img/sharp-win32-ia32": ["@img/sharp-win32-ia32@0.34.5", "", { "os": "win32", "cpu": "ia32" }, "sha512-FV9m/7NmeCmSHDD5j4+4pNI8Cp3aW+JvLoXcTUo0IqyjSfAZJ8dIUmijx1qaJsIiU+Hosw6xM5KijAWRJCSgNg=="],
+
+    "@img/sharp-win32-x64": ["@img/sharp-win32-x64@0.34.5", "", { "os": "win32", "cpu": "x64" }, "sha512-+29YMsqY2/9eFEiW93eqWnuLcWcufowXewwSNIT6UwZdUUCrM3oFjMWH/Z6/TMmb4hlFenmfAVbpWeup2jryCw=="],
+
    "@isaacs/balanced-match": ["@isaacs/balanced-match@4.0.1", "", {}, "sha512-yzMTt9lEb8Gv7zRioUilSglI0c0smZ9k5D65677DLWLtWJaXIS3CqcGyUFByYKlnUj6TkjLVs54fBl6+TiGQDQ=="],

    "@isaacs/brace-expansion": ["@isaacs/brace-expansion@5.0.0", "", { "dependencies": { "@isaacs/balanced-match": "^4.0.1" } }, "sha512-ZT55BDLV0yv0RBm2czMiZ+SqCGO7AvmOM3G/w2xhVPH+te0aKgFjmBvGlL1dH+ql2tgGO3MVrbb3jCKyvpgnxA=="],
@@ -96,6 +149,8 @@

    "define-lazy-prop": ["define-lazy-prop@3.0.0", "", {}, "sha512-N+MeXYoqr3pOgn8xfyRPREN7gHakLYjhsHhWGT3fWAiL4IkAt0iDw14QiiEm2bE30c5XX5q0FtAA3CK5f9/BUg=="],

+    "detect-libc": ["detect-libc@2.1.2", "", {}, "sha512-Btj2BOOO83o3WyH59e8MgXsxEQVcarkUOpEYrubB0urwnN10yQ364rsiByU11nZlqWYZm05i/of7io4mzihBtQ=="],
+
    "diff": ["diff@8.0.2", "", {}, "sha512-sSuxWU5j5SR9QQji/o2qMvqRNYRDOcBTgsJ/DeCf4iSN4gW+gNMXM7wFIP+fdXZxoNiAnHUTGjCr+TSWXdRDKg=="],

    "emoji-regex": ["emoji-regex@10.6.0", "", {}, "sha512-toUI84YS5YmxW219erniWD0CIVOo46xGKColeNQRgOzDorgBi1v4D71/OFzgD9GO2UGKIv1C3Sp8DAn0+j5w7A=="],
@@ -198,6 +253,10 @@

    "scheduler": ["scheduler@0.23.2", "", { "dependencies": { "loose-envify": "^1.1.0" } }, "sha512-UOShsPwz7NrMUqhR6t0hWjFduvOzbtv7toDH1/hIrfRNIDBnnBWd0CwJTGvTpngVlmwGCdP9/Zl/tVrDqcuYzQ=="],

+    "semver": ["semver@7.7.3", "", { "bin": { "semver": "bin/semver.js" } }, "sha512-SdsKMrI9TdgjdweUSR9MweHA4EJ8YxHn8DFaDisvhVlUOe4BF1tLD7GAj0lIqWVl+dPb/rExr0Btby5loQm20Q=="],
+
+    "sharp": ["sharp@0.34.5", "", { "dependencies": { "@img/colour": "^1.0.0", "detect-libc": "^2.1.2", "semver": "^7.7.3" }, "optionalDependencies": { "@img/sharp-darwin-arm64": "0.34.5", "@img/sharp-darwin-x64": "0.34.5", "@img/sharp-libvips-darwin-arm64": "1.2.4", "@img/sharp-libvips-darwin-x64": "1.2.4", "@img/sharp-libvips-linux-arm": "1.2.4", "@img/sharp-libvips-linux-arm64": "1.2.4", "@img/sharp-libvips-linux-ppc64": "1.2.4", "@img/sharp-libvips-linux-riscv64": "1.2.4", "@img/sharp-libvips-linux-s390x": "1.2.4", "@img/sharp-libvips-linux-x64": "1.2.4", "@img/sharp-libvips-linuxmusl-arm64": "1.2.4", "@img/sharp-libvips-linuxmusl-x64": "1.2.4", "@img/sharp-linux-arm": "0.34.5", "@img/sharp-linux-arm64": "0.34.5", "@img/sharp-linux-ppc64": "0.34.5", "@img/sharp-linux-riscv64": "0.34.5", "@img/sharp-linux-s390x": "0.34.5", "@img/sharp-linux-x64": "0.34.5", "@img/sharp-linuxmusl-arm64": "0.34.5", "@img/sharp-linuxmusl-x64": "0.34.5", "@img/sharp-wasm32": "0.34.5", "@img/sharp-win32-arm64": "0.34.5", "@img/sharp-win32-ia32": "0.34.5", "@img/sharp-win32-x64": "0.34.5" } }, "sha512-Ou9I5Ft9WNcCbXrU9cMgPBcCK8LiwLqcbywW3t4oDV37n1pzpuNLsYiAV8eODnjbtQlSDwZ2cUEeQz4E54Hltg=="],
+
    "signal-exit": ["signal-exit@3.0.7", "", {}, "sha512-wnD2ZE+l+SPC/uoS0vXeE9L1+0wuaMqKlfz9AMUo38JsyLSBWSFcHR1Rri62LZc12vLr1gb3jl7iwQhgwpAbGQ=="],

    "slice-ansi": ["slice-ansi@7.1.2", "", { "dependencies": { "ansi-styles": "^6.2.1", "is-fullwidth-code-point": "^5.0.0" } }, "sha512-iOBWFgUX7caIZiuutICxVgX1SdxwAVFFKwt1EvMYYec/NWO5meOJ6K5uQxhrYBdQJne4KxiqZc+KptFOWFSI9w=="],
@@ -218,6 +277,8 @@

    "to-regex-range": ["to-regex-range@5.0.1", "", { "dependencies": { "is-number": "^7.0.0" } }, "sha512-65P7iz6X5yEr1cwcgvQxbbIw7Uk3gOy5dIdtZ4rDveLqhrdJP+Li/Hx6tyK0NEb+2GCyneCMJiGqrADCSNk8sQ=="],

+    "tslib": ["tslib@2.8.1", "", {}, "sha512-oJFu94HQb+KVduSUQL7wnpmqnfmLsOA/nAh6b6EH0wCEoK0/mPeXU6c3wKDV83MkOuHPRHtSXKKU99IBazS/2w=="],
+
    "type-fest": ["type-fest@4.41.0", "", {}, "sha512-TeTSQ6H5YHvpqVwBRcnLDCBnDOHWYu7IvGbHT6N8AOymcr9PJGjc1GTtiWZTYg0NCgYwvnYWEkVChQAr9bjfwA=="],

    "typescript": ["typescript@5.9.3", "", { "bin": { "tsc": "bin/tsc", "tsserver": "bin/tsserver" } }, "sha512-jl1vZzPDinLr9eUt3J/t7V6FgNEw9QjvBPdysz9KfQDD41fQrC2Y4vKQdiaUpFT4bXlb1RHhLpp8wtm6M5TgSw=="],
--- a/package.json
+++ b/package.json
@@ -33,7 +33,8 @@
    "@letta-ai/letta-client": "^1.6.8",
    "glob": "^13.0.0",
    "ink-link": "^5.0.0",
-    "open": "^10.2.0"
+    "open": "^10.2.0",
+    "sharp": "^0.34.5"
  },
  "optionalDependencies": {
    "@vscode/ripgrep": "^1.17.0"
--- a/src/cli/App.tsx
+++ b/src/cli/App.tsx
@@ -2957,6 +2957,21 @@ export default function App({
    setMessageQueue([]);
  }, []);

+  // Handle paste errors (e.g., image too large)
+  const handlePasteError = useCallback(
+    (message: string) => {
+      const statusId = uid("status");
+      buffersRef.current.byId.set(statusId, {
+        kind: "status",
+        id: statusId,
+        lines: [`⚠️ ${message}`],
+      });
+      buffersRef.current.order.push(statusId);
+      refreshDerived();
+    },
+    [refreshDerived],
+  );
+
  const handleInterrupt = useCallback(async () => {
    // If we're executing client-side tools, abort them AND the main stream
    const hasTrackedTools =
@@ -8028,6 +8043,7 @@ Plan file path: ${planFilePath}`;
                ralphPendingYolo={pendingRalphConfig?.isYolo ?? false}
                onRalphExit={handleRalphExit}
                conversationId={conversationId}
+                onPasteError={handlePasteError}
              />
            </Box>

--- a/src/cli/components/InputRich.tsx
+++ b/src/cli/components/InputRich.tsx
@@ -139,6 +139,7 @@ export function Input({
  ralphPendingYolo = false,
  onRalphExit,
  conversationId,
+  onPasteError,
 }: {
  visible?: boolean;
  streaming: boolean;
@@ -163,6 +164,7 @@ export function Input({
  ralphPendingYolo?: boolean;
  onRalphExit?: () => void;
  conversationId?: string;
+  onPasteError?: (message: string) => void;
 }) {
  const [value, setValue] = useState("");
  const [escapePressed, setEscapePressed] = useState(false);
@@ -815,6 +817,7 @@ export function Input({
              focus={!onEscapeCancel}
              onBangAtEmpty={handleBangAtEmpty}
              onBackspaceAtEmpty={handleBackspaceAtEmpty}
+              onPasteError={onPasteError}
            />
          </Box>
        </Box>
--- a/src/cli/components/PasteAwareTextInput.tsx
+++ b/src/cli/components/PasteAwareTextInput.tsx
@@ -41,6 +41,11 @@ interface PasteAwareTextInputProps {
   * Return true to consume the keystroke.
   */
  onBackspaceAtEmpty?: () => boolean;
+
+  /**
+   * Called when an image paste fails (e.g., image too large).
+   */
+  onPasteError?: (message: string) => void;
 }

 function countLines(text: string): number {
@@ -122,6 +127,7 @@ export function PasteAwareTextInput({
  onCursorMove,
  onBangAtEmpty,
  onBackspaceAtEmpty,
+  onPasteError,
 }: PasteAwareTextInputProps) {
  const { internal_eventEmitter } = useStdin();
  const [displayValue, setDisplayValue] = useState(value);
@@ -209,26 +215,34 @@ export function PasteAwareTextInput({
      // Native terminals don't send image data via bracketed paste, so we need
      // to explicitly check the clipboard when Ctrl+V is pressed.
      if (key.ctrl && input === "v") {
-        const clip = tryImportClipboardImageMac();
-        if (clip) {
-          const at = Math.max(
-            0,
-            Math.min(caretOffsetRef.current, displayValueRef.current.length),
-          );
-          const newDisplay =
-            displayValueRef.current.slice(0, at) +
-            clip +
-            displayValueRef.current.slice(at);
-          displayValueRef.current = newDisplay;
-          setDisplayValue(newDisplay);
-          setActualValue(newDisplay);
-          onChangeRef.current(newDisplay);
-          const nextCaret = at + clip.length;
-          setNudgeCursorOffset(nextCaret);
-          caretOffsetRef.current = nextCaret;
-        }
-        // Don't return - let it fall through to normal paste handling
-        // in case there's also text in the clipboard
+        // Fire async handler (can't await in useInput callback)
+        (async () => {
+          const result = await tryImportClipboardImageMac();
+          if (result) {
+            if ("error" in result) {
+              // Report the error via callback
+              onPasteErrorRef.current?.(result.error);
+              return;
+            }
+            // Success - insert the placeholder
+            const clip = result.placeholder;
+            const at = Math.max(
+              0,
+              Math.min(caretOffsetRef.current, displayValueRef.current.length),
+            );
+            const newDisplay =
+              displayValueRef.current.slice(0, at) +
+              clip +
+              displayValueRef.current.slice(at);
+            displayValueRef.current = newDisplay;
+            setDisplayValue(newDisplay);
+            setActualValue(newDisplay);
+            onChangeRef.current(newDisplay);
+            const nextCaret = at + clip.length;
+            setNudgeCursorOffset(nextCaret);
+            caretOffsetRef.current = nextCaret;
+          }
+        })();
        return;
      }

@@ -239,27 +253,22 @@ export function PasteAwareTextInput({

        const payload = typeof input === "string" ? input : "";
        // Translate any image payloads in the paste (OSC 1337, data URLs, file paths)
-        let translated = translatePasteForImages(payload);
-        // If paste event carried no text (common for image-only clipboard), try macOS import
-        if ((!translated || translated.length === 0) && payload.length === 0) {
-          const clip = tryImportClipboardImageMac();
-          if (clip) translated = clip;
-        }
+        const translated = translatePasteForImages(payload);

-        if (translated && translated.length > 0) {
-          // Insert at current caret position
+        // Helper to insert translated content
+        const insertTranslated = (text: string) => {
          const at = Math.max(
            0,
            Math.min(caretOffsetRef.current, displayValue.length),
          );
-          const isLarge = countLines(translated) > 5 || translated.length > 500;
+          const isLarge = countLines(text) > 5 || text.length > 500;
          if (isLarge) {
-            const pasteId = allocatePaste(translated);
-            const placeholder = `[Pasted text #${pasteId} +${countLines(translated)} lines]`;
+            const pasteId = allocatePaste(text);
+            const placeholder = `[Pasted text #${pasteId} +${countLines(text)} lines]`;
            const newDisplay =
              displayValue.slice(0, at) + placeholder + displayValue.slice(at);
            const newActual =
-              actualValue.slice(0, at) + translated + actualValue.slice(at);
+              actualValue.slice(0, at) + text + actualValue.slice(at);
            setDisplayValue(newDisplay);
            setActualValue(newActual);
            onChange(newDisplay);
@@ -267,11 +276,11 @@ export function PasteAwareTextInput({
            setNudgeCursorOffset(nextCaret);
            caretOffsetRef.current = nextCaret;
          } else {
-            const displayText = sanitizeForDisplay(translated);
+            const displayText = sanitizeForDisplay(text);
            const newDisplay =
              displayValue.slice(0, at) + displayText + displayValue.slice(at);
            const newActual =
-              actualValue.slice(0, at) + translated + actualValue.slice(at);
+              actualValue.slice(0, at) + text + actualValue.slice(at);
            setDisplayValue(newDisplay);
            setActualValue(newActual);
            onChange(newDisplay);
@@ -279,6 +288,26 @@ export function PasteAwareTextInput({
            setNudgeCursorOffset(nextCaret);
            caretOffsetRef.current = nextCaret;
          }
+        };
+
+        // If paste event carried no text (common for image-only clipboard), try macOS import
+        if ((!translated || translated.length === 0) && payload.length === 0) {
+          // Fire async handler
+          (async () => {
+            const clipResult = await tryImportClipboardImageMac();
+            if (clipResult) {
+              if ("error" in clipResult) {
+                onPasteErrorRef.current?.(clipResult.error);
+                return;
+              }
+              insertTranslated(clipResult.placeholder);
+            }
+          })();
+          return;
+        }
+
+        if (translated && translated.length > 0) {
+          insertTranslated(translated);
          return;
        }
        // If nothing to insert, fall through
@@ -288,23 +317,31 @@ export function PasteAwareTextInput({
        (key.meta && (input === "v" || input === "V")) ||
        (key.ctrl && key.shift && (input === "v" || input === "V"))
      ) {
-        const placeholder = tryImportClipboardImageMac();
-        if (placeholder) {
-          const at = Math.max(
-            0,
-            Math.min(caretOffsetRef.current, displayValue.length),
-          );
-          const newDisplay =
-            displayValue.slice(0, at) + placeholder + displayValue.slice(at);
-          const newActual =
-            actualValue.slice(0, at) + placeholder + actualValue.slice(at);
-          setDisplayValue(newDisplay);
-          setActualValue(newActual);
-          onChange(newDisplay);
-          const nextCaret = at + placeholder.length;
-          setNudgeCursorOffset(nextCaret);
-          caretOffsetRef.current = nextCaret;
-        }
+        // Fire async handler
+        (async () => {
+          const result = await tryImportClipboardImageMac();
+          if (result) {
+            if ("error" in result) {
+              onPasteErrorRef.current?.(result.error);
+              return;
+            }
+            const placeholder = result.placeholder;
+            const at = Math.max(
+              0,
+              Math.min(caretOffsetRef.current, displayValue.length),
+            );
+            const newDisplay =
+              displayValue.slice(0, at) + placeholder + displayValue.slice(at);
+            const newActual =
+              actualValue.slice(0, at) + placeholder + actualValue.slice(at);
+            setDisplayValue(newDisplay);
+            setActualValue(newActual);
+            onChange(newDisplay);
+            const nextCaret = at + placeholder.length;
+            setNudgeCursorOffset(nextCaret);
+            caretOffsetRef.current = nextCaret;
+          }
+        })();
      }

      // Backspace on empty input - handle here since handleChange won't fire
@@ -330,6 +367,11 @@ export function PasteAwareTextInput({
    onBackspaceAtEmptyRef.current = onBackspaceAtEmpty;
  }, [onBackspaceAtEmpty]);

+  const onPasteErrorRef = useRef(onPasteError);
+  useEffect(() => {
+    onPasteErrorRef.current = onPasteError;
+  }, [onPasteError]);
+
  // Consolidated raw stdin handler for Option+Arrow navigation and Option+Delete
  // Uses internal_eventEmitter (Ink's private API) for escape sequences that useInput doesn't parse correctly.
  // Falls back gracefully if internal_eventEmitter is unavailable (useInput handler above still works for some cases).
--- a/src/cli/helpers/clipboard.ts
+++ b/src/cli/helpers/clipboard.ts
@@ -1,9 +1,22 @@
 // Clipboard utilities for detecting and importing images from system clipboard
 import { execFileSync } from "node:child_process";
-import { existsSync, readFileSync, statSync } from "node:fs";
-import { basename, extname, isAbsolute, resolve } from "node:path";
+import { existsSync, readFileSync, statSync, unlinkSync } from "node:fs";
+import { tmpdir } from "node:os";
+import { basename, extname, isAbsolute, join, resolve } from "node:path";
+import { resizeImageIfNeeded } from "./imageResize";
 import { allocateImage } from "./pasteRegistry";

+/**
+ * Result type for clipboard image import.
+ * - placeholder: Successfully imported, contains [Image #N]
+ * - error: Failed with an error message
+ * - null: No image in clipboard
+ */
+export type ClipboardImageResult =
+  | { placeholder: string; resized: boolean; width: number; height: number }
+  | { error: string }
+  | null;
+
 /**
 * Copy text to system clipboard
 * Returns true if successful, false otherwise
@@ -158,50 +171,116 @@ export function translatePasteForImages(paste: string): string {
  return s;
 }

-// Attempt to import an image directly from OS clipboard on macOS via JXA (built-in)
-export function tryImportClipboardImageMac(): string | null {
+/**
+ * Read image from macOS clipboard to a temp file.
+ * Returns the temp file path and UTI, or null if no image in clipboard.
+ */
+function getClipboardImageToTempFile(): {
+  tempPath: string;
+  uti: string;
+} | null {
  if (process.platform !== "darwin") return null;
+
+  const tempPath = join(tmpdir(), `letta-clipboard-${Date.now()}.bin`);
+
  try {
+    // JXA script that writes clipboard image to temp file and returns UTI
+    // This avoids stdout buffer limits for large images
    const jxa = `
      ObjC.import('AppKit');
+      ObjC.import('Foundation');
      (function() {
        var pb = $.NSPasteboard.generalPasteboard;
-        var types = ['public.png','public.jpeg','public.tiff','public.heic','public.heif','public.bmp','public.gif','public.svg-image'];
+        var types = ['public.png','public.jpeg','public.tiff','public.heic','public.heif','public.bmp','public.gif'];
        for (var i = 0; i < types.length; i++) {
          var t = types[i];
          var d = pb.dataForType(t);
-          if (d) {
-            var b64 = d.base64EncodedStringWithOptions(0).js;
-            return t + '|' + b64;
+          if (d && d.length > 0) {
+            d.writeToFileAtomically($('${tempPath}'), true);
+            return t;
          }
        }
        return '';
      })();
    `;
-    const out = execFileSync("osascript", ["-l", "JavaScript", "-e", jxa], {
+
+    const uti = execFileSync("osascript", ["-l", "JavaScript", "-e", jxa], {
      encoding: "utf8",
      stdio: ["ignore", "pipe", "ignore"],
    }).trim();
-    if (!out) return null;
-    const idx = out.indexOf("|");
-    if (idx <= 0) return null;
-    const uti = out.slice(0, idx);
-    const b64 = out.slice(idx + 1);
-    if (!b64) return null;
-    const map: Record<string, string> = {
-      "public.png": "image/png",
-      "public.jpeg": "image/jpeg",
-      "public.tiff": "image/tiff",
-      "public.heic": "image/heic",
-      "public.heif": "image/heif",
-      "public.bmp": "image/bmp",
-      "public.gif": "image/gif",
-      "public.svg-image": "image/svg+xml",
-    };
-    const mediaType = map[uti] || "image/png";
-    const id = allocateImage({ data: b64, mediaType });
-    return `[Image #${id}]`;
+
+    if (!uti || !existsSync(tempPath)) return null;
+
+    return { tempPath, uti };
  } catch {
+    // Clean up temp file on error
+    if (existsSync(tempPath)) {
+      try {
+        unlinkSync(tempPath);
+      } catch {}
+    }
    return null;
  }
 }
+
+const UTI_TO_MEDIA_TYPE: Record<string, string> = {
+  "public.png": "image/png",
+  "public.jpeg": "image/jpeg",
+  "public.tiff": "image/tiff",
+  "public.heic": "image/heic",
+  "public.heif": "image/heif",
+  "public.bmp": "image/bmp",
+  "public.gif": "image/gif",
+};
+
+/**
+ * Import image from macOS clipboard, resize if needed, return placeholder.
+ * Uses temp file approach to avoid stdout buffer limits.
+ * Resizes large images to fit within API limits (2048x2048).
+ */
+export async function tryImportClipboardImageMac(): Promise<ClipboardImageResult> {
+  if (process.platform !== "darwin") return null;
+
+  const clipboardResult = getClipboardImageToTempFile();
+  if (!clipboardResult) return null;
+
+  const { tempPath, uti } = clipboardResult;
+
+  try {
+    // Read the temp file
+    const buffer = readFileSync(tempPath);
+
+    // Clean up temp file immediately after reading
+    try {
+      unlinkSync(tempPath);
+    } catch {}
+
+    const mediaType = UTI_TO_MEDIA_TYPE[uti] || "image/png";
+
+    // Resize if needed (handles large retina screenshots, HEIC conversion, etc.)
+    const resized = await resizeImageIfNeeded(buffer, mediaType);
+
+    // Store in registry
+    const id = allocateImage({
+      data: resized.data,
+      mediaType: resized.mediaType,
+    });
+
+    return {
+      placeholder: `[Image #${id}]`,
+      resized: resized.resized,
+      width: resized.width,
+      height: resized.height,
+    };
+  } catch (err) {
+    // Clean up temp file on error
+    if (existsSync(tempPath)) {
+      try {
+        unlinkSync(tempPath);
+      } catch {}
+    }
+
+    const message = err instanceof Error ? err.message : String(err);
+    return { error: `Image paste failed: ${message}` };
+  }
+}
--- a/src/cli/helpers/imageResize.ts
+++ b/src/cli/helpers/imageResize.ts
@@ -0,0 +1,90 @@
+// Image resizing utilities for clipboard paste
+// Follows Codex CLI's approach (codex-rs/utils/image/src/lib.rs)
+import sharp from "sharp";
+
+// Conservative limits that work with Anthropic's API (max 8000x8000)
+// Codex uses 2048x768, we use 2048x2048 for more flexibility with tall screenshots
+export const MAX_IMAGE_WIDTH = 2048;
+export const MAX_IMAGE_HEIGHT = 2048;
+
+export interface ResizeResult {
+  data: string; // base64 encoded
+  mediaType: string;
+  width: number;
+  height: number;
+  resized: boolean;
+}
+
+/**
+ * Resize image if it exceeds MAX_IMAGE_WIDTH or MAX_IMAGE_HEIGHT.
+ * Uses 'inside' fit to preserve aspect ratio (like Codex's resize behavior).
+ * Returns original if already within limits and format is supported.
+ */
+export async function resizeImageIfNeeded(
+  buffer: Buffer,
+  inputMediaType: string,
+): Promise<ResizeResult> {
+  const image = sharp(buffer);
+  const metadata = await image.metadata();
+  const width = metadata.width ?? 0;
+  const height = metadata.height ?? 0;
+  const format = metadata.format;
+
+  const needsResize = width > MAX_IMAGE_WIDTH || height > MAX_IMAGE_HEIGHT;
+
+  // Determine if we can pass through the original format
+  const isPassthroughFormat = format === "png" || format === "jpeg";
+
+  if (!needsResize && isPassthroughFormat) {
+    // No resize needed and format is supported - return original bytes
+    return {
+      data: buffer.toString("base64"),
+      mediaType: inputMediaType,
+      width,
+      height,
+      resized: false,
+    };
+  }
+
+  if (needsResize) {
+    // Resize preserving aspect ratio
+    // Use 'inside' fit which is equivalent to Codex's resize behavior
+    const resized = image.resize(MAX_IMAGE_WIDTH, MAX_IMAGE_HEIGHT, {
+      fit: "inside",
+      withoutEnlargement: true,
+    });
+
+    // Output as PNG for lossless quality (or JPEG if input was JPEG)
+    let outputBuffer: Buffer;
+    let outputMediaType: string;
+
+    if (format === "jpeg") {
+      // Preserve JPEG format with good quality (Codex uses 85)
+      outputBuffer = await resized.jpeg({ quality: 85 }).toBuffer();
+      outputMediaType = "image/jpeg";
+    } else {
+      // Default to PNG for everything else
+      outputBuffer = await resized.png().toBuffer();
+      outputMediaType = "image/png";
+    }
+
+    const resizedMeta = await sharp(outputBuffer).metadata();
+    return {
+      data: outputBuffer.toString("base64"),
+      mediaType: outputMediaType,
+      width: resizedMeta.width ?? 0,
+      height: resizedMeta.height ?? 0,
+      resized: true,
+    };
+  }
+
+  // No resize needed but format needs conversion (e.g., HEIC, TIFF, etc.)
+  const outputBuffer = await image.png().toBuffer();
+  return {
+    data: outputBuffer.toString("base64"),
+    mediaType: "image/png",
+    width,
+    height,
+    resized: false,
+  };
+}