fix: sanitize oversized image payloads

CHANGELOG.md

@@ -16,6 +16,7 @@ Docs: https://docs.clawd.bot
 
 ### Fixes
 - Auth profiles: keep auto-pinned preference while allowing rotation on failover; user pins stay locked. (#1138) — thanks @cheeeee.
+- Agents: sanitize oversized image payloads before send and surface image-dimension errors.
 - macOS: avoid touching launchd in Remote over SSH so quitting the app no longer disables the remote gateway. (#1105)
 - Memory: index atomically so failed reindex preserves the previous memory database. (#1151)
 - Memory: avoid sqlite-vec unique constraint failures when reindexing duplicate chunk ids. (#1151)

src/agents/pi-embedded-helpers.classifyfailoverreason.test.ts

@@ -26,6 +26,11 @@ describe("classifyFailoverReason", () => {
     expect(classifyFailoverReason("deadline exceeded")).toBe("timeout");
     expect(classifyFailoverReason("string should match pattern")).toBe("format");
     expect(classifyFailoverReason("bad request")).toBeNull();
+    expect(
+      classifyFailoverReason(
+        "messages.84.content.1.image.source.base64.data: At least one of the image dimensions exceed max allowed size for many-image requests: 2000 pixels",
+      ),
+    ).toBeNull();
   });
   it("classifies OpenAI usage limit errors as rate_limit", () => {
     expect(classifyFailoverReason("You have hit your ChatGPT usage limit (plus plan)")).toBe(

src/agents/pi-embedded-helpers.image-dimension-error.test.ts

@@ -0,0 +1,16 @@
+import { describe, expect, it } from "vitest";
+
+import { isImageDimensionErrorMessage, parseImageDimensionError } from "./pi-embedded-helpers.js";
+
+describe("image dimension errors", () => {
+  it("parses anthropic image dimension errors", () => {
+    const raw =
+      "400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"messages.84.content.1.image.source.base64.data: At least one of the image dimensions exceed max allowed size for many-image requests: 2000 pixels\"}}";
+    const parsed = parseImageDimensionError(raw);
+    expect(parsed).not.toBeNull();
+    expect(parsed?.maxDimensionPx).toBe(2000);
+    expect(parsed?.messageIndex).toBe(84);
+    expect(parsed?.contentIndex).toBe(1);
+    expect(isImageDimensionErrorMessage(raw)).toBe(true);
+  });
+});

src/agents/pi-embedded-helpers.iscloudcodeassistformaterror.test.ts

@@ -23,5 +23,10 @@ describe("isCloudCodeAssistFormatError", () => {
   });
   it("ignores unrelated errors", () => {
     expect(isCloudCodeAssistFormatError("rate limit exceeded")).toBe(false);
+    expect(
+      isCloudCodeAssistFormatError(
+        "400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"messages.84.content.1.image.source.base64.data: At least one of the image dimensions exceed max allowed size for many-image requests: 2000 pixels\"}}",
+      ),
+    ).toBe(false);
   });
 });

src/agents/pi-embedded-helpers.ts

@@ -21,11 +21,13 @@ export {
   isContextOverflowError,
   isFailoverAssistantError,
   isFailoverErrorMessage,
+  isImageDimensionErrorMessage,
   isOverloadedErrorMessage,
   isRawApiErrorPayload,
   isRateLimitAssistantError,
   isRateLimitErrorMessage,
   isTimeoutErrorMessage,
+  parseImageDimensionError,
 } from "./pi-embedded-helpers/errors.js";
 export {
   downgradeGeminiHistory,

src/agents/pi-embedded-helpers/errors.ts

@@ -339,7 +339,6 @@ const ERROR_PATTERNS = {
     "no api key found",
   ],
   format: [
-    "invalid_request_error",
     "string should match pattern",
     "tool_use.id",
     "tool_use_id",
@@ -348,6 +347,10 @@ const ERROR_PATTERNS = {
   ],
 } as const;
 
+const IMAGE_DIMENSION_ERROR_RE =
+  /image dimensions exceed max allowed size for many-image requests:\s*(\d+)\s*pixels/i;
+const IMAGE_DIMENSION_PATH_RE = /messages\.(\d+)\.content\.(\d+)\.image/i;
+
 function matchesErrorPatterns(raw: string, patterns: readonly ErrorPattern[]): boolean {
   if (!raw) return false;
   const value = raw.toLowerCase();
@@ -390,8 +393,31 @@ export function isOverloadedErrorMessage(raw: string): boolean {
   return matchesErrorPatterns(raw, ERROR_PATTERNS.overloaded);
 }
 
+export function parseImageDimensionError(raw: string): {
+  maxDimensionPx?: number;
+  messageIndex?: number;
+  contentIndex?: number;
+  raw: string;
+} | null {
+  if (!raw) return null;
+  const lower = raw.toLowerCase();
+  if (!lower.includes("image dimensions exceed max allowed size")) return null;
+  const limitMatch = raw.match(IMAGE_DIMENSION_ERROR_RE);
+  const pathMatch = raw.match(IMAGE_DIMENSION_PATH_RE);
+  return {
+    maxDimensionPx: limitMatch?.[1] ? Number.parseInt(limitMatch[1], 10) : undefined,
+    messageIndex: pathMatch?.[1] ? Number.parseInt(pathMatch[1], 10) : undefined,
+    contentIndex: pathMatch?.[2] ? Number.parseInt(pathMatch[2], 10) : undefined,
+    raw,
+  };
+}
+
+export function isImageDimensionErrorMessage(raw: string): boolean {
+  return Boolean(parseImageDimensionError(raw));
+}
+
 export function isCloudCodeAssistFormatError(raw: string): boolean {
-  return matchesErrorPatterns(raw, ERROR_PATTERNS.format);
+  return !isImageDimensionErrorMessage(raw) && matchesErrorPatterns(raw, ERROR_PATTERNS.format);
 }
 
 export function isAuthAssistantError(msg: AssistantMessage | undefined): boolean {
@@ -400,6 +426,7 @@ export function isAuthAssistantError(msg: AssistantMessage | undefined): boolean
 }
 
 export function classifyFailoverReason(raw: string): FailoverReason | null {
+  if (isImageDimensionErrorMessage(raw)) return null;
   if (isRateLimitErrorMessage(raw)) return "rate_limit";
   if (isOverloadedErrorMessage(raw)) return "rate_limit";
   if (isCloudCodeAssistFormatError(raw)) return "format";

src/agents/pi-embedded-runner/run.ts

@@ -31,6 +31,7 @@ import {
   isContextOverflowError,
   isFailoverAssistantError,
   isFailoverErrorMessage,
+  parseImageDimensionError,
   isRateLimitAssistantError,
   isTimeoutErrorMessage,
   pickFallbackThinkingLevel,
@@ -357,6 +358,26 @@ export async function runEmbeddedPiAgent(
           const failoverFailure = isFailoverAssistantError(lastAssistant);
           const assistantFailoverReason = classifyFailoverReason(lastAssistant?.errorMessage ?? "");
           const cloudCodeAssistFormatError = attempt.cloudCodeAssistFormatError;
+          const imageDimensionError = parseImageDimensionError(lastAssistant?.errorMessage ?? "");
+
+          if (imageDimensionError && lastProfileId) {
+            const details = [
+              imageDimensionError.messageIndex !== undefined
+                ? `message=${imageDimensionError.messageIndex}`
+                : null,
+              imageDimensionError.contentIndex !== undefined
+                ? `content=${imageDimensionError.contentIndex}`
+                : null,
+              imageDimensionError.maxDimensionPx !== undefined
+                ? `limit=${imageDimensionError.maxDimensionPx}px`
+                : null,
+            ]
+              .filter(Boolean)
+              .join(" ");
+            log.warn(
+              `Profile ${lastProfileId} rejected image payload${details ? ` (${details})` : ""}.`,
+            );
+          }
 
           // Treat timeout as potential rate limit (Antigravity hangs on rate limit)
           const shouldRotate = (!aborted && failoverFailure) || timedOut;

src/agents/pi-embedded-runner/run/images.ts

@@ -5,6 +5,7 @@ import { fileURLToPath } from "node:url";
 import type { ImageContent } from "@mariozechner/pi-ai";
 
 import { assertSandboxPath } from "../../sandbox-paths.js";
+import { sanitizeImageBlocks } from "../../tool-images.js";
 import { extractTextFromMessage } from "../../../tui/tui-formatters.js";
 import { loadWebMedia } from "../../../web/media.js";
 import { resolveUserPath } from "../../../utils.js";
@@ -48,6 +49,17 @@ function isImageExtension(filePath: string): boolean {
   return IMAGE_EXTENSIONS.has(ext);
 }
 
+async function sanitizeImagesWithLog(
+  images: ImageContent[],
+  label: string,
+): Promise<ImageContent[]> {
+  const { images: sanitized, dropped } = await sanitizeImageBlocks(images, label);
+  if (dropped > 0) {
+    log.warn(`Native image: dropped ${dropped} image(s) after sanitization (${label}).`);
+  }
+  return sanitized;
+}
+
 /**
  * Detects image references in a user prompt.
  *
@@ -392,9 +404,18 @@ export async function detectAndLoadPromptImages(params: {
     }
   }
 
+  const sanitizedPromptImages = await sanitizeImagesWithLog(promptImages, "prompt:images");
+  const sanitizedHistoryImagesByIndex = new Map<number, ImageContent[]>();
+  for (const [index, images] of historyImagesByIndex) {
+    const sanitized = await sanitizeImagesWithLog(images, `history:images:${index}`);
+    if (sanitized.length > 0) {
+      sanitizedHistoryImagesByIndex.set(index, sanitized);
+    }
+  }
+
   return {
-    images: promptImages,
+    images: sanitizedPromptImages,
-    historyImagesByIndex,
+    historyImagesByIndex: sanitizedHistoryImagesByIndex,
     detectedRefs: allRefs,
     loadedCount,
     skippedCount,

src/agents/tool-images.test.ts

@@ -1,7 +1,7 @@
 import sharp from "sharp";
 import { describe, expect, it } from "vitest";
 
-import { sanitizeContentBlocksImages } from "./tool-images.js";
+import { sanitizeContentBlocksImages, sanitizeImageBlocks } from "./tool-images.js";
 
 describe("tool image sanitizing", () => {
   it("shrinks oversized images to <=5MB", async () => {
@@ -33,6 +33,56 @@ describe("tool image sanitizing", () => {
     expect(image.mimeType).toBe("image/jpeg");
   }, 20_000);
 
+  it("sanitizes image arrays and reports drops", async () => {
+    const width = 2600;
+    const height = 400;
+    const raw = Buffer.alloc(width * height * 3, 0x7f);
+    const png = await sharp(raw, {
+      raw: { width, height, channels: 3 },
+    })
+      .png({ compressionLevel: 9 })
+      .toBuffer();
+
+    const images = [
+      { type: "image" as const, data: png.toString("base64"), mimeType: "image/png" },
+    ];
+    const { images: out, dropped } = await sanitizeImageBlocks(images, "test");
+    expect(dropped).toBe(0);
+    expect(out.length).toBe(1);
+    const meta = await sharp(Buffer.from(out[0].data, "base64")).metadata();
+    expect(meta.width).toBeLessThanOrEqual(2000);
+    expect(meta.height).toBeLessThanOrEqual(2000);
+  }, 20_000);
+
+  it("shrinks images that exceed max dimension even if size is small", async () => {
+    const width = 2600;
+    const height = 400;
+    const raw = Buffer.alloc(width * height * 3, 0x7f);
+    const png = await sharp(raw, {
+      raw: { width, height, channels: 3 },
+    })
+      .png({ compressionLevel: 9 })
+      .toBuffer();
+
+    const blocks = [
+      {
+        type: "image" as const,
+        data: png.toString("base64"),
+        mimeType: "image/png",
+      },
+    ];
+
+    const out = await sanitizeContentBlocksImages(blocks, "test");
+    const image = out.find((b) => b.type === "image");
+    if (!image || image.type !== "image") {
+      throw new Error("expected image block");
+    }
+    const meta = await sharp(Buffer.from(image.data, "base64")).metadata();
+    expect(meta.width).toBeLessThanOrEqual(2000);
+    expect(meta.height).toBeLessThanOrEqual(2000);
+    expect(image.mimeType).toBe("image/jpeg");
+  }, 20_000);
+
   it("corrects mismatched jpeg mimeType", async () => {
     const jpeg = await sharp({
       create: {

src/agents/tool-images.ts

@@ -1,5 +1,7 @@
 import type { AgentToolResult } from "@mariozechner/pi-agent-core";
+import type { ImageContent } from "@mariozechner/pi-ai";
 
+import { createSubsystemLogger } from "../logging.js";
 import { getImageMetadata, resizeToJpeg } from "../media/image-ops.js";
 
 type ToolContentBlock = AgentToolResult<unknown>["content"][number];
@@ -14,6 +16,7 @@ type TextContentBlock = Extract<ToolContentBlock, { type: "text" }>;
 // and recompress base64 image blocks when they exceed these limits.
 const MAX_IMAGE_DIMENSION_PX = 2000;
 const MAX_IMAGE_BYTES = 5 * 1024 * 1024;
+const log = createSubsystemLogger("agents/tool-images");
 
 function isImageBlock(block: unknown): block is ImageContentBlock {
   if (!block || typeof block !== "object") return false;
@@ -41,26 +44,41 @@ async function resizeImageBase64IfNeeded(params: {
   mimeType: string;
   maxDimensionPx: number;
   maxBytes: number;
-}): Promise<{ base64: string; mimeType: string; resized: boolean }> {
+  label?: string;
+}): Promise<{
+  base64: string;
+  mimeType: string;
+  resized: boolean;
+  width?: number;
+  height?: number;
+}> {
   const buf = Buffer.from(params.base64, "base64");
   const meta = await getImageMetadata(buf);
   const width = meta?.width;
   const height = meta?.height;
   const overBytes = buf.byteLength > params.maxBytes;
-  const maxDim = Math.max(width ?? 0, height ?? 0);
+  const hasDimensions = typeof width === "number" && typeof height === "number";
-  if (typeof width !== "number" || typeof height !== "number") {
+  if (hasDimensions && !overBytes && width <= params.maxDimensionPx && height <= params.maxDimensionPx) {
-    if (!overBytes) {
+    return {
-      return {
+      base64: params.base64,
-        base64: params.base64,
+      mimeType: params.mimeType,
-        mimeType: params.mimeType,
+      resized: false,
-        resized: false,
+      width,
-      };
+      height,
-    }
+    };
-  } else if (!overBytes && width <= params.maxDimensionPx && height <= params.maxDimensionPx) {
+  }
-    return { base64: params.base64, mimeType: params.mimeType, resized: false };
+  if (hasDimensions && (width > params.maxDimensionPx || height > params.maxDimensionPx || overBytes)) {
+    log.warn("Image exceeds limits; resizing", {
+      label: params.label,
+      width,
+      height,
+      maxDimensionPx: params.maxDimensionPx,
+      maxBytes: params.maxBytes,
+    });
   }
 
   const qualities = [85, 75, 65, 55, 45, 35];
+  const maxDim = hasDimensions ? Math.max(width ?? 0, height ?? 0) : params.maxDimensionPx;
   const sideStart = maxDim > 0 ? Math.min(params.maxDimensionPx, maxDim) : params.maxDimensionPx;
   const sideGrid = [sideStart, 1800, 1600, 1400, 1200, 1000, 800]
     .map((v) => Math.min(params.maxDimensionPx, v))
@@ -80,10 +98,23 @@ async function resizeImageBase64IfNeeded(params: {
         smallest = { buffer: out, size: out.byteLength };
       }
       if (out.byteLength <= params.maxBytes) {
+        log.info("Image resized", {
+          label: params.label,
+          width,
+          height,
+          maxDimensionPx: params.maxDimensionPx,
+          maxBytes: params.maxBytes,
+          originalBytes: buf.byteLength,
+          resizedBytes: out.byteLength,
+          quality,
+          side,
+        });
         return {
           base64: out.toString("base64"),
           mimeType: "image/jpeg",
           resized: true,
+          width,
+          height,
         };
       }
     }
@@ -127,6 +158,7 @@ export async function sanitizeContentBlocksImages(
         mimeType,
         maxDimensionPx,
         maxBytes,
+        label,
       });
       out.push({
         ...block,
@@ -144,6 +176,17 @@ export async function sanitizeContentBlocksImages(
   return out;
 }
 
+export async function sanitizeImageBlocks(
+  images: ImageContent[],
+  label: string,
+  opts: { maxDimensionPx?: number; maxBytes?: number } = {},
+): Promise<{ images: ImageContent[]; dropped: number }> {
+  if (images.length === 0) return { images, dropped: 0 };
+  const sanitized = await sanitizeContentBlocksImages(images as ToolContentBlock[], label, opts);
+  const next = sanitized.filter(isImageBlock) as ImageContent[];
+  return { images: next, dropped: Math.max(0, images.length - next.length) };
+}
+
 export async function sanitizeToolResultImages(
   result: AgentToolResult<unknown>,
   label: string,