diff --git a/packages/adapters/claude-local/src/server/execute.ts b/packages/adapters/claude-local/src/server/execute.ts
index 6086cc3e..a2656061 100644
--- a/packages/adapters/claude-local/src/server/execute.ts
+++ b/packages/adapters/claude-local/src/server/execute.ts
@@ -55,6 +55,7 @@ import {
   isClaudeTransientUpstreamError,
   isClaudeUnknownSessionError,
   isClaudePoisonedPreviousMessageIdError,
+  isClaudeImageProcessingError,
 } from "./parse.js";
 import { prepareClaudeConfigSeed, resolveSharedClaudeConfigDir } from "./claude-config.js";
 import { resolveClaudeDesiredSkillNames } from "./skills.js";
@@ -983,6 +984,8 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
           ? "unknown"
           : isClaudePoisonedPreviousMessageIdError(initial.parsed)
           ? "poisoned"
+          : isClaudeImageProcessingError(initial.parsed)
+          ? "image"
           : null
         : null;
 
@@ -990,6 +993,8 @@ export async function execute(ctx: AdapterExecutionContext): Promise<AdapterExec
       const reason =
         sessionErrorKind === "poisoned"
           ? "returned a poisoned message-id"
+          : sessionErrorKind === "image"
+          ? "contains an unprocessable image"
           : "is unavailable";
       await onLog(
         "stdout",
diff --git a/packages/adapters/claude-local/src/server/parse.test.ts b/packages/adapters/claude-local/src/server/parse.test.ts
index d8cd65b0..0b79edb0 100644
--- a/packages/adapters/claude-local/src/server/parse.test.ts
+++ b/packages/adapters/claude-local/src/server/parse.test.ts
@@ -4,6 +4,7 @@ import {
   isClaudeTransientUpstreamError,
   isClaudePoisonedPreviousMessageIdError,
   isClaudeUnknownSessionError,
+  isClaudeImageProcessingError,
 } from "./parse.js";
 
 describe("isClaudeTransientUpstreamError", () => {
@@ -185,6 +186,50 @@ describe("isClaudeUnknownSessionError", () => {
   });
 });
 
+describe("isClaudeImageProcessingError", () => {
+  it("detects the 'Could not process image' 400 error in the result field", () => {
+    expect(
+      isClaudeImageProcessingError({
+        subtype: "success",
+        is_error: true,
+        result: "API Error: 400 Could not process image: image source URL has expired",
+      }),
+    ).toBe(true);
+  });
+
+  it("detects the error in the errors array", () => {
+    expect(
+      isClaudeImageProcessingError({
+        is_error: true,
+        result: "",
+        errors: [{ message: "400 Could not process image" }],
+      }),
+    ).toBe(true);
+  });
+
+  it("is case-insensitive", () => {
+    expect(
+      isClaudeImageProcessingError({
+        is_error: true,
+        result: "could not process image attached to message",
+      }),
+    ).toBe(true);
+  });
+
+  it("returns false for unrelated errors", () => {
+    expect(
+      isClaudeImageProcessingError({
+        is_error: true,
+        result: "No conversation found with session id abc-123",
+      }),
+    ).toBe(false);
+  });
+
+  it("returns false for empty parsed result", () => {
+    expect(isClaudeImageProcessingError({})).toBe(false);
+  });
+});
+
 describe("extractClaudeRetryNotBefore", () => {
   it("parses the 'resets 4pm' hint in its explicit timezone", () => {
     const now = new Date("2026-04-22T15:15:00.000Z");
diff --git a/packages/adapters/claude-local/src/server/parse.ts b/packages/adapters/claude-local/src/server/parse.ts
index 36d13fd6..fbf66f79 100644
--- a/packages/adapters/claude-local/src/server/parse.ts
+++ b/packages/adapters/claude-local/src/server/parse.ts
@@ -209,6 +209,17 @@ export function isClaudePoisonedPreviousMessageIdError(parsed: Record<string, un
   );
 }
 
+export function isClaudeImageProcessingError(parsed: Record<string, unknown>): boolean {
+  const resultText = asString(parsed.result, "").trim();
+  const allMessages = [resultText, ...extractClaudeErrorMessages(parsed)]
+    .map((msg) => msg.trim())
+    .filter(Boolean);
+
+  return allMessages.some((msg) =>
+    /could not process image/i.test(msg),
+  );
+}
+
 function buildClaudeTransientHaystack(input: {
   parsed?: Record<string, unknown> | null;
   stdout?: string | null;
@@ -388,7 +399,7 @@ export function isClaudeTransientUpstreamError(input: {
 }): boolean {
   const parsed = input.parsed ?? null;
   // Deterministic failures are handled by their own classifiers.
-  if (parsed && (isClaudeMaxTurnsResult(parsed) || isClaudeUnknownSessionError(parsed) || isClaudePoisonedPreviousMessageIdError(parsed))) {
+  if (parsed && (isClaudeMaxTurnsResult(parsed) || isClaudeUnknownSessionError(parsed) || isClaudePoisonedPreviousMessageIdError(parsed) || isClaudeImageProcessingError(parsed))) {
     return false;
   }
   const loginMeta = detectClaudeLoginRequired({