diff --git a/CHANGELOG.md b/CHANGELOG.md
index 61327e5c5..9e39702f6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -69,6 +69,7 @@ Status: unreleased.
 - **BREAKING:** Gateway auth mode "none" is removed; gateway now requires token/password (Tailscale Serve identity still allowed).
 
 ### Fixes
+- Agents: prevent retries on oversized image errors and surface size limits. (#2871) Thanks @Suksham-sharma.
 - Agents: inherit provider baseUrl/api for inline models. (#2740) Thanks @lploc94.
 - Memory Search: keep auto provider model defaults and only include remote when configured. (#2576) Thanks @papago2355.
 - macOS: auto-scroll to bottom when sending a new message while scrolled up. (#2471) Thanks @kennyklee.
diff --git a/src/agents/pi-embedded-helpers.classifyfailoverreason.test.ts b/src/agents/pi-embedded-helpers.classifyfailoverreason.test.ts
index bb449a6e4..749a52414 100644
--- a/src/agents/pi-embedded-helpers.classifyfailoverreason.test.ts
+++ b/src/agents/pi-embedded-helpers.classifyfailoverreason.test.ts
@@ -31,6 +31,7 @@ describe("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();
+    expect(classifyFailoverReason("image exceeds 5 MB maximum")).toBeNull();
   });
   it("classifies OpenAI usage limit errors as rate_limit", () => {
     expect(classifyFailoverReason("You have hit your ChatGPT usage limit (plus plan)")).toBe(
diff --git a/src/agents/pi-embedded-helpers.image-size-error.test.ts b/src/agents/pi-embedded-helpers.image-size-error.test.ts
new file mode 100644
index 000000000..75b165d8d
--- /dev/null
+++ b/src/agents/pi-embedded-helpers.image-size-error.test.ts
@@ -0,0 +1,14 @@
+import { describe, expect, it } from "vitest";
+
+import { parseImageSizeError } from "./pi-embedded-helpers.js";
+
+describe("parseImageSizeError", () => {
+  it("parses max MB values from error text", () => {
+    expect(parseImageSizeError("image exceeds 5 MB maximum")?.maxMb).toBe(5);
+    expect(parseImageSizeError("Image exceeds 5.5 MB limit")?.maxMb).toBe(5.5);
+  });
+
+  it("returns null for unrelated errors", () => {
+    expect(parseImageSizeError("context overflow")).toBeNull();
+  });
+});