From ac09ec00e8f524b5069cb94f631eda761159d522 Mon Sep 17 00:00:00 2001
From: Paul Frederiksen <paul@paulfrederiksen.com>
Date: Mon, 4 May 2026 05:06:26 +0000
Subject: [PATCH] fix(media): tolerate missing image optimizer for in-limit
 images

---
 src/media/web-media.test.ts | 47 +++++++++++++++++++++++++++++++++++++
 src/media/web-media.ts      | 37 ++++++++++++++++++++++++++++-
 2 files changed, 83 insertions(+), 1 deletion(-)

diff --git a/src/media/web-media.test.ts b/src/media/web-media.test.ts
index 146ae374b65..634b1763fe0 100644
--- a/src/media/web-media.test.ts
+++ b/src/media/web-media.test.ts
@@ -163,6 +163,53 @@ describe("loadWebMedia", () => {
     );
   });
 
+  async function withUnavailableImageOptimizer<T>(fn: () => Promise<T>): Promise<T> {
+    vi.resetModules();
+    vi.doMock("./image-ops.js", () => ({
+      convertHeicToJpeg: vi.fn(async (buffer: Buffer) => buffer),
+      hasAlphaChannel: vi.fn(async () => {
+        throw new Error(
+          "Optional dependency sharp is required for image attachment processing | Cannot find package 'sharp' imported from image-ops.js",
+        );
+      }),
+      optimizeImageToPng: vi.fn(async () => {
+        throw new Error("should not optimize png");
+      }),
+      resizeToJpeg: vi.fn(async () => {
+        throw new Error("should not resize jpeg");
+      }),
+    }));
+    try {
+      return await fn();
+    } finally {
+      vi.doUnmock("./image-ops.js");
+      vi.resetModules();
+    }
+  }
+
+  it("sends an in-limit original image when optional sharp optimization is unavailable", async () => {
+    await withUnavailableImageOptimizer(async () => {
+      const { loadWebMedia: loadWebMediaWithMissingOptimizer } = await import("./web-media.js");
+      const result = await loadWebMediaWithMissingOptimizer(
+        tinyPngFile,
+        createLocalWebMediaOptions(),
+      );
+      expect(result.kind).toBe("image");
+      expect(result.contentType).toBe("image/png");
+      expect(result.fileName).toBe("tiny.png");
+      expect(result.buffer.equals(Buffer.from(TINY_PNG_BASE64, "base64"))).toBe(true);
+    });
+  });
+
+  it("does not bypass the size cap when optional sharp optimization is unavailable", async () => {
+    await withUnavailableImageOptimizer(async () => {
+      const { loadWebMedia: loadWebMediaWithMissingOptimizer } = await import("./web-media.js");
+      await expect(
+        loadWebMediaWithMissingOptimizer(tinyPngFile, { maxBytes: 8, localRoots: [fixtureRoot] }),
+      ).rejects.toThrow(/Optional dependency sharp is required/);
+    });
+  });
+
   it("resolves relative local media paths against the provided workspace directory", async () => {
     const result = await loadWebMedia("chart.png", {
       maxBytes: 1024 * 1024,
diff --git a/src/media/web-media.ts b/src/media/web-media.ts
index e7bf75c440e..f77661680ff 100644
--- a/src/media/web-media.ts
+++ b/src/media/web-media.ts
@@ -205,6 +205,23 @@ function formatCapReduce(label: string, cap: number, size: number): string {
   return `${label} could not be reduced below ${formatMb(cap, 0)}MB (got ${formatMb(size)}MB)`;
 }
 
+function isOptionalImageOptimizerUnavailable(err: unknown): boolean {
+  const messages: string[] = [];
+  let current: unknown = err;
+  while (current instanceof Error) {
+    messages.push(current.message);
+    current = current.cause;
+  }
+  const detail = messages.join("\n").toLowerCase();
+  return (
+    detail.includes("optional dependency sharp is required") ||
+    detail.includes("cannot find package 'sharp'") ||
+    detail.includes('cannot find package "sharp"') ||
+    detail.includes("cannot find module 'sharp'") ||
+    detail.includes('cannot find module "sharp"')
+  );
+}
+
 function isHeicSource(opts: { contentType?: string; fileName?: string }): boolean {
   if (opts.contentType && HEIC_MIME_RE.test(opts.contentType.trim())) {
     return true;
@@ -392,7 +409,25 @@ async function loadWebMediaInternal(
     meta?: { contentType?: string; fileName?: string },
   ) => {
     const originalSize = buffer.length;
-    const optimized = await optimizeImageWithFallback({ buffer, cap, meta });
+    let optimized: OptimizedImage;
+    try {
+      optimized = await optimizeImageWithFallback({ buffer, cap, meta });
+    } catch (err) {
+      if (isOptionalImageOptimizerUnavailable(err) && buffer.length <= cap) {
+        if (shouldLogVerbose()) {
+          logVerbose(
+            `Image optimizer unavailable; sending original ${formatMb(buffer.length)}MB media without optimization`,
+          );
+        }
+        return {
+          buffer,
+          contentType: meta?.contentType,
+          kind: "image" as const,
+          fileName: meta?.fileName,
+        };
+      }
+      throw err;
+    }
     logOptimizedImage({ originalSize, optimized });
 
     if (optimized.buffer.length > cap) {