diff --git a/apps/api/src/media/upload.test.ts b/apps/api/src/media/upload.test.ts
index a24b242c4..160ec8951 100644
--- a/apps/api/src/media/upload.test.ts
+++ b/apps/api/src/media/upload.test.ts
@@ -38,7 +38,11 @@ async function createUploader() {
   return user;
 }
 import * as s3 from "./s3";
-import { handleUploadImage } from "./upload";
+import {
+  handleUploadError,
+  handleUploadImage,
+  UnsupportedMimeTypeError,
+} from "./upload";
 import {
   ALLOWED_IMAGE_MIME_TYPES,
   MAX_IMAGE_BYTES,
@@ -343,6 +347,24 @@ describe("handleUploadImage", () => {
     expect((res.jsonBody as { name: string }).name).toBe("Lemon");
   });
 
+  test("415 with allowed list when fileFilter rejects the claimed MIME", () => {
+    const res = mockRes();
+    const next = vi.fn();
+    handleUploadError(
+      new UnsupportedMimeTypeError("image/svg+xml"),
+      mockReq({}),
+      res as unknown as Response,
+      next,
+    );
+    expect(res.statusCode).toBe(StatusCodes.UNSUPPORTED_MEDIA_TYPE);
+    const body = res.jsonBody as { error: string; details: string };
+    expect(body.error).toBe("Unsupported image type");
+    expect(body.details).toBe(
+      "Allowed: image/jpeg, image/png, image/webp, image/gif",
+    );
+    expect(next).not.toHaveBeenCalled();
+  });
+
   test("rolls back the DB row and best-effort deletes S3 when putImage throws", async () => {
     const user = await createUploader();
     vi.mocked(s3.putImage).mockRejectedValue(new Error("S3 down"));
diff --git a/apps/api/src/media/upload.ts b/apps/api/src/media/upload.ts
index 09c25481e..8283fbaff 100644
--- a/apps/api/src/media/upload.ts
+++ b/apps/api/src/media/upload.ts
@@ -29,6 +29,16 @@ const FORMAT_INFO: Record<string, { mime: string; ext: string }> = {
   gif: { mime: "image/gif", ext: "gif" },
 };
 
+// Thrown by the multer fileFilter so handleUploadError can surface a 415
+// with the actual claimed type and the allowed list, instead of the generic
+// "missing file" fallback that fires when the filter silently drops the file.
+export class UnsupportedMimeTypeError extends Error {
+  constructor(public readonly claimedMimeType: string) {
+    super(`Unsupported image type: ${claimedMimeType}`);
+    this.name = "UnsupportedMimeTypeError";
+  }
+}
+
 export const uploadImageMulter = multer({
   storage: multer.memoryStorage(),
   limits: { fileSize: MAX_IMAGE_BYTES, files: 1 },
@@ -38,7 +48,7 @@ export const uploadImageMulter = multer({
     ) {
       cb(null, true);
     } else {
-      cb(null, false);
+      cb(new UnsupportedMimeTypeError(file.mimetype));
     }
   },
 });
@@ -159,6 +169,13 @@ export function handleUploadError(
   res: Response,
   next: (err?: unknown) => void,
 ) {
+  if (err instanceof UnsupportedMimeTypeError) {
+    res.status(StatusCodes.UNSUPPORTED_MEDIA_TYPE).json({
+      error: "Unsupported image type",
+      details: `Allowed: ${ALLOWED_IMAGE_MIME_TYPES.join(", ")}`,
+    });
+    return;
+  }
   if (err instanceof multer.MulterError) {
     if (err.code === "LIMIT_FILE_SIZE") {
       res.status(StatusCodes.REQUEST_TOO_LONG).json({