diff --git a/apps/web/src/lib/desktop-repository.test.mjs b/apps/web/src/lib/desktop-repository.test.mjs
index c7ff3984..72800660 100644
--- a/apps/web/src/lib/desktop-repository.test.mjs
+++ b/apps/web/src/lib/desktop-repository.test.mjs
@@ -13,6 +13,7 @@ globalThis.window = {
     sidecarRequest: async (method, params) => {
       lastRequest = { method, params };
       if (method === "memo.get") {
+        const filename = params.memoId === "memo_wechat" ? "微信图片_202609231723_1.jpg" : "screenshot.webp";
         return {
           memo: {
             id: params.memoId,
@@ -20,10 +21,10 @@ globalThis.window = {
               type: "doc",
               content: [{
                 type: "image",
-                attrs: { alt: "screenshot.webp", src: "edgeever-staged://stage_dead" },
+                attrs: { alt: filename, src: "edgeever-staged://stage_dead" },
               }],
             },
-            contentMarkdown: "![screenshot.webp](edgeever-staged://stage_dead)\n\n",
+            contentMarkdown: `![${filename}](edgeever-staged://stage_dead)\n\n`,
           },
         };
       }
@@ -35,8 +36,14 @@ globalThis.window = {
             kind: "image",
             filename: "screenshot.webp",
             url: "/api/v1/resources/res_shot/blob",
+          }, {
+            id: "res_wechat",
+            memoId: "memo_wechat",
+            kind: "image",
+            filename: "微信图片_202609231723_1.webp",
+            url: "/api/v1/resources/res_wechat/blob",
           }],
-          summary: { totalCount: 1, totalBytes: 1, imageCount: 1, attachmentCount: 0 },
+          summary: { totalCount: 2, totalBytes: 2, imageCount: 2, attachmentCount: 0 },
         };
       }
       if (method === "memo.update") {
@@ -132,4 +139,10 @@ describe("desktop repository memo reads", () => {
     expect(result.memo.contentMarkdown).not.toContain("edgeever-staged://");
     expect(result.memo.contentJson.content[0].attrs.src).toBe("edgeever-resource://resource/res_shot");
   });
+
+  test("recovers an imported WeChat image after jpg compression changed its extension", async () => {
+    const result = await createDesktopRepository().getMemo("memo_wechat");
+    expect(result.memo.contentJson.content[0].attrs.src).toBe("edgeever-resource://resource/res_wechat");
+    expect(result.memo.contentMarkdown).toContain("edgeever-resource://resource/res_wechat");
+  });
 });
diff --git a/apps/web/src/lib/staged-resource-repair.test.mjs b/apps/web/src/lib/staged-resource-repair.test.mjs
index caabbc3c..db62c7be 100644
--- a/apps/web/src/lib/staged-resource-repair.test.mjs
+++ b/apps/web/src/lib/staged-resource-repair.test.mjs
@@ -81,6 +81,36 @@ describe("staged resource repair", () => {
       .toEqual([]);
   });
 
+  test("recovers a WeChat image whose uploaded filename changed from jpg to webp", () => {
+    const memo = {
+      contentJson: { type: "doc", content: [{ type: "image", attrs: {
+        alt: "微信图片_202609231723_1.jpg",
+        src: "edgeever-staged://stage_missing",
+        width: 35,
+      } }] },
+      contentMarkdown: "![微信图片_202609231723_1.jpg](edgeever-staged://stage_missing)",
+    };
+    const resourceUrl = "/api/v1/resources/res_wechat/blob";
+    const repaired = repairMemoStagedResourceUrls(memo, [{
+      url: resourceUrl,
+      filename: "微信图片_202609231723_1.webp",
+      kind: "image",
+    }]);
+    expect(repaired.contentJson.content[0].attrs).toEqual({
+      alt: "微信图片_202609231723_1.jpg",
+      src: resourceUrl,
+      width: 35,
+    });
+    expect(repaired.contentMarkdown).toBe(`![微信图片_202609231723_1.jpg](${resourceUrl})`);
+  });
+
+  test("does not guess between resources with the same filename stem", () => {
+    expect(findMatchingMemoResource([
+      { url: "/api/v1/resources/res_a/blob", filename: "image.jpg", kind: "image" },
+      { url: "/api/v1/resources/res_b/blob", filename: "image.webp", kind: "image" },
+    ], "image.png", "image")).toBeNull();
+  });
+
   test("does not guess when a memo has several images and the placeholder has no filename", () => {
     expect(findMatchingMemoResource([
       screenshotResource,
diff --git a/apps/web/src/lib/staged-resource-repair.ts b/apps/web/src/lib/staged-resource-repair.ts
index d06cbdf3..8ea79892 100644
--- a/apps/web/src/lib/staged-resource-repair.ts
+++ b/apps/web/src/lib/staged-resource-repair.ts
@@ -106,7 +106,13 @@ export const findMatchingMemoResource = (
   const normalizedFilename = filename?.trim();
   if (normalizedFilename) {
     const named = pool.filter((resource) => resource.filename === normalizedFilename);
-    return named[0] ?? null;
+    if (named.length === 1) return named[0];
+    if (named.length > 1) return null;
+    // Image compression may change only the extension (for example, .jpg to
+    // .webp) while the editor keeps the original filename as the image alt.
+    const stem = normalizedFilename.replace(/\.[^.]+$/, "");
+    const sameStem = pool.filter((resource) => resource.filename?.replace(/\.[^.]+$/, "") === stem);
+    return sameStem.length === 1 ? sameStem[0] : null;
   }
   if (pool.length === 1) return pool[0];
   return null;