diff --git a/src/sessions/user-turn-transcript.test.ts b/src/sessions/user-turn-transcript.test.ts
index 9354e6d302f..fee5ca45728 100644
--- a/src/sessions/user-turn-transcript.test.ts
+++ b/src/sessions/user-turn-transcript.test.ts
@@ -83,6 +83,19 @@ describe("user turn transcript persistence", () => {
       ]);
     });
 
+    it("does not reuse singular media type for later media paths", () => {
+      expect(
+        buildPersistedUserTurnMediaInputsFromFields({
+          MediaPath: "/tmp/a.png",
+          MediaPaths: ["/tmp/a.png", "/tmp/report.pdf"],
+          MediaType: "image/png",
+        }),
+      ).toEqual([
+        { path: "/tmp/a.png", contentType: "image/png" },
+        { path: "/tmp/report.pdf", contentType: "application/pdf" },
+      ]);
+    });
+
     it("resolves staged relative media paths against the media workspace", () => {
       const workspaceDir = createTempDir("openclaw-user-turn-media-");
 
diff --git a/src/sessions/user-turn-transcript.ts b/src/sessions/user-turn-transcript.ts
index 705281b7a96..d69b7d2da64 100644
--- a/src/sessions/user-turn-transcript.ts
+++ b/src/sessions/user-turn-transcript.ts
@@ -250,7 +250,7 @@ export function buildPersistedUserTurnMediaInputsFromFields(
       ...(mediaPath ? { path: mediaPath } : {}),
       ...(url ? { url } : {}),
       contentType: resolveTranscriptMediaType({
-        explicitType: types[index] ?? singleType,
+        explicitType: types[index] ?? (index === 0 ? singleType : undefined),
         mediaPath,
         mediaUrl: url,
       }),