diff --git a/ui/goose2/src/features/chat/lib/__tests__/attachments.test.ts b/ui/goose2/src/features/chat/lib/__tests__/attachments.test.ts
index 2e15253035..9e5583eaa4 100644
--- a/ui/goose2/src/features/chat/lib/__tests__/attachments.test.ts
+++ b/ui/goose2/src/features/chat/lib/__tests__/attachments.test.ts
@@ -121,4 +121,30 @@ describe("rebuildAttachmentDrafts", () => {
     expect(drafts[0].kind).toBe("file");
     expect(drafts[0].name).toBe("photo.jpg");
   });
+
+  it("preserves pathless browser-uploaded file attachments", () => {
+    const msg: Message = {
+      id: "m4",
+      role: "user",
+      created: Date.now(),
+      content: [{ type: "text", text: "see attached" }],
+      metadata: {
+        userVisible: true,
+        agentVisible: true,
+        attachments: [
+          {
+            type: "file",
+            name: "report.pdf",
+            mimeType: "application/pdf",
+          },
+        ],
+      },
+    };
+
+    const drafts = rebuildAttachmentDrafts(msg);
+
+    expect(drafts).toHaveLength(1);
+    expect(drafts[0].kind).toBe("file");
+    expect(drafts[0].name).toBe("report.pdf");
+  });
 });
diff --git a/ui/goose2/src/features/chat/lib/attachments.ts b/ui/goose2/src/features/chat/lib/attachments.ts
index c102a88d02..0358e94800 100644
--- a/ui/goose2/src/features/chat/lib/attachments.ts
+++ b/ui/goose2/src/features/chat/lib/attachments.ts
@@ -112,14 +112,14 @@ export function rebuildAttachmentDrafts(
         name: att.name,
         path: att.path,
       });
-    } else if (att.type === "file" && att.path) {
+    } else if (att.type === "file") {
       // Skip image file entries when content blocks already provide the base64
       if (hasImageDrafts && att.mimeType?.startsWith("image/")) continue;
       drafts.push({
         id: crypto.randomUUID(),
         kind: "file",
         name: att.name,
-        path: att.path,
+        ...(att.path ? { path: att.path } : {}),
         mimeType: att.mimeType,
       });
     }