diff --git a/packages/cli/src/commands/asset.spec.ts b/packages/cli/src/commands/asset.spec.ts
index 7e582039ba..a105d09d40 100644
--- a/packages/cli/src/commands/asset.spec.ts
+++ b/packages/cli/src/commands/asset.spec.ts
@@ -385,8 +385,7 @@ describe('findSidecar', () => {
     fs.writeFileSync(sidecarPath2, 'xmp data 2');
 
     const result = findSidecar(testFilePath);
-    // Should return the first one found (photo.xmp) based on the order in the code
-    expect(result).toBe(sidecarPath1);
+    expect(result).toBe(sidecarPath2);
   });
 
   it('should return undefined when no sidecar file exists', () => {
diff --git a/packages/cli/src/commands/asset.ts b/packages/cli/src/commands/asset.ts
index 6aab96dc30..ac6f5eb990 100644
--- a/packages/cli/src/commands/asset.ts
+++ b/packages/cli/src/commands/asset.ts
@@ -445,8 +445,8 @@ export const findSidecar = (filepath: string): string | undefined => {
   const assetPath = path.parse(filepath);
   const noExtension = path.join(assetPath.dir, assetPath.name);
 
-  // XMP sidecars can come in two filename formats. For a photo named photo.ext, the filenames are photo.ext.xmp and photo.xmp
-  for (const sidecarPath of [`${noExtension}.xmp`, `${filepath}.xmp`]) {
+  // Prefer photo.ext.xmp over photo.xmp, matching the server's sidecar precedence.
+  for (const sidecarPath of [`${filepath}.xmp`, `${noExtension}.xmp`]) {
     if (existsSync(sidecarPath)) {
       return sidecarPath;
     }