diff --git a/server/src/services/metadata.service.spec.ts b/server/src/services/metadata.service.spec.ts
index 57c029961e..8f7fe71be9 100644
--- a/server/src/services/metadata.service.spec.ts
+++ b/server/src/services/metadata.service.spec.ts
@@ -1836,6 +1836,36 @@ describe(MetadataService.name, () => {
       );
     });
 
+    it('should still swap width/height using EXIF Orientation for a .heic-named file that is actually JPEG', async () => {
+      const asset = AssetFactory.create({ originalFileName: 'IMG_1.heic' });
+      mocks.assetJob.getForMetadataExtraction.mockResolvedValue(getForMetadataExtraction(asset));
+      // no QuickTime `Rotation` tag and FileTypeExtension `jpg` - this is what ExifTool reports
+      // for a file that was converted to JPEG in place but kept its .heic extension/filename.
+      mockReadTags({ ImageWidth: 1000, ImageHeight: 2000, Orientation: 6, FileTypeExtension: 'jpg' });
+
+      await sut.handleMetadataExtraction({ id: asset.id });
+      expect(mocks.asset.update).toHaveBeenCalledWith(
+        expect.objectContaining({
+          width: 2000,
+          height: 1000,
+        }),
+      );
+    });
+
+    it('should ignore EXIF Orientation and use QuickTime Rotation for a genuine HEIC file', async () => {
+      const asset = AssetFactory.create({ originalFileName: 'IMG_1.heic' });
+      mocks.assetJob.getForMetadataExtraction.mockResolvedValue(getForMetadataExtraction(asset));
+      mockReadTags({ ImageWidth: 1000, ImageHeight: 2000, Orientation: 6, FileTypeExtension: 'heic', Rotation: 0 });
+
+      await sut.handleMetadataExtraction({ id: asset.id });
+      expect(mocks.asset.update).toHaveBeenCalledWith(
+        expect.objectContaining({
+          width: 1000,
+          height: 2000,
+        }),
+      );
+    });
+
     it('should overwrite existing width/height for unedited assets', async () => {
       const asset = AssetFactory.create({ width: 1920, height: 1080, isEdited: false });
       mocks.assetJob.getForMetadataExtraction.mockResolvedValue(getForMetadataExtraction(asset));
diff --git a/server/src/services/metadata.service.ts b/server/src/services/metadata.service.ts
index a95d1f1497..57257c9af2 100644
--- a/server/src/services/metadata.service.ts
+++ b/server/src/services/metadata.service.ts
@@ -603,7 +603,16 @@ export class MetadataService extends BaseService {
 
     // don't use Exif Orientation for HEIF based images, it's usually missing or invalid.
     // prefer irot (ExifTool QuickTime:Rotation) mapped to ExifOrientation.
-    if (mimeTypes.isHeifImage(asset.originalPath)) {
+    //
+    // Some files carry a .heic/.heif/.avif extension without actually being encoded
+    // as such (e.g. converted to JPEG in place by external tools before being
+    // imported). Trusting the filename alone would discard a perfectly valid EXIF
+    // Orientation tag below and lead to a squished/stretched thumbnail, since the
+    // dimensions never get swapped for the sideways rotation. ExifTool's own
+    // content-detected FileTypeExtension is the source of truth here, not the name.
+    const isActuallyHeif =
+      mimeTypes.isHeifImage(asset.originalPath) && mimeTypes.isHeifImage(`file.${mediaTags.FileTypeExtension ?? ''}`);
+    if (isActuallyHeif) {
       const orientation = this.getHeifOrientation(mediaTags);
       if (orientation === null) {
         delete mediaTags.Orientation;