diff --git a/CHANGES.md b/CHANGES.md
index 5f18bb47..0ea15e72 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -6,6 +6,11 @@ Version 0.3.2
 
 To be released.
 
+ -  Fixed a bug where generated thumbnails had not copied the EXIF orientation
+    metadata from the original image.  [[#76]]
+
+[#76]: https://github.com/dahlia/hollo/issues/76
+
 
 Version 0.3.1
 -------------
diff --git a/src/media.ts b/src/media.ts
index 8abf0f73..9b209cc0 100644
--- a/src/media.ts
+++ b/src/media.ts
@@ -22,12 +22,21 @@ export async function uploadThumbnail(
   thumbnailArea = DEFAULT_THUMBNAIL_AREA,
 ): Promise<Thumbnail> {
   const originalMetadata = await original.metadata();
-  const thumbnailSize = calculateThumbnailSize(
-    originalMetadata.width!,
-    originalMetadata.height!,
-    thumbnailArea,
-  );
-  const thumbnail = await original.resize(thumbnailSize).webp().toBuffer();
+  let width = originalMetadata.width!;
+  let height = originalMetadata.height!;
+  if (originalMetadata.orientation !== 1) {
+    // biome-ignore lint/style/noParameterAssign:
+    original = original.clone();
+    original.rotate();
+    if (originalMetadata.orientation !== 3) {
+      [width, height] = [height, width];
+    }
+  }
+  const thumbnailSize = calculateThumbnailSize(width, height, thumbnailArea);
+  const thumbnail = await original
+    .resize(thumbnailSize)
+    .webp({ nearLossless: true })
+    .toBuffer();
   const content = new Uint8Array(thumbnail);
   try {
     await disk.put(`media/${id}/thumbnail.webp`, content, {