diff --git a/server/router/api/v1/attachment_service.go b/server/router/api/v1/attachment_service.go
index 1efbf4a82..64f342904 100644
--- a/server/router/api/v1/attachment_service.go
+++ b/server/router/api/v1/attachment_service.go
@@ -558,7 +558,7 @@ func (s *APIV1Service) getOrGenerateThumbnail(attachment *store.Attachment) ([]b
 
 		// Only resize if the image is larger than thumbnailMaxSize
 		if max(width, height) > thumbnailMaxSize {
-			if width > height {
+			if width >= height {
 				// Landscape or square - constrain width, maintain aspect ratio for height
 				thumbnailWidth = thumbnailMaxSize
 				thumbnailHeight = 0
diff --git a/web/src/components/MemoAttachmentListView.tsx b/web/src/components/MemoAttachmentListView.tsx
index 08ddfb98f..7749fb0e2 100644
--- a/web/src/components/MemoAttachmentListView.tsx
+++ b/web/src/components/MemoAttachmentListView.tsx
@@ -1,7 +1,7 @@
 import { memo, useState } from "react";
 import { cn } from "@/lib/utils";
 import { Attachment } from "@/types/proto/api/v1/attachment_service";
-import { getAttachmentType, getAttachmentUrl, getAttachmentThumbnailUrl } from "@/utils/attachment";
+import { getAttachmentThumbnailUrl, getAttachmentType, getAttachmentUrl } from "@/utils/attachment";
 import MemoAttachment from "./MemoAttachment";
 import PreviewImageDialog from "./PreviewImageDialog";