diff --git a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/image-preview.tsx b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/image-preview.tsx
index 0bac2180bed..e4ba8033261 100644
--- a/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/image-preview.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/files/components/file-viewer/image-preview.tsx
@@ -7,7 +7,11 @@ import { ZoomablePreview } from './zoomable-preview'
 
 export const ImagePreview = memo(function ImagePreview({ file }: { file: WorkspaceFileRecord }) {
   const source = useFileContentSource()
-  const serveUrl = source.buildUrl(file.key)
+  // Version the URL on updatedAt: overwrites keep the same storage key, so an unversioned
+  // URL would resolve to a previously cached copy instead of the rewritten bytes.
+  const serveUrl = source.buildUrl(file.key, {
+    version: Number(new Date(file.updatedAt)) || file.size,
+  })
 
   return (
     <ZoomablePreview className='flex flex-1' contentClassName='h-full w-full'>
diff --git a/apps/sim/next.config.ts b/apps/sim/next.config.ts
index 1d42e1c7c22..5f760789c4f 100644
--- a/apps/sim/next.config.ts
+++ b/apps/sim/next.config.ts
@@ -177,7 +177,7 @@ const nextConfig: NextConfig = {
   async headers() {
     return [
       {
-        source: '/:all*(svg|jpg|jpeg|png|gif|ico|webp|avif|woff|woff2|ttf|eot)',
+        source: '/((?!api/).*\\.(?:svg|jpg|jpeg|png|gif|ico|webp|avif|woff|woff2|ttf|eot))',
         headers: [
           {
             key: 'Cache-Control',