diff --git a/apps/business/src/components/WebsiteStaticImageGallery.module.css b/apps/business/src/components/WebsiteStaticImageGallery.module.css
index dd8c462..b905b8b 100644
--- a/apps/business/src/components/WebsiteStaticImageGallery.module.css
+++ b/apps/business/src/components/WebsiteStaticImageGallery.module.css
@@ -65,6 +65,18 @@
   cursor: pointer;
 }
 
+/* Checkerboard so white/transparent PNG icons stay visible in the CMS. */
+.imageButtonTransparent {
+  background-color: #64748b;
+  background-image:
+    linear-gradient(45deg, #475569 25%, transparent 25%),
+    linear-gradient(-45deg, #475569 25%, transparent 25%),
+    linear-gradient(45deg, transparent 75%, #475569 75%),
+    linear-gradient(-45deg, transparent 75%, #475569 75%);
+  background-size: 16px 16px;
+  background-position: 0 0, 0 8px, 8px -8px, -8px 0;
+}
+
 .image {
   width: 100%;
   height: 100%;
diff --git a/apps/business/src/components/WebsiteStaticImageGallery.tsx b/apps/business/src/components/WebsiteStaticImageGallery.tsx
index f820bb4..d566c91 100644
--- a/apps/business/src/components/WebsiteStaticImageGallery.tsx
+++ b/apps/business/src/components/WebsiteStaticImageGallery.tsx
@@ -3,6 +3,7 @@ import { useLocale } from '@meshkee/dashboard-ui'
 import { useT } from '../i18n/useT'
 import type { WebsiteStaticImageItem } from '../types/websiteStaticImage'
 import { cssAspectRatio, slotPreviewSize } from '../utils/aspectRatio'
+import { isPngImageUrl } from '../utils/imageUpload'
 import { Tooltip } from './Tooltip'
 import controlStyles from './CategoryRow.module.css'
 import styles from './WebsiteStaticImageGallery.module.css'
@@ -106,7 +107,7 @@ export function WebsiteStaticImageGallery({
               <article className={styles.card}>
                 <button
                   type="button"
-                  className={styles.imageButton}
+                  className={`${styles.imageButton} ${isPngImageUrl(image.url) ? styles.imageButtonTransparent : ''}`}
                   onClick={() => onAddAt(index)}
                   aria-label={replaceLabel}
                   style={{ aspectRatio: cssAspect }}
diff --git a/apps/business/src/pages/WebsiteStaticImagesPage.tsx b/apps/business/src/pages/WebsiteStaticImagesPage.tsx
index 34f2cdd..45ccc88 100644
--- a/apps/business/src/pages/WebsiteStaticImagesPage.tsx
+++ b/apps/business/src/pages/WebsiteStaticImagesPage.tsx
@@ -20,6 +20,7 @@ import type { BusinessMessageKey } from '../i18n/messages'
 import { ApiError } from '../lib/api'
 import { getBusinessDomain } from '../lib/config'
 import { resolveDataUrlToMediaId } from '../services/mediaService'
+import { uploadFilenameForImageDataUrl } from '../utils/imageUpload'
 import {
   deleteWebsiteStaticImageSlot,
   listWebsiteStaticImageSlots,
@@ -230,7 +231,7 @@ export function WebsiteStaticImagesPage() {
       const occupying = occupyingImage(slot, index)
       const imageMediaId = await resolveDataUrlToMediaId(
         data.image,
-        'static-image.jpg',
+        uploadFilenameForImageDataUrl(data.image ?? '', 'static-image'),
         occupying?.imageMediaId,
       )
       if (!imageMediaId) {
diff --git a/apps/business/src/utils/imageUpload.ts b/apps/business/src/utils/imageUpload.ts
index 0e9f7a5..22bd331 100644
--- a/apps/business/src/utils/imageUpload.ts
+++ b/apps/business/src/utils/imageUpload.ts
@@ -98,3 +98,21 @@ export async function ensureJpegUploadFile(
       : `${filename.replace(/\.[^.]+$/, '') || 'image'}.jpg`,
   )
 }
+
+/** Pick .png vs .jpg from a data URL so PNG transparency is not flattened to JPEG. */
+export function uploadFilenameForImageDataUrl(
+  dataUrl: string,
+  baseName: string,
+): string {
+  const safe = baseName.replace(/\.[^.]+$/, '') || 'image'
+  return /^data:image\/png/i.test(dataUrl) ? `${safe}.png` : `${safe}.jpg`
+}
+
+export function isPngImageUrl(url: string): boolean {
+  if (/^data:image\/png/i.test(url)) return true
+  try {
+    return new URL(url, 'https://local').pathname.toLowerCase().endsWith('.png')
+  } catch {
+    return /\.png(\?|#|$)/i.test(url)
+  }
+}