Upload Media: stop propagating -scaled to sub-size filenames

packages/upload-media/CHANGELOG.md

@@ -2,6 +2,10 @@
 
 ## Unreleased
 
+### Bug Fix
+
+- Fix `-scaled` suffix propagating to every sub-size filename when an image exceeds `big_image_size_threshold`. Threshold scaling now runs as a sideload after the original is uploaded, so sub-sizes inherit the un-suffixed basename — matching WordPress core's `wp_create_image_subsizes()` naming.
+
 ## 0.31.0 (2026-05-14)
 
 ## 0.30.0 (2026-04-29)

packages/upload-media/src/store/private-actions.ts

@@ -665,30 +665,21 @@ export function prepareItem( id: QueueItemId ) {
 		);
 		const isHeic = HEIC_MIME_TYPES.includes( file.type );
 
-		// For images that can be processed by vips, check if we need to scale down based on threshold.
+		// For images that can be processed by vips, upload the original and
+		// let generateThumbnails() handle threshold scaling as a sideload.
+		//
+		// Uploading the original (rather than a pre-scaled copy) preserves
+		// the un-suffixed basename in attachment.filename, so sub-size
+		// names are derived from the original — matching WordPress core's
+		// wp_create_image_subsizes() naming convention where only the
+		// scaled-down full-size copy carries the `-scaled` suffix and the
+		// original is kept alongside it as `original_image`.
+		//
+		// Main-file format conversion is handled server-side via the
+		// image_editor_output_format filter during create_item.
+		// The response carries image_output_format so generateThumbnails
+		// can transcode sub-sizes to the same target format.
 		if ( isImage && isVipsSupported ) {
-			const { bigImageSizeThreshold } = settings;
-
-			// If a threshold is set, add a resize operation to scale down large images.
-			// This matches WordPress core's behavior in wp_create_image_subsizes().
-			if ( bigImageSizeThreshold ) {
-				operations.push( [
-					OperationType.ResizeCrop,
-					{
-						resize: {
-							width: bigImageSizeThreshold,
-							height: bigImageSizeThreshold,
-						},
-						isThresholdResize: true,
-					},
-				] );
-			}
-
-			// Main-file format conversion is handled server-side via the
-			// image_editor_output_format filter during create_item.
-			// The response carries image_output_format so generateThumbnails
-			// can transcode sub-sizes to the same target format.
-
 			operations.push(
 				OperationType.Upload,
 				OperationType.ThumbnailGeneration,

packages/upload-media/src/store/test/actions.ts

@@ -1085,5 +1085,137 @@ describe( 'actions', () => {
 			// Exactly at threshold means no scaling (condition is > not >=).
 			expect( scaledItems ).toHaveLength( 0 );
 		} );
+
+		// Sub-size and scaled-sideload naming uses attachment.filename
+		// verbatim. The cases below cover both the everyday filename and
+		// edge cases that previously broke with a client-side strip:
+		//   - a legitimate `-scaled` suffix in the user's filename
+		//   - the literal basename `scaled.jpg`
+		//   - `-scaled` appearing mid-name
+		//   - the server's numeric conflict-resolution suffix
+		//   - mixed case and multi-dot filenames
+		it.each( [
+			'IMG_2300.jpg',
+			'foo-scaled.jpg',
+			'scaled.jpg',
+			'my-scaled-image.jpg',
+			'IMG_2300-1.jpg',
+			'IMG-scaled-2.jpg',
+			'image.with.dots.jpg',
+			'FOO-SCALED.JPG',
+			'photo.jpeg',
+		] )( 'uses %s verbatim for thumbnail sideloads', async ( filename ) => {
+			mockCreateImageBitmap( 800, 600 );
+
+			unlock( registry.dispatch( uploadStore ) ).updateSettings( {
+				bigImageSizeThreshold: 2560,
+				allImageSizes: {
+					thumbnail: { width: 150, height: 150 },
+					medium: { width: 300, height: 300 },
+				},
+			} );
+
+			const item = await setupItemForThumbnailGeneration( {
+				attachment: { filename },
+			} );
+			await unlock( registry.dispatch( uploadStore ) ).generateThumbnails(
+				item.id
+			);
+
+			const thumbnailItems = unlock( registry.select( uploadStore ) )
+				.getAllItems()
+				.filter(
+					( i ) =>
+						i.additionalData?.image_size === 'thumbnail' ||
+						i.additionalData?.image_size === 'medium'
+				);
+			expect( thumbnailItems ).toHaveLength( 2 );
+			for ( const sideload of thumbnailItems ) {
+				expect( sideload.file.name ).toBe( filename );
+			}
+		} );
+
+		it.each( [
+			'IMG_2300.jpg',
+			'foo-scaled.jpg',
+			'scaled.jpg',
+			'IMG_2300-1.jpg',
+			'image.with.dots.jpg',
+		] )(
+			'uses %s verbatim for the scaled sideload when above threshold',
+			async ( filename ) => {
+				// Image above threshold triggers the scaled sideload path.
+				mockCreateImageBitmap( 4000, 3000 );
+
+				unlock( registry.dispatch( uploadStore ) ).updateSettings( {
+					bigImageSizeThreshold: 2560,
+					allImageSizes: {
+						thumbnail: { width: 150, height: 150 },
+					},
+				} );
+
+				const item = await setupItemForThumbnailGeneration( {
+					attachment: {
+						filename,
+						missing_image_sizes: [ 'thumbnail' ],
+					},
+				} );
+				await unlock(
+					registry.dispatch( uploadStore )
+				).generateThumbnails( item.id );
+
+				const scaledItems = unlock( registry.select( uploadStore ) )
+					.getAllItems()
+					.filter(
+						( i ) => i.additionalData?.image_size === 'scaled'
+					);
+				expect( scaledItems ).toHaveLength( 1 );
+				// vipsResizeImage adds the `-scaled` suffix during the
+				// ResizeCrop op; the sideload enters the queue under the
+				// server's filename so the resulting file matches WP core's
+				// naming (e.g. foo-scaled.jpg → foo-scaled-scaled.jpg, which
+				// is correct because the user really did have `-scaled` in
+				// their original name and the file was just scaled again).
+				expect( scaledItems[ 0 ].file.name ).toBe( filename );
+			}
+		);
+	} );
+
+	describe( 'prepareItem big image threshold', () => {
+		it( 'should not pre-scale the main upload when bigImageSizeThreshold is set', async () => {
+			// Pre-scaling the main upload would cause the server-returned
+			// attachment.filename to carry `-scaled`, which would then leak
+			// into every sub-size name. Threshold scaling must happen as a
+			// sideload so the original is uploaded with its un-suffixed
+			// basename.
+			unlock( registry.dispatch( uploadStore ) ).updateSettings( {
+				bigImageSizeThreshold: 2560,
+			} );
+			unlock( registry.dispatch( uploadStore ) ).addItem( {
+				file: jpegFile,
+			} );
+
+			const item = unlock(
+				registry.select( uploadStore )
+			).getAllItems()[ 0 ];
+
+			await unlock( registry.dispatch( uploadStore ) ).prepareItem(
+				item.id
+			);
+
+			const updatedItem = unlock(
+				registry.select( uploadStore )
+			).getAllItems()[ 0 ];
+
+			expect( updatedItem.operations ).not.toEqual(
+				expect.arrayContaining( [ OperationType.ResizeCrop ] )
+			);
+			expect( updatedItem.operations ).toEqual(
+				expect.arrayContaining( [
+					OperationType.Upload,
+					OperationType.ThumbnailGeneration,
+				] )
+			);
+		} );
 	} );
 } );