diff --git a/packages/e2e-tests/specs/editor/various/__snapshots__/multi-block-selection.test.js.snap b/packages/e2e-tests/specs/editor/various/__snapshots__/multi-block-selection.test.js.snap
index 5d4499423f1eb0..3964a7ccae7609 100644
--- a/packages/e2e-tests/specs/editor/various/__snapshots__/multi-block-selection.test.js.snap
+++ b/packages/e2e-tests/specs/editor/various/__snapshots__/multi-block-selection.test.js.snap
@@ -70,6 +70,30 @@ exports[`Multi-block selection should cut and paste 2`] = `
 <!-- /wp:paragraph -->"
 `;
 
+exports[`Multi-block selection should gradually multi-select 1`] = `
+"<!-- wp:columns -->
+<div class=\\"wp-block-columns\\"><!-- wp:column -->
+<div class=\\"wp-block-column\\"><!-- wp:paragraph -->
+<p>1</p>
+<!-- /wp:paragraph -->
+
+<!-- wp:paragraph -->
+<p>2</p>
+<!-- /wp:paragraph --></div>
+<!-- /wp:column -->
+
+<!-- wp:column -->
+<div class=\\"wp-block-column\\"></div>
+<!-- /wp:column --></div>
+<!-- /wp:columns -->"
+`;
+
+exports[`Multi-block selection should gradually multi-select 2`] = `
+"<!-- wp:columns -->
+<div class=\\"wp-block-columns\\"></div>
+<!-- /wp:columns -->"
+`;
+
 exports[`Multi-block selection should not multi select single block 1`] = `
 "<!-- wp:paragraph -->
 <p></p>
diff --git a/packages/e2e-tests/specs/editor/various/multi-block-selection.test.js b/packages/e2e-tests/specs/editor/various/multi-block-selection.test.js
index eba80dd658a89b..af70fa0b93b211 100644
--- a/packages/e2e-tests/specs/editor/various/multi-block-selection.test.js
+++ b/packages/e2e-tests/specs/editor/various/multi-block-selection.test.js
@@ -591,7 +591,7 @@ describe( 'Multi-block selection', () => {
 		expect( await getEditedPostContent() ).toMatchSnapshot();
 	} );
 
-	// Previously we would unexpectedly duplicated the block on Enter.
+	// Previously we would unexpectedly duplicate the block on Enter.
 	it( 'should not multi select single block', async () => {
 		await clickBlockAppender();
 		await page.keyboard.type( '1' );
@@ -601,4 +601,44 @@ describe( 'Multi-block selection', () => {
 
 		expect( await getEditedPostContent() ).toMatchSnapshot();
 	} );
+
+	it( 'should gradually multi-select', async () => {
+		await clickBlockAppender();
+		await page.keyboard.type( '/columns' );
+		await page.keyboard.press( 'Enter' );
+		// Select two columns.
+		await page.keyboard.press( 'ArrowRight' );
+		await page.keyboard.press( 'ArrowRight' );
+		await page.keyboard.press( 'Enter' );
+		// Navigate to appender.
+		await page.keyboard.press( 'ArrowRight' );
+		await page.keyboard.press( 'Enter' );
+		// Select a paragraph.
+		await page.keyboard.press( 'Tab' );
+		await page.keyboard.press( 'Enter' );
+		await page.keyboard.type( '1' );
+		await page.keyboard.press( 'Enter' );
+		await page.keyboard.type( '2' );
+
+		// Confirm correct setup: two columns with two paragraphs in the first.
+		expect( await getEditedPostContent() ).toMatchSnapshot();
+
+		await pressKeyWithModifier( 'primary', 'a' );
+		await pressKeyWithModifier( 'primary', 'a' );
+
+		await page.waitForSelector(
+			'[data-type="core/paragraph"].is-multi-selected'
+		);
+
+		await pressKeyWithModifier( 'primary', 'a' );
+
+		await page.waitForSelector(
+			'[data-type="core/column"].is-multi-selected'
+		);
+
+		await page.keyboard.press( 'Backspace' );
+
+		// Expect both columns to be deleted.
+		expect( await getEditedPostContent() ).toMatchSnapshot();
+	} );
 } );