diff --git a/packages/dom/src/dom.js b/packages/dom/src/dom.js
index e52fb4d7908b24..579e10af1e6d04 100644
--- a/packages/dom/src/dom.js
+++ b/packages/dom/src/dom.js
@@ -93,7 +93,8 @@ function isEdge( container, isReverse, onlyVertical ) {
 		return false;
 	}
 
-	const range = selection.getRangeAt( 0 ).cloneRange();
+	const originalRange = selection.getRangeAt( 0 );
+	const range = originalRange.cloneRange();
 	const isForward = isSelectionForward( selection );
 	const isCollapsed = selection.isCollapsed;
 
@@ -131,9 +132,10 @@ function isEdge( container, isReverse, onlyVertical ) {
 	// over its line boundary.
 	const buffer = 3 * parseInt( lineHeight, 10 ) / 4;
 	const containerRect = container.getBoundingClientRect();
+	const originalRangeRect = getRectangleFromRange( originalRange );
 	const verticalEdge = isReverse ?
-		containerRect.top + padding > rangeRect.top - buffer :
-		containerRect.bottom - padding < rangeRect.bottom + buffer;
+		containerRect.top + padding > originalRangeRect.top - buffer :
+		containerRect.bottom - padding < originalRangeRect.bottom + buffer;
 
 	if ( ! verticalEdge ) {
 		return false;
diff --git a/packages/e2e-tests/specs/editor/various/__snapshots__/writing-flow.test.js.snap b/packages/e2e-tests/specs/editor/various/__snapshots__/writing-flow.test.js.snap
index c6c4bf5e8528e3..5fd746b9aaf4e7 100644
--- a/packages/e2e-tests/specs/editor/various/__snapshots__/writing-flow.test.js.snap
+++ b/packages/e2e-tests/specs/editor/various/__snapshots__/writing-flow.test.js.snap
@@ -24,6 +24,16 @@ exports[`Writing Flow Should navigate inner blocks with arrow keys 1`] = `
 <!-- /wp:paragraph -->"
 `;
 
+exports[`Writing Flow should allow selecting entire list with longer last item 1`] = `
+"<!-- wp:paragraph -->
+<p>a</p>
+<!-- /wp:paragraph -->
+
+<!-- wp:list -->
+<ul><li></li></ul>
+<!-- /wp:list -->"
+`;
+
 exports[`Writing Flow should create valid paragraph blocks when rapidly pressing Enter 1`] = `
 "<!-- wp:paragraph -->
 <p></p>
diff --git a/packages/e2e-tests/specs/editor/various/writing-flow.test.js b/packages/e2e-tests/specs/editor/various/writing-flow.test.js
index 661267778b6cad..db15f1f29d6ad0 100644
--- a/packages/e2e-tests/specs/editor/various/writing-flow.test.js
+++ b/packages/e2e-tests/specs/editor/various/writing-flow.test.js
@@ -440,4 +440,21 @@ describe( 'Writing Flow', () => {
 
 		expect( await getEditedPostContent() ).toMatchSnapshot();
 	} );
+
+	it( 'should allow selecting entire list with longer last item', async () => {
+		await page.keyboard.press( 'Enter' );
+		await page.keyboard.type( 'a' );
+		await page.keyboard.press( 'Enter' );
+		await page.keyboard.type( '* b' );
+		await page.keyboard.press( 'Enter' );
+		await page.keyboard.type( 'cd' );
+		await pressKeyWithModifier( 'shift', 'ArrowUp' );
+		await pressKeyWithModifier( 'shift', 'ArrowUp' );
+
+		// Ensure multi selection is not triggered and selection stays within
+		// the list.
+		await page.keyboard.press( 'Backspace' );
+
+		expect( await getEditedPostContent() ).toMatchSnapshot();
+	} );
 } );