diff --git a/packages/e2e-tests/specs/blocks/__snapshots__/list.test.js.snap b/packages/e2e-tests/specs/blocks/__snapshots__/list.test.js.snap
index a7212afc153e6f..9ce876ee4aebec 100644
--- a/packages/e2e-tests/specs/blocks/__snapshots__/list.test.js.snap
+++ b/packages/e2e-tests/specs/blocks/__snapshots__/list.test.js.snap
@@ -212,6 +212,12 @@ exports[`List should outdent with children 2`] = `
 <!-- /wp:list -->"
 `;
 
+exports[`List should place the caret in the right place with nested list 1`] = `
+"<!-- wp:list -->
+<ul><li>1</li><li>2<ul><li>a</li></ul></li></ul>
+<!-- /wp:list -->"
+`;
+
 exports[`List should split indented list item 1`] = `
 "<!-- wp:list -->
 <ul><li>one<ul><li>two</li><li>three</li></ul></li></ul>
diff --git a/packages/e2e-tests/specs/blocks/list.test.js b/packages/e2e-tests/specs/blocks/list.test.js
index 776483ae4eb6a2..54d726aca6ae84 100644
--- a/packages/e2e-tests/specs/blocks/list.test.js
+++ b/packages/e2e-tests/specs/blocks/list.test.js
@@ -358,4 +358,17 @@ describe( 'List', () => {
 		// That's 9 key presses to create the list, and 9 key presses to remove
 		// the list. ;)
 	} );
+
+	it( 'should place the caret in the right place with nested list', async () => {
+		await clickBlockAppender();
+		await page.keyboard.type( '* 1' );
+		await page.keyboard.press( 'Enter' );
+		await page.keyboard.type( ' a' );
+		await page.keyboard.press( 'ArrowUp' );
+		await page.keyboard.press( 'Enter' );
+		// The caret should land in the second item.
+		await page.keyboard.type( '2' );
+
+		expect( await getEditedPostContent() ).toMatchSnapshot();
+	} );
 } );