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 71118e8d65118c..ef176d16bb9d75 100644
--- a/packages/e2e-tests/specs/blocks/__snapshots__/list.test.js.snap
+++ b/packages/e2e-tests/specs/blocks/__snapshots__/list.test.js.snap
@@ -144,6 +144,18 @@ exports[`List should indent and outdent level 2 3`] = `
 <!-- /wp:list -->"
 `;
 
+exports[`List should insert a line break on shift+enter 1`] = `
+"<!-- wp:list -->
+<ul><li>a<br><br></li></ul>
+<!-- /wp:list -->"
+`;
+
+exports[`List should insert a line break on shift+enter in a non trailing list item 1`] = `
+"<!-- wp:list -->
+<ul><li>a</li><li>b<br><br></li><li>c</li></ul>
+<!-- /wp:list -->"
+`;
+
 exports[`List should outdent with children 1`] = `
 "<!-- wp:list -->
 <ul><li>a<ul><li>b<ul><li>c</li></ul></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 98b7f74bd25362..915c9da4f537a5 100644
--- a/packages/e2e-tests/specs/blocks/list.test.js
+++ b/packages/e2e-tests/specs/blocks/list.test.js
@@ -280,4 +280,25 @@ describe( 'List', () => {
 
 		expect( await getEditedPostContent() ).toMatchSnapshot();
 	} );
+
+	it( 'should insert a line break on shift+enter', async () => {
+		await insertBlock( 'List' );
+		await page.keyboard.type( 'a' );
+		await pressKeyWithModifier( 'shift', 'Enter' );
+
+		expect( await getEditedPostContent() ).toMatchSnapshot();
+	} );
+
+	it( 'should insert a line break on shift+enter in a non trailing list item', async () => {
+		await insertBlock( 'List' );
+		await page.keyboard.type( 'a' );
+		await page.keyboard.press( 'Enter' );
+		await page.keyboard.type( 'b' );
+		await page.keyboard.press( 'Enter' );
+		await page.keyboard.type( 'c' );
+		await page.keyboard.press( 'ArrowUp' );
+		await pressKeyWithModifier( 'shift', 'Enter' );
+
+		expect( await getEditedPostContent() ).toMatchSnapshot();
+	} );
 } );
diff --git a/packages/editor/src/components/rich-text/index.js b/packages/editor/src/components/rich-text/index.js
index f91f5f77b17a42..59ba6e6e4225ce 100644
--- a/packages/editor/src/components/rich-text/index.js
+++ b/packages/editor/src/components/rich-text/index.js
@@ -33,6 +33,7 @@ import {
 	toHTMLString,
 	getTextContent,
 	insert,
+	insertLineBreak,
 	insertLineSeparator,
 	isEmptyLine,
 	unstableToDom,
@@ -599,27 +600,15 @@ export class RichText extends Component {
 			}
 
 			if ( this.multilineTag ) {
-				if ( this.onSplit && isEmptyLine( record ) ) {
+				if ( event.shiftKey ) {
+					this.onChange( insertLineBreak( record ) );
+				} else if ( this.onSplit && isEmptyLine( record ) ) {
 					this.onSplit( ...split( record ).map( this.valueToFormat ) );
 				} else {
 					this.onChange( insertLineSeparator( record ) );
 				}
 			} else if ( event.shiftKey || ! this.onSplit ) {
-				const text = getTextContent( record );
-				const length = text.length;
-				let toInsert = '\n';
-
-				// If the caret is at the end of the text, and there is no
-				// trailing line break or no text at all, we have to insert two
-				// line breaks in order to create a new line visually and place
-				// the caret there.
-				if ( record.end === length && (
-					text.charAt( length - 1 ) !== '\n' || length === 0
-				) ) {
-					toInsert = '\n\n';
-				}
-
-				this.onChange( insert( record, toInsert ) );
+				this.onChange( insertLineBreak( record ) );
 			} else {
 				this.splitContent();
 			}
diff --git a/packages/rich-text/src/index.js b/packages/rich-text/src/index.js
index 7ce8ed970e6ebe..423046079132bd 100644
--- a/packages/rich-text/src/index.js
+++ b/packages/rich-text/src/index.js
@@ -19,6 +19,7 @@ export { removeFormat } from './remove-format';
 export { remove } from './remove';
 export { replace } from './replace';
 export { insert } from './insert';
+export { insertLineBreak } from './insert-line-break';
 export { insertLineSeparator } from './insert-line-separator';
 export { insertObject } from './insert-object';
 export { slice } from './slice';
diff --git a/packages/rich-text/src/insert-line-break.js b/packages/rich-text/src/insert-line-break.js
new file mode 100644
index 00000000000000..540214d614f3c6
--- /dev/null
+++ b/packages/rich-text/src/insert-line-break.js
@@ -0,0 +1,34 @@
+/**
+ * Internal dependencies
+ */
+
+import { insert } from './insert';
+import { LINE_SEPARATOR } from './special-characters';
+
+/**
+ * Inserts a line break at the given or selected position. Inserts two line
+ * breaks if at the end of a line.
+ *
+ * @param {Object} value Value to modify.
+ *
+ * @return {Object} The value with the line break(s) inserted.
+ */
+export function insertLineBreak( value ) {
+	const { text, end } = value;
+	const length = text.length;
+
+	let toInsert = '\n';
+
+	// If the caret is at the end of the text, and there is no
+	// trailing line break or no text at all, we have to insert two
+	// line breaks in order to create a new line visually and place
+	// the caret there.
+	if (
+		( end === length || text[ end ] === LINE_SEPARATOR ) &&
+		( text[ end - 1 ] !== '\n' || length === 0 )
+	) {
+		toInsert = '\n\n';
+	}
+
+	return insert( value, toInsert );
+}