diff --git a/packages/block-editor/src/components/writing-flow/use-clipboard-handler.js b/packages/block-editor/src/components/writing-flow/use-clipboard-handler.js
index 56583447d3f0e9..bed07b183cc0cc 100644
--- a/packages/block-editor/src/components/writing-flow/use-clipboard-handler.js
+++ b/packages/block-editor/src/components/writing-flow/use-clipboard-handler.js
@@ -6,6 +6,7 @@ import {
 	findTransform,
 	getBlockTransforms,
 	hasBlockSupport,
+	switchToBlockType,
 } from '@wordpress/blocks';
 import {
 	documentHasSelection,
@@ -208,15 +209,36 @@ export default function useClipboardHandler() {
 					firstSelectedClientId
 				);
 
-				if (
-					! blocks.every( ( block ) =>
-						canInsertBlockType( block.name, rootClientId )
-					)
-				) {
-					return;
+				const newBlocks = [];
+
+				for ( const block of blocks ) {
+					if ( canInsertBlockType( block.name, rootClientId ) ) {
+						newBlocks.push( block );
+					} else {
+						// If a block cannot be inserted in a root block, try
+						// converting it to that root block type and insert the
+						// inner blocks.
+						// Example: paragraphs cannot be inserted into a list,
+						// so convert the paragraphs to a list for list items.
+						const rootBlockName = getBlockName( rootClientId );
+						const switchedBlocks =
+							block.name !== rootBlockName
+								? switchToBlockType( block, rootBlockName )
+								: [ block ];
+
+						if ( ! switchedBlocks ) {
+							return;
+						}
+
+						for ( const switchedBlock of switchedBlocks ) {
+							for ( const innerBlock of switchedBlock.innerBlocks ) {
+								newBlocks.push( innerBlock );
+							}
+						}
+					}
 				}
 
-				__unstableSplitSelection( blocks );
+				__unstableSplitSelection( newBlocks );
 				event.preventDefault();
 			}
 		}
diff --git a/test/e2e/specs/editor/various/__snapshots__/Copy-cut-paste-should-paste-list-in-list-1-chromium.txt b/test/e2e/specs/editor/various/__snapshots__/Copy-cut-paste-should-paste-list-in-list-1-chromium.txt
new file mode 100644
index 00000000000000..7f74d7fd8b3d03
--- /dev/null
+++ b/test/e2e/specs/editor/various/__snapshots__/Copy-cut-paste-should-paste-list-in-list-1-chromium.txt
@@ -0,0 +1,9 @@
+<!-- wp:list -->
+<ul class="wp-block-list"><!-- wp:list-item -->
+<li>x</li>
+<!-- /wp:list-item -->
+
+<!-- wp:list-item -->
+<li>y‸</li>
+<!-- /wp:list-item --></ul>
+<!-- /wp:list -->
\ No newline at end of file
diff --git a/test/e2e/specs/editor/various/__snapshots__/Copy-cut-paste-should-paste-paragraphs-in-list-1-chromium.txt b/test/e2e/specs/editor/various/__snapshots__/Copy-cut-paste-should-paste-paragraphs-in-list-1-chromium.txt
new file mode 100644
index 00000000000000..7f74d7fd8b3d03
--- /dev/null
+++ b/test/e2e/specs/editor/various/__snapshots__/Copy-cut-paste-should-paste-paragraphs-in-list-1-chromium.txt
@@ -0,0 +1,9 @@
+<!-- wp:list -->
+<ul class="wp-block-list"><!-- wp:list-item -->
+<li>x</li>
+<!-- /wp:list-item -->
+
+<!-- wp:list-item -->
+<li>y‸</li>
+<!-- /wp:list-item --></ul>
+<!-- /wp:list -->
\ No newline at end of file
diff --git a/test/e2e/specs/editor/various/copy-cut-paste.spec.js b/test/e2e/specs/editor/various/copy-cut-paste.spec.js
index 48392170e66dde..4951f99fb6b5b2 100644
--- a/test/e2e/specs/editor/various/copy-cut-paste.spec.js
+++ b/test/e2e/specs/editor/various/copy-cut-paste.spec.js
@@ -494,6 +494,32 @@ test.describe( 'Copy/cut/paste', () => {
 		expect( await editor.getEditedPostContent() ).toMatchSnapshot();
 	} );
 
+	test( 'should paste list in list', async ( {
+		page,
+		pageUtils,
+		editor,
+	} ) => {
+		pageUtils.setClipboardData( { html: '<ul><li>x</li><li>y</li></ul>' } );
+		await editor.insertBlock( { name: 'core/list' } );
+		await pageUtils.pressKeys( 'primary+v' );
+		// Ensure the selection is correct.
+		await page.keyboard.type( '‸' );
+		expect( await editor.getEditedPostContent() ).toMatchSnapshot();
+	} );
+
+	test( 'should paste paragraphs in list', async ( {
+		page,
+		pageUtils,
+		editor,
+	} ) => {
+		pageUtils.setClipboardData( { html: '<p>x</p><p>y</p>' } );
+		await editor.insertBlock( { name: 'core/list' } );
+		await pageUtils.pressKeys( 'primary+v' );
+		// Ensure the selection is correct.
+		await page.keyboard.type( '‸' );
+		expect( await editor.getEditedPostContent() ).toMatchSnapshot();
+	} );
+
 	test( 'should link selection', async ( { pageUtils, editor } ) => {
 		await editor.insertBlock( {
 			name: 'core/paragraph',