diff --git a/packages/block-editor/src/store/selectors.js b/packages/block-editor/src/store/selectors.js
index 5a88b6fb09b0a..5adbb72d542cb 100644
--- a/packages/block-editor/src/store/selectors.js
+++ b/packages/block-editor/src/store/selectors.js
@@ -1255,11 +1255,20 @@ const canInsertBlockTypeUnmemoized = (
 	);
 
 	const blockAllowedParentBlocks = blockType.parent;
-	const parentName = getBlockName( state, rootClientId );
-	const hasBlockAllowedParent = checkAllowList(
-		blockAllowedParentBlocks,
-		parentName
-	);
+	let hasBlockAllowedParent = null;
+	if ( blockAllowedParentBlocks ) {
+		const parents = [
+			rootClientId,
+			...getBlockParents( state, rootClientId ),
+		];
+
+		hasBlockAllowedParent = some( parents, ( parentClientId ) =>
+			checkAllowList(
+				blockAllowedParentBlocks,
+				getBlockName( state, parentClientId )
+			)
+		);
+	}
 
 	const canInsert =
 		( hasParentAllowedBlock === null && hasBlockAllowedParent === null ) ||
diff --git a/packages/block-editor/src/store/test/selectors.js b/packages/block-editor/src/store/test/selectors.js
index a9baaec53d346..db6562dfb8784 100644
--- a/packages/block-editor/src/store/test/selectors.js
+++ b/packages/block-editor/src/store/test/selectors.js
@@ -2248,6 +2248,7 @@ describe( 'selectors', () => {
 				blocks: {
 					byClientId: {},
 					attributes: {},
+					parents: {},
 				},
 				blockListSettings: {},
 				settings: {},
@@ -2284,6 +2285,7 @@ describe( 'selectors', () => {
 					attributes: {
 						block1: {},
 					},
+					parents: {},
 				},
 				blockListSettings: {
 					block1: {},
@@ -2304,6 +2306,7 @@ describe( 'selectors', () => {
 					attributes: {
 						block1: {},
 					},
+					parents: {},
 				},
 				blockListSettings: {
 					block1: {},
@@ -2368,6 +2371,7 @@ describe( 'selectors', () => {
 					attributes: {
 						block1: {},
 					},
+					parents: {},
 				},
 				blockListSettings: {
 					block1: {
@@ -2404,6 +2408,7 @@ describe( 'selectors', () => {
 				blocks: {
 					byClientId: {},
 					attributes: {},
+					parents: {},
 				},
 				blockListSettings: {},
 				settings: {},
@@ -2428,6 +2433,7 @@ describe( 'selectors', () => {
 						2: {},
 						3: {},
 					},
+					parents: {},
 				},
 				blockListSettings: {
 					1: {
@@ -2465,6 +2471,32 @@ describe( 'selectors', () => {
 			};
 			expect( canInsertBlocks( state, [ '2', '3' ], '1' ) ).toBe( false );
 		} );
+
+		it( 'should allow blocks to be inserted into any parent if an ancestor allows it', () => {
+			const state = {
+				blocks: {
+					byClientId: {
+						block1: { name: 'core/test-block-b' },
+						block2: { name: 'core/test-block-a' },
+					},
+					attributes: {
+						block1: {},
+						block2: {},
+					},
+					parents: {
+						block2: 'block1',
+					},
+				},
+				blockListSettings: {
+					block1: {},
+					block2: {},
+				},
+				settings: {},
+			};
+			expect(
+				canInsertBlockType( state, 'core/test-block-c', 'block2' )
+			).toBe( true );
+		} );
 	} );
 
 	describe( 'getInserterItems', () => {
@@ -2664,6 +2696,7 @@ describe( 'selectors', () => {
 						},
 					},
 					controlledInnerBlocks: {},
+					parents: {},
 				},
 				preferences: {
 					insertUsage: {},
@@ -2872,6 +2905,7 @@ describe( 'selectors', () => {
 						},
 					},
 					controlledInnerBlocks: {},
+					parents: {},
 				},
 				preferences: {
 					insertUsage: {},