diff --git a/packages/block-library/src/image/index.js b/packages/block-library/src/image/index.js
index 92b9af7ec9a42c..ace6b55f31636b 100644
--- a/packages/block-library/src/image/index.js
+++ b/packages/block-library/src/image/index.js
@@ -123,6 +123,25 @@ function getFirstAnchorAttributeFormHTML( html, attributeName ) {
 	}
 }
 
+export function stripFirstImage( attributes, { shortcode } ) {
+	const { body } = document.implementation.createHTMLDocument( '' );
+
+	body.innerHTML = shortcode.content;
+
+	let nodeToRemove = body.querySelector( 'img' );
+
+	// if an image has parents, find the topmost node to remove
+	while ( nodeToRemove && nodeToRemove.parentNode && nodeToRemove.parentNode !== body ) {
+		nodeToRemove = nodeToRemove.parentNode;
+	}
+
+	if ( nodeToRemove ) {
+		nodeToRemove.parentNode.removeChild( nodeToRemove );
+	}
+
+	return body.innerHTML.trim();
+}
+
 export const settings = {
 	title: __( 'Image' ),
 
@@ -196,14 +215,7 @@ export const settings = {
 						selector: 'img',
 					},
 					caption: {
-						shortcode: ( attributes, { shortcode } ) => {
-							const { body } = document.implementation.createHTMLDocument( '' );
-
-							body.innerHTML = shortcode.content;
-							body.removeChild( body.firstElementChild );
-
-							return body.innerHTML.trim();
-						},
+						shortcode: stripFirstImage,
 					},
 					href: {
 						shortcode: ( attributes, { shortcode } ) => {
diff --git a/packages/block-library/src/image/test/index.js b/packages/block-library/src/image/test/index.js
new file mode 100644
index 00000000000000..5b21dcefdf6ebd
--- /dev/null
+++ b/packages/block-library/src/image/test/index.js
@@ -0,0 +1,32 @@
+/**
+ * Internal dependencies
+ */
+import { stripFirstImage } from '../';
+
+describe( 'stripFirstImage', () => {
+	test( 'should do nothing if no image is present', () => {
+		expect( stripFirstImage( {}, { shortcode: { content: '' } } ) ).toEqual( '' );
+		expect( stripFirstImage( {}, { shortcode: { content: 'Tucson' } } ) ).toEqual( 'Tucson' );
+		expect( stripFirstImage( {}, { shortcode: { content: '<em>Tucson</em>' } } ) ).toEqual( '<em>Tucson</em>' );
+	} );
+
+	test( 'should strip out image when leading as expected', () => {
+		expect( stripFirstImage( {}, { shortcode: { content: '<img>' } } ) ).toEqual( '' );
+		expect( stripFirstImage( {}, { shortcode: { content: '<img>Image!' } } ) ).toEqual( 'Image!' );
+		expect( stripFirstImage( {}, { shortcode: { content: '<img src="image.png">Image!' } } ) ).toEqual( 'Image!' );
+	} );
+
+	test( 'should strip out image when not in leading position as expected', () => {
+		expect( stripFirstImage( {}, { shortcode: { content: 'Before<img>' } } ) ).toEqual( 'Before' );
+		expect( stripFirstImage( {}, { shortcode: { content: 'Before<img>Image!' } } ) ).toEqual( 'BeforeImage!' );
+		expect( stripFirstImage( {}, { shortcode: { content: 'Before<img src="image.png">Image!' } } ) ).toEqual( 'BeforeImage!' );
+	} );
+
+	test( 'should strip out only the first of many images', () => {
+		expect( stripFirstImage( {}, { shortcode: { content: '<img><img>' } } ) ).toEqual( '<img>' );
+	} );
+
+	test( 'should strip out the first image and its wrapping parents', () => {
+		expect( stripFirstImage( {}, { shortcode: { content: '<p><a><img></a></p><p><img></p>' } } ) ).toEqual( '<p><img></p>' );
+	} );
+} );