diff --git a/extensions/blocks/calendly/edit.js b/extensions/blocks/calendly/edit.js
index b0e994ee0386..7db04d81371f 100644
--- a/extensions/blocks/calendly/edit.js
+++ b/extensions/blocks/calendly/edit.js
@@ -15,11 +15,12 @@ import {
 	Notice,
 	PanelBody,
 	Placeholder,
+	Spinner,
 	ToggleControl,
 	Toolbar,
 	withNotices,
 } from '@wordpress/components';
-import { useState } from '@wordpress/element';
+import { useEffect, useState } from '@wordpress/element';
 import { __, _x } from '@wordpress/i18n';
 import { getBlockDefaultClassName } from '@wordpress/blocks';
 
@@ -34,6 +35,8 @@ import { getValidatedAttributes } from '../../shared/get-validated-attributes';
 import SubmitButton from '../../shared/submit-button';
 import { getAttributesFromEmbedCode } from './utils';
 import BlockStylesSelector from '../../shared/components/block-styles-selector';
+import { CALENDLY_EXAMPLE_URL } from './';
+import testEmbedUrl from '../../shared/test-embed-url';
 
 function CalendlyEdit( props ) {
 	const {
@@ -62,6 +65,7 @@ function CalendlyEdit( props ) {
 		url,
 	} = validatedAttributes;
 	const [ embedCode, setEmbedCode ] = useState( '' );
+	const [ isResolvingUrl, setIsResolvingUrl ] = useState( false );
 
 	const setErrorNotice = () => {
 		noticeOperations.removeAllNotices();
@@ -70,6 +74,16 @@ function CalendlyEdit( props ) {
 		);
 	};
 
+	useEffect( () => {
+		if ( ! url || CALENDLY_EXAMPLE_URL === url || 'link' === style ) {
+			return;
+		}
+		testEmbedUrl( url, setIsResolvingUrl ).catch( () => {
+			setAttributes( { url: undefined } );
+			setErrorNotice();
+		} );
+	}, [] );
+
 	const parseEmbedCode = event => {
 		if ( ! event ) {
 			setErrorNotice();
@@ -84,10 +98,16 @@ function CalendlyEdit( props ) {
 			return;
 		}
 
-		const newValidatedAttributes = getValidatedAttributes( attributeDetails, newAttributes );
-
-		setAttributes( newValidatedAttributes );
-		noticeOperations.removeAllNotices();
+		testEmbedUrl( newAttributes.url, setIsResolvingUrl )
+			.then( () => {
+				const newValidatedAttributes = getValidatedAttributes( attributeDetails, newAttributes );
+				setAttributes( newValidatedAttributes );
+				noticeOperations.removeAllNotices();
+			} )
+			.catch( () => {
+				setAttributes( { url: undefined } );
+				setErrorNotice();
+			} );
 	};
 
 	const embedCodeForm = (
@@ -115,6 +135,13 @@ function CalendlyEdit( props ) {
 		</>
 	);
 
+	const blockEmbedding = (
+		<div className="wp-block-embed is-loading">
+			<Spinner />
+			<p>{ __( 'Embedding…', 'jetpack' ) }</p>
+		</div>
+	);
+
 	const blockPlaceholder = (
 		<Placeholder
 			label={ __( 'Calendly', 'jetpack' ) }
@@ -257,6 +284,10 @@ function CalendlyEdit( props ) {
 		</InspectorControls>
 	);
 
+	if ( isResolvingUrl ) {
+		return blockEmbedding;
+	}
+
 	const classes = `${ className } calendly-style-${ style }`;
 
 	return (
diff --git a/extensions/blocks/calendly/index.js b/extensions/blocks/calendly/index.js
index ae56a7f4b34a..243d598a9a0e 100644
--- a/extensions/blocks/calendly/index.js
+++ b/extensions/blocks/calendly/index.js
@@ -17,6 +17,8 @@ import { getAttributesFromEmbedCode, REGEX } from './utils';
  */
 import './editor.scss';
 
+export const CALENDLY_EXAMPLE_URL = 'https://calendly.com/wordpresscom/jetpack-block-example';
+
 export const name = 'calendly';
 export const title = __( 'Calendly', 'jetpack' );
 export const settings = {
@@ -44,7 +46,7 @@ export const settings = {
 			submitButtonText: __( 'Schedule time with me', 'jetpack' ),
 			hideEventTypeDetails: false,
 			style: 'inline',
-			url: 'https://calendly.com/wordpresscom/jetpack-block-example',
+			url: CALENDLY_EXAMPLE_URL,
 		},
 	},
 	transforms: {
diff --git a/extensions/shared/test-embed-url.js b/extensions/shared/test-embed-url.js
new file mode 100644
index 000000000000..b594f84b7c7d
--- /dev/null
+++ b/extensions/shared/test-embed-url.js
@@ -0,0 +1,41 @@
+/**
+ * External dependencies
+ */
+import { noop } from 'lodash';
+
+/**
+ * WordPress dependencies
+ */
+import apiFetch from '@wordpress/api-fetch';
+
+/**
+ * Test if a URL is accessible and respond with status code < 400.
+ *
+ * @example
+ * const [ isResolvingUrl, setIsResolvingUrl ] = useState();
+ * testEmbedUrl( url, setIsResolvingUrl )
+ *   .then( () => setAttributes( url ) )
+ *   .catch( () => setErrorNotice() );
+ *
+ * @param {String} url The URL to test.
+ * @param {Function} [setIsResolvingUrl=noop] An optional function to track the resolving state. Typically used to update the calling component's state.
+ * @returns {Promise} Resolve if the URL is valid, reject otherwise.
+ */
+export default function testEmbedUrl( url, setIsResolvingUrl = noop ) {
+	setIsResolvingUrl( true );
+	return new Promise( async ( resolve, reject ) => {
+		try {
+			const response = await apiFetch( { path: `/wpcom/v2/resolve-redirect/${ url }` } );
+			setIsResolvingUrl( false );
+			const responseStatusCode = response.status ? parseInt( response.status, 10 ) : null;
+			if ( responseStatusCode && responseStatusCode >= 400 ) {
+				reject();
+			} else {
+				resolve();
+			}
+		} catch ( error ) {
+			setIsResolvingUrl( false );
+			reject();
+		}
+	} );
+}