diff --git a/lib/class-wp-rest-url-details-controller.php b/lib/class-wp-rest-url-details-controller.php
new file mode 100644
index 00000000000000..158e9e6c5adf22
--- /dev/null
+++ b/lib/class-wp-rest-url-details-controller.php
@@ -0,0 +1,122 @@
+<?php
+/**
+ *
+ *
+ * @package gutenberg
+ * @since 5.?.0
+ */
+
+/**
+ * Controller which provides REST endpoint for retrieving information
+ * from a remote site's HTML response.
+ *
+ * @since 5.?.0
+ *
+ * @see WP_REST_Controller
+ */
+class WP_REST_URL_Details_Controller extends WP_REST_Controller {
+
+	/**
+	 * Constructs the controller.
+	 *
+	 * @access public
+	 */
+	public function __construct() {
+		$this->namespace = '__experimental';
+		$this->rest_base = 'url-details';
+	}
+
+	/**
+	 * Registers the necessary REST API routes.
+	 *
+	 * @access public
+	 */
+	public function register_routes() {
+		register_rest_route(
+			$this->namespace,
+			'/' . $this->rest_base . '/title',
+			array(
+				array(
+					'methods'             => WP_REST_Server::READABLE,
+					'callback'            => array( $this, 'get_title' ),
+					'args' => array(
+						'url' => array(
+							'validate_callback' => 'wp_http_validate_url',
+							'sanitize_callback' => 'esc_url_raw',
+						),
+					),
+					'permission_callback' => array( $this, 'get_remote_url_permissions_check' ),
+				),
+			)
+		);
+	}
+
+	/**
+	 * Retrieves the contents of the <title> tag from the HTML
+	 * response.
+	 *
+	 * @access public
+	 * @param WP_REST_REQUEST $request Full details about the request.
+	 * @return String|WP_Error The title text or an error.
+	 */
+	public function get_title( $request ) {
+		$url   = $request->get_param( 'url' );
+		$title = $this->get_remote_url_title( $url );
+
+		return rest_ensure_response( $title );
+	}
+
+	/**
+	 * Checks whether a given request has permission to read remote urls.
+	 *
+	 * @return WP_Error|bool True if the request has access, WP_Error object otherwise.
+	 */
+	public function get_remote_url_permissions_check() {
+		if ( ! current_user_can( 'edit_posts' ) ) {
+			return new WP_Error(
+				'rest_user_cannot_view',
+				__( 'Sorry, you are not allowed to access remote urls.', 'gutenberg' )
+			);
+		}
+
+		return true;
+	}
+
+	/**
+	 * Retrieves the document title from a remote URL.
+	 *
+	 * @param string $url The website url whose HTML we want to access.
+	 * @return string|WP_Error The URL's document title on success, WP_Error on failure.
+	 */
+	private function get_remote_url_title( $url ) {
+		// Transient per URL.
+		$cache_key = 'g_url_details_response_' . hash( 'crc32b', $url );
+
+		// Attempt to retrieve cached response.
+		$title = get_transient( $cache_key );
+
+		if ( empty( $title ) ) {
+			$request                = wp_safe_remote_get( $url, array(
+				'timeout'             => 10,
+				'limit_response_size' => 153600, // 150 KB.
+			) );
+			$remote_source = wp_remote_retrieve_body( $request );
+
+			if ( ! $remote_source ) {
+				return new WP_Error( 'no_response', __( 'The source URL does not exist.', 'gutenberg' ), array( 'status' => 404 ) );
+			}
+
+			preg_match( '|<title>([^<]*?)</title>|is', $remote_source, $match_title );
+			$title = isset( $match_title[1] ) ? trim( $match_title[1] ) : '';
+
+			if ( empty( $title ) ) {
+				return new WP_Error( 'no_title', __( 'No document title at remote url.', 'gutenberg' ), array( 'status' => 404 ) );
+			}
+
+			// Only cache valid responses.
+			set_transient( $cache_key, $title, HOUR_IN_SECONDS );
+		}
+
+		return $title;
+	}
+}
diff --git a/lib/load.php b/lib/load.php
index 7076be29f63127..e3ee9b3a894d69 100644
--- a/lib/load.php
+++ b/lib/load.php
@@ -43,6 +43,11 @@ function gutenberg_is_experiment_enabled( $name ) {
 	* End: Include for phase 2
 	*/
 
+	if ( ! class_exists( 'WP_REST_URL_Details_Controller' ) ) {
+		require dirname( __FILE__ ) . '/class-wp-rest-url-details-controller.php';
+	}
+
+
 	require dirname( __FILE__ ) . '/rest-api.php';
 }
 
diff --git a/lib/rest-api.php b/lib/rest-api.php
index e0b6e7be592e7b..f1b97b4bf86969 100644
--- a/lib/rest-api.php
+++ b/lib/rest-api.php
@@ -54,6 +54,17 @@ function gutenberg_filter_oembed_result( $response, $handler, $request ) {
 
 
 
+/**
+ * Registers the REST API routes for URL Details.
+ *
+ * @since 5.0.0
+ */
+function gutenberg_register_url_details_routes() {
+	$url_details_controller = new WP_REST_URL_Details_Controller();
+	$url_details_controller->register_routes();
+}
+add_action( 'rest_api_init', 'gutenberg_register_url_details_routes' );
+
 /**
  * Start: Include for phase 2
  */
diff --git a/packages/block-editor/src/components/link-control/index.js b/packages/block-editor/src/components/link-control/index.js
index 18ae9da7c5401b..fcabde566ccc41 100644
--- a/packages/block-editor/src/components/link-control/index.js
+++ b/packages/block-editor/src/components/link-control/index.js
@@ -40,13 +40,13 @@ import LinkControlSearchItem from './search-item';
 import LinkControlSearchInput from './search-input';
 
 const MODE_EDIT = 'edit';
-// const MODE_SHOW = 'show';
 
 function LinkControl( {
 	className,
 	currentLink,
 	currentSettings,
 	fetchSearchSuggestions,
+	fetchRemoteURLTitle,
 	instanceId,
 	onClose = noop,
 	onChangeMode = noop,
@@ -112,7 +112,7 @@ function LinkControl( {
 		setInputValue( '' );
 	};
 
-	const handleDirectEntry = ( value ) => {
+	const handleDirectEntry = async ( value, { fetchUrlInfo = true } = {} ) => {
 		let type = 'URL';
 
 		const protocol = getProtocol( value ) || '';
@@ -129,24 +129,42 @@ function LinkControl( {
 			type = 'internal';
 		}
 
-		return Promise.resolve(
-			[ {
-				id: '-1',
-				title: value,
-				url: type === 'URL' ? prependHTTP( value ) : value,
-				type,
-			} ]
-		);
+		const defaultResponse = {
+			id: '-1',
+			title: value,
+			url: type === 'URL' ? prependHTTP( value ) : value,
+			type,
+		};
+
+		// If it's a URL then request the `<title>` tag
+		// Todo:
+		// * avoid invalid requests for incomplete URLS
+		// * avoid concurrent requests - cancel existing AJAX requests if already pending
+		if ( fetchUrlInfo && type === 'URL' && isURL( prependHTTP( value ) ) && value.length > 3 ) {
+			try {
+				const urlTitle = await fetchRemoteURLTitle( value );
+				return [ {
+					...defaultResponse,
+					title: urlTitle || value,
+				} ];
+			} catch ( error ) {
+				return [ defaultResponse ];
+			}
+		}
+
+		return [ defaultResponse ];
 	};
 
 	const handleEntitySearch = async ( value ) => {
+		const couldBeURL = ! value.includes( ' ' );
+
 		const results = await Promise.all( [
 			fetchSearchSuggestions( value ),
-			handleDirectEntry( value ),
+			handleDirectEntry( value, {
+				fetchUrlInfo: couldBeURL,
+			} ),
 		] );
 
-		const couldBeURL = ! value.includes( ' ' );
-
 		// If it's potentially a URL search then concat on a URL search suggestion
 		// just for good measure. That way once the actual results run out we always
 		// have a URL option to fallback on.
@@ -264,6 +282,7 @@ export default compose(
 		const { getSettings } = select( 'core/block-editor' );
 		return {
 			fetchSearchSuggestions: getSettings().__experimentalFetchLinkSuggestions,
+			fetchRemoteURLTitle: getSettings().__experimentalFetchRemoteURLTitle,
 		};
 	} )
 )( LinkControl );
diff --git a/packages/block-editor/src/components/link-control/search-item.js b/packages/block-editor/src/components/link-control/search-item.js
index 7b086860d30560..d28992fd1a645e 100644
--- a/packages/block-editor/src/components/link-control/search-item.js
+++ b/packages/block-editor/src/components/link-control/search-item.js
@@ -36,7 +36,7 @@ export const LinkControlSearchItem = ( { itemProps, suggestion, isSelected = fal
 				<span aria-hidden={ ! isURL } className="block-editor-link-control__search-item-info">
 					{ ! isURL && ( safeDecodeURI( suggestion.url ) || '' ) }
 					{ isURL && (
-						__( 'Press ENTER to add this link' )
+						`${ safeDecodeURI( suggestion.url ) } - ${ __( 'press ENTER to add this link' ) }`
 					) }
 				</span>
 			</span>
diff --git a/packages/editor/src/components/provider/index.js b/packages/editor/src/components/provider/index.js
index 1d3714e5c09885..df4e395b3196ac 100644
--- a/packages/editor/src/components/provider/index.js
+++ b/packages/editor/src/components/provider/index.js
@@ -14,7 +14,7 @@ import { __ } from '@wordpress/i18n';
 import { EntityProvider } from '@wordpress/core-data';
 import { BlockEditorProvider, transformStyles } from '@wordpress/block-editor';
 import apiFetch from '@wordpress/api-fetch';
-import { addQueryArgs } from '@wordpress/url';
+import { addQueryArgs, prependHTTP } from '@wordpress/url';
 import { decodeEntities } from '@wordpress/html-entities';
 
 /**
@@ -42,6 +42,18 @@ const fetchLinkSuggestions = async ( search ) => {
 	} ) );
 };
 
+const fetchRemoteURLTitle = async ( url ) => {
+	const endpoint = '/__experimental/url-details/title';
+
+	const args = {
+		url: prependHTTP( url ),
+	};
+
+	return apiFetch( {
+		path: addQueryArgs( endpoint, args ),
+	} );
+};
+
 class EditorProvider extends Component {
 	constructor( props ) {
 		super( ...arguments );
@@ -118,6 +130,7 @@ class EditorProvider extends Component {
 			__experimentalFetchReusableBlocks,
 			__experimentalFetchLinkSuggestions: fetchLinkSuggestions,
 			__experimentalCanUserUseUnfilteredHTML: canUserUseUnfilteredHTML,
+			__experimentalFetchRemoteURLTitle: fetchRemoteURLTitle,
 		};
 	}