diff --git a/modules/masterbar/masterbar.php b/modules/masterbar/masterbar.php
index 6a378b892c5ec..55e00143dcba2 100644
--- a/modules/masterbar/masterbar.php
+++ b/modules/masterbar/masterbar.php
@@ -141,6 +141,30 @@ public function __construct() {
 			// Override Notification module to include RTL styles.
 			add_action( 'a8c_wpcom_masterbar_enqueue_rtl_notification_styles', '__return_true' );
 		}
+
+		add_action( 'wp_logout', array( $this, 'maybe_logout_user_from_wpcom' ) );
+	}
+
+	/**
+	 * Log out from WordPress.com when logging out of the local site.
+	 */
+	public function maybe_logout_user_from_wpcom() {
+		/**
+		 * Whether we should sign out from wpcom too when signing out from the masterbar.
+		 *
+		 * @since 5.9.0
+		 *
+		 * @param bool $masterbar_should_logout_from_wpcom True by default.
+		 */
+		$masterbar_should_logout_from_wpcom = apply_filters( 'jetpack_masterbar_should_logout_from_wpcom', true );
+		if (
+			// No need to check for a nonce here, it happens further up.
+			isset( $_GET['context'] ) // phpcs:ignore WordPress.Security.NonceVerification.Recommended
+			&& 'masterbar' === $_GET['context'] // phpcs:ignore WordPress.Security.NonceVerification.Recommended
+			&& $masterbar_should_logout_from_wpcom
+		) {
+			do_action( 'wp_masterbar_logout' );
+		}
 	}
 
 	/**
@@ -287,9 +311,6 @@ public function build_wpcom_masterbar( $wp_admin_bar ) {
 
 		$this->add_me_submenu( $wp_admin_bar );
 		$this->add_write_button( $wp_admin_bar );
-
-		// Add a sidebar toggle on mobile.
-		wp_admin_bar_sidebar_toggle( $wp_admin_bar );
 	}
 
 	/**
@@ -344,45 +365,140 @@ public function add_notifications( $wp_admin_bar ) {
 	}
 
 	/**
-	 * Add the "My Site" menu item in the root default group.
+	 * Add the "Reader" menu item in the root default group.
 	 *
 	 * @param WP_Admin_Bar $wp_admin_bar Admin Bar instance.
 	 */
-	public function add_my_sites_submenu( $wp_admin_bar ) {
+	public function add_reader_submenu( $wp_admin_bar ) {
 		$wp_admin_bar->add_menu(
 			array(
 				'parent' => 'root-default',
-				'id'     => 'blog',
-				'title'  => _n( 'My Site', 'My Sites', $this->user_site_count, 'jetpack' ),
-				'href'   => 'https://wordpress.com/stats/' . esc_attr( $this->primary_site_slug ),
+				'id'     => 'newdash',
+				'title'  => esc_html__( 'Reader', 'jetpack' ),
+				'href'   => '#',
 				'meta'   => array(
-					'class' => 'my-sites mb-trackable',
+					'class' => 'mb-trackable',
 				),
 			)
 		);
-	}
 
-	/**
-	 * Add the "Reader" menu item in the root default group.
-	 *
-	 * @param WP_Admin_Bar $wp_admin_bar Admin Bar instance.
-	 */
-	public function add_reader_submenu( $wp_admin_bar ) {
 		$wp_admin_bar->add_menu(
 			array(
-				'parent' => 'root-default',
-				'id'     => 'newdash',
-				'title'  => esc_html__( 'Reader', 'jetpack' ),
-				'href'   => 'https://wordpress.com/',
+				'parent' => 'newdash',
+				'id'     => 'streams-header',
+				'title'  => esc_html_x(
+					'Streams',
+					'Title for Reader sub-menu that contains followed sites, likes, and recommendations',
+					'jetpack'
+				),
 				'meta'   => array(
-					'class' => 'mb-trackable',
+					'class' => 'ab-submenu-header',
+				),
+			)
+		);
+
+		$following_title = $this->create_menu_item_pair(
+			array(
+				'url'   => 'https://wordpress.com/',
+				'id'    => 'wp-admin-bar-followed-sites',
+				'label' => esc_html__( 'Followed Sites', 'jetpack' ),
+			),
+			array(
+				'url'   => 'https://wordpress.com/following/edit',
+				'id'    => 'wp-admin-bar-reader-followed-sites-manage',
+				'label' => esc_html__( 'Manage', 'jetpack' ),
+			)
+		);
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => 'newdash',
+				'id'     => 'following',
+				'title'  => $following_title,
+				'meta'   => array( 'class' => 'inline-action' ),
+			)
+		);
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => 'newdash',
+				'id'     => 'discover-discover',
+				'title'  => esc_html__( 'Discover', 'jetpack' ),
+				'href'   => 'https://wordpress.com/discover',
+				'meta'   => array(
+					'class' => 'mb-icon-spacer',
+				),
+			)
+		);
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => 'newdash',
+				'id'     => 'discover-search',
+				'title'  => esc_html__( 'Search', 'jetpack' ),
+				'href'   => 'https://wordpress.com/read/search',
+				'meta'   => array(
+					'class' => 'mb-icon-spacer',
+				),
+			)
+		);
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => 'newdash',
+				'id'     => 'discover-recommended-blogs',
+				'title'  => esc_html__( 'Recommendations', 'jetpack' ),
+				'href'   => 'https://wordpress.com/recommendations',
+				'meta'   => array(
+					'class' => 'mb-icon-spacer',
 				),
 			)
 		);
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => 'newdash',
+				'id'     => 'my-activity-my-likes',
+				'title'  => esc_html__( 'My Likes', 'jetpack' ),
+				'href'   => 'https://wordpress.com/activities/likes',
+				'meta'   => array(
+					'class' => 'mb-icon-spacer',
+				),
+			)
+		);
+
+	}
+
+	/**
+	 * Merge 2 menu items together into 2 link tags.
+	 *
+	 * @param array $primary   Array of menu information.
+	 * @param array $secondary Array of menu information.
+	 */
+	public function create_menu_item_pair( $primary, $secondary ) {
+		$primary_class   = 'ab-item ab-primary mb-icon';
+		$secondary_class = 'ab-secondary';
+
+		$primary_anchor   = $this->create_menu_item_anchor( $primary_class, $primary['url'], $primary['label'], $primary['id'] );
+		$secondary_anchor = $this->create_menu_item_anchor( $secondary_class, $secondary['url'], $secondary['label'], $secondary['id'] );
+
+		return $primary_anchor . $secondary_anchor;
 	}
 
 	/**
-	 * Define main groups used in our admin bar.
+	 * Create a link tag based on information about a menu item.
+	 *
+	 * @param string $class Menu item CSS class.
+	 * @param string $url   URL you go to when clicking on the menu item.
+	 * @param string $label Menu item title.
+	 * @param string $id    Menu item slug.
+	 */
+	public function create_menu_item_anchor( $class, $url, $label, $id ) {
+		return '<a href="' . $url . '" class="' . $class . '" id="' . $id . '">' . $label . '</a>';
+	}
+
+	/**
+	 * Add Secondary groups for submenu items.
 	 *
 	 * @param WP_Admin_Bar $wp_admin_bar Admin Bar instance.
 	 */
@@ -396,6 +512,16 @@ public function wpcom_adminbar_add_secondary_groups( $wp_admin_bar ) {
 			)
 		);
 
+		$wp_admin_bar->add_group(
+			array(
+				'parent' => 'blog',
+				'id'     => 'blog-secondary',
+				'meta'   => array(
+					'class' => 'ab-sub-secondary',
+				),
+			)
+		);
+
 		$wp_admin_bar->add_group(
 			array(
 				'id'   => 'top-secondary',
@@ -426,12 +552,163 @@ public function add_me_submenu( $wp_admin_bar ) {
 				'id'     => 'my-account',
 				'parent' => 'top-secondary',
 				'title'  => $avatar . '<span class="ab-text">' . esc_html__( 'Me', 'jetpack' ) . '</span>',
-				'href'   => 'https://wordpress.com/me/account',
+				'href'   => '#',
 				'meta'   => array(
 					'class' => $class,
 				),
 			)
 		);
+
+		$id = 'user-actions';
+		$wp_admin_bar->add_group(
+			array(
+				'parent' => 'my-account',
+				'id'     => $id,
+			)
+		);
+
+		$settings_url = 'https://wordpress.com/me/account';
+
+		$logout_url = wp_logout_url();
+		$logout_url = add_query_arg( 'context', 'masterbar', $logout_url );
+
+		$user_info  = get_avatar( $this->user_email, 128, 'mm', '', array( 'force_display' => true ) );
+		$user_info .= '<span class="display-name">' . $this->display_name . '</span>';
+		$user_info .= '<a class="username" href="http://gravatar.com/' . $this->user_login . '">@' . $this->user_login . '</a>';
+
+		$user_info .= sprintf(
+			'<div><a href="%s" class="ab-sign-out">%s</a></div>',
+			$logout_url,
+			esc_html__( 'Sign Out', 'jetpack' )
+		);
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => $id,
+				'id'     => 'user-info',
+				'title'  => $user_info,
+				'meta'   => array(
+					'class'    => 'user-info user-info-item',
+					'tabindex' => -1,
+				),
+			)
+		);
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => $id,
+				'id'     => 'profile-header',
+				'title'  => esc_html__( 'Profile', 'jetpack' ),
+				'meta'   => array(
+					'class' => 'ab-submenu-header',
+				),
+			)
+		);
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => $id,
+				'id'     => 'my-profile',
+				'title'  => esc_html__( 'My Profile', 'jetpack' ),
+				'href'   => 'https://wordpress.com/me',
+				'meta'   => array(
+					'class' => 'mb-icon',
+				),
+			)
+		);
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => $id,
+				'id'     => 'account-settings',
+				'title'  => esc_html__( 'Account Settings', 'jetpack' ),
+				'href'   => $settings_url,
+				'meta'   => array(
+					'class' => 'mb-icon',
+				),
+			)
+		);
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => $id,
+				'id'     => 'billing',
+				'title'  => esc_html__( 'Manage Purchases', 'jetpack' ),
+				'href'   => 'https://wordpress.com/me/purchases',
+				'meta'   => array(
+					'class' => 'mb-icon',
+				),
+			)
+		);
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => $id,
+				'id'     => 'security',
+				'title'  => esc_html__( 'Security', 'jetpack' ),
+				'href'   => 'https://wordpress.com/me/security',
+				'meta'   => array(
+					'class' => 'mb-icon',
+				),
+			)
+		);
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => $id,
+				'id'     => 'notifications',
+				'title'  => esc_html__( 'Notifications', 'jetpack' ),
+				'href'   => 'https://wordpress.com/me/notifications',
+				'meta'   => array(
+					'class' => 'mb-icon',
+				),
+			)
+		);
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => $id,
+				'id'     => 'special-header',
+				'title'  => esc_html_x(
+					'Special',
+					'Title for Me sub-menu that contains Get Apps, Next Steps, and Help options',
+					'jetpack'
+				),
+				'meta'   => array(
+					'class' => 'ab-submenu-header',
+				),
+			)
+		);
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => $id,
+				'id'     => 'get-apps',
+				'title'  => esc_html__( 'Get Apps', 'jetpack' ),
+				'href'   => 'https://wordpress.com/me/get-apps',
+				'meta'   => array(
+					'class' => 'mb-icon user-info-item',
+				),
+			)
+		);
+
+		$help_link = 'https://jetpack.com/support/';
+
+		if ( jetpack_is_atomic_site() ) {
+			$help_link = 'https://wordpress.com/help';
+		}
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => $id,
+				'id'     => 'help',
+				'title'  => esc_html__( 'Help', 'jetpack' ),
+				'href'   => $help_link,
+				'meta'   => array(
+					'class' => 'mb-icon user-info-item',
+				),
+			)
+		);
 	}
 
 	/**
@@ -467,4 +744,557 @@ public function add_write_button( $wp_admin_bar ) {
 			)
 		);
 	}
+
+	/**
+	 * Add the "My Site" menu item in the root default group.
+	 *
+	 * @param WP_Admin_Bar $wp_admin_bar Admin Bar instance.
+	 */
+	public function add_my_sites_submenu( $wp_admin_bar ) {
+		$current_user = wp_get_current_user();
+
+		$blog_name = get_bloginfo( 'name' );
+		if ( empty( $blog_name ) ) {
+			$blog_name = $this->primary_site_slug;
+		}
+
+		if ( mb_strlen( $blog_name ) > 20 ) {
+			$blog_name = mb_substr( html_entity_decode( $blog_name, ENT_QUOTES ), 0, 20 ) . '&hellip;';
+		}
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => 'root-default',
+				'id'     => 'blog',
+				'title'  => _n( 'My Site', 'My Sites', $this->user_site_count, 'jetpack' ),
+				'href'   => '#',
+				'meta'   => array(
+					'class' => 'my-sites mb-trackable',
+				),
+			)
+		);
+
+		if ( $this->user_site_count > 1 ) {
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'blog',
+					'id'     => 'switch-site',
+					'title'  => esc_html__( 'Switch Site', 'jetpack' ),
+					'href'   => 'https://wordpress.com/sites',
+				)
+			);
+		} else {
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'blog',
+					'id'     => 'new-site',
+					'title'  => esc_html__( '+ Add New WordPress', 'jetpack' ),
+					'href'   => 'https://wordpress.com/start?ref=admin-bar-logged-in',
+				)
+			);
+		}
+
+		if ( is_user_member_of_blog( $current_user->ID ) ) {
+			$blavatar = '';
+			$class    = 'current-site';
+
+			if ( has_site_icon() ) {
+				$src      = get_site_icon_url();
+				$blavatar = '<img class="avatar" src="' . esc_attr( $src ) . '" alt="Current site avatar">';
+				$class    = 'has-blavatar';
+			}
+
+			$blog_info  = '<div class="ab-site-icon">' . $blavatar . '</div>';
+			$blog_info .= '<span class="ab-site-title">' . esc_html( $blog_name ) . '</span>';
+			$blog_info .= '<span class="ab-site-description">' . esc_html( $this->primary_site_url ) . '</span>';
+
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'blog',
+					'id'     => 'blog-info',
+					'title'  => $blog_info,
+					'href'   => esc_url( trailingslashit( $this->primary_site_url ) ),
+					'meta'   => array(
+						'class' => $class,
+					),
+				)
+			);
+		}
+
+		// Site Preview.
+		if ( is_admin() ) {
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'blog',
+					'id'     => 'site-view',
+					'title'  => __( 'View Site', 'jetpack' ),
+					'href'   => home_url(),
+					'meta'   => array(
+						'class'  => 'mb-icon',
+						'target' => '_blank',
+					),
+				)
+			);
+		}
+
+		// Stats.
+		if ( Jetpack::is_module_active( 'stats' ) ) {
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'blog',
+					'id'     => 'blog-stats',
+					'title'  => esc_html__( 'Stats', 'jetpack' ),
+					'href'   => 'https://wordpress.com/stats/' . esc_attr( $this->primary_site_slug ),
+					'meta'   => array(
+						'class' => 'mb-icon',
+					),
+				)
+			);
+		}
+
+		if ( current_user_can( 'manage_options' ) ) {
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'blog',
+					'id'     => 'activity',
+					'title'  => esc_html__( 'Activity', 'jetpack' ),
+					'href'   => 'https://wordpress.com/activity-log/' . esc_attr( $this->primary_site_slug ),
+					'meta'   => array(
+						'class' => 'mb-icon',
+					),
+				)
+			);
+		}
+
+		// Add Calypso plans link and plan type indicator.
+		if ( is_user_member_of_blog( $current_user->ID ) ) {
+			$plans_url = 'https://wordpress.com/plans/' . esc_attr( $this->primary_site_slug );
+			$label     = esc_html__( 'Plan', 'jetpack' );
+			$plan      = Jetpack_Plan::get();
+
+			$plan_title = $this->create_menu_item_pair(
+				array(
+					'url'   => $plans_url,
+					'id'    => 'wp-admin-bar-plan',
+					'label' => $label,
+				),
+				array(
+					'url'   => $plans_url,
+					'id'    => 'wp-admin-bar-plan-badge',
+					'label' => $plan['product_name_short'],
+				)
+			);
+
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'blog',
+					'id'     => 'plan',
+					'title'  => $plan_title,
+					'meta'   => array(
+						'class' => 'inline-action',
+					),
+				)
+			);
+		}
+
+		// Publish group.
+		$wp_admin_bar->add_group(
+			array(
+				'parent' => 'blog',
+				'id'     => 'publish',
+			)
+		);
+
+		// Publish header.
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => 'publish',
+				'id'     => 'publish-header',
+				'title'  => esc_html_x( 'Manage', 'admin bar menu group label', 'jetpack' ),
+				'meta'   => array(
+					'class' => 'ab-submenu-header',
+				),
+			)
+		);
+
+		// Pages.
+		$pages_title = $this->create_menu_item_pair(
+			array(
+				'url'   => 'https://wordpress.com/pages/' . esc_attr( $this->primary_site_slug ),
+				'id'    => 'wp-admin-bar-edit-page',
+				'label' => esc_html__( 'Site Pages', 'jetpack' ),
+			),
+			array(
+				'url'   => 'https://wordpress.com/page/' . esc_attr( $this->primary_site_slug ),
+				'id'    => 'wp-admin-bar-new-page-badge',
+				'label' => esc_html_x( 'Add', 'admin bar menu new item label', 'jetpack' ),
+			)
+		);
+
+		if ( ! current_user_can( 'edit_pages' ) ) {
+			$pages_title = $this->create_menu_item_anchor(
+				'ab-item ab-primary mb-icon',
+				'https://wordpress.com/pages/' . esc_attr( $this->primary_site_slug ),
+				esc_html__( 'Site Pages', 'jetpack' ),
+				'wp-admin-bar-edit-page'
+			);
+		}
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => 'publish',
+				'id'     => 'new-page',
+				'title'  => $pages_title,
+				'meta'   => array(
+					'class' => 'inline-action',
+				),
+			)
+		);
+
+		// Blog Posts.
+		$posts_title = $this->create_menu_item_pair(
+			array(
+				'url'   => 'https://wordpress.com/posts/' . esc_attr( $this->primary_site_slug ),
+				'id'    => 'wp-admin-bar-edit-post',
+				'label' => esc_html__( 'Blog Posts', 'jetpack' ),
+			),
+			array(
+				'url'   => 'https://wordpress.com/post/' . esc_attr( $this->primary_site_slug ),
+				'id'    => 'wp-admin-bar-new-post-badge',
+				'label' => esc_html_x( 'Add', 'admin bar menu new item label', 'jetpack' ),
+			)
+		);
+
+		if ( ! current_user_can( 'edit_posts' ) ) {
+			$posts_title = $this->create_menu_item_anchor(
+				'ab-item ab-primary mb-icon',
+				'https://wordpress.com/posts/' . esc_attr( $this->primary_site_slug ),
+				esc_html__( 'Blog Posts', 'jetpack' ),
+				'wp-admin-bar-edit-post'
+			);
+		}
+
+		$wp_admin_bar->add_menu(
+			array(
+				'parent' => 'publish',
+				'id'     => 'new-post',
+				'title'  => $posts_title,
+				'meta'   => array(
+					'class' => 'inline-action mb-trackable',
+				),
+			)
+		);
+
+		// Comments.
+		if ( current_user_can( 'moderate_comments' ) ) {
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'publish',
+					'id'     => 'comments',
+					'title'  => __( 'Comments', 'jetpack' ),
+					'href'   => 'https://wordpress.com/comments/' . esc_attr( $this->primary_site_slug ),
+					'meta'   => array(
+						'class' => 'mb-icon',
+					),
+				)
+			);
+		}
+
+		// Testimonials.
+		if ( Jetpack::is_module_active( 'custom-content-types' ) && get_option( 'jetpack_testimonial' ) ) {
+			$testimonials_title = $this->create_menu_item_pair(
+				array(
+					'url'   => 'https://wordpress.com/types/jetpack-testimonial/' . esc_attr( $this->primary_site_slug ),
+					'id'    => 'wp-admin-bar-edit-testimonial',
+					'label' => esc_html__( 'Testimonials', 'jetpack' ),
+				),
+				array(
+					'url'   => 'https://wordpress.com/edit/jetpack-testimonial/' . esc_attr( $this->primary_site_slug ),
+					'id'    => 'wp-admin-bar-new-testimonial',
+					'label' => esc_html_x( 'Add', 'Button label for adding a new item via the toolbar menu', 'jetpack' ),
+				)
+			);
+
+			if ( ! current_user_can( 'edit_pages' ) ) {
+				$testimonials_title = $this->create_menu_item_anchor(
+					'ab-item ab-primary mb-icon',
+					'https://wordpress.com/types/jetpack-testimonial/' . esc_attr( $this->primary_site_slug ),
+					esc_html__( 'Testimonials', 'jetpack' ),
+					'wp-admin-bar-edit-testimonial'
+				);
+			}
+
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'publish',
+					'id'     => 'new-jetpack-testimonial',
+					'title'  => $testimonials_title,
+					'meta'   => array(
+						'class' => 'inline-action',
+					),
+				)
+			);
+		}
+
+		// Portfolio.
+		if ( Jetpack::is_module_active( 'custom-content-types' ) && get_option( 'jetpack_portfolio' ) ) {
+			$portfolios_title = $this->create_menu_item_pair(
+				array(
+					'url'   => 'https://wordpress.com/types/jetpack-portfolio/' . esc_attr( $this->primary_site_slug ),
+					'id'    => 'wp-admin-bar-edit-portfolio',
+					'label' => esc_html__( 'Portfolio', 'jetpack' ),
+				),
+				array(
+					'url'   => 'https://wordpress.com/edit/jetpack-portfolio/' . esc_attr( $this->primary_site_slug ),
+					'id'    => 'wp-admin-bar-new-portfolio',
+					'label' => esc_html_x( 'Add', 'Button label for adding a new item via the toolbar menu', 'jetpack' ),
+				)
+			);
+
+			if ( ! current_user_can( 'edit_pages' ) ) {
+				$portfolios_title = $this->create_menu_item_anchor(
+					'ab-item ab-primary mb-icon',
+					'https://wordpress.com/types/jetpack-portfolio/' . esc_attr( $this->primary_site_slug ),
+					esc_html__( 'Portfolio', 'jetpack' ),
+					'wp-admin-bar-edit-portfolio'
+				);
+			}
+
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'publish',
+					'id'     => 'new-jetpack-portfolio',
+					'title'  => $portfolios_title,
+					'meta'   => array(
+						'class' => 'inline-action',
+					),
+				)
+			);
+		}
+
+		if ( current_user_can( 'edit_theme_options' ) ) {
+			// Look and Feel group.
+			$wp_admin_bar->add_group(
+				array(
+					'parent' => 'blog',
+					'id'     => 'look-and-feel',
+				)
+			);
+
+			// Look and Feel header.
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'look-and-feel',
+					'id'     => 'look-and-feel-header',
+					'title'  => esc_html_x( 'Personalize', 'admin bar menu group label', 'jetpack' ),
+					'meta'   => array(
+						'class' => 'ab-submenu-header',
+					),
+				)
+			);
+
+			if ( is_admin() ) {
+				// In wp-admin the `return` query arg will return to that page after closing the Customizer.
+				$customizer_url = add_query_arg(
+					array(
+						'return' => rawurlencode( site_url( $_SERVER['REQUEST_URI'] ) ),
+					),
+					wp_customize_url()
+				);
+			} else {
+				/*
+				 * On the frontend the `url` query arg will load that page in the Customizer
+				 * and also return to it after closing
+				 * non-home URLs won't work unless we undo domain mapping
+				 * since the Customizer preview is unmapped to always have HTTPS.
+				 */
+				$current_page   = '//' . $this->primary_site_slug . $_SERVER['REQUEST_URI'];
+				$customizer_url = add_query_arg( array( 'url' => rawurlencode( $current_page ) ), wp_customize_url() );
+			}
+
+			$theme_title = $this->create_menu_item_pair(
+				array(
+					'url'   => $customizer_url,
+					'id'    => 'wp-admin-bar-cmz',
+					'label' => esc_html_x( 'Customize', 'admin bar customize item label', 'jetpack' ),
+				),
+				array(
+					'url'   => 'https://wordpress.com/themes/' . esc_attr( $this->primary_site_slug ),
+					'id'    => 'wp-admin-bar-themes',
+					'label' => esc_html__( 'Themes', 'jetpack' ),
+				)
+			);
+			$meta        = array(
+				'class' => 'mb-icon',
+				'class' => 'inline-action',
+			);
+			$href        = false;
+
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'look-and-feel',
+					'id'     => 'themes',
+					'title'  => $theme_title,
+					'href'   => $href,
+					'meta'   => $meta,
+				)
+			);
+		}
+
+		if ( current_user_can( 'manage_options' ) ) {
+			// Configuration group.
+			$wp_admin_bar->add_group(
+				array(
+					'parent' => 'blog',
+					'id'     => 'configuration',
+				)
+			);
+
+			// Configuration header.
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'configuration',
+					'id'     => 'configuration-header',
+					'title'  => esc_html_x( 'Configure', 'admin bar menu group label', 'jetpack' ),
+					'meta'   => array(
+						'class' => 'ab-submenu-header',
+					),
+				)
+			);
+
+			if ( Jetpack::is_module_active( 'publicize' ) || Jetpack::is_module_active( 'sharedaddy' ) ) {
+				$wp_admin_bar->add_menu(
+					array(
+						'parent' => 'configuration',
+						'id'     => 'sharing',
+						'title'  => esc_html__( 'Sharing', 'jetpack' ),
+						'href'   => 'https://wordpress.com/sharing/' . esc_attr( $this->primary_site_slug ),
+						'meta'   => array(
+							'class' => 'mb-icon',
+						),
+					)
+				);
+			}
+
+			$people_title = $this->create_menu_item_pair(
+				array(
+					'url'   => 'https://wordpress.com/people/team/' . esc_attr( $this->primary_site_slug ),
+					'id'    => 'wp-admin-bar-people',
+					'label' => esc_html__( 'People', 'jetpack' ),
+				),
+				array(
+					'url'   => admin_url( 'user-new.php' ),
+					'id'    => 'wp-admin-bar-people-add',
+					'label' => esc_html_x( 'Add', 'admin bar people item label', 'jetpack' ),
+				)
+			);
+
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'configuration',
+					'id'     => 'users-toolbar',
+					'title'  => $people_title,
+					'href'   => false,
+					'meta'   => array(
+						'class' => 'inline-action',
+					),
+				)
+			);
+
+			$plugins_title = $this->create_menu_item_pair(
+				array(
+					'url'   => 'https://wordpress.com/plugins/' . esc_attr( $this->primary_site_slug ),
+					'id'    => 'wp-admin-bar-plugins',
+					'label' => esc_html__( 'Plugins', 'jetpack' ),
+				),
+				array(
+					'url'   => 'https://wordpress.com/plugins/manage/' . esc_attr( $this->primary_site_slug ),
+					'id'    => 'wp-admin-bar-plugins-add',
+					'label' => esc_html_x( 'Manage', 'Label for the button on the Masterbar to manage plugins', 'jetpack' ),
+				)
+			);
+
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'configuration',
+					'id'     => 'plugins',
+					'title'  => $plugins_title,
+					'href'   => false,
+					'meta'   => array(
+						'class' => 'inline-action',
+					),
+				)
+			);
+
+			if ( jetpack_is_atomic_site() ) {
+				$domain_title = $this->create_menu_item_pair(
+					array(
+						'url'   => 'https://wordpress.com/domains/' . esc_attr( $this->primary_site_slug ),
+						'id'    => 'wp-admin-bar-domains',
+						'label' => esc_html__( 'Domains', 'jetpack' ),
+					),
+					array(
+						'url'   => 'https://wordpress.com/domains/add/' . esc_attr( $this->primary_site_slug ),
+						'id'    => 'wp-admin-bar-domains-add',
+						'label' => esc_html_x( 'Add', 'Label for the button on the Masterbar to add a new domain', 'jetpack' ),
+					)
+				);
+				$wp_admin_bar->add_menu(
+					array(
+						'parent' => 'configuration',
+						'id'     => 'domains',
+						'title'  => $domain_title,
+						'href'   => false,
+						'meta'   => array(
+							'class' => 'inline-action',
+						),
+					)
+				);
+			}
+
+			$wp_admin_bar->add_menu(
+				array(
+					'parent' => 'configuration',
+					'id'     => 'blog-settings',
+					'title'  => esc_html__( 'Settings', 'jetpack' ),
+					'href'   => 'https://wordpress.com/settings/general/' . esc_attr( $this->primary_site_slug ),
+					'meta'   => array(
+						'class' => 'mb-icon',
+					),
+				)
+			);
+
+			if ( ! is_admin() ) {
+				$wp_admin_bar->add_menu(
+					array(
+						'parent' => 'configuration',
+						'id'     => 'legacy-dashboard',
+						'title'  => esc_html__( 'Dashboard', 'jetpack' ),
+						'href'   => admin_url(),
+						'meta'   => array(
+							'class' => 'mb-icon',
+						),
+					)
+				);
+			}
+
+			// Restore dashboard menu toggle that is needed on mobile views.
+			if ( is_admin() ) {
+				$wp_admin_bar->add_menu(
+					array(
+						'id'    => 'menu-toggle',
+						'title' => '<span class="ab-icon"></span><span class="screen-reader-text">' . esc_html__( 'Menu', 'jetpack' ) . '</span>',
+						'href'  => '#',
+					)
+				);
+			}
+
+			/**
+			 * Fires when menu items are added to the masterbar "My Sites" menu.
+			 *
+			 * @since 5.4.0
+			 */
+			do_action( 'jetpack_masterbar' );
+		}
+	}
 }
diff --git a/modules/masterbar/tracks-events.js b/modules/masterbar/tracks-events.js
index 8364266cfd26c..a8993999f8e6c 100644
--- a/modules/masterbar/tracks-events.js
+++ b/modules/masterbar/tracks-events.js
@@ -9,6 +9,55 @@
 		'wp-admin-bar-ab-new-post': 'write_button',
 		'wp-admin-bar-my-account': 'my_account',
 		'wp-admin-bar-notes': 'notifications',
+		//my sites - top items
+		'wp-admin-bar-switch-site': 'my_sites_switch_site',
+		'wp-admin-bar-blog-info': 'my_sites_blog_info',
+		'wp-admin-bar-site-view': 'my_sites_view_site',
+		'wp-admin-bar-blog-stats': 'my_sites_blog_stats',
+		'wp-admin-bar-activity': 'my_sites_activity',
+		'wp-admin-bar-plan': 'my_sites_plan',
+		'wp-admin-bar-plan-badge': 'my_sites_plan_badge',
+		//my sites - manage
+		'wp-admin-bar-edit-page': 'my_sites_manage_site_pages',
+		'wp-admin-bar-new-page-badge': 'my_sites_manage_add_page',
+		'wp-admin-bar-edit-post': 'my_sites_manage_blog_posts',
+		'wp-admin-bar-new-post-badge': 'my_sites_manage_add_new_post',
+		'wp-admin-bar-edit-attachment': 'my_sites_manage_media',
+		'wp-admin-bar-new-attachment-badge': 'my_sites_manage_add_media',
+		'wp-admin-bar-comments': 'my_sites_manage_comments',
+		'wp-admin-bar-edit-testimonial': 'my_sites_manage_testimonials',
+		'wp-admin-bar-new-testimonial': 'my_sites_manage_add_testimonial',
+		'wp-admin-bar-edit-portfolio': 'my_sites_manage_portfolio',
+		'wp-admin-bar-new-portfolio': 'my_sites_manage_add_portfolio',
+		//my sites - personalize
+		'wp-admin-bar-themes': 'my_sites_personalize_themes',
+		'wp-admin-bar-cmz': 'my_sites_personalize_themes_customize',
+		//my sites - configure
+		'wp-admin-bar-sharing': 'my_sites_configure_sharing',
+		'wp-admin-bar-people': 'my_sites_configure_people',
+		'wp-admin-bar-people-add': 'my_sites_configure_people_add_button',
+		'wp-admin-bar-plugins': 'my_sites_configure_plugins',
+		'wp-admin-bar-plugins-add': 'my_sites_configure_manage_plugins',
+		'wp-admin-bar-blog-settings': 'my_sites_configure_settings',
+		//reader
+		'wp-admin-bar-followed-sites': 'reader_followed_sites',
+		'wp-admin-bar-reader-followed-sites-manage': 'reader_manage_followed_sites',
+		'wp-admin-bar-discover-discover': 'reader_discover',
+		'wp-admin-bar-discover-search': 'reader_search',
+		'wp-admin-bar-discover-recommended-blogs': 'reader_recommendations',
+		'wp-admin-bar-my-activity-my-likes': 'reader_my_likes',
+		//account
+		'wp-admin-bar-user-info': 'my_account_user_name',
+		// account - profile
+		'wp-admin-bar-my-profile': 'my_account_profile_my_profile',
+		'wp-admin-bar-account-settings': 'my_account_profile_account_settings',
+		'wp-admin-bar-billing': 'my_account_profile_manage_purchases',
+		'wp-admin-bar-security': 'my_account_profile_security',
+		'wp-admin-bar-notifications': 'my_account_profile_notifications',
+		//account - special
+		'wp-admin-bar-get-apps': 'my_account_special_get_apps',
+		'wp-admin-bar-next-steps': 'my_account_special_next_steps',
+		'wp-admin-bar-help': 'my_account_special_help',
 	};
 
 	var notesTracksEvents = {
diff --git a/sync/class.jetpack-sync-module-users.php b/sync/class.jetpack-sync-module-users.php
index e74d7116c6328..f1cb47325c9bd 100644
--- a/sync/class.jetpack-sync-module-users.php
+++ b/sync/class.jetpack-sync-module-users.php
@@ -55,6 +55,7 @@ public function init_listeners( $callable ) {
 		add_action( 'jetpack_wp_login', $callable, 10, 3 );
 
 		add_action( 'wp_logout', $callable, 10, 0 );
+		add_action( 'wp_masterbar_logout', $callable, 10, 0 );
 
 		// Add on init
 		add_filter( 'jetpack_sync_before_enqueue_jetpack_sync_add_user', array( $this, 'expand_action' ) );