diff --git a/projects/packages/protect/changelog/update-protect-monitor-card-failure-states-JETPACK-2963 b/projects/packages/protect/changelog/update-protect-monitor-card-failure-states-JETPACK-2963
new file mode 100644
index 00000000000..d41913b1cc5
--- /dev/null
+++ b/projects/packages/protect/changelog/update-protect-monitor-card-failure-states-JETPACK-2963
@@ -0,0 +1,4 @@
+Significance: patch
+Type: changed
+
+Protect dashboard: Tell the Monitor card's failures apart, with a link to connect a WordPress.com account and a way to retry.
diff --git a/projects/packages/protect/routes/dashboard/sections/monitor/monitor-card.tsx b/projects/packages/protect/routes/dashboard/sections/monitor/monitor-card.tsx
index e37a6b8e46e..ff69d5b7732 100644
--- a/projects/packages/protect/routes/dashboard/sections/monitor/monitor-card.tsx
+++ b/projects/packages/protect/routes/dashboard/sections/monitor/monitor-card.tsx
@@ -1,9 +1,9 @@
 import apiFetch from '@wordpress/api-fetch';
 import { getSettings, gmdateI18n } from '@wordpress/date';
-import { useEffect, useState } from '@wordpress/element';
+import { useCallback, useEffect, useState } from '@wordpress/element';
 import { __, _n, sprintf } from '@wordpress/i18n';
 import { seen } from '@wordpress/icons';
-import { Skeleton, Stack, Text, VisuallyHidden } from '@wordpress/ui';
+import { Button, Link, Skeleton, Stack, Text, VisuallyHidden } from '@wordpress/ui';
 import { CardRow, ProtectCard } from '../../components/card';
 import TabLink from '../../components/tab-link';
 import isModuleActive from '../../data/is-module-active';
@@ -11,6 +11,9 @@ import type { MonitorContext, Uptime, UptimeDay } from './types';
 import type { CardStatus } from '../../components/card';
 import './style.scss';
 
+const UPTIME_PATH = '/jetpack/v4/protect-dashboard/uptime';
+const CONNECT_URL = 'admin.php?page=my-jetpack#/connection';
+
 /**
  * Text for one day's bar.
  *
@@ -46,6 +49,7 @@ function describeDay( day: UptimeDay ): string {
  *
  * @param available - Whether Monitor can run on this site.
  * @param active    - Whether Monitor is on.
+ * @param connected - Whether the user has a WordPress.com connection.
  * @param uptime    - The uptime response, once loaded.
  * @param failed    - Whether loading it failed.
  * @return The badge, if any.
@@ -53,6 +57,7 @@ function describeDay( day: UptimeDay ): string {
 function getStatus(
 	available: boolean,
 	active: boolean,
+	connected: boolean,
 	uptime: Uptime | null,
 	failed: boolean
 ): CardStatus | undefined {
@@ -62,6 +67,9 @@ function getStatus(
 	if ( ! active ) {
 		return { label: __( 'Off', 'jetpack-protect-pkg' ), intent: 'draft' };
 	}
+	if ( ! connected ) {
+		return { label: __( 'On', 'jetpack-protect-pkg' ), intent: 'none' };
+	}
 	if ( uptime?.isUp === true ) {
 		return { label: __( 'Operational', 'jetpack-protect-pkg' ), intent: 'stable' };
 	}
@@ -90,23 +98,36 @@ export default function MonitorCard( { state: monitor, settings, openTab }: Moni
 		available &&
 		! settings.isSaving( 'monitor' ) &&
 		isModuleActive( settings.settings, 'monitor', Boolean( monitor?.active ) );
+	const { refresh } = settings;
 	const [ uptime, setUptime ] = useState< Uptime | null >( null );
-	const [ failed, setFailed ] = useState( false );
+	const [ error, setError ] = useState< string | null >( null );
+	const [ retries, setRetries ] = useState( 0 );
+	const connected = Boolean( monitor?.userConnected ) && error !== 'not_connected';
+	const failed = connected && error !== null;
+	const canLoad = active && Boolean( monitor?.userConnected );
+	const retry = useCallback( () => setRetries( count => count + 1 ), [] );
 
 	useEffect( () => {
-		if ( ! active ) {
+		if ( ! canLoad ) {
 			return;
 		}
 		let current = true;
 		setUptime( null );
-		setFailed( false );
-		apiFetch< Uptime >( { path: '/jetpack/v4/protect-dashboard/uptime' } )
+		setError( null );
+		// A retry skips the failure the server remembers for a minute.
+		apiFetch< Uptime >( { path: retries ? `${ UPTIME_PATH }?retry=1` : UPTIME_PATH } )
 			.then( response => current && setUptime( response ) )
-			.catch( () => current && setFailed( true ) );
+			.catch( async ( e: { code?: string } ) => {
+				// Monitor was turned off elsewhere: re-read it so the card and its toggle show Off.
+				if ( e?.code === 'monitor_inactive' ) {
+					await refresh( [ 'monitor' ] );
+				}
+				return current && setError( e?.code ?? 'uptime_unavailable' );
+			} );
 		return () => {
 			current = false;
 		};
-	}, [ active ] );
+	}, [ canLoad, retries, refresh ] );
 
 	const days = uptime?.days;
 	const count = ( status: UptimeDay[ 'status' ] ) =>
@@ -144,26 +165,48 @@ export default function MonitorCard( { state: monitor, settings, openTab }: Moni
 		<ProtectCard
 			icon={ seen }
 			title={ __( 'Monitor', 'jetpack-protect-pkg' ) }
-			status={ getStatus( available, active, uptime, failed ) }
+			status={ getStatus( available, active, connected, uptime, failed ) }
 		>
 			<CardRow>
 				{ ! active && <Text variant="body-md">{ body }</Text> }
 				{ active && (
 					<Stack direction="column" gap="md">
-						<Text variant="body-md">
-							{ sprintf(
-								/* translators: %d is a number of days. */
-								__( 'Uptime, last %d days (UTC)', 'jetpack-protect-pkg' ),
-								days?.length ?? monitor?.uptimeDays ?? 0
-							) }
-						</Text>
-						{ failed && (
+						{ connected && (
 							<Text variant="body-md">
-								{ __( 'Uptime history is unavailable right now.', 'jetpack-protect-pkg' ) }
+								{ sprintf(
+									/* translators: %d is a number of days. */
+									__( 'Uptime, last %d days (UTC)', 'jetpack-protect-pkg' ),
+									days?.length ?? monitor?.uptimeDays ?? 0
+								) }
 							</Text>
 						) }
-						{ ! failed && ! days && <Skeleton className="jp-protect-uptime__skeleton" /> }
-						{ ! failed && days && (
+						{ ! connected && (
+							<>
+								<Text variant="body-md">
+									{ __(
+										'Your site is being monitored. Connect your WordPress.com account to see its uptime history.',
+										'jetpack-protect-pkg'
+									) }
+								</Text>
+								<Link href={ CONNECT_URL }>
+									{ __( 'Connect your account', 'jetpack-protect-pkg' ) }
+								</Link>
+							</>
+						) }
+						{ failed && (
+							<Stack direction="row" gap="sm" align="center">
+								<Text variant="body-md">
+									{ __( 'Uptime history is unavailable right now.', 'jetpack-protect-pkg' ) }
+								</Text>
+								<Button variant="minimal" size="compact" onClick={ retry }>
+									{ __( 'Try again', 'jetpack-protect-pkg' ) }
+								</Button>
+							</Stack>
+						) }
+						{ connected && ! failed && ! days && (
+							<Skeleton className="jp-protect-uptime__skeleton" />
+						) }
+						{ connected && ! failed && days && (
 							<>
 								<div className="jp-protect-uptime" aria-hidden="true">
 									{ days.map( day => (
diff --git a/projects/packages/protect/routes/dashboard/sections/monitor/test/monitor-card.test.tsx b/projects/packages/protect/routes/dashboard/sections/monitor/test/monitor-card.test.tsx
index cf3d8c391ba..ec52887f5bb 100644
--- a/projects/packages/protect/routes/dashboard/sections/monitor/test/monitor-card.test.tsx
+++ b/projects/packages/protect/routes/dashboard/sections/monitor/test/monitor-card.test.tsx
@@ -1,7 +1,9 @@
 import { render, screen } from '@testing-library/react';
+import userEvent from '@testing-library/user-event';
 import apiFetch from '@wordpress/api-fetch';
+import { useCallback, useState } from '@wordpress/element';
 import MonitorCard from '../monitor-card';
-import type { ProtectSettingsData } from '../../../data/use-protect-settings';
+import type { ProtectSettings, ProtectSettingsData } from '../../../data/use-protect-settings';
 import type { MonitorState, UptimeDay } from '../types';
 
 jest.mock( '@wordpress/api-fetch', () => ( { __esModule: true, default: jest.fn() } ) );
@@ -21,7 +23,14 @@ const renderCard = (
 	render(
 		<MonitorCard
 			state={ { available: true, active: true, uptimeDays: 40, userConnected: true, ...state } }
-			settings={ { settings: null, isSaving: () => false, ...settings } as ProtectSettingsData }
+			settings={
+				{
+					settings: null,
+					isSaving: () => false,
+					refresh: jest.fn(),
+					...settings,
+				} as ProtectSettingsData
+			}
 			openTab={ jest.fn() }
 		/>
 	);
@@ -61,15 +70,64 @@ describe( 'MonitorCard', () => {
 		expect( mockApiFetch ).not.toHaveBeenCalled();
 	} );
 
-	it( 'says the history is unavailable when it cannot be loaded', async () => {
-		mockApiFetch.mockRejectedValue( { code: 'not_connected' } );
+	it( 'offers a retry that skips the remembered failure when WordPress.com fails', async () => {
+		mockApiFetch.mockRejectedValueOnce( { code: 'uptime_unavailable' } );
+		mockApiFetch.mockResolvedValue( { days, isUp: true } );
 		renderCard();
 
 		await expect(
 			screen.findByText( 'Uptime history is unavailable right now.' )
 		).resolves.toBeInTheDocument();
 		expect( screen.getByText( 'Status unknown' ) ).toBeInTheDocument();
-		expect( screen.queryByRole( 'listitem' ) ).not.toBeInTheDocument();
+		await userEvent.click( screen.getByRole( 'button', { name: 'Try again' } ) );
+
+		await expect( screen.findByText( 'Operational' ) ).resolves.toBeInTheDocument();
+		expect( mockApiFetch ).toHaveBeenLastCalledWith( {
+			path: '/jetpack/v4/protect-dashboard/uptime?retry=1',
+		} );
+	} );
+
+	it.each( [
+		[ 'at page load', { userConnected: false }, 0 ],
+		[ 'since page load', {}, 1 ],
+	] )(
+		'points a user who is not connected %s to the connection page',
+		async ( _name, state, requests ) => {
+			mockApiFetch.mockRejectedValue( { code: 'not_connected' } );
+			renderCard( {}, state );
+
+			await expect(
+				screen.findByRole( 'link', { name: 'Connect your account' } )
+			).resolves.toHaveAttribute( 'href', 'admin.php?page=my-jetpack#/connection' );
+			expect( screen.getByText( 'On' ) ).toBeInTheDocument();
+			expect( screen.queryByText( /^Uptime, last/ ) ).not.toBeInTheDocument();
+			expect( screen.queryByRole( 'button', { name: 'Try again' } ) ).not.toBeInTheDocument();
+			expect( mockApiFetch ).toHaveBeenCalledTimes( requests );
+		}
+	);
+
+	it( 'shows Off when the server says Monitor was turned off elsewhere', async () => {
+		mockApiFetch.mockRejectedValue( { code: 'monitor_inactive' } );
+		const Card = () => {
+			const [ live, setLive ] = useState< ProtectSettings | null >( null );
+			const refresh = useCallback( async () => setLive( { monitor: false } ), [] );
+			return (
+				<MonitorCard
+					state={ { available: true, active: true, uptimeDays: 40, userConnected: true } }
+					settings={
+						{ settings: live, isSaving: () => false, refresh } as unknown as ProtectSettingsData
+					}
+					openTab={ jest.fn() }
+				/>
+			);
+		};
+		render( <Card /> );
+
+		await expect( screen.findByText( 'Off' ) ).resolves.toBeInTheDocument();
+		expect( screen.getByText( 'Turn on in Settings' ) ).toBeInTheDocument();
+		expect(
+			screen.queryByText( 'Uptime history is unavailable right now.' )
+		).not.toBeInTheDocument();
 	} );
 
 	it( 'waits for a Monitor save to finish before asking for uptime', () => {
diff --git a/projects/packages/protect/src/sections/class-monitor.php b/projects/packages/protect/src/sections/class-monitor.php
index 55187d4ed62..821474483f8 100644
--- a/projects/packages/protect/src/sections/class-monitor.php
+++ b/projects/packages/protect/src/sections/class-monitor.php
@@ -13,6 +13,7 @@
 use Automattic\Jetpack\Protect\Dashboard_Section;
 use Jetpack_Options;
 use WP_Error;
+use WP_REST_Request;
 use WP_REST_Server;
 
 if ( ! defined( 'ABSPATH' ) ) {
@@ -85,6 +86,13 @@ public function register_routes() {
 				'methods'             => WP_REST_Server::READABLE,
 				'callback'            => array( $this, 'get_uptime' ),
 				'permission_callback' => array( Dashboard::class, 'can_manage' ),
+				'args'                => array(
+					'retry' => array(
+						'description' => __( 'Ask WordPress.com again, even if it failed in the last minute.', 'jetpack-protect-pkg' ),
+						'type'        => 'boolean',
+						'default'     => false,
+					),
+				),
 			)
 		);
 	}
@@ -92,9 +100,10 @@ public function register_routes() {
 	/**
 	 * Daily uptime for the last UPTIME_DAYS days (oldest first) and the current status, from WordPress.com.
 	 *
+	 * @param WP_REST_Request|null $request The request; its `retry` flag skips a remembered failure.
 	 * @return array|WP_Error
 	 */
-	public function get_uptime() {
+	public function get_uptime( $request = null ) {
 		if ( ! Dashboard::get_module_state( 'monitor' )['active'] ) {
 			return new WP_Error( 'monitor_inactive', __( 'Downtime monitoring is off.', 'jetpack-protect-pkg' ), array( 'status' => 409 ) );
 		}
@@ -108,7 +117,7 @@ public function get_uptime() {
 		if ( is_array( $cached ) ) {
 			return $cached;
 		}
-		if ( 'failed' === $cached ) {
+		if ( 'failed' === $cached && ! ( $request && $request['retry'] ) ) {
 			return $this->unavailable_error();
 		}
 
diff --git a/projects/packages/protect/tests/php/Monitor_Test.php b/projects/packages/protect/tests/php/Monitor_Test.php
index c6a0c2cfe74..ca1cf672974 100644
--- a/projects/packages/protect/tests/php/Monitor_Test.php
+++ b/projects/packages/protect/tests/php/Monitor_Test.php
@@ -247,6 +247,18 @@ public function test_get_uptime_is_a_502_when_the_history_is_unusable_and_caches
 		$this->assertCount( $requests, $this->requests );
 	}
 
+	public function test_get_uptime_asks_wpcom_again_on_a_retry_despite_a_cached_failure() {
+		$this->uptime_response = self::json_response( array(), 500 );
+		$monitor               = new Monitor();
+		$monitor->get_uptime();
+		$this->uptime_response = self::json_response( array( '2026-10-01' => array( 'status' => 'up' ) ) );
+		$request               = new \WP_REST_Request( 'GET', '/jetpack/v4/protect-dashboard/uptime' );
+		$request->set_param( 'retry', true );
+
+		$this->assertInstanceOf( WP_Error::class, $monitor->get_uptime() );
+		$this->assertCount( 1, $monitor->get_uptime( $request )['days'] );
+	}
+
 	public function test_get_uptime_refuses_a_disconnected_user_even_with_a_warm_cache() {
 		$monitor = new Monitor();
 		$monitor->get_uptime();
diff --git a/projects/plugins/jetpack/changelog/update-protect-monitor-card-failure-states-JETPACK-2963 b/projects/plugins/jetpack/changelog/update-protect-monitor-card-failure-states-JETPACK-2963
new file mode 100644
index 00000000000..a911f33cb7a
--- /dev/null
+++ b/projects/plugins/jetpack/changelog/update-protect-monitor-card-failure-states-JETPACK-2963
@@ -0,0 +1,4 @@
+Significance: patch
+Type: other
+
+Protect: Tell the Monitor card's failures apart on the Protect dashboard, with a link to connect a WordPress.com account and a way to retry.