diff --git a/tests/vip-jetpack/connection-pilot/test-class-jetpack-connection-pilot.php b/tests/vip-jetpack/connection-pilot/test-class-jetpack-connection-pilot.php
index a16ff95fae..02f587b84a 100644
--- a/tests/vip-jetpack/connection-pilot/test-class-jetpack-connection-pilot.php
+++ b/tests/vip-jetpack/connection-pilot/test-class-jetpack-connection-pilot.php
@@ -20,46 +20,57 @@ protected static function getMethod( $name ) {
 	/**
 	 * @group jetpack-required
 	 * @preserveGlobalState disabled
-	 * @dataProvider get_test_data__update_backoff_factor
+	 * @dataProvider get_test_data__update_heartbeat_on_failure
 	 */
-	public function test__update_backoff_factor( ?int $backoff_factor, int $expected ) {
-		$option = array(
-			'site_url'        => get_site_url(),
-			'hashed_site_url' => md5( get_site_url() ),
-			'cache_site_id'   => (int) \Jetpack_Options::get_option( 'id', - 1 ),
-			'timestamp'       => time(),
-			'backoff_factor'  => $backoff_factor,
-		);
-		update_option( 'vip_jetpack_connection_pilot_heartbeat', $option, false );
-
-		$cp                    = Connection_Pilot::instance();
-		$update_backoff_factor = self::getMethod( 'update_backoff_factor' );
-		$update_backoff_factor->invoke( $cp );
-
-		$option = get_option( 'vip_jetpack_connection_pilot_heartbeat' );
-		$this->assertEquals( $expected, $option['backoff_factor'] );
+	public function test__update_heartbeat_on_failure( ?int $backoff_factor, int $expected_backoff, int $failed_attempts ) {
+		$last_failure = time() - 1000;
+
+		$this->set_heartbeat( [
+			'site_url'          => 'example.com',
+			'backoff_factor'    => $backoff_factor,
+			'failed_attempts'   => $failed_attempts,
+			'failure_timestamp' => $last_failure,
+		] );
+
+		$connection_pilot      = Connection_Pilot::instance();
+		$update_backoff_factor = self::getMethod( 'update_heartbeat_on_failure' );
+		$update_backoff_factor->invoke( $connection_pilot );
+
+		$option = $this->get_heartbeat();
+		$this->assertEquals( $expected_backoff, $option['backoff_factor'] );
+		$this->assertEquals( $failed_attempts + 1, $option['failed_attempts'] );
+		$this->assertTrue( $option['failure_timestamp'] > $last_failure );
+
+		// Doesn't change.
+		$this->assertEquals( 'example.com', $option['site_url'] );
 	}
 
 	/**
 	 * @group jetpack-required
 	 * @preserveGlobalState disabled
-	 * @dataProvider get_test_data__update_heartbeat
 	 */
-	public function test__update_heartbeat( ?int $backoff_factor, array $expected ) {
-		$cp               = Connection_Pilot::instance();
-		$update_heartbeat = self::getMethod( 'update_heartbeat' );
-
-		if ( $backoff_factor ) {
-			$update_heartbeat->invokeArgs( $cp, [ $backoff_factor ] );
-		} else {
-			$update_heartbeat->invoke( $cp );
-		}
+	public function test__update_heartbeat_on_success() {
+		$this->set_heartbeat( [
+			'site_url'          => 'example.com',
+			'cache_site_id'     => 22,
+			'backoff_factor'    => 24,
+			'failed_attempts'   => 2,
+			'failure_timestamp' => time() - 1000,
+		] );
 
-		$option = get_option( 'vip_jetpack_connection_pilot_heartbeat' );
-		$this->assertEquals( $expected['site_url'], $option['site_url'] );
-		$this->assertEquals( $expected['hashed_site_url'], $option['hashed_site_url'] );
-		$this->assertEquals( $expected['cache_site_id'], $option['cache_site_id'] );
-		$this->assertEquals( $expected['backoff_factor'], $option['backoff_factor'] );
+		$connection_pilot = Connection_Pilot::instance();
+		$update_heartbeat = self::getMethod( 'update_heartbeat_on_success' );
+		$update_heartbeat->invoke( $connection_pilot );
+
+		$option = $this->get_heartbeat();
+		$this->assertEquals( get_site_url(), $option['site_url'] );
+		$this->assertEquals( md5( get_site_url() ), $option['hashed_site_url'] );
+		$this->assertEquals( \Jetpack_Options::get_option( 'id', - 1 ), $option['cache_site_id'] );
+
+		// Resets.
+		$this->assertEquals( 0, $option['backoff_factor'] );
+		$this->assertEquals( 0, $option['failed_attempts'] );
+		$this->assertEquals( 0, $option['failure_timestamp'] );
 	}
 
 	/**
@@ -67,27 +78,22 @@ public function test__update_heartbeat( ?int $backoff_factor, array $expected )
 	 * @preserveGlobalState disabled
 	 * @dataProvider get_test_data__should_back_off
 	 */
-	public function test__should_back_off( ?int $backoff_factor, DateTime $dt, bool $expected ) {
+	public function test__should_back_off( ?int $backoff_factor, ?DateTime $failure_time, ?DateTime $legacy_time, int $failed_attempts, bool $expected ) {
 		if ( null !== $backoff_factor ) {
-			$option = array(
-				'site_url'        => get_site_url(),
-				'hashed_site_url' => md5( get_site_url() ),
-				'cache_site_id'   => (int) \Jetpack_Options::get_option( 'id', - 1 ),
-				'timestamp'       => $dt->getTimestamp(),
-				'backoff_factor'  => $backoff_factor,
-			);
-			update_option( 'vip_jetpack_connection_pilot_heartbeat', $option, false );
+			$this->set_heartbeat( [
+				'backoff_factor'    => $backoff_factor,
+				'failed_attempts'   => $failed_attempts,
+				'failure_timestamp' => null === $failure_time ? $legacy_time->getTimestamp() : $failure_time->getTimestamp(),
+			] );
 		}
 
-		$cp              = Connection_Pilot::instance();
-		$should_back_off = self::getMethod( 'should_back_off' );
-
-		$result = $should_back_off->invoke( $cp );
+		$connection_pilot = Connection_Pilot::instance();
+		$should_back_off  = self::getMethod( 'should_back_off' );
 
-		$this->assertEquals( $expected, $result );
+		$this->assertEquals( $expected, $should_back_off->invoke( $connection_pilot ) );
 	}
 
-	public function get_test_data__update_backoff_factor() {
+	public function get_test_data__update_heartbeat_on_failure() {
 		$connection_pilot = Connection_Pilot::instance();
 		$increments       = $connection_pilot::BACKOFF_INCREMENTS;
 		$max_increment    = $connection_pilot::MAX_BACKOFF_FACTOR;
@@ -95,61 +101,53 @@ public function get_test_data__update_backoff_factor() {
 		$test_data = [];
 		foreach ( $increments as $key => $increment ) {
 			if ( isset( $increments[ $key + 1 ] ) ) {
-				$test_data[ 'increment_' . $key ] = [ $increment, $increments[ $key + 1 ] ];
+				$test_data[ 'increment_' . $key ] = [ $increment, $increments[ $key + 1 ], $key ];
 			}
 		}
 
-		$test_data['null']     = [ null, $increments[0] ];
-		$test_data['zero']     = [ 0, $increments[0] ];
-		$test_data['max']      = [ $max_increment, $max_increment ];
-		$test_data['over_max'] = [ $max_increment + 1000, $max_increment ];
+		$test_data['null']     = [ null, $increments[0], 1 ];
+		$test_data['zero']     = [ 0, $increments[0], 2 ];
+		$test_data['max']      = [ $max_increment, $max_increment, 3 ];
+		$test_data['over_max'] = [ $max_increment + 1000, $max_increment, 4 ];
 
 		return $test_data;
 	}
 
-	public function get_test_data__update_heartbeat() {
+	public function get_test_data__should_back_off() {
+		$connection_pilot = Connection_Pilot::instance();
+		$max_retries      = $connection_pilot::MAX_RETRIES;
+
+		// [ current backoff factor, last failure's timestamp, legacy timestamp, failed attempts, expected result ]
 		return [
-			'null' => [
-				null,
-				array(
-					'site_url'        => get_site_url(),
-					'hashed_site_url' => md5( get_site_url() ),
-					'cache_site_id'   => (int) \Jetpack_Options::get_option( 'id', - 1 ),
-					'timestamp'       => time(),
-					'backoff_factor'  => 0,
-				),
-			],
-			'zero' => [
-				0,
-				array(
-					'site_url'        => get_site_url(),
-					'hashed_site_url' => md5( get_site_url() ),
-					'cache_site_id'   => (int) \Jetpack_Options::get_option( 'id', - 1 ),
-					'timestamp'       => time(),
-					'backoff_factor'  => 0,
-				),
-			],
-			'one'  => [
-				1,
-				array(
-					'site_url'        => get_site_url(),
-					'hashed_site_url' => md5( get_site_url() ),
-					'cache_site_id'   => (int) \Jetpack_Options::get_option( 'id', - 1 ),
-					'timestamp'       => time(),
-					'backoff_factor'  => 1,
-				),
-			],
+			'null'                     => [ null, new DateTime(), null, 0, false ],
+			'zero'                     => [ 0, new DateTime(), null, 0, false ],
+			'one-hour-true'            => [ 1, new DateTime(), null, 0, true ],
+			'one-hour-false'           => [ 1, ( new DateTime() )->modify( '-2 hours' ), null, 0, false ],
+			'eight-hours-true'         => [ 8, new DateTime(), null, 0, true ],
+			'eight-hours-false'        => [ 8, ( new DateTime() )->modify( '-9 hours' ), null, 0, false ],
+			'eight-hours-legacy-true'  => [ 8, null, new DateTime(), 0, true ],
+			'eight-hours-legacy-false' => [ 8, null, ( new DateTime() )->modify( '-9 hours' ), 0, false ],
+			'exceeds-retry-limit-true' => [ 8, ( new DateTime() )->modify( '-9 hours' ), null, $max_retries + 1, true ],
 		];
 	}
 
-	public function get_test_data__should_back_off() {
-		return [
-			'null'              => [ null, new DateTime(), false ],
-			'zero'              => [ 0, new DateTime(), false ],
-			'one-hour-true'     => [ 1, new DateTime(), true ],
-			'one-hour-false'    => [ 1, ( new DateTime() )->modify( '-2 hours' ), false ],
-			'eight-hours-true'  => [ 8, new DateTime(), true ],
-			'eight-hours-false' => [ 8, ( new DateTime() )->modify( '-9 hours' ), false ],
-		];
+	private function get_heartbeat() {
+		return get_option( 'vip_jetpack_connection_pilot_heartbeat', [] );
+	}
+
+	private function set_heartbeat( $values = [] ) {
+		$saved = update_option( 'vip_jetpack_connection_pilot_heartbeat', [
+			'site_url'          => $values['site_url'] ?? get_site_url(),
+			'hashed_site_url'   => isset( $values['site_url'] ) ? md5( $values['site_url'] ) : md5( get_site_url() ),
+			'cache_site_id'     => $values['cache_site_id'] ?? (int) \Jetpack_Options::get_option( 'id', - 1 ),
+			'success_timestamp' => $values['success_timestamp'] ?? time(),
+			'backoff_factor'    => $values['backoff_factor'] ?? 0,
+			'failed_attempts'   => $values['failed_attempts'] ?? 0,
+			'failure_timestamp' => $values['failure_timestamp'] ?? 0,
+		], false );
+
+		if ( ! $saved ) {
+			throw new Error( 'Failed to set heartbeat' );
+		}
 	}
 }
diff --git a/vip-jetpack/connection-pilot/class-jetpack-connection-pilot.php b/vip-jetpack/connection-pilot/class-jetpack-connection-pilot.php
index 6693ec8891..8e1a27e6dc 100644
--- a/vip-jetpack/connection-pilot/class-jetpack-connection-pilot.php
+++ b/vip-jetpack/connection-pilot/class-jetpack-connection-pilot.php
@@ -38,12 +38,12 @@ class Connection_Pilot {
 	 */
 	const BACKOFF_INCREMENTS = [ 1, 12, 24, 48, 96, self::MAX_BACKOFF_FACTOR ];
 
+	const MAX_RETRIES = 1;
+
 	/**
 	 * The healtcheck option's current data.
 	 *
-	 * Example: [ 'site_url' => 'https://example.go-vip.co', 'hashed_site_url' => '371a92eb7d5d63007db216dbd3b49187', 'cache_site_id' => 1234, 'timestamp' => 1555124370 ]
-	 *
-	 * @var mixed False if doesn't exist, else an array with the data shown above.
+	 * @var array Connection-related data.
 	 */
 	private $last_heartbeat;
 
@@ -120,7 +120,7 @@ public function run_connection_pilot() {
 
 		if ( true === $is_connected ) {
 			// Everything checks out. Update the heartbeat option and move on.
-			$this->update_heartbeat();
+			$this->update_heartbeat_on_success();
 
 			// Attempting Akismet connection given that Jetpack is connected.
 			$skip_akismet = defined( 'VIP_AKISMET_SKIP_LOAD' ) && VIP_AKISMET_SKIP_LOAD;
@@ -176,7 +176,7 @@ public function reconnect( $prev_connection_error = null ) {
 
 		// Reconnection failed.
 		$this->send_alert( 'Jetpack (re)connection attempt failed.' . $prev_connection_error_message, $connection_attempt );
-		$this->update_backoff_factor();
+		$this->update_heartbeat_on_failure();
 	}
 
 	/**
@@ -185,21 +185,32 @@ public function reconnect( $prev_connection_error = null ) {
 	 * @return bool True if CP should back off, false otherwise.
 	 */
 	private function should_back_off(): bool {
-		if ( ! empty( $this->last_heartbeat['backoff_factor'] ) && ! empty( $this->last_heartbeat['timestamp'] ) ) {
-			$backoff_factor = min( $this->last_heartbeat['backoff_factor'], self::MAX_BACKOFF_FACTOR );
+		if ( empty( $this->last_heartbeat['backoff_factor'] ) ) {
+			return false;
+		}
+
+		$backoff_factor = min( $this->last_heartbeat['backoff_factor'], self::MAX_BACKOFF_FACTOR );
+		if ( $backoff_factor <= 0 ) {
+			return false;
+		}
 
-			if ( $backoff_factor > 0 ) {
-				$seconds_elapsed = time() - $this->last_heartbeat['timestamp'];
-				$hours_elapsed   = $seconds_elapsed / HOUR_IN_SECONDS;
+		$failed_attempts = $this->last_heartbeat['failed_attempts'] ?? 0;
+		if ( $failed_attempts >= self::MAX_RETRIES + 1 ) {
+			return true;
+		}
 
-				if ( $backoff_factor > $hours_elapsed ) {
-					// We're still in the backoff period.
-					return true;
-				}
-			}
+		$last_failure = 0;
+		if ( isset( $this->last_heartbeat['failure_timestamp'] ) ) {
+			$last_failure = $this->last_heartbeat['failure_timestamp'];
+		} elseif ( ! empty( $this->last_heartbeat['timestamp'] ) ) {
+			// Backwards compat.
+			$last_failure = $this->last_heartbeat['timestamp'];
 		}
 
-		return false;
+		$hours_elapsed = ( time() - $last_failure ) / HOUR_IN_SECONDS;
+
+		// We'll backoff (not attempt reconnection) until the hours elapsed exceeds the backoff factor.
+		return $backoff_factor > $hours_elapsed;
 	}
 
 	/**
@@ -207,7 +218,7 @@ private function should_back_off(): bool {
 	 *
 	 * @return void
 	 */
-	private function update_backoff_factor(): void {
+	private function update_heartbeat_on_failure(): void {
 		$current_backoff_factor = isset( $this->last_heartbeat['backoff_factor'] ) ? (int) $this->last_heartbeat['backoff_factor'] : 0;
 
 		$new_backoff_factor = self::MAX_BACKOFF_FACTOR;
@@ -219,22 +230,32 @@ private function update_backoff_factor(): void {
 			}
 		}
 
-		$this->update_heartbeat( min( $new_backoff_factor, self::MAX_BACKOFF_FACTOR ) );
+		$new_heartbeat = $this->last_heartbeat;
+
+		// Just want to update some values, not overwrite them all.
+		$new_heartbeat['backoff_factor']    = $new_backoff_factor;
+		$new_heartbeat['failed_attempts']   = isset( $new_heartbeat['failed_attempts'] ) ? $new_heartbeat['failed_attempts'] + 1 : 1;
+		$new_heartbeat['failure_timestamp'] = time();
+
+		$update = update_option( self::HEARTBEAT_OPTION_NAME, $new_heartbeat, false );
+		if ( $update ) {
+			$this->last_heartbeat = $new_heartbeat;
+		}
 	}
 
-	/**
-	 * @param int $backoff_factor
-	 *
-	 * @return void
-	 */
-	private function update_heartbeat( int $backoff_factor = 0 ): void {
+	private function update_heartbeat_on_success(): void {
 		$option = array(
-			'site_url'        => get_site_url(),
-			'hashed_site_url' => md5( get_site_url() ), // used to protect against S&Rs/imports/syncs
-			'cache_site_id'   => (int) \Jetpack_Options::get_option( 'id', -1 ), // if no id can be retrieved, we'll fall back to -1
-			'timestamp'       => time(),
-			'backoff_factor'  => $backoff_factor,
+			'site_url'          => get_site_url(),
+			'hashed_site_url'   => md5( get_site_url() ), // used to protect against S&Rs/imports/syncs
+			'cache_site_id'     => (int) \Jetpack_Options::get_option( 'id', -1 ),
+			'success_timestamp' => time(),
 		);
+
+		// Reset these, as we're now successfully connected.
+		$option['backoff_factor']    = 0;
+		$option['failed_attempts']   = 0;
+		$option['failure_timestamp'] = 0;
+
 		$update = update_option( self::HEARTBEAT_OPTION_NAME, $option, false );
 		if ( $update ) {
 			$this->last_heartbeat = $option;
@@ -308,10 +329,10 @@ protected function send_alert( $message = '', $wp_error = null ) {
 		$message .= sprintf( ' Site: %s (ID %d).', get_site_url(), defined( 'VIP_GO_APP_ID' ) ? VIP_GO_APP_ID : 0 );
 
 		$last_heartbeat = $this->last_heartbeat;
-		if ( isset( $last_heartbeat['site_url'], $last_heartbeat['cache_site_id'], $last_heartbeat['timestamp'] ) && -1 != $last_heartbeat['cache_site_id'] ) {
+		if ( isset( $last_heartbeat['site_url'], $last_heartbeat['cache_site_id'], $last_heartbeat['success_timestamp'] ) && -1 != $last_heartbeat['cache_site_id'] ) {
 			$message .= sprintf(
 				' The last known connection was on %s UTC to Cache Site ID %d (%s).',
-				gmdate( 'F j, H:i', $last_heartbeat['timestamp'] ), $last_heartbeat['cache_site_id'], $last_heartbeat['site_url']
+				gmdate( 'F j, H:i', $last_heartbeat['success_timestamp'] ), $last_heartbeat['cache_site_id'], $last_heartbeat['site_url']
 			);
 		}
 
@@ -319,6 +340,10 @@ protected function send_alert( $message = '', $wp_error = null ) {
 			$message .= sprintf( ' Backoff Factor: %s hours.', $last_heartbeat['backoff_factor'] );
 		}
 
+		if ( isset( $last_heartbeat['failed_attempts'] ) && $last_heartbeat['failed_attempts'] > 0 ) {
+			$message .= sprintf( ' Failed Attempts: %s.', $last_heartbeat['failed_attempts'] );
+		}
+
 		if ( is_wp_error( $wp_error ) ) {
 			$message .= sprintf( ' Error: [%s] %s', $wp_error->get_error_code(), $wp_error->get_error_message() );
 		}