diff --git a/projects/plugins/jetpack/changelog/fix-premium-content-refresh-before-deny b/projects/plugins/jetpack/changelog/fix-premium-content-refresh-before-deny
new file mode 100644
index 000000000000..f9e5b9c5bb60
--- /dev/null
+++ b/projects/plugins/jetpack/changelog/fix-premium-content-refresh-before-deny
@@ -0,0 +1,4 @@
+Significance: patch
+Type: bugfix
+
+Paid Content block: refresh the subscription token on-demand when it contains a stale end_date, preventing lockout after a subscription renewal.
diff --git a/projects/plugins/jetpack/extensions/blocks/premium-content/_inc/subscription-service/class-abstract-token-subscription-service.php b/projects/plugins/jetpack/extensions/blocks/premium-content/_inc/subscription-service/class-abstract-token-subscription-service.php
index 36d653e5b2a8..dd5c8d821ce8 100644
--- a/projects/plugins/jetpack/extensions/blocks/premium-content/_inc/subscription-service/class-abstract-token-subscription-service.php
+++ b/projects/plugins/jetpack/extensions/blocks/premium-content/_inc/subscription-service/class-abstract-token-subscription-service.php
@@ -76,6 +76,103 @@ public function get_and_set_token_from_request() {
 		return $this->token_from_cookie();
 	}
 
+	/**
+	 * Attempt to refresh the current token against the WordPress.com refresh endpoint
+	 * and, on success, persist the fresh token in the cookie and return the decoded
+	 * payload.
+	 *
+	 * This is called when a subscriber has a JWT token whose subscription data is
+	 * stale (e.g. the cookie contains an old end_date from before a Stripe renewal).
+	 * The refresh endpoint accepts the existing token, re-queries billing, and
+	 * returns a fresh token reflecting current subscription state.
+	 *
+	 * @return array|null Decoded fresh payload on success, null on any failure.
+	 */
+	protected function refresh_token_payload() {
+		$current_token = $this->get_and_set_token_from_request();
+		if ( empty( $current_token ) ) {
+			return null;
+		}
+
+		$fresh_token = $this->fetch_refreshed_token( $current_token );
+		if ( empty( $fresh_token ) ) {
+			return null;
+		}
+
+		$fresh_payload = $this->decode_token( $fresh_token );
+		if ( empty( $fresh_payload ) ) {
+			return null;
+		}
+
+		$this->set_token_cookie( $fresh_token );
+		return $fresh_payload;
+	}
+
+	/**
+	 * POST the current token to the WordPress.com refresh endpoint and return a
+	 * fresh JWT string, or null on any failure.
+	 *
+	 * Response handling:
+	 *  - 200 with jwt_token → return fresh token string.
+	 *  - 400 (iat expired) / 401 (bad signature) → deterministic failure: clear the
+	 *    cookie so the visitor is routed through the normal auth flow on the next
+	 *    page load, and return null.
+	 *  - Any other non-200 / WP_Error / network timeout → transient failure: leave
+	 *    the cookie alone so a temporary endpoint outage does not mass-log-out
+	 *    subscribers, and return null.
+	 *
+	 * @param string $current_token The token to present for refresh.
+	 * @return string|null Fresh token string, or null on failure.
+	 */
+	protected function fetch_refreshed_token( $current_token ) {
+		$response = wp_remote_post(
+			self::REST_URL_ORIGIN . 'memberships/jwt/refresh',
+			array(
+				'timeout' => 10,
+				'headers' => array( 'Content-Type' => 'application/json' ),
+				'body'    => wp_json_encode(
+					array(
+						'token'   => $current_token,
+						'site_id' => $this->get_site_id(),
+					),
+					JSON_UNESCAPED_SLASHES
+				),
+			)
+		);
+
+		if ( is_wp_error( $response ) ) {
+			// Transient (network error / timeout). Leave cookie, deny.
+			return null;
+		}
+
+		$code = (int) wp_remote_retrieve_response_code( $response );
+
+		if ( 200 === $code ) {
+			$body = json_decode( wp_remote_retrieve_body( $response ), true );
+			if ( is_array( $body ) && ! empty( $body['token'] ) && is_string( $body['token'] ) ) {
+				return $body['token'];
+			}
+			// Malformed 200 — treat as transient.
+			return null;
+		}
+
+		if ( 400 === $code || 401 === $code ) {
+			// Deterministic failure — clear cookie so the subscriber re-authenticates.
+			self::clear_token_cookie();
+			return null;
+		}
+
+		// Any other status (5xx, 403, 404, etc.) — transient. Leave cookie, deny.
+		return null;
+	}
+
+	/**
+	 * Get the site ID for the current site.
+	 *
+	 * @return int
+	 */
+	abstract public function get_site_id();
+
 	/**
 	 * Get the token payload .
 	 *
@@ -156,6 +253,19 @@ public function visitor_can_view_content( $valid_plan_ids, $access_level ) {
 			);
 			$subscriptions      = (array) $payload['subscriptions'];
 			$is_paid_subscriber = static::validate_subscriptions( $valid_plan_ids, $subscriptions );
+
+			// If the token's subscriptions do not satisfy the required plans (e.g. the token has a
+			// stale end_date from before a subscription renewal), attempt a single refresh against
+			// the WordPress.com refresh endpoint before denying access.
+			if ( ! $is_paid_subscriber && ! empty( $valid_plan_ids ) ) {
+				$fresh_payload = $this->refresh_token_payload();
+				if ( ! empty( $fresh_payload ) ) {
+					$payload            = $fresh_payload;
+					$is_blog_subscriber = isset( $payload['blog_sub'] ) && self::BLOG_SUB_ACTIVE === $payload['blog_sub'];
+					$subscriptions      = isset( $payload['subscriptions'] ) ? (array) $payload['subscriptions'] : array();
+					$is_paid_subscriber = static::validate_subscriptions( $valid_plan_ids, $subscriptions );
+				}
+			}
 		}
 
 		$has_access = $this->user_has_access( $access_level, $is_blog_subscriber, $is_paid_subscriber, get_the_ID(), $subscriptions );
diff --git a/projects/plugins/jetpack/tests/php/extensions/blocks/premium-content/Jetpack_Premium_Content_Test.php b/projects/plugins/jetpack/tests/php/extensions/blocks/premium-content/Jetpack_Premium_Content_Test.php
index a5d1dfc10b9e..eef5ca96e362 100644
--- a/projects/plugins/jetpack/tests/php/extensions/blocks/premium-content/Jetpack_Premium_Content_Test.php
+++ b/projects/plugins/jetpack/tests/php/extensions/blocks/premium-content/Jetpack_Premium_Content_Test.php
@@ -22,6 +22,14 @@ class Jetpack_Premium_Content_Test extends WP_UnitTestCase {
 
 	protected $product_id = 1234;
 
+	/**
+	 * Optional override for the refresh endpoint response. If null, refresh is blocked
+	 * (simulates a transient 500). Tests can set this to control refresh behavior.
+	 *
+	 * @var array|null
+	 */
+	protected $refresh_response_override = null;
+
 	public function set_up() {
 		parent::set_up();
 		Jetpack_Subscriptions::init();
@@ -32,6 +40,8 @@ function () {
 				return new Test_Jetpack_Token_Subscription_Service();
 			}
 		);
+		// Block or mock refresh endpoint HTTP calls in tests.
+		add_filter( 'pre_http_request', array( $this, 'mock_refresh_endpoint' ), 10, 3 );
 	}
 
 	public function tear_down() {
@@ -39,9 +49,39 @@ public function tear_down() {
 		remove_all_filters( 'earn_get_user_subscriptions_for_site_id' );
 		remove_all_filters( 'jetpack_is_connection_ready' );
 		remove_all_filters( PAYWALL_FILTER );
+		remove_all_filters( 'pre_http_request' );
+		$this->refresh_response_override = null;
+		unset( $_COOKIE['wp-jp-premium-content-session'] );
 		parent::tear_down();
 	}
 
+	/**
+	 * Intercept HTTP calls to the refresh endpoint. Returns the override if set,
+	 * otherwise a transient 500 so refresh fails and existing behavior is preserved.
+	 *
+	 * @param mixed  $preempt Current preempt value.
+	 * @param array  $args    Request args.
+	 * @param string $url     Request URL.
+	 * @return mixed
+	 */
+	public function mock_refresh_endpoint( $preempt, $args, $url ) {
+		if ( false !== strpos( $url, 'memberships/jwt/refresh' ) ) {
+			if ( null !== $this->refresh_response_override ) {
+				return $this->refresh_response_override;
+			}
+			return array(
+				'response' => array(
+					'code'    => 500,
+					'message' => 'blocked in tests',
+				),
+				'body'     => '',
+				'headers'  => array(),
+				'cookies'  => array(),
+			);
+		}
+		return $preempt;
+	}
+
 	/**
 	 * Retrieves payload for JWT token
 	 *
@@ -195,4 +235,198 @@ public function test_access_check_current_visitor_can_access_passing_plan_id() {
 		$this->assertTrue( current_visitor_can_access( array( 'selectedPlanIds' => array( $plan_id ) ), array() ) );
 		$this->assertTrue( current_visitor_can_access( array(), (object) array( 'context' => array( 'premium-content/planIds' => array( $plan_id ) ) ) ) );
 	}
+
+	/**
+	 * Helper: build a mock 200 response from the refresh endpoint with a fresh JWT
+	 * containing a subscription that expires in the future.
+	 *
+	 * @return array
+	 */
+	private function build_refresh_success_response() {
+		$service       = subscription_service();
+		$fresh_payload = array(
+			'blog_sub'      => 'active',
+			'subscriptions' => array(
+				$this->product_id => array(
+					'status'     => 'active',
+					'end_date'   => time() + HOUR_IN_SECONDS,
+					'product_id' => $this->product_id,
+				),
+			),
+		);
+		$fresh_token   = JWT::encode( $fresh_payload, $service->get_key() );
+		return array(
+			'response' => array(
+				'code'    => 200,
+				'message' => 'OK',
+			),
+			'body'     => wp_json_encode( array( 'token' => $fresh_token ), JSON_UNESCAPED_SLASHES ),
+			'headers'  => array(),
+			'cookies'  => array(),
+		);
+	}
+
+	/**
+	 * When the token contains a stale (expired) end_date and the refresh endpoint
+	 * returns a fresh token with a valid subscription, access should be granted.
+	 * This covers the core renewal lockout bug.
+	 *
+	 * @return void
+	 */
+	public function test_refresh_before_deny_grants_access_on_successful_refresh() {
+		$users_plans        = $this->set_up_users_and_plans();
+		$paid_subscriber_id = $users_plans[2];
+		$plan_id            = $users_plans[3];
+
+		wp_set_current_user( $paid_subscriber_id );
+		// Stale token — end_date in the past.
+		$stale_payload = $this->get_payload( true, true, time() - HOUR_IN_SECONDS );
+		$this->set_returned_token( $stale_payload );
+
+		// Refresh endpoint returns a fresh token with a valid future end_date.
+		$this->refresh_response_override = $this->build_refresh_success_response();
+
+		$this->assertTrue( current_visitor_can_access( array( 'selectedPlanIds' => array( $plan_id ) ), array() ) );
+	}
+
+	/**
+	 * When the refresh endpoint returns 200 with a token whose subscriptions no
+	 * longer include the required plan (e.g. the subscription was cancelled),
+	 * access should be denied.
+	 *
+	 * @return void
+	 */
+	public function test_refresh_before_deny_denies_when_fresh_token_has_no_subscription() {
+		$users_plans        = $this->set_up_users_and_plans();
+		$paid_subscriber_id = $users_plans[2];
+		$plan_id            = $users_plans[3];
+
+		wp_set_current_user( $paid_subscriber_id );
+		$stale_payload = $this->get_payload( true, true, time() - HOUR_IN_SECONDS );
+		$this->set_returned_token( $stale_payload );
+
+		// Refresh returns a token with no subscriptions (cancelled).
+		$service                         = subscription_service();
+		$empty_token                     = JWT::encode(
+			array(
+				'blog_sub'      => 'active',
+				'subscriptions' => array(),
+			),
+			$service->get_key()
+		);
+		$this->refresh_response_override = array(
+			'response' => array(
+				'code'    => 200,
+				'message' => 'OK',
+			),
+			'body'     => wp_json_encode( array( 'token' => $empty_token ), JSON_UNESCAPED_SLASHES ),
+			'headers'  => array(),
+			'cookies'  => array(),
+		);
+
+		$this->assertFalse( current_visitor_can_access( array( 'selectedPlanIds' => array( $plan_id ) ), array() ) );
+	}
+
+	/**
+	 * When the refresh endpoint returns a transient failure (5xx), the original
+	 * stale token behavior should apply — access denied, cookie left alone.
+	 *
+	 * @return void
+	 */
+	public function test_refresh_before_deny_denies_on_transient_failure() {
+		$users_plans        = $this->set_up_users_and_plans();
+		$paid_subscriber_id = $users_plans[2];
+		$plan_id            = $users_plans[3];
+
+		wp_set_current_user( $paid_subscriber_id );
+		$stale_payload = $this->get_payload( true, true, time() - HOUR_IN_SECONDS );
+		$this->set_returned_token( $stale_payload );
+
+		// Refresh endpoint returns a 500 (the default mock behavior).
+		$this->refresh_response_override = array(
+			'response' => array(
+				'code'    => 500,
+				'message' => 'Server Error',
+			),
+			'body'     => '',
+			'headers'  => array(),
+			'cookies'  => array(),
+		);
+
+		$this->assertFalse( current_visitor_can_access( array( 'selectedPlanIds' => array( $plan_id ) ), array() ) );
+	}
+
+	/**
+	 * When the refresh endpoint returns 401 (bad signature), access is denied
+	 * AND the cookie is cleared so the subscriber re-authenticates on next visit.
+	 *
+	 * @return void
+	 */
+	public function test_refresh_before_deny_clears_cookie_on_unauthorized() {
+		$users_plans        = $this->set_up_users_and_plans();
+		$paid_subscriber_id = $users_plans[2];
+		$plan_id            = $users_plans[3];
+
+		wp_set_current_user( $paid_subscriber_id );
+		$stale_payload                            = $this->get_payload( true, true, time() - HOUR_IN_SECONDS );
+		$service                                  = subscription_service();
+		$token_string                             = JWT::encode( $stale_payload, $service->get_key() );
+		$_COOKIE['wp-jp-premium-content-session'] = $token_string;
+		$_GET['token']                            = $token_string;
+
+		$this->refresh_response_override = array(
+			'response' => array(
+				'code'    => 401,
+				'message' => 'Unauthorized',
+			),
+			'body'     => '',
+			'headers'  => array(),
+			'cookies'  => array(),
+		);
+
+		$this->assertFalse( current_visitor_can_access( array( 'selectedPlanIds' => array( $plan_id ) ), array() ) );
+		// Cookie should be cleared from $_COOKIE (cannot assert setcookie header from PHPUnit).
+		$this->assertArrayNotHasKey( 'wp-jp-premium-content-session', $_COOKIE );
+	}
+
+	/**
+	 * A WP_Error from the HTTP layer (e.g. network timeout) is treated as a
+	 * transient failure — deny access, leave cookie alone.
+	 *
+	 * @return void
+	 */
+	public function test_refresh_before_deny_treats_wp_error_as_transient() {
+		$users_plans        = $this->set_up_users_and_plans();
+		$paid_subscriber_id = $users_plans[2];
+		$plan_id            = $users_plans[3];
+
+		wp_set_current_user( $paid_subscriber_id );
+		$stale_payload = $this->get_payload( true, true, time() - HOUR_IN_SECONDS );
+		$this->set_returned_token( $stale_payload );
+
+		$this->refresh_response_override = new WP_Error( 'http_request_failed', 'cURL error 28: Operation timed out' );
+
+		$this->assertFalse( current_visitor_can_access( array( 'selectedPlanIds' => array( $plan_id ) ), array() ) );
+	}
+
+	/**
+	 * An active subscription with a future end_date should not trigger a refresh
+	 * at all — no HTTP call is made.
+	 *
+	 * @return void
+	 */
+	public function test_refresh_not_called_when_subscription_is_active() {
+		$users_plans        = $this->set_up_users_and_plans();
+		$paid_subscriber_id = $users_plans[2];
+		$plan_id            = $users_plans[3];
+
+		wp_set_current_user( $paid_subscriber_id );
+		$valid_payload = $this->get_payload( true, true, time() + HOUR_IN_SECONDS );
+		$this->set_returned_token( $valid_payload );
+
+		// If a refresh call were made, this override would throw — proving it is not called.
+		$this->refresh_response_override = new WP_Error( 'should_not_be_called', 'refresh should not be called for valid token' );
+
+		$this->assertTrue( current_visitor_can_access( array( 'selectedPlanIds' => array( $plan_id ) ), array() ) );
+	}
 }
diff --git a/projects/plugins/jetpack/tests/php/modules/subscriptions/Jetpack_Subscriptions_Test.php b/projects/plugins/jetpack/tests/php/modules/subscriptions/Jetpack_Subscriptions_Test.php
index b9a31c71a8fe..56fac5380e10 100644
--- a/projects/plugins/jetpack/tests/php/modules/subscriptions/Jetpack_Subscriptions_Test.php
+++ b/projects/plugins/jetpack/tests/php/modules/subscriptions/Jetpack_Subscriptions_Test.php
@@ -35,6 +35,9 @@ public function set_up() {
 		parent::set_up();
 		Jetpack_Subscriptions::init();
 		add_filter( 'jetpack_is_connection_ready', '__return_true' );
+		// Block refresh endpoint HTTP calls in tests by default so stale tokens deny
+		// access (existing test expectations). Individual refresh tests can override.
+		add_filter( 'pre_http_request', array( $this, 'block_refresh_endpoint' ), 10, 3 );
 		$this->set_up_users();
 	}
 
@@ -42,10 +45,36 @@ public function tear_down() {
 		// Clean up
 		remove_all_filters( 'earn_get_user_subscriptions_for_site_id' );
 		remove_all_filters( 'jetpack_is_connection_ready' );
+		remove_all_filters( 'pre_http_request' );
 
 		parent::tear_down();
 	}
 
+	/**
+	 * Default pre_http_request mock for the refresh endpoint — returns a 500 so that
+	 * refresh attempts fail transiently and the existing "expired subscription denies
+	 * access" expectations in the access matrix still hold.
+	 *
+	 * @param mixed  $preempt Current preempt value.
+	 * @param array  $args    Request args.
+	 * @param string $url     Request URL.
+	 * @return mixed
+	 */
+	public function block_refresh_endpoint( $preempt, $args, $url ) {
+		if ( false !== strpos( $url, 'memberships/jwt/refresh' ) ) {
+			return array(
+				'response' => array(
+					'code'    => 500,
+					'message' => 'blocked in tests',
+				),
+				'body'     => '',
+				'headers'  => array(),
+				'cookies'  => array(),
+			);
+		}
+		return $preempt;
+	}
+
 	private function set_up_users() {
 		$this->regular_non_subscriber_id = $this->factory->user->create(
 			array(