diff --git a/classes/gateways/class.pmprogateway_stripe.php b/classes/gateways/class.pmprogateway_stripe.php
index fcccbd5e2..bab2718de 100644
--- a/classes/gateways/class.pmprogateway_stripe.php
+++ b/classes/gateways/class.pmprogateway_stripe.php
@@ -1611,6 +1611,7 @@ static function pmpro_checkout_before_change_membership_level( $user_id, $morder
 			if (
 				empty( $level->trial_limit ) && // Check if there is a trial period.
 				$filtered_trial_period_days === $unfiltered_trial_period_days && // Check if the trial period is the same as the filtered trial period.
+				empty( $level->profile_start_date ) && // Check if the profile start date set directly on the level is empty.
 				( ! empty( $initial_payment_amount ) && $initial_payment_amount === $recurring_payment_amount ) // Check if the initial payment and recurring payment prices are the same.
 				) {
 				// We can combine the initial payment and the recurring payment.
diff --git a/includes/checkout.php b/includes/checkout.php
index f5c03f1fb..e2dc93c25 100644
--- a/includes/checkout.php
+++ b/includes/checkout.php
@@ -15,8 +15,14 @@ function pmpro_calculate_profile_start_date( $order, $date_format, $filter = tru
 	// Get the checkout level.
 	$level = $order->getMembershipLevelAtCheckout();
 
-	// Calculate the profile start date.
-	$profile_start_date = date_i18n( 'Y-m-d H:i:s', strtotime( '+ ' . $level->cycle_number . ' ' . $level->cycle_period ) );
+	// If the level already has a profile start date set, use it. Otherwise, calculate it based on the cycle number and period.
+	if ( ! empty( $level->profile_start_date ) ) {
+		// Use the profile start date that is already set.
+		$profile_start_date = date_i18n( 'Y-m-d H:i:s', strtotime( $level->profile_start_date ) );
+	} else {
+		// Calculate the profile start date based on the cycle number and period.
+		$profile_start_date = date_i18n( 'Y-m-d H:i:s', strtotime( '+ ' . $level->cycle_number . ' ' . $level->cycle_period ) );
+	}
 
 	// Filter the profile start date if needed.
 	if ( $filter ) {
@@ -28,13 +34,14 @@ function pmpro_calculate_profile_start_date( $order, $date_format, $filter = tru
 		 * to use that format in case we update this code in the future.
 		 *
 		 * @since 1.4
+		 * @deprecated TBD Set the 'profile_start_date' property on the checkout level object instead.
 		 *
 		 * @param string $profile_start_date The profile start date in UTC YYYY-MM-DD HH:MM:SS format.
 		 * @param MemberOrder $order         The order that the profile start date is being calculated for.
 		 *
 		 * @return string The profile start date in UTC YYYY-MM-DD HH:MM:SS format.
 		 */
-		$profile_start_date = apply_filters( 'pmpro_profile_start_date', $profile_start_date, $order );
+		$profile_start_date = apply_filters_deprecated( 'pmpro_profile_start_date', array( $profile_start_date, $order ), 'TBD' );
 	}
 
 	// Convert $profile_start_date to correct format.