diff --git a/changelog/add-woopay-direct-checkout-eligibility-flag b/changelog/add-woopay-direct-checkout-eligibility-flag
new file mode 100644
index 00000000000..dc736bf3648
--- /dev/null
+++ b/changelog/add-woopay-direct-checkout-eligibility-flag
@@ -0,0 +1,4 @@
+Significance: minor
+Type: add
+
+Add WooPay direct checkout flow behind a server-side feature flag.
diff --git a/includes/class-wc-payments-features.php b/includes/class-wc-payments-features.php
index 715b38b2872..57dbad4a32f 100644
--- a/includes/class-wc-payments-features.php
+++ b/includes/class-wc-payments-features.php
@@ -262,7 +262,11 @@ public static function is_woopay_first_party_auth_enabled() {
 	 * @return bool
 	 */
 	public static function is_woopay_direct_checkout_enabled() {
-		return '1' === get_option( self::WOOPAY_DIRECT_CHECKOUT_FLAG_NAME, '0' ) && self::is_woopay_first_party_auth_enabled();
+		$account_cache                   = WC_Payments::get_database_cache()->get( WCPay\Database_Cache::ACCOUNT_KEY, true );
+		$is_direct_checkout_eligible     = is_array( $account_cache ) && ( $account_cache['platform_direct_checkout_eligible'] ?? false );
+		$is_direct_checkout_flag_enabled = '1' === get_option( self::WOOPAY_DIRECT_CHECKOUT_FLAG_NAME, '0' );
+
+		return ( $is_direct_checkout_eligible || $is_direct_checkout_flag_enabled ) && self::is_woopay_first_party_auth_enabled();
 	}
 
 	/**