diff --git a/projects/packages/connection/changelog/fix-jetpack-sso-wpcom-classic b/projects/packages/connection/changelog/fix-jetpack-sso-wpcom-classic
new file mode 100644
index 0000000000000..8f406c00c798d
--- /dev/null
+++ b/projects/packages/connection/changelog/fix-jetpack-sso-wpcom-classic
@@ -0,0 +1,4 @@
+Significance: patch
+Type: removed
+
+SSO: Removed the ability to skip the automatic login if site uses the WP.com classic interface
diff --git a/projects/packages/connection/src/sso/class-sso.php b/projects/packages/connection/src/sso/class-sso.php
index 2c04f13c7820e..b1c69934c0d16 100644
--- a/projects/packages/connection/src/sso/class-sso.php
+++ b/projects/packages/connection/src/sso/class-sso.php
@@ -446,13 +446,6 @@ private function wants_to_login() {
 		return $wants_to_login;
 	}
 
-	/**
-	 * Checks to determine if the user has indicated they want to use the wp-admin interface.
-	 */
-	private function use_wp_admin_interface() {
-		return 'wp-admin' === get_option( 'wpcom_admin_interface' );
-	}
-
 	/**
 	 * Initialization for a SSO request.
 	 */
@@ -510,7 +503,7 @@ public function login_init() {
 			 * to the WordPress.com login page AND  that the request to wp-login.php
 			 * is not something other than login (Like logout!)
 			 */
-			if ( ! $this->use_wp_admin_interface() && Helpers::bypass_login_forward_wpcom() && $this->wants_to_login() ) {
+			if ( Helpers::bypass_login_forward_wpcom() && $this->wants_to_login() ) {
 				add_filter( 'allowed_redirect_hosts', array( Helpers::class, 'allowed_redirect_hosts' ) );
 				$reauth  = ! empty( $_GET['force_reauth'] ); // phpcs:ignore WordPress.Security.NonceVerification.Recommended
 				$sso_url = $this->get_sso_url_or_die( $reauth );
diff --git a/projects/plugins/wpcomsh/changelog/fix-jetpack-sso-wpcom-classic b/projects/plugins/wpcomsh/changelog/fix-jetpack-sso-wpcom-classic
new file mode 100644
index 0000000000000..0bab71346e03c
--- /dev/null
+++ b/projects/plugins/wpcomsh/changelog/fix-jetpack-sso-wpcom-classic
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+SSO: Automatic logic for Calypso users of classic sites
diff --git a/projects/plugins/wpcomsh/composer.json b/projects/plugins/wpcomsh/composer.json
index a242491ec9760..ad1e0de5a4658 100644
--- a/projects/plugins/wpcomsh/composer.json
+++ b/projects/plugins/wpcomsh/composer.json
@@ -127,7 +127,7 @@
 			"composer/installers": true,
 			"roots/wordpress-core-installer": true
 		},
-		"autoloader-suffix": "26841ac2064774301cbe06d174833bfc_wpcomshⓥ5_5_1_alpha"
+		"autoloader-suffix": "26841ac2064774301cbe06d174833bfc_wpcomshⓥ5_6_0_alpha"
 	},
 	"extra": {
 		"mirror-repo": "Automattic/wpcom-site-helper",
diff --git a/projects/plugins/wpcomsh/package.json b/projects/plugins/wpcomsh/package.json
index c8a90ec001440..58970450f0966 100644
--- a/projects/plugins/wpcomsh/package.json
+++ b/projects/plugins/wpcomsh/package.json
@@ -3,7 +3,7 @@
 	"name": "@automattic/jetpack-wpcomsh",
 	"description": "A helper for connecting WordPress.com sites to external host infrastructure.",
 	"homepage": "https://jetpack.com",
-	"version": "5.5.1-alpha",
+	"version": "5.6.0-alpha",
 	"bugs": {
 		"url": "https://github.com/Automattic/jetpack/labels/[Plugin] Wpcomsh"
 	},
diff --git a/projects/plugins/wpcomsh/wpcomsh.php b/projects/plugins/wpcomsh/wpcomsh.php
index 927e38334a506..b4fa84bbc9465 100644
--- a/projects/plugins/wpcomsh/wpcomsh.php
+++ b/projects/plugins/wpcomsh/wpcomsh.php
@@ -2,14 +2,14 @@
 /**
  * Plugin Name: WordPress.com Site Helper
  * Description: A helper for connecting WordPress.com sites to external host infrastructure.
- * Version: 5.5.1-alpha
+ * Version: 5.6.0-alpha
  * Author: Automattic
  * Author URI: http://automattic.com/
  *
  * @package wpcomsh
  */
 
-define( 'WPCOMSH_VERSION', '5.5.1-alpha' );
+define( 'WPCOMSH_VERSION', '5.6.0-alpha' );
 
 // If true, Typekit fonts will be available in addition to Google fonts
 add_filter( 'jetpack_fonts_enable_typekit', '__return_true' );
@@ -217,9 +217,29 @@ function wpcomsh_jetpack_sso_auth_cookie_expiration( $seconds ) {
 add_filter( 'jetpack_sso_auth_cookie_expiration', 'wpcomsh_jetpack_sso_auth_cookie_expiration' );
 
 /**
- * If a user is logged in to WordPress.com, log him in automatically to wp-login
+ * Determine if users who are already logged in to WordPress.com are automatically logged in to wp-admin.
  */
-add_filter( 'jetpack_sso_bypass_login_forward_wpcom', '__return_true' );
+function wpcomsh_bypass_jetpack_sso_login() {
+	/**
+	 * Sites with the classic interface:
+	 * - Automatic login if they come from Calypso.
+	 * - Otherwise we display the login form, so they can decide whether to use a WP.com account or a local account.
+	 */
+	if ( 'wp-admin' === get_option( 'wpcom_admin_interface' ) ) {
+		$calypso_domains = array(
+			'https://wordpress.com/',
+			'https://horizon.wordpress.com/',
+			'https://wpcalypso.wordpress.com/',
+			'http://calypso.localhost:3000/',
+			'http://127.0.0.1:41050/', // Desktop App.
+		);
+		return in_array( wp_get_referer(), $calypso_domains, true );
+	}
+
+	// Users of sites with the default interface are always logged in automatically.
+	return true;
+}
+add_filter( 'jetpack_sso_bypass_login_forward_wpcom', 'wpcomsh_bypass_jetpack_sso_login' );
 
 /**
  * Overwrite the default value of SSO "Match by Email" setting.