diff --git a/projects/packages/jitm/changelog/add-jitm-sideload-backup-plugin b/projects/packages/jitm/changelog/add-jitm-sideload-backup-plugin
new file mode 100644
index 000000000000..cff1da4a8e0b
--- /dev/null
+++ b/projects/packages/jitm/changelog/add-jitm-sideload-backup-plugin
@@ -0,0 +1,4 @@
+Significance: minor
+Type: added
+
+Adds filters to allow sideloading of the Jetpack Backup plugin through JITMs.
diff --git a/projects/packages/jitm/composer.json b/projects/packages/jitm/composer.json
index 7970580b3afc..05f75e7f3273 100644
--- a/projects/packages/jitm/composer.json
+++ b/projects/packages/jitm/composer.json
@@ -67,7 +67,7 @@
 			"link-template": "https://github.com/Automattic/jetpack-jitm/compare/v${old}...v${new}"
 		},
 		"branch-alias": {
-			"dev-master": "2.0.x-dev"
+			"dev-master": "2.1.x-dev"
 		}
 	}
 }
diff --git a/projects/packages/jitm/src/class-jitm.php b/projects/packages/jitm/src/class-jitm.php
index d77cc3aae6a6..7f7f6333ea77 100644
--- a/projects/packages/jitm/src/class-jitm.php
+++ b/projects/packages/jitm/src/class-jitm.php
@@ -20,7 +20,7 @@
  */
 class JITM {
 
-	const PACKAGE_VERSION = '2.0.8';
+	const PACKAGE_VERSION = '2.1.0-alpha';
 
 	/**
 	 * The configuration method that is called from the jetpack-config package.
diff --git a/projects/packages/jitm/src/class-post-connection-jitm.php b/projects/packages/jitm/src/class-post-connection-jitm.php
index 3d2bbc60f194..8a2d1a2684f8 100644
--- a/projects/packages/jitm/src/class-post-connection-jitm.php
+++ b/projects/packages/jitm/src/class-post-connection-jitm.php
@@ -161,6 +161,40 @@ public static function jitm_jetpack_creative_mail_activate() {
 		);
 	}
 
+	/**
+	 * A special filter used in the CTA of a JITM offering to install the Jetpack Backup plugin.
+	 *
+	 * @return string The new CTA
+	 */
+	public static function jitm_jetpack_backup_install() {
+		return wp_nonce_url(
+			add_query_arg(
+				array(
+					'jetpack-backup-action' => 'install',
+				),
+				admin_url( 'admin.php?page=jetpack' )
+			),
+			'jetpack-backup-install'
+		);
+	}
+
+	/**
+	 * A special filter used in the CTA of a JITM offering to activate the Jetpack Backup plugin.
+	 *
+	 * @return string The new CTA
+	 */
+	public static function jitm_jetpack_backup_activate() {
+		return wp_nonce_url(
+			add_query_arg(
+				array(
+					'jetpack-backup-action' => 'activate',
+				),
+				admin_url( 'admin.php?page=jetpack' )
+			),
+			'jetpack-backup-install'
+		);
+	}
+
 	/**
 	 * This is an entire admin notice dedicated to messaging and handling of the case where a user is trying to delete
 	 * the connection owner.
@@ -366,6 +400,10 @@ public function get_messages( $message_path, $query, $full_jp_logo_exists ) {
 		add_filter( 'jitm_jetpack_creative_mail_install', array( $this, 'jitm_jetpack_creative_mail_install' ) );
 		add_filter( 'jitm_jetpack_creative_mail_activate', array( $this, 'jitm_jetpack_creative_mail_activate' ) );
 
+		// Jetpack Backup.
+		add_filter( 'jitm_jetpack_backup_install', array( $this, 'jitm_jetpack_backup_install' ) );
+		add_filter( 'jitm_jetpack_backup_activate', array( $this, 'jitm_jetpack_backup_activate' ) );
+
 		$user = wp_get_current_user();
 
 		// Unauthenticated or invalid requests just bail.
diff --git a/projects/plugins/jetpack/3rd-party/3rd-party.php b/projects/plugins/jetpack/3rd-party/3rd-party.php
index dc84bba3d41b..c8c6dd8d768a 100644
--- a/projects/plugins/jetpack/3rd-party/3rd-party.php
+++ b/projects/plugins/jetpack/3rd-party/3rd-party.php
@@ -24,6 +24,7 @@ function load_3rd_party() {
 		'class-jetpack-crm-data.php',
 		'class-jetpack-modules-overrides.php', // Special case. Tools to be used to override module settings.
 		'creative-mail.php',
+		'jetpack-backup.php',
 		'debug-bar.php',
 		'class-domain-mapping.php',
 		'crowdsignal.php',
diff --git a/projects/plugins/jetpack/3rd-party/jetpack-backup.php b/projects/plugins/jetpack/3rd-party/jetpack-backup.php
new file mode 100644
index 000000000000..ec1880b3a181
--- /dev/null
+++ b/projects/plugins/jetpack/3rd-party/jetpack-backup.php
@@ -0,0 +1,105 @@
+<?php
+/**
+ * Compatibility functions for the Jetpack Backup plugin.
+ * https://wordpress.org/plugins/jetpack-backup/
+ *
+ * @since 10.4
+ *
+ * @package automattic/jetpack
+ */
+
+namespace Automattic\Jetpack\Jetpack_Backup;
+
+if ( ! defined( 'ABSPATH' ) ) {
+	exit;
+}
+
+const PLUGIN_SLUG = 'jetpack-backup';
+const PLUGIN_FILE = 'jetpack-backup/jetpack-backup.php';
+
+add_action( 'admin_notices', __NAMESPACE__ . '\error_notice' );
+add_action( 'admin_init', __NAMESPACE__ . '\try_install' );
+
+/**
+ * Verify the intent to install Jetpack Backup, and kick off installation.
+ *
+ * This works in tandem with a JITM set up in the JITM package.
+ */
+function try_install() {
+	if ( ! isset( $_GET['jetpack-backup-action'] ) ) {
+		return;
+	}
+
+	check_admin_referer( 'jetpack-backup-install' );
+
+	$result = false;
+	// If the plugin install fails, redirect to plugin install page pre-populated with jetpack-backup search term.
+	$redirect_on_error = admin_url( 'plugin-install.php?s=jetpack-backup&tab=search&type=term' );
+
+	// Attempt to install and activate the plugin.
+	if ( current_user_can( 'activate_plugins' ) ) {
+		switch ( $_GET['jetpack-backup-action'] ) {
+			case 'install':
+				$result = install_and_activate();
+				break;
+			case 'activate':
+				$result = activate();
+				break;
+		}
+	}
+
+	if ( $result ) {
+		/** This action is already documented in _inc/lib/class.core-rest-api-endpoints.php */
+		do_action( 'jetpack_activated_plugin', PLUGIN_FILE, 'jitm' );
+		$redirect = admin_url( 'admin.php?page=jetpack-backup' );
+	} else {
+		$redirect = add_query_arg( 'jetpack-backup-install-error', true, $redirect_on_error );
+	}
+
+	wp_safe_redirect( $redirect );
+
+	exit;
+}
+
+/**
+ * Install and activate the Jetpack Backup plugin.
+ *
+ * @return bool result of installation
+ */
+function install_and_activate() {
+	jetpack_require_lib( 'plugins' );
+	$result = \Jetpack_Plugins::install_and_activate_plugin( PLUGIN_SLUG );
+
+	if ( is_wp_error( $result ) ) {
+		return false;
+	} else {
+		return true;
+	}
+}
+
+/**
+ * Activate the Jetpack Backup plugin.
+ *
+ * @return bool result of activation
+ */
+function activate() {
+	$result = activate_plugin( PLUGIN_FILE );
+
+	// Activate_plugin() returns null on success.
+	return is_null( $result );
+}
+
+/**
+ * Notify the user that the installation of Jetpack Backup failed.
+ */
+function error_notice() {
+	if ( empty( $_GET['jetpack-backup-install-error'] ) ) { // phpcs:ignore WordPress.Security.NonceVerification.Recommended
+		return;
+	}
+
+	?>
+	<div class="notice notice-error is-dismissible">
+		<p><?php esc_html_e( 'There was an error installing Jetpack Backup. Please try again.', 'jetpack' ); ?></p>
+	</div>
+	<?php
+}
diff --git a/projects/plugins/jetpack/changelog/add-jitm-sideload-backup-plugin b/projects/plugins/jetpack/changelog/add-jitm-sideload-backup-plugin
new file mode 100644
index 000000000000..cd6e1f2b3b34
--- /dev/null
+++ b/projects/plugins/jetpack/changelog/add-jitm-sideload-backup-plugin
@@ -0,0 +1,4 @@
+Significance: minor
+Type: compat
+
+Jetpack Backup: Add considtions that allow sideloading of Jetpack Backup plugin via JITMs.
diff --git a/projects/plugins/jetpack/changelog/add-jitm-sideload-backup-plugin#2 b/projects/plugins/jetpack/changelog/add-jitm-sideload-backup-plugin#2
new file mode 100644
index 000000000000..1eaea6a769e8
--- /dev/null
+++ b/projects/plugins/jetpack/changelog/add-jitm-sideload-backup-plugin#2
@@ -0,0 +1,4 @@
+Significance: patch
+Type: other
+
+Updated package dependencies.
diff --git a/projects/plugins/jetpack/composer.json b/projects/plugins/jetpack/composer.json
index 26824bd96412..17986aae2699 100644
--- a/projects/plugins/jetpack/composer.json
+++ b/projects/plugins/jetpack/composer.json
@@ -26,7 +26,7 @@
 		"automattic/jetpack-error": "1.3.x-dev",
 		"automattic/jetpack-heartbeat": "1.3.x-dev",
 		"automattic/jetpack-identity-crisis": "0.4.x-dev",
-		"automattic/jetpack-jitm": "2.0.x-dev",
+		"automattic/jetpack-jitm": "2.1.x-dev",
 		"automattic/jetpack-lazy-images": "2.0.x-dev",
 		"automattic/jetpack-licensing": "1.5.x-dev",
 		"automattic/jetpack-logo": "1.5.x-dev",
diff --git a/projects/plugins/jetpack/composer.lock b/projects/plugins/jetpack/composer.lock
index 19d1b1a051f9..69c866b13222 100644
--- a/projects/plugins/jetpack/composer.lock
+++ b/projects/plugins/jetpack/composer.lock
@@ -4,7 +4,7 @@
         "Read more about it at https://getcomposer.org/doc/01-basic-usage.md#installing-dependencies",
         "This file is @generated automatically"
     ],
-    "content-hash": "2145ecdbbd72d981d6667cd908f08e30",
+    "content-hash": "0be3edf262cfcfe2d899e5a136e8415a",
     "packages": [
         {
             "name": "automattic/jetpack-a8c-mc-stats",
@@ -870,7 +870,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/jitm",
-                "reference": "f72b99550e4c894841a5b070a518e677cd162a1f"
+                "reference": "54ee594e9f467dd332ed584d435cf2c0d4e42a6b"
             },
             "require": {
                 "automattic/jetpack-a8c-mc-stats": "^1.4",
@@ -900,7 +900,7 @@
                     "link-template": "https://github.com/Automattic/jetpack-jitm/compare/v${old}...v${new}"
                 },
                 "branch-alias": {
-                    "dev-master": "2.0.x-dev"
+                    "dev-master": "2.1.x-dev"
                 }
             },
             "autoload": {