diff --git a/projects/packages/sync/changelog/update-sync-add-links-when-expanding-posts-in-before-send b/projects/packages/sync/changelog/update-sync-add-links-when-expanding-posts-in-before-send
new file mode 100644
index 0000000000000..dd77887df297a
--- /dev/null
+++ b/projects/packages/sync/changelog/update-sync-add-links-when-expanding-posts-in-before-send
@@ -0,0 +1,4 @@
+Significance: patch
+Type: changed
+
+Sync:Moved the add links part of the expand posts functionality in dedicated sync requests to before_send insetad of before_enqueue  
diff --git a/projects/packages/sync/src/class-package-version.php b/projects/packages/sync/src/class-package-version.php
index 83ee4058665aa..9a90505729922 100644
--- a/projects/packages/sync/src/class-package-version.php
+++ b/projects/packages/sync/src/class-package-version.php
@@ -12,7 +12,7 @@
  */
 class Package_Version {
 
-	const PACKAGE_VERSION = '3.1.3';
+	const PACKAGE_VERSION = '3.1.4-alpha';
 
 	const PACKAGE_SLUG = 'sync';
 
diff --git a/projects/packages/sync/src/modules/class-posts.php b/projects/packages/sync/src/modules/class-posts.php
index 0c087ceea6ded..1fd15afd5c2b9 100644
--- a/projects/packages/sync/src/modules/class-posts.php
+++ b/projects/packages/sync/src/modules/class-posts.php
@@ -227,6 +227,10 @@ public function init_full_sync_listeners( $callable ) {
 	 * @access public
 	 */
 	public function init_before_send() {
+
+		add_filter( 'jetpack_sync_before_send_jetpack_sync_save_post', array( $this, 'filter_jetpack_sync_before_send_jetpack_sync_save_post' ) );
+		add_filter( 'jetpack_sync_before_send_jetpack_published_post', array( $this, 'filter_jetpack_sync_before_send_jetpack_published_post' ) );
+
 		// meta.
 		add_filter( 'jetpack_sync_before_send_added_post_meta', array( $this, 'trim_post_meta' ) );
 		add_filter( 'jetpack_sync_before_send_updated_post_meta', array( $this, 'trim_post_meta' ) );
@@ -324,18 +328,6 @@ public function trim_post_meta( $args ) {
 		return array( $meta_id, $object_id, $meta_key, $meta_value );
 	}
 
-	/**
-	 * Process content before send.
-	 *
-	 * @param array $args Arguments of the `wp_insert_post` hook.
-	 *
-	 * @return array
-	 */
-	public function expand_jetpack_sync_save_post( $args ) {
-		list( $post_id, $post, $update, $previous_state ) = $args;
-		return array( $post_id, $this->filter_post_content_and_add_links( $post ), $update, $previous_state );
-	}
-
 	/**
 	 * Filter all blacklisted post types and add filtered post content.
 	 *
@@ -349,7 +341,7 @@ public function filter_jetpack_sync_before_enqueue_jetpack_sync_save_post( $args
 			return false;
 		}
 
-		return array( $post_id, $this->filter_post_content_and_add_links( $post ), $update, $previous_state );
+		return array( $post_id, $this->filter_post_content( $post ), $update, $previous_state );
 	}
 
 	/**
@@ -360,8 +352,32 @@ public function filter_jetpack_sync_before_enqueue_jetpack_sync_save_post( $args
 	 */
 	public function filter_jetpack_sync_before_enqueue_jetpack_published_post( $args ) {
 		list( $post_id, $flags, $post ) = $args;
+		if ( in_array( $post->post_type, Settings::get_setting( 'post_types_blacklist' ), true ) ) {
+			return false;
+		}
+		return array( $post_id, $flags, $this->filter_post_content( $post ) );
+	}
+
+	/**
+	 * Add filtered post content.
+	 *
+	 * @param array $args Hook arguments.
+	 * @return array Hook arguments.
+	 */
+	public function filter_jetpack_sync_before_send_jetpack_published_post( $args ) {
+		list( $post_id, $flags, $filtered_post ) = $args;
+		return array( $post_id, $flags, $this->add_links( $filtered_post ) );
+	}
 
-		return array( $post_id, $flags, $this->filter_post_content_and_add_links( $post ) );
+	/**
+	 * Add filtered post content.
+	 *
+	 * @param array $args Hook arguments.
+	 * @return array Hook arguments.
+	 */
+	public function filter_jetpack_sync_before_send_jetpack_sync_save_post( $args ) {
+		list( $post_id, $filtered_post, $update, $previous_state ) = $args;
+		return array( $post_id, $this->add_links( $filtered_post ), $update, $previous_state );
 	}
 
 	/**
@@ -451,11 +467,21 @@ public function add_embed() {
 	}
 
 	/**
-	 * Expands wp_insert_post to include filtered content
+	 * Expands wp_insert_post to include filtered content andd add links
 	 *
 	 * @param \WP_Post $post_object Post object.
 	 */
 	public function filter_post_content_and_add_links( $post_object ) {
+		$filtered_post = $this->filter_post_content( $post_object );
+		return $this->add_links( $filtered_post );
+	}
+
+	/**
+	 * Expands wp_insert_post to include filtered content
+	 *
+	 * @param \WP_Post $post_object Post object.
+	 */
+	public function filter_post_content( $post_object ) {
 		global $post;
 
 		// Used to restore the post global.
@@ -572,6 +598,27 @@ public function filter_post_content_and_add_links( $post_object ) {
 
 		$this->add_embed();
 
+		$filtered_post = $post;
+
+		// Restore global post.
+		// phpcs:ignore WordPress.WP.GlobalVariablesOverride.Prohibited
+		$post = $current_post;
+
+		return $filtered_post;
+	}
+
+	/**
+	 * Add links to the post object.
+	 *
+	 * @param \WP_Post $post Post object.
+	 * @return \WP_Post Post object with added links.
+	 */
+	public function add_links( $post ) {
+
+		if ( isset( $post->post_status ) && in_array( $post->post_status, array( 'jetpack_sync_non_registered_post_type', 'jetpack_sync_blocked' ), true ) ) {
+			return $post;
+		}
+
 		if ( has_post_thumbnail( $post->ID ) ) {
 			$image_attributes = wp_get_attachment_image_src( get_post_thumbnail_id( $post->ID ), 'full' );
 			if ( is_array( $image_attributes ) && isset( $image_attributes[0] ) ) {
@@ -585,14 +632,7 @@ public function filter_post_content_and_add_links( $post_object ) {
 		if ( function_exists( 'amp_get_permalink' ) ) {
 			$post->amp_permalink = amp_get_permalink( $post->ID );
 		}
-
-		$filtered_post = $post;
-
-		// Restore global post.
-		// phpcs:ignore WordPress.WP.GlobalVariablesOverride.Prohibited
-		$post = $current_post;
-
-		return $filtered_post;
+		return $post;
 	}
 
 	/**
@@ -742,7 +782,6 @@ public function send_published( $post_ID, $post ) {
 
 		// Only Send Pulished Post event if post_type is not blacklisted.
 		if ( ! in_array( $post->post_type, Settings::get_setting( 'post_types_blacklist' ), true ) ) {
-
 			/**
 			 * Action that gets synced when a post type gets published.
 			 *
diff --git a/projects/plugins/jetpack/changelog/update-sync-add-links-when-expanding-posts-in-before-send b/projects/plugins/jetpack/changelog/update-sync-add-links-when-expanding-posts-in-before-send
new file mode 100644
index 0000000000000..dfd0a85dcdb68
--- /dev/null
+++ b/projects/plugins/jetpack/changelog/update-sync-add-links-when-expanding-posts-in-before-send
@@ -0,0 +1,4 @@
+Significance: patch
+Type: major
+
+Sync:Moved the add links part of the expand posts functionality in dedicated sync requests to before_send instead of before_enqueue
diff --git a/projects/plugins/jetpack/tests/php/sync/test_class.jetpack-sync-base.php b/projects/plugins/jetpack/tests/php/sync/test_class.jetpack-sync-base.php
index 3f8dc2dd57a2e..36a9898f0569d 100644
--- a/projects/plugins/jetpack/tests/php/sync/test_class.jetpack-sync-base.php
+++ b/projects/plugins/jetpack/tests/php/sync/test_class.jetpack-sync-base.php
@@ -138,7 +138,14 @@ protected function assertDataIsSynced() {
 		$local_posts = array_map(
 			array(
 				$posts_sync_module,
-				'filter_post_content_and_add_links',
+				'filter_post_content',
+			),
+			$local->get_posts()
+		);
+		$local_posts = array_map(
+			array(
+				$posts_sync_module,
+				'add_links',
 			),
 			$local->get_posts()
 		);
diff --git a/projects/plugins/jetpack/tests/php/sync/test_class.jetpack-sync-posts.php b/projects/plugins/jetpack/tests/php/sync/test_class.jetpack-sync-posts.php
index 024801a6ac248..b6067215149ad 100644
--- a/projects/plugins/jetpack/tests/php/sync/test_class.jetpack-sync-posts.php
+++ b/projects/plugins/jetpack/tests/php/sync/test_class.jetpack-sync-posts.php
@@ -51,11 +51,11 @@ public function test_post_content_limit() {
 		'@phan-var \Automattic\Jetpack\Sync\Modules\Posts $post_sync_module';
 
 		$this->post->post_content = str_repeat( 'X', Automattic\Jetpack\Sync\Modules\Posts::MAX_POST_CONTENT_LENGTH - 1 );
-		$filtered_post            = $post_sync_module->filter_post_content_and_add_links( $this->post );
+		$filtered_post            = $post_sync_module->filter_post_content( $this->post );
 		$this->assertNotEmpty( $filtered_post->post_content, 'Filtered post content is empty for stings of allowed length.' );
 
 		$this->post->post_content = str_repeat( 'X', Automattic\Jetpack\Sync\Modules\Posts::MAX_POST_CONTENT_LENGTH );
-		$filtered_post            = $post_sync_module->filter_post_content_and_add_links( $this->post );
+		$filtered_post            = $post_sync_module->filter_post_content( $this->post );
 		$this->assertEmpty( $filtered_post->post_content, 'Filtered post content is not truncated (empty) for stings larger than allowed length.' );
 	}
 
@@ -523,13 +523,13 @@ public function test_sync_post_filter_restores_global_post() {
 
 		$post_sync_module = Modules::get_module( 'posts' );
 		'@phan-var \Automattic\Jetpack\Sync\Modules\Posts $post_sync_module';
-		$post_sync_module->filter_post_content_and_add_links( $this->post );
+		$post_sync_module->filter_post_content( $this->post );
 
 		$this->assertSame( $post_id, $post->ID );
 
 		// Test with post global not set.
 		$post = null;
-		$post_sync_module->filter_post_content_and_add_links( $this->post );
+		$post_sync_module->filter_post_content( $this->post );
 		$this->assertNull( $post );
 	}
 
@@ -666,6 +666,8 @@ public function test_do_not_sync_non_existant_post_types() {
 		$this->assertSame( '', $synced_post->post_content_filtered );
 		$this->assertSame( '', $synced_post->post_excerpt_filtered );
 		$this->assertEquals( 'does_not_exist', $synced_post->post_type );
+		$this->assertObjectNotHasProperty( 'permalink', $synced_post );
+		$this->assertObjectNotHasProperty( 'shortlink', $synced_post );
 	}
 
 	/**
@@ -721,6 +723,8 @@ public function test_sync_post_jetpack_sync_prevent_sending_post_data_filter() {
 		$this->assertTrue( strtotime( $this->post->post_modified_gmt ) <= strtotime( $post->post_modified_gmt ) );
 		$this->assertEquals( 'jetpack_sync_blocked', $post->post_status );
 		$this->assertEquals( 'post', $post->post_type );
+		$this->assertObjectNotHasProperty( 'permalink', $post );
+		$this->assertObjectNotHasProperty( 'shortlink', $post );
 
 		// Since the filter is not there any more the sync should happen as expected.
 		$this->post->post_content = 'foo bar';
@@ -730,6 +734,8 @@ public function test_sync_post_jetpack_sync_prevent_sending_post_data_filter() {
 		$synced_post = $this->server_replica_storage->get_post( $this->post->ID );
 		// no we sync the content and it looks like what we expect to be.
 		$this->assertEquals( $this->post->post_content, $synced_post->post_content );
+		$this->assertObjectHasProperty( 'permalink', $synced_post );
+		$this->assertObjectHasProperty( 'shortlink', $synced_post );
 	}
 
 	/**