diff --git a/includes/classes/Indexable/Post/SyncManager.php b/includes/classes/Indexable/Post/SyncManager.php
index a5feafcaa..5f998fa1e 100644
--- a/includes/classes/Indexable/Post/SyncManager.php
+++ b/includes/classes/Indexable/Post/SyncManager.php
@@ -300,7 +300,7 @@ public function action_delete_post( $post_id ) {
 		Indexables::factory()->get( $this->indexable_slug )->delete( $post_id, false );
 
 		/**
-		 * Make sure to remove this post from the sync queue in case an shutdown happens
+		 * Make sure to remove this post from the sync queue in case a shutdown happens
 		 * before a redirect when a redirect has already been triggered.
 		 */
 		$this->remove_from_queue( $post_id );
@@ -533,6 +533,7 @@ public function action_set_object_terms( $post_id, $terms, $tt_ids, $taxonomy, $
 		}
 
 		if ( ! $this->should_reindex_post( $post_id, $taxonomy ) ) {
+			$this->remove_from_queue( $post_id );
 			return;
 		}
 
@@ -629,6 +630,7 @@ public function action_edited_term( $term_id, $tt_id, $taxonomy ) {
 		// Add all of them to the queue
 		foreach ( $object_ids as $post_id ) {
 			if ( ! $this->should_reindex_post( $post_id, $taxonomy ) ) {
+				$this->remove_from_queue( $post_id );
 				continue;
 			}
 
@@ -693,6 +695,7 @@ public function action_deleted_term_relationships( $post_id, $tt_ids, $taxonomy
 		}
 
 		if ( ! $this->should_reindex_post( $post_id, $taxonomy ) ) {
+			$this->remove_from_queue( $post_id );
 			return;
 		}
 
diff --git a/includes/classes/SyncManager.php b/includes/classes/SyncManager.php
index 1f2e54ce3..ea0068767 100644
--- a/includes/classes/SyncManager.php
+++ b/includes/classes/SyncManager.php
@@ -131,6 +131,10 @@ public function remove_from_queue( $object_id ) {
 			return false;
 		}
 
+		if ( ! isset( $this->sync_queue[ $object_id ] ) ) {
+			return false;
+		}
+
 		$current_blog_id = get_current_blog_id();
 		if ( ! isset( $this->sync_queue[ $current_blog_id ] ) ) {
 			$this->sync_queue[ $current_blog_id ] = [];
diff --git a/tests/cypress/integration/features/protected-content-removal.cy.js b/tests/cypress/integration/features/protected-content-removal.cy.js
new file mode 100644
index 000000000..d10261874
--- /dev/null
+++ b/tests/cypress/integration/features/protected-content-removal.cy.js
@@ -0,0 +1,47 @@
+describe('Set password on post', () => {
+	it('Removes Post from Index when Password is Set', () => {
+		cy.login();
+		cy.maybeDisableFeature('protected_content');
+
+		// Delete previous posts, so we can be sure we just expect 1 post.
+		cy.wpCli('post list --format=ids').then((wpCliResponse) => {
+			if (wpCliResponse.stdout !== '') {
+				cy.wpCli(`post delete ${wpCliResponse.stdout}`);
+			}
+		});
+
+		cy.publishPost({
+			title: 'Protected Post Removal Test',
+		});
+
+		/**
+		 * Give Elasticsearch some time to process the new post.
+		 *
+		 * @todo instead of waiting for an arbitrary time, we should ensure the post is stored.
+		 */
+		// eslint-disable-next-line cypress/no-unnecessary-waiting
+		cy.wait(2000);
+
+		// Post is indexed
+		cy.visit('/?s=Protected+Post+Removal+Test');
+		cy.contains('.site-content article h2', 'Protected Post Removal Test').should('exist');
+
+		cy.wpCli('post list --format=ids').then((wpCliResponse) => {
+			if (wpCliResponse.stdout !== '') {
+				cy.postSetPassword(wpCliResponse.stdout, 'enter');
+			}
+		});
+
+		/**
+		 * Give Elasticsearch some time to process the update.
+		 *
+		 * @todo instead of waiting for an arbitrary time, we should ensure the post is stored.
+		 */
+		// eslint-disable-next-line cypress/no-unnecessary-waiting
+		cy.wait(2000);
+
+		// Post is removed from index
+		cy.visit('/?s=Protected+Post+Removal+Test');
+		cy.contains('.site-content article h2', 'Protected Post Removal Test').should('not.exist');
+	});
+});
diff --git a/tests/cypress/support/commands.js b/tests/cypress/support/commands.js
index c8f415be3..df863039c 100644
--- a/tests/cypress/support/commands.js
+++ b/tests/cypress/support/commands.js
@@ -197,6 +197,26 @@ Cypress.Commands.add('publishPost', (postData, viewPost) => {
 	cy.wait(2000);
 });
 
+Cypress.Commands.add('postSetPassword', (id, password) => {
+	cy.visitAdminPage(`post.php?post=${id}&action=edit`);
+	cy.get('h1.editor-post-title__input').click();
+	cy.get('body').then(($body) => {
+		const $button = $body.find('.edit-post-post-visibility__toggle');
+		if (!$button.is(':visible')) {
+			cy.get('.edit-post-header__settings button[aria-label="Settings"]').click();
+		}
+	});
+	cy.get('.edit-post-post-visibility__toggle').click();
+	cy.get('.editor-post-visibility__dialog-radio, .editor-post-visibility__radio').check(
+		'password',
+	);
+	cy.get(
+		'.editor-post-visibility__dialog-password-input, .editor-post-visibility__password-input',
+	).type(password);
+
+	cy.get('.editor-post-publish-button').click();
+});
+
 Cypress.Commands.add('updateFeatures', (featureName, newValues) => {
 	const escapedNewValues = JSON.stringify(newValues);