diff --git a/RELEASE-NOTES.txt b/RELEASE-NOTES.txt
index c1d7847d3a..2c4633641d 100644
--- a/RELEASE-NOTES.txt
+++ b/RELEASE-NOTES.txt
@@ -1,5 +1,6 @@
 Unreleased
 ---
+* [**] Introduce VideoPress v5 support, to fix issues using video block with dotcom and Jetpack sites [https://github.com/wordpress-mobile/gutenberg-mobile/pull/6634]
 * [*] Prevent crash when autoscrolling to blocks [https://github.com/WordPress/gutenberg/pull/59110]
 * [*] Remove opacity change when images are being uploaded [https://github.com/WordPress/gutenberg/pull/59264]
 * [*] Media & Text blocks correctly show an error message when the attached video upload fails [https://github.com/WordPress/gutenberg/pull/59288]
diff --git a/bundle/android/strings.xml b/bundle/android/strings.xml
index 67a72b61f0..bc92b80078 100644
--- a/bundle/android/strings.xml
+++ b/bundle/android/strings.xml
@@ -48,6 +48,7 @@
     <!-- translators: displays audio file extension. e.g. MP3 audio file -->
     <string name="gutenberg_native_audio_file" tools:ignore="UnusedResources">audio file</string>
     <string name="gutenberg_native_audio_player" tools:ignore="UnusedResources">Audio Player</string>
+    <string name="gutenberg_native_autoplay_may_cause_usability_issues_for_some_users" tools:ignore="UnusedResources">Autoplay may cause usability issues for some users</string>
     <string name="gutenberg_native_block_cannot_be_rendered_because_it_is_deeply_nested_tap_here_for" tools:ignore="UnusedResources">Block cannot be rendered because it is deeply nested. Tap here for more details.</string>
     <!-- translators: displayed right after the block is copied. -->
     <string name="gutenberg_native_block_copied" tools:ignore="UnusedResources">Block copied</string>
@@ -160,6 +161,7 @@
     <string name="gutenberg_native_edit_media" tools:ignore="UnusedResources">Edit media</string>
     <string name="gutenberg_native_edit_using_web_editor" tools:ignore="UnusedResources">Edit using web editor</string>
     <string name="gutenberg_native_edit_video" tools:ignore="UnusedResources">Edit video</string>
+    <string name="gutenberg_native_edit_video_024aee6d" tools:ignore="UnusedResources">Edit video</string>
     <!-- translators: %s: name of the host app (e.g. WordPress) -->
     <string name="gutenberg_native_editing_synced_patterns_is_not_yet_supported_on_s_for_android" tools:ignore="UnusedResources">Editing synced patterns is not yet supported on %s for Android</string>
     <!-- translators: %s: name of the host app (e.g. WordPress) -->
@@ -389,10 +391,13 @@ translators: %s: Select control option value e.g: "Auto, 25%". -->
     <string name="gutenberg_native_upgrade_your_plan_to_use_video_covers" tools:ignore="UnusedResources">Upgrade your plan to use video covers</string>
     <string name="gutenberg_native_uploading" tools:ignore="UnusedResources">Uploading…</string>
     <string name="gutenberg_native_use_icon_button" tools:ignore="UnusedResources">Use icon button</string>
-    <!-- translators: accessibility text. Empty video caption. -->
     <string name="gutenberg_native_video_caption_empty" tools:ignore="UnusedResources">Video caption. Empty</string>
+    <!-- translators: accessibility text. Empty video caption. -->
+    <string name="gutenberg_native_video_caption_empty_663aab49" tools:ignore="UnusedResources">Video caption. Empty</string>
     <!-- translators: accessibility text. %s: video caption. -->
     <string name="gutenberg_native_video_caption_s" tools:ignore="UnusedResources">Video caption. %s</string>
+    <!-- translators: accessibility text. %s: video caption. -->
+    <string name="gutenberg_native_video_caption_s_0141bd20" tools:ignore="UnusedResources">Video caption. %s</string>
     <string name="gutenberg_native_waiting_for_connection" tools:ignore="UnusedResources">Waiting for connection</string>
     <string name="gutenberg_native_warning_message" tools:ignore="UnusedResources">Warning message</string>
     <string name="gutenberg_native_we_are_working_hard_to_add_more_blocks_with_each_release" tools:ignore="UnusedResources">We are working hard to add more blocks with each release.</string>
diff --git a/bundle/ios/GutenbergNativeTranslations.swift b/bundle/ios/GutenbergNativeTranslations.swift
index 8ac86e4842..f702168650 100644
--- a/bundle/ios/GutenbergNativeTranslations.swift
+++ b/bundle/ios/GutenbergNativeTranslations.swift
@@ -54,6 +54,7 @@ private func dummy() {
     _ = NSLocalizedString("Audio caption. Empty", comment: "translators: accessibility text. Empty Audio caption.")
     _ = NSLocalizedString("audio file", comment: "translators: displays audio file extension. e.g. MP3 audio file")
     _ = NSLocalizedString("Audio Player", comment: "")
+    _ = NSLocalizedString("Autoplay may cause usability issues for some users", comment: "")
     _ = NSLocalizedString("Block cannot be rendered because it is deeply nested. Tap here for more details.", comment: "")
     _ = NSLocalizedString("Block copied", comment: "translators: displayed right after the block is copied.")
     _ = NSLocalizedString("Block cut", comment: "translators: displayed right after the block is cut.")
diff --git a/gutenberg b/gutenberg
index 57470e9e5e..44d4886d6a 160000
--- a/gutenberg
+++ b/gutenberg
@@ -1 +1 @@
-Subproject commit 57470e9e5e2c38c93b4f1771a867ed7159c354da
+Subproject commit 44d4886d6a11bdc27d528ff62be488a8edf0b44f
diff --git a/jetpack b/jetpack
index 76a55b3290..68f87a4058 160000
--- a/jetpack
+++ b/jetpack
@@ -1 +1 @@
-Subproject commit 76a55b3290233c809eb3094f838a6cf8478f940d
+Subproject commit 68f87a40581c6ed07e22cbb25f51194fdb736b85
diff --git a/src/jetpack-editor-setup.js b/src/jetpack-editor-setup.js
index ff9f9cd262..edda77d5a7 100644
--- a/src/jetpack-editor-setup.js
+++ b/src/jetpack-editor-setup.js
@@ -17,7 +17,6 @@ import {
 	registerLoomVariation,
 	registerSmartframeVariation,
 } from '../jetpack/projects/plugins/jetpack/extensions/extended-blocks/core-embed';
-import '../jetpack/projects/plugins/jetpack/extensions/blocks/videopress/editor';
 
 // When adding new blocks to this list please also consider updating `./block-support/supported-blocks.json`
 const supportedJetpackBlocks = {
@@ -129,6 +128,14 @@ export function registerJetpackEmbedVariations( { capabilities } ) {
 	} );
 }
 
+export function enableVideoPressV5Support( { capabilities } ) {
+	if ( ! isActive() || ! capabilities.videoPressV5Support ) {
+		return;
+	}
+
+	require( '../jetpack/projects/plugins/jetpack/extensions/blocks/videopress/editor' );
+}
+
 const setupHooks = () => {
 	// Hook triggered before the editor is rendered
 	addAction( 'native.pre-render', 'gutenberg-mobile-jetpack', ( props ) => {
@@ -142,6 +149,11 @@ const setupHooks = () => {
 		// block type registration, so it’s required to add them before
 		// the core blocks are registered.
 		registerJetpackEmbedVariations( props );
+
+		// VideoPress v5 conversion also uses WP hooks that are attached to
+		// block type registration, so it’s required to add them before
+		// the core blocks are registered.
+		enableVideoPressV5Support( props );
 	} );
 
 	// Hook triggered after the editor is rendered