From e60727733b66f69c2632cb50b92c10d8b0157f0e Mon Sep 17 00:00:00 2001
From: Mikael Korpela <mikael.korpela@automattic.com>
Date: Thu, 2 Apr 2026 22:13:30 +0300
Subject: [PATCH 1/9] Sidebar upsell nudge: update visually

---
 pnpm-lock.yaml                                |  3 ++
 projects/packages/admin-ui/composer.json      |  4 ++
 projects/packages/admin-ui/package.json       |  1 +
 .../admin-ui/src/admin-ui-upgrade-menu.scss   | 46 +++++--------------
 4 files changed, 20 insertions(+), 34 deletions(-)

diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 734ce5c750f1..dab575af3409 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -1824,6 +1824,9 @@ importers:
 
   projects/packages/admin-ui:
     devDependencies:
+      '@automattic/jetpack-base-styles':
+        specifier: workspace:*
+        version: link:../../js-packages/base-styles
       '@automattic/jetpack-webpack-config':
         specifier: workspace:*
         version: link:../../js-packages/webpack-config
diff --git a/projects/packages/admin-ui/composer.json b/projects/packages/admin-ui/composer.json
index 4719275ecb81..de9a08edfe43 100644
--- a/projects/packages/admin-ui/composer.json
+++ b/projects/packages/admin-ui/composer.json
@@ -38,6 +38,10 @@
 		],
 		"test-php": [
 			"@composer phpunit"
+		],
+		"watch": [
+			"Composer\\Config::disableProcessTimeout",
+			"pnpm run watch"
 		]
 	},
 	"repositories": [
diff --git a/projects/packages/admin-ui/package.json b/projects/packages/admin-ui/package.json
index f2f9b3af09b6..5de0ec2495fc 100644
--- a/projects/packages/admin-ui/package.json
+++ b/projects/packages/admin-ui/package.json
@@ -25,6 +25,7 @@
 		"extends @wordpress/browserslist-config"
 	],
 	"devDependencies": {
+		"@automattic/jetpack-base-styles": "workspace:*",
 		"@automattic/jetpack-webpack-config": "workspace:*",
 		"@wordpress/browserslist-config": "6.42.0",
 		"sass-embedded": "1.97.3",
diff --git a/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss b/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
index 6ac09f5db748..7fbd57cc521f 100644
--- a/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
+++ b/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
@@ -1,41 +1,19 @@
+@use "@automattic/jetpack-base-styles/root-variables";
+
 // Keep the slug in sync with `UPGRADE_MENU_SLUG` at class-admin-menu.php
 $upgrade-menu-slug: jetpack-wpadmin-sidebar-free-plan-upsell-menu-item;
-$upgrade-menu-default-color: #069e08;
-$upgrade-menu-default-color-schemes: fresh, light, modern;
-$upgrade-menu-special-color-schemes: (
-	coffee: #9ea476,
-	ectoplasm: #a3b745,
-	midnight: #e14d43,
-);
-
-@mixin upgrade-menu-item-link-selector {
-	#adminmenu li.#{$upgrade-menu-slug} > a,
-	#adminmenu li.#{$upgrade-menu-slug} > a:hover {
-		@content;
-	}
-}
-
-@mixin upgrade-menu-item-theme-selector($theme) {
-	body.admin-color-#{$theme} #adminmenu li.#{$upgrade-menu-slug} > a,
-	body.admin-color-#{$theme} #adminmenu li.#{$upgrade-menu-slug} > a:hover {
-		@content;
-	}
-}
 
-@include upgrade-menu-item-link-selector {
+#adminmenu li.#{$upgrade-menu-slug} > a,
+#adminmenu li.#{$upgrade-menu-slug} > a:hover {
+	background: var(--jp-green-40) !important;
+	border-radius: var(--jp-border-radius) !important;
+	box-shadow: none !important;
+	color: var(--jp-white) !important;
 	font-weight: 600;
+	margin-left: 5px;
+	margin-right: 5px;
 }
 
-@each $theme in $upgrade-menu-default-color-schemes {
-
-	@include upgrade-menu-item-theme-selector($theme) {
-		color: $upgrade-menu-default-color !important;
-	}
-}
-
-@each $theme, $color in $upgrade-menu-special-color-schemes {
-
-	@include upgrade-menu-item-theme-selector($theme) {
-		color: $color !important;
-	}
+#adminmenu li.#{$upgrade-menu-slug} > a:hover {
+	background: var(--jp-green-30) !important;
 }

From b5359529a56830512fcdc459816a81ddaacc2d44 Mon Sep 17 00:00:00 2001
From: Mikael Korpela <mikael.korpela@automattic.com>
Date: Thu, 2 Apr 2026 22:27:45 +0300
Subject: [PATCH 2/9] Adjust spacing and enforce single row

---
 projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss | 8 +++++---
 1 file changed, 5 insertions(+), 3 deletions(-)

diff --git a/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss b/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
index 7fbd57cc521f..1b4eeff947de 100644
--- a/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
+++ b/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
@@ -9,9 +9,11 @@ $upgrade-menu-slug: jetpack-wpadmin-sidebar-free-plan-upsell-menu-item;
 	border-radius: var(--jp-border-radius) !important;
 	box-shadow: none !important;
 	color: var(--jp-white) !important;
-	font-weight: 600;
-	margin-left: 5px;
-	margin-right: 5px;
+	margin: 2px 4px;
+	max-width: 250px;
+	overflow: hidden;
+	text-overflow: ellipsis;
+	white-space: nowrap;
 }
 
 #adminmenu li.#{$upgrade-menu-slug} > a:hover {

From 7d14a7accea4bf24d7a1cb026042c9332ac8b74d Mon Sep 17 00:00:00 2001
From: Mikael Korpela <mikael.korpela@automattic.com>
Date: Thu, 2 Apr 2026 22:34:34 +0300
Subject: [PATCH 3/9] Nest, it's sass

---
 .../admin-ui/src/admin-ui-upgrade-menu.scss   | 32 +++++++++++--------
 1 file changed, 18 insertions(+), 14 deletions(-)

diff --git a/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss b/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
index 1b4eeff947de..2cad0264b086 100644
--- a/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
+++ b/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
@@ -3,19 +3,23 @@
 // Keep the slug in sync with `UPGRADE_MENU_SLUG` at class-admin-menu.php
 $upgrade-menu-slug: jetpack-wpadmin-sidebar-free-plan-upsell-menu-item;
 
-#adminmenu li.#{$upgrade-menu-slug} > a,
-#adminmenu li.#{$upgrade-menu-slug} > a:hover {
-	background: var(--jp-green-40) !important;
-	border-radius: var(--jp-border-radius) !important;
-	box-shadow: none !important;
-	color: var(--jp-white) !important;
-	margin: 2px 4px;
-	max-width: 250px;
-	overflow: hidden;
-	text-overflow: ellipsis;
-	white-space: nowrap;
-}
+#adminmenu li.#{$upgrade-menu-slug} > a {
+
+	&,
+	&:hover {
+		background: var(--jp-green-40) !important;
+		border-radius: var(--jp-border-radius) !important;
+		box-shadow: none !important;
+		color: var(--jp-white) !important;
+		margin: 2px 4px;
+		max-width: 250px;
+		overflow: hidden;
+		text-overflow: ellipsis;
+		white-space: nowrap;
+	}
+
+	&:hover {
+		background: var(--jp-green-30) !important;
+	}
 
-#adminmenu li.#{$upgrade-menu-slug} > a:hover {
-	background: var(--jp-green-30) !important;
 }

From ed8ce48a502cf9aaa1302a38506140b184c6ac89 Mon Sep 17 00:00:00 2001
From: Mikael Korpela <mikael.korpela@automattic.com>
Date: Thu, 2 Apr 2026 22:35:24 +0300
Subject: [PATCH 4/9] simplify

---
 projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss | 4 +---
 1 file changed, 1 insertion(+), 3 deletions(-)

diff --git a/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss b/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
index 2cad0264b086..3e9fbd7aae17 100644
--- a/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
+++ b/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
@@ -1,9 +1,7 @@
 @use "@automattic/jetpack-base-styles/root-variables";
 
 // Keep the slug in sync with `UPGRADE_MENU_SLUG` at class-admin-menu.php
-$upgrade-menu-slug: jetpack-wpadmin-sidebar-free-plan-upsell-menu-item;
-
-#adminmenu li.#{$upgrade-menu-slug} > a {
+#adminmenu li.jetpack-wpadmin-sidebar-free-plan-upsell-menu-item > a {
 
 	&,
 	&:hover {

From 05315f5f618147dd06e7f721f6ddffad1a56a44d Mon Sep 17 00:00:00 2001
From: Mikael Korpela <mikael.korpela@automattic.com>
Date: Thu, 2 Apr 2026 22:51:46 +0300
Subject: [PATCH 5/9] Align center

---
 projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss | 1 +
 1 file changed, 1 insertion(+)

diff --git a/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss b/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
index 3e9fbd7aae17..c67351f3ec1b 100644
--- a/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
+++ b/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
@@ -12,6 +12,7 @@
 		margin: 2px 4px;
 		max-width: 250px;
 		overflow: hidden;
+		text-align: center;
 		text-overflow: ellipsis;
 		white-space: nowrap;
 	}

From b84392d0fb3d808cfd0aff3a2295dd54fa23978b Mon Sep 17 00:00:00 2001
From: Mikael Korpela <mikael.korpela@automattic.com>
Date: Thu, 2 Apr 2026 23:04:19 +0300
Subject: [PATCH 6/9] Don't enforce single line

---
 projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss | 5 +----
 1 file changed, 1 insertion(+), 4 deletions(-)

diff --git a/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss b/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
index c67351f3ec1b..810c0e7c8fcb 100644
--- a/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
+++ b/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
@@ -10,11 +10,8 @@
 		box-shadow: none !important;
 		color: var(--jp-white) !important;
 		margin: 2px 4px;
-		max-width: 250px;
-		overflow: hidden;
 		text-align: center;
-		text-overflow: ellipsis;
-		white-space: nowrap;
+		text-wrap: pretty;
 	}
 
 	&:hover {

From 6ca3c52d37c0e1727d51acfbd18e098b270f6466 Mon Sep 17 00:00:00 2001
From: Mikael Korpela <mikael.korpela@automattic.com>
Date: Thu, 2 Apr 2026 23:12:36 +0300
Subject: [PATCH 7/9] Try text-wrap balance

---
 projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss b/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
index 810c0e7c8fcb..f04b3481ed17 100644
--- a/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
+++ b/projects/packages/admin-ui/src/admin-ui-upgrade-menu.scss
@@ -11,7 +11,7 @@
 		color: var(--jp-white) !important;
 		margin: 2px 4px;
 		text-align: center;
-		text-wrap: pretty;
+		text-wrap: balance;
 	}
 
 	&:hover {

From 84b0698f5ff0add8fb4fbdd2bd78f642dfa756f2 Mon Sep 17 00:00:00 2001
From: Mikael Korpela <mikael.korpela@automattic.com>
Date: Fri, 3 Apr 2026 11:51:58 +0300
Subject: [PATCH 8/9] =?UTF-8?q?Remove=20=E2=86=97?=
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

---
 projects/packages/admin-ui/src/class-admin-menu.php | 5 ++---
 1 file changed, 2 insertions(+), 3 deletions(-)

diff --git a/projects/packages/admin-ui/src/class-admin-menu.php b/projects/packages/admin-ui/src/class-admin-menu.php
index 4345817319d7..7bb688972160 100644
--- a/projects/packages/admin-ui/src/class-admin-menu.php
+++ b/projects/packages/admin-ui/src/class-admin-menu.php
@@ -320,12 +320,11 @@ private static function maybe_add_upgrade_menu_item() {
 			? \Automattic\Jetpack\Redirect::get_url( self::UPGRADE_MENU_SLUG )
 			: self::UPGRADE_MENU_FALLBACK_URL;
 
-		$menu_title = esc_html__( 'Upgrade Jetpack', 'jetpack-admin-ui' )
-			. ' <span aria-hidden="true">↗</span>';
+		$menu_title = esc_html__( 'Upgrade Jetpack', 'jetpack-admin-ui' );
 
 		add_submenu_page(
 			'jetpack',
-			__( 'Upgrade Jetpack', 'jetpack-admin-ui' ),
+			$menu_title,
 			$menu_title,
 			'manage_options',
 			esc_url( $upgrade_url ),

From 4a51025a247493fae6088ece9ceebb894ad6d917 Mon Sep 17 00:00:00 2001
From: Mikael Korpela <mikael.korpela@automattic.com>
Date: Fri, 3 Apr 2026 13:21:28 +0300
Subject: [PATCH 9/9] Lockfiles

---
 .../admin-ui/changelog/update-sidebar-upsell-visual-update  | 4 ++++
 .../changelog/update-sidebar-upsell-visual-update           | 4 ++++
 .../plugins/automattic-for-agencies-client/composer.lock    | 6 +++++-
 .../backup/changelog/update-sidebar-upsell-visual-update    | 4 ++++
 projects/plugins/backup/composer.lock                       | 6 +++++-
 .../beta/changelog/update-sidebar-upsell-visual-update      | 4 ++++
 projects/plugins/beta/composer.lock                         | 6 +++++-
 .../boost/changelog/update-sidebar-upsell-visual-update     | 4 ++++
 projects/plugins/boost/composer.lock                        | 6 +++++-
 .../changelog/update-sidebar-upsell-visual-update           | 4 ++++
 projects/plugins/classic-theme-helper-plugin/composer.lock  | 6 +++++-
 .../inspect/changelog/update-sidebar-upsell-visual-update   | 4 ++++
 projects/plugins/inspect/composer.lock                      | 6 +++++-
 .../jetpack/changelog/update-sidebar-upsell-visual-update   | 4 ++++
 projects/plugins/jetpack/composer.lock                      | 6 +++++-
 .../changelog/update-sidebar-upsell-visual-update           | 4 ++++
 projects/plugins/mu-wpcom-plugin/composer.lock              | 6 +++++-
 .../changelog/update-sidebar-upsell-visual-update           | 4 ++++
 projects/plugins/paypal-payment-buttons/composer.lock       | 6 +++++-
 .../protect/changelog/update-sidebar-upsell-visual-update   | 4 ++++
 projects/plugins/protect/composer.lock                      | 6 +++++-
 .../search/changelog/update-sidebar-upsell-visual-update    | 4 ++++
 projects/plugins/search/composer.lock                       | 6 +++++-
 .../social/changelog/update-sidebar-upsell-visual-update    | 4 ++++
 projects/plugins/social/composer.lock                       | 6 +++++-
 .../changelog/update-sidebar-upsell-visual-update           | 4 ++++
 projects/plugins/starter-plugin/composer.lock               | 6 +++++-
 .../changelog/update-sidebar-upsell-visual-update           | 4 ++++
 projects/plugins/videopress/composer.lock                   | 6 +++++-
 .../changelog/update-sidebar-upsell-visual-update           | 4 ++++
 projects/plugins/wpcloud-sso/composer.lock                  | 6 +++++-
 .../wpcomsh/changelog/update-sidebar-upsell-visual-update   | 4 ++++
 projects/plugins/wpcomsh/composer.lock                      | 6 +++++-
 33 files changed, 148 insertions(+), 16 deletions(-)
 create mode 100644 projects/packages/admin-ui/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/automattic-for-agencies-client/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/backup/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/beta/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/boost/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/classic-theme-helper-plugin/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/inspect/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/jetpack/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/mu-wpcom-plugin/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/paypal-payment-buttons/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/protect/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/search/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/social/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/starter-plugin/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/videopress/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/wpcloud-sso/changelog/update-sidebar-upsell-visual-update
 create mode 100644 projects/plugins/wpcomsh/changelog/update-sidebar-upsell-visual-update

diff --git a/projects/packages/admin-ui/changelog/update-sidebar-upsell-visual-update b/projects/packages/admin-ui/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/packages/admin-ui/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/automattic-for-agencies-client/changelog/update-sidebar-upsell-visual-update b/projects/plugins/automattic-for-agencies-client/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/automattic-for-agencies-client/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/automattic-for-agencies-client/composer.lock b/projects/plugins/automattic-for-agencies-client/composer.lock
index 4d5f9fc1df02..f67354217c8c 100644
--- a/projects/plugins/automattic-for-agencies-client/composer.lock
+++ b/projects/plugins/automattic-for-agencies-client/composer.lock
@@ -66,7 +66,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -118,6 +118,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/backup/changelog/update-sidebar-upsell-visual-update b/projects/plugins/backup/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/backup/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/backup/composer.lock b/projects/plugins/backup/composer.lock
index 06c9f20fd8fd..92a71d80faf0 100644
--- a/projects/plugins/backup/composer.lock
+++ b/projects/plugins/backup/composer.lock
@@ -66,7 +66,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -118,6 +118,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/beta/changelog/update-sidebar-upsell-visual-update b/projects/plugins/beta/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/beta/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/beta/composer.lock b/projects/plugins/beta/composer.lock
index 5d8dee531158..4339413b28ac 100644
--- a/projects/plugins/beta/composer.lock
+++ b/projects/plugins/beta/composer.lock
@@ -12,7 +12,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -64,6 +64,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/boost/changelog/update-sidebar-upsell-visual-update b/projects/plugins/boost/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/boost/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/boost/composer.lock b/projects/plugins/boost/composer.lock
index 2a944ca2e914..3bbd398a61f2 100644
--- a/projects/plugins/boost/composer.lock
+++ b/projects/plugins/boost/composer.lock
@@ -66,7 +66,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -118,6 +118,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/classic-theme-helper-plugin/changelog/update-sidebar-upsell-visual-update b/projects/plugins/classic-theme-helper-plugin/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/classic-theme-helper-plugin/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/classic-theme-helper-plugin/composer.lock b/projects/plugins/classic-theme-helper-plugin/composer.lock
index 9873d0cfe0f7..31af601877b8 100644
--- a/projects/plugins/classic-theme-helper-plugin/composer.lock
+++ b/projects/plugins/classic-theme-helper-plugin/composer.lock
@@ -130,7 +130,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -182,6 +182,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/inspect/changelog/update-sidebar-upsell-visual-update b/projects/plugins/inspect/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/inspect/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/inspect/composer.lock b/projects/plugins/inspect/composer.lock
index f95f05b56b7a..a5a3a6dd6ebc 100644
--- a/projects/plugins/inspect/composer.lock
+++ b/projects/plugins/inspect/composer.lock
@@ -66,7 +66,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -118,6 +118,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/jetpack/changelog/update-sidebar-upsell-visual-update b/projects/plugins/jetpack/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..f2fa2824ffa7
--- /dev/null
+++ b/projects/plugins/jetpack/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: other
+
+ Update design of the sidebar upsell.
diff --git a/projects/plugins/jetpack/composer.lock b/projects/plugins/jetpack/composer.lock
index 9561e06b6a99..389af2605b4b 100644
--- a/projects/plugins/jetpack/composer.lock
+++ b/projects/plugins/jetpack/composer.lock
@@ -199,7 +199,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -251,6 +251,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/mu-wpcom-plugin/changelog/update-sidebar-upsell-visual-update b/projects/plugins/mu-wpcom-plugin/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/mu-wpcom-plugin/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/mu-wpcom-plugin/composer.lock b/projects/plugins/mu-wpcom-plugin/composer.lock
index 87f688548444..d0573ca295df 100644
--- a/projects/plugins/mu-wpcom-plugin/composer.lock
+++ b/projects/plugins/mu-wpcom-plugin/composer.lock
@@ -130,7 +130,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -182,6 +182,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/paypal-payment-buttons/changelog/update-sidebar-upsell-visual-update b/projects/plugins/paypal-payment-buttons/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/paypal-payment-buttons/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/paypal-payment-buttons/composer.lock b/projects/plugins/paypal-payment-buttons/composer.lock
index 5236044f8eb7..e42a53bc287c 100644
--- a/projects/plugins/paypal-payment-buttons/composer.lock
+++ b/projects/plugins/paypal-payment-buttons/composer.lock
@@ -66,7 +66,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -118,6 +118,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/protect/changelog/update-sidebar-upsell-visual-update b/projects/plugins/protect/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/protect/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/protect/composer.lock b/projects/plugins/protect/composer.lock
index 69e8c03669b4..f5edfd164e58 100644
--- a/projects/plugins/protect/composer.lock
+++ b/projects/plugins/protect/composer.lock
@@ -135,7 +135,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -187,6 +187,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/search/changelog/update-sidebar-upsell-visual-update b/projects/plugins/search/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/search/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/search/composer.lock b/projects/plugins/search/composer.lock
index 48753c36ca4c..b460d7498b11 100644
--- a/projects/plugins/search/composer.lock
+++ b/projects/plugins/search/composer.lock
@@ -66,7 +66,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -118,6 +118,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/social/changelog/update-sidebar-upsell-visual-update b/projects/plugins/social/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/social/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/social/composer.lock b/projects/plugins/social/composer.lock
index 34e51f5e5d26..bc71aba2fd8e 100644
--- a/projects/plugins/social/composer.lock
+++ b/projects/plugins/social/composer.lock
@@ -130,7 +130,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -182,6 +182,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/starter-plugin/changelog/update-sidebar-upsell-visual-update b/projects/plugins/starter-plugin/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/starter-plugin/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/starter-plugin/composer.lock b/projects/plugins/starter-plugin/composer.lock
index fb0f2403070d..4ac1587b0f4c 100644
--- a/projects/plugins/starter-plugin/composer.lock
+++ b/projects/plugins/starter-plugin/composer.lock
@@ -66,7 +66,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -118,6 +118,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/videopress/changelog/update-sidebar-upsell-visual-update b/projects/plugins/videopress/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/videopress/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/videopress/composer.lock b/projects/plugins/videopress/composer.lock
index cb4b57d3331c..90755e7ee69e 100644
--- a/projects/plugins/videopress/composer.lock
+++ b/projects/plugins/videopress/composer.lock
@@ -66,7 +66,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -118,6 +118,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/wpcloud-sso/changelog/update-sidebar-upsell-visual-update b/projects/plugins/wpcloud-sso/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/wpcloud-sso/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/wpcloud-sso/composer.lock b/projects/plugins/wpcloud-sso/composer.lock
index 5d2e8e6a00a8..8c041daf4ff8 100644
--- a/projects/plugins/wpcloud-sso/composer.lock
+++ b/projects/plugins/wpcloud-sso/composer.lock
@@ -66,7 +66,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -118,6 +118,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [
diff --git a/projects/plugins/wpcomsh/changelog/update-sidebar-upsell-visual-update b/projects/plugins/wpcomsh/changelog/update-sidebar-upsell-visual-update
new file mode 100644
index 000000000000..c219724eb996
--- /dev/null
+++ b/projects/plugins/wpcomsh/changelog/update-sidebar-upsell-visual-update
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Update design of the sidebar upsell.
diff --git a/projects/plugins/wpcomsh/composer.lock b/projects/plugins/wpcomsh/composer.lock
index a547d4febfdf..000460aedd0d 100644
--- a/projects/plugins/wpcomsh/composer.lock
+++ b/projects/plugins/wpcomsh/composer.lock
@@ -198,7 +198,7 @@
             "dist": {
                 "type": "path",
                 "url": "../../packages/admin-ui",
-                "reference": "d71575c86c7f4cec8c3354e21c15db817b966515"
+                "reference": "b85d3fbbc9298316d8cd1d3e35f50a6e0b17c07c"
             },
             "require": {
                 "automattic/jetpack-redirect": "@dev",
@@ -250,6 +250,10 @@
                 ],
                 "test-php": [
                     "@composer phpunit"
+                ],
+                "watch": [
+                    "Composer\\Config::disableProcessTimeout",
+                    "pnpm run watch"
                 ]
             },
             "license": [