diff --git a/extensions/shared/register-jetpack-block.js b/extensions/shared/register-jetpack-block.js
index 06bbd9263163a..24fe4efda95ad 100644
--- a/extensions/shared/register-jetpack-block.js
+++ b/extensions/shared/register-jetpack-block.js
@@ -45,9 +45,7 @@ export default function registerJetpackBlock( name, settings, childBlocks = [] )
 	const result = registerBlockType( `jetpack/${ name }`, {
 		...settings,
 		title: betaExtensions.includes( name ) ? `${ settings.title } (beta)` : settings.title,
-		edit: requiredPlan
-			? wrapPaidBlock( { feature: details.required_feature, requiredPlan } )( settings.edit )
-			: settings.edit,
+		edit: requiredPlan ? wrapPaidBlock( { requiredPlan } )( settings.edit ) : settings.edit,
 	} );
 
 	// Register child blocks. Using `registerBlockType()` directly avoids availability checks -- if
diff --git a/extensions/shared/upgrade-nudge/index.jsx b/extensions/shared/upgrade-nudge/index.jsx
index b88b97cdc7b5f..320514e772385 100644
--- a/extensions/shared/upgrade-nudge/index.jsx
+++ b/extensions/shared/upgrade-nudge/index.jsx
@@ -1,7 +1,7 @@
 /**
  * External dependencies
  */
-import { get } from 'lodash';
+import { get, startsWith } from 'lodash';
 import { __, sprintf } from '@wordpress/i18n';
 import { addQueryArgs } from '@wordpress/url';
 import { Button } from '@wordpress/components';
@@ -16,7 +16,7 @@ import './store';
 
 import './style.scss';
 
-const UpgradeNudge = ( { feature, plan, planName } ) => (
+const UpgradeNudge = ( { planName, planPathSlug, postId, postType } ) => (
 	<div className="jetpack-upgrade-nudge">
 		<Gridicon className="jetpack-upgrade-nudge__icon" icon="star" size={ 18 } />
 		<div className="jetpack-upgrade-nudge__info">
@@ -31,10 +31,12 @@ const UpgradeNudge = ( { feature, plan, planName } ) => (
 		</div>
 		<Button
 			className="jetpack-upgrade-nudge__button"
-			href={ addQueryArgs( `https://wordpress.com/plans/${ getSiteFragment() }`, {
-				feature,
-				plan,
-			} ) }
+			href={ addQueryArgs(
+				`https://wordpress.com/checkout/${ getSiteFragment() }/${ planPathSlug }`,
+				{
+					redirect_to: `/${ postType }/${ getSiteFragment() }/${ postId }`,
+				}
+			) }
 			isDefault
 		>
 			{ __( 'Upgrade', 'jetpack' ) }
@@ -43,5 +45,17 @@ const UpgradeNudge = ( { feature, plan, planName } ) => (
 );
 export default withSelect( ( select, { plan: planSlug } ) => {
 	const plan = select( 'wordpress-com/plans' ).getPlan( planSlug );
-	return { planName: get( plan, [ 'product_name_short' ] ) };
+
+	// WP.com plan objects have a dedicated `path_slug` field, Jetpack plan objects don't
+	// For Jetpack, we thus use the plan slug with the 'jetpack_' prefix removed.
+	const planPathSlug = startsWith( planSlug, 'jetpack_' )
+		? planSlug.substr( 'jetpack_'.length )
+		: get( plan, [ 'path_slug' ] );
+
+	return {
+		planName: get( plan, [ 'product_name_short' ] ),
+		planPathSlug,
+		postId: select( 'core/editor' ).getCurrentPostId(),
+		postType: select( 'core/editor' ).getCurrentPostType(),
+	};
 } )( UpgradeNudge );
diff --git a/extensions/shared/wrap-paid-block/index.jsx b/extensions/shared/wrap-paid-block/index.jsx
index 25294b362a789..8668563878957 100644
--- a/extensions/shared/wrap-paid-block/index.jsx
+++ b/extensions/shared/wrap-paid-block/index.jsx
@@ -11,12 +11,12 @@ import UpgradeNudge from '../upgrade-nudge';
 
 import './style.scss';
 
-export default ( { feature, requiredPlan } ) =>
+export default ( { requiredPlan } ) =>
 	createHigherOrderComponent(
 		WrappedComponent => props => (
 			// Wraps the input component in a container, without mutating it. Good!
 			<div className="jetpack-paid-block__wrapper">
-				<UpgradeNudge feature={ feature } plan={ requiredPlan } />
+				<UpgradeNudge plan={ requiredPlan } />
 				<div className="jetpack-paid-block__disabled">
 					<WrappedComponent { ...props } />
 				</div>