diff --git a/app/controllers/webhooks_controller.rb b/app/controllers/webhooks_controller.rb
index 1f1b3c01..3afb8141 100644
--- a/app/controllers/webhooks_controller.rb
+++ b/app/controllers/webhooks_controller.rb
@@ -10,17 +10,15 @@ def invoice_payment_succeeded
   end
 
   def customer_subscription_deleted
-    Subscription.find_by(stripe_user_id: @customer.id)
-                .update(active: false, percent_off: 0)
+    subscription = Subscription.find_by(stripe_user_id: @customer.id)
+    subscription.update(active: false, percent_off: 0)
+    subscription.recipient.users.each do |user|
+      SubscriptionMailer.deactivated(user).deliver_now
+    end
   rescue NoMethodError
     nil
   end
 
-  def subscription_expired
-    # TODO: deactivate Beehive::Subscription at_period_end
-    # TODO: send reminder emails
-  end
-
   private
 
     def load_customer
diff --git a/app/mailers/subscription_mailer.rb b/app/mailers/subscription_mailer.rb
new file mode 100644
index 00000000..c97f68a5
--- /dev/null
+++ b/app/mailers/subscription_mailer.rb
@@ -0,0 +1,6 @@
+class SubscriptionMailer < ApplicationMailer
+  def deactivated(user)
+    @user = user
+    mail(to: @user.email, subject: 'Subscription Expired - Beehive')
+  end
+end
diff --git a/app/views/subscription_mailer/deactivated.text.erb b/app/views/subscription_mailer/deactivated.text.erb
new file mode 100644
index 00000000..039acf28
--- /dev/null
+++ b/app/views/subscription_mailer/deactivated.text.erb
@@ -0,0 +1,17 @@
+Hi <%= @user&.first_name %>
+
+Your 'Pro' subscription on www.beehivegiving.org (Beehive) has now come to an end.
+
+As Beehive is a project of a charity, we really appreciate that you upgraded your account a year ago. Your contribution has helped us sustain the project and provide our grant funding suitability checking service to many more fund seekers - thank you!
+
+We know there is plenty we could do to improve our service, and as a valued customer we'd love to ask you a few brief questions about this.
+
+To say thank you for your feedback and support, we'll happily extend your 'Pro' subscription for another year (free of charge).
+
+Just reply to this email and let us know you'd be happy to answer some questions.
+
+Big thanks,
+The Beehive Team
+
+--
+This is an automated message from www.beehivegiving.org
diff --git a/spec/features/subscriptions_spec.rb b/spec/features/subscriptions_spec.rb
index 44d4d6de..541c3b09 100644
--- a/spec/features/subscriptions_spec.rb
+++ b/spec/features/subscriptions_spec.rb
@@ -157,11 +157,11 @@
 
       scenario 'webhook customer-subscription-deleted', type: :request do
         Subscription.last.update(percent_off: 10)
+        status = helper.stripe_subscription(@db[:recipient]).status
 
-        expect(Subscription.last.active).to eq true
-        expect(Subscription.last.percent_off).to eq 10
-        expect(helper.stripe_subscription(@db[:recipient]).status)
-          .to eq 'active'
+        expect(Subscription.last.active).to eq(true)
+        expect(Subscription.last.percent_off).to eq(10)
+        expect(status).to eq('active')
 
         event = StripeMock.mock_webhook_event(
           'customer.subscription.deleted',
@@ -172,16 +172,13 @@
              params: event.to_json,
              headers: { 'Content-Type': 'application/json' }
 
-        expect(Subscription.last.active).to eq false
-        expect(Subscription.last.percent_off).to eq 0
-        expect(event.data.object.status).to eq 'canceled'
-      end
+        expect(Subscription.last.active).to eq(false)
+        expect(Subscription.last.percent_off).to eq(0)
+        expect(event.data.object.status).to eq('canceled')
 
-      scenario 'remaining free checks hidden' do
-        @app.setup_funds
-        @db[:proposal].save!
-        visit fund_path(Fund.first, @db[:proposal])
-        expect(page).not_to have_button 'Check eligibility (3 left)'
+        deliveries = ActionMailer::Base.deliveries
+        expect(deliveries.size).to eq(1)
+        expect(deliveries.last.subject).to eq('Subscription Expired - Beehive')
       end
     end
   end
diff --git a/spec/mailers/previews/subscription_mailer_preview.rb b/spec/mailers/previews/subscription_mailer_preview.rb
new file mode 100644
index 00000000..4da09d92
--- /dev/null
+++ b/spec/mailers/previews/subscription_mailer_preview.rb
@@ -0,0 +1,6 @@
+class SubscriptionMailerPreview < ActionMailer::Preview
+  def deactivated
+    user = OpenStruct.new(email: 'email@example.com', first_name: 'John')
+    SubscriptionMailer.deactivated(user)
+  end
+end