Retry outbound emails

app/jobs/entry_job.rb

@@ -0,0 +1,16 @@
+class EntryJob < ActiveJob::Base
+  queue_as :default
+
+  retry_on RestClient::Unauthorized, wait: 5.minutes, attempts: 3
+
+  def perform(user_id, random_inspiration_id, sent_in_hour)
+    user = User.find(user_id)
+    random_inspiration = Inspiration.find(random_inspiration_id)
+    EntryMailer.send_entry(user, random_inspiration).deliver_now
+  rescue StandardError => e
+    Sentry.set_user(id: user.id, email: user.email)
+    Sentry.set_tags(plan: user.plan)
+    Sentry.capture_exception(e, extra: { sent_in_hour: sent_in_hour })
+    raise
+  end
+end

lib/tasks/entry.rake

@@ -5,7 +5,7 @@ namespace :entry do
   # rake entry:send_entries_test
   task :send_entries_test => :environment do
     user = User.where(:email=>"[email protected]").first
-    EntryMailer.send_entry(user, Inspiration.random).deliver_now
+    EntryJob.perform_later(user.id, Inspiration.random.id, 0)
   end
 
   # TRIGGERED MANUALLY
@@ -186,7 +186,7 @@ namespace :entry do
         if user.is_free? && user.emails_sent > 6 && user.entries.count == 0 && ENV['FREE_WEEK'] != 'true'
           user.update_columns(frequency: [], previous_frequency: user.frequency)
         elsif user.is_pro? || (user.is_free? && Time.now.strftime("%U").to_i % 2 == 0) || ENV['FREE_WEEK'] == 'true' # Every other week for free users
-          EntryMailer.send_entry(user, random_inspiration).deliver_now
+          EntryJob.perform_later(user.id, random_inspiration.id, sent_in_hour)
           sent_in_hour += 1
         end
       rescue => error