diff --git a/app/jobs/send_three_month_email_job.rb b/app/jobs/send_three_month_email_job.rb
new file mode 100644
index 000000000..29c250500
--- /dev/null
+++ b/app/jobs/send_three_month_email_job.rb
@@ -0,0 +1,9 @@
+# frozen_string_literal: true
+
+class SendThreeMonthEmailJob < ApplicationJob
+  queue_as :default
+
+  def perform
+    ThreeMonthEmailService.send_chaser
+  end
+end
diff --git a/app/mailers/concerns/email_delivery.rb b/app/mailers/concerns/email_delivery.rb
new file mode 100644
index 000000000..f39bf581a
--- /dev/null
+++ b/app/mailers/concerns/email_delivery.rb
@@ -0,0 +1,19 @@
+module EmailDelivery
+  extend ActiveSupport::Concern
+
+    private
+
+    def log_sent_email
+      member = params[:member]
+      return unless member
+
+      MemberEmailDelivery.create!(
+        member: member,
+        subject: mail.subject,
+        body: mail.body.to_s,
+        to: mail.to,
+        cc: mail.cc,
+        bcc: mail.bcc
+      )
+    end
+end
diff --git a/app/mailers/member_mailer.rb b/app/mailers/member_mailer.rb
index ebc5e4850..fa1c8425f 100644
--- a/app/mailers/member_mailer.rb
+++ b/app/mailers/member_mailer.rb
@@ -1,5 +1,16 @@
 class MemberMailer < ApplicationMailer
   include EmailHeaderHelper
+  include EmailDelivery
+
+  after_deliver :log_sent_email, only: [:chaser]
+
+  def chaser
+    @member = params[:member]
+    subject = "It’s been a while, how are you doing? ♥️"
+    mail mail_args(@member, subject, 'hello@codebar.io', 'hello@codebar.io') do |format|
+      format.html {render 'three_month_chaser'}
+    end
+  end
 
   def welcome(member)
     if member.student?
diff --git a/app/models/member.rb b/app/models/member.rb
index b6be0e8a3..13e36fd70 100644
--- a/app/models/member.rb
+++ b/app/models/member.rb
@@ -22,6 +22,7 @@ class Member < ApplicationRecord
   has_many :chapters, -> { distinct }, through: :groups
   has_many :announcements, -> { distinct }, through: :groups
   has_many :meeting_invitations
+  has_many :member_email_deliveries
 
   validates :auth_services, presence: true
   validates :name, :surname, :email, :about_you, presence: true, if: :can_log_in?
diff --git a/app/models/member_email_delivery.rb b/app/models/member_email_delivery.rb
new file mode 100644
index 000000000..f6d836129
--- /dev/null
+++ b/app/models/member_email_delivery.rb
@@ -0,0 +1,3 @@
+class MemberEmailDelivery < ApplicationRecord
+  belongs_to :member, polymorphic: true, optional: true
+end
diff --git a/app/services/three_month_email_service.rb b/app/services/three_month_email_service.rb
new file mode 100644
index 000000000..20d3c1585
--- /dev/null
+++ b/app/services/three_month_email_service.rb
@@ -0,0 +1,35 @@
+# frozen_string_literal: true
+
+class ThreeMonthEmailService
+  def self.send_chaser
+    three_month_cutoff = 3.months.ago.beginning_of_day
+    one_year_cutoff = 1.year.ago.beginning_of_day
+
+    recent_attendee_ids = WorkshopInvitation.to_students
+                                            .attended
+                                            .joins(:workshop)
+                                            .where('workshops.date_and_time >= ?', three_month_cutoff)
+                                            .select(:member_id)
+
+    past_year_attendee_ids = WorkshopInvitation.to_students
+                                               .attended
+                                               .joins(:workshop)
+                                               .where('workshops.date_and_time >= ?', one_year_cutoff)
+                                               .select(:member_id)
+
+    members = Member.not_banned
+                    .accepted_toc
+                    .joins(:groups)
+                    .merge(Group.students)
+                    .left_joins(:member_email_deliveries)
+                    .where(member_email_deliveries: { id: nil })
+                    .where.not(id: recent_attendee_ids)
+                    .where(id: past_year_attendee_ids)
+                    .distinct
+    return if members.empty?
+
+    members.find_each do |member|
+      MemberMailer.with(member: member).chaser.deliver_later
+    end
+  end
+end
diff --git a/app/views/member_mailer/three_month_chaser.html.haml b/app/views/member_mailer/three_month_chaser.html.haml
new file mode 100644
index 000000000..93fcfde68
--- /dev/null
+++ b/app/views/member_mailer/three_month_chaser.html.haml
@@ -0,0 +1,21 @@
+%h1 Hi #{@member.name},
+
+%p
+  We’ve noticed you haven’t been to a codebar workshop in a little while, and we just wanted to check in. We know life gets busy, but we’d love to understand how things are going for you and whether there’s anything we can do to make it easier or more valuable for you to join again.
+%p
+  If you have a minute, could you please share your thoughts in this short form? 👉 https://forms.gle/tEETvC3zYP9mcLar7
+
+%p
+  Or, if you’re thinking about coming back soon, we’ve got some great upcoming workshops and events you might like to join 👉https://codebar.io/events/
+
+%p
+  Your feedback really helps us make codebar more welcoming and useful for everyone in our community 💜
+
+%p
+  We’d love to see you again soon!
+
+%p
+  #{"-- "}
+%br
+Warmly,
+The Codebar Team
diff --git a/config/application.rb b/config/application.rb
index a8af5e442..e84652355 100644
--- a/config/application.rb
+++ b/config/application.rb
@@ -33,6 +33,9 @@ class Application < Rails::Application
 
     config.active_record.belongs_to_required_by_default = true
 
+    # let's start using Active Job!
+    config.active_job.queue_adapter = :delayed_job
+
     if ENV["RAILS_LOG_TO_STDOUT"].present?
       $stdout.sync = true
       config.rails_semantic_logger.add_file_appender = false
diff --git a/config/environments/test.rb b/config/environments/test.rb
index 7b18fa6e0..3afe8b20f 100644
--- a/config/environments/test.rb
+++ b/config/environments/test.rb
@@ -1,5 +1,6 @@
 require "active_support/core_ext/integer/time"
 require "timecop"
+require "active_job/test_helper"
 
 # The test environment is used exclusively to run your application's
 # test suite. You never need to work with it otherwise. Remember that
@@ -55,6 +56,8 @@
   # Raise error when a before_action's only/except options reference missing actions.
   config.action_controller.raise_on_missing_callback_actions = true
 
+  config.active_job.queue_adapter = :test
+
   # Fake omniauth for testing
   OmniAuth.config.test_mode = true
 
diff --git a/lib/tasks/chaser.rake b/lib/tasks/chaser.rake
new file mode 100644
index 000000000..d06134aa5
--- /dev/null
+++ b/lib/tasks/chaser.rake
@@ -0,0 +1,7 @@
+namespace :chaser do
+  desc "Send emails to users who've not attended in a while"
+
+  task three_months: :environment do
+    SendThreeMonthEmailJob.perform_later
+  end
+end
diff --git a/spec/fabricators/member_email_delivery_fabricator.rb b/spec/fabricators/member_email_delivery_fabricator.rb
new file mode 100644
index 000000000..f633b7a35
--- /dev/null
+++ b/spec/fabricators/member_email_delivery_fabricator.rb
@@ -0,0 +1,6 @@
+Fabricator(:member_email_delivery) do
+  member(fabricator: :member)
+  subject("Chaser")
+  body("Lorem ipsum")
+  to(["test_email@address"])
+end
diff --git a/spec/mailers/member_mailer_spec.rb b/spec/mailers/member_mailer_spec.rb
index b09ed32f6..77c6566ff 100644
--- a/spec/mailers/member_mailer_spec.rb
+++ b/spec/mailers/member_mailer_spec.rb
@@ -115,4 +115,21 @@
       end.to change { ActionMailer::Base.deliveries.count }.by 1
     end
   end
+
+  describe "#chaser" do
+    it "logs the sent email" do
+      expect do
+        MemberMailer
+          .with(member: member)
+          .chaser
+          .deliver_now
+        end.to change(MemberEmailDelivery, :count).by(1)
+
+      log = MemberEmailDelivery.last!
+
+      expect(log.member).to eq(member)
+      expect(log.subject).to eq("It’s been a while, how are you doing? ♥️")
+      expect(log.to).to eq([member.email])
+    end
+  end
 end
diff --git a/spec/services/three_month_email_service_spec.rb b/spec/services/three_month_email_service_spec.rb
new file mode 100644
index 000000000..4117bb819
--- /dev/null
+++ b/spec/services/three_month_email_service_spec.rb
@@ -0,0 +1,200 @@
+RSpec.describe ThreeMonthEmailService, type: :service do
+  describe "#send_chaser" do
+    subject(:call) { described_class.send_chaser }
+
+    let(:chapter) { Fabricate(:chapter) }
+    let(:students_group) { Fabricate(:group, name: "Students", chapter: chapter) }
+    let(:coaches_group) { Fabricate(:group, name: "Coaches", chapter: chapter) }
+
+    let!(:eligible_student) do
+      member = Fabricate(:member)
+      Fabricate(:subscription, member: member, group: students_group)
+      Fabricate(
+        :workshop_invitation,
+        member: member,
+        workshop: Fabricate(:workshop, chapter: chapter, date_and_time: 6.months.ago),
+        role: "Student",
+        attended: true
+      )
+      member
+    end
+
+    let!(:already_emailed_student) do
+      member = Fabricate(:member)
+      Fabricate(:subscription, member: member, group: students_group)
+      Fabricate(:member_email_delivery, member: member)
+      member
+    end
+
+    let!(:student_with_recent_attendance) do
+      member = Fabricate(:member)
+      Fabricate(:subscription, member: member, group: students_group)
+      Fabricate(
+        :workshop_invitation,
+        member: member,
+        workshop: Fabricate(:workshop, chapter: chapter, date_and_time: 1.month.ago),
+        role: "Student",
+        attended: true
+      )
+      member
+    end
+
+    let!(:student_with_old_attendance) do
+      member = Fabricate(:member)
+      Fabricate(:subscription, member: member, group: students_group)
+      Fabricate(
+        :workshop_invitation,
+        member: member,
+        workshop: Fabricate(:workshop, chapter: chapter, date_and_time: 4.months.ago),
+        role: "Student",
+        attended: true
+      )
+      member
+    end
+
+    let!(:coach_member) do
+      member = Fabricate(:member)
+      Fabricate(:subscription, member: member, group: coaches_group)
+      member
+    end
+
+    let!(:unsubscribed_member) { Fabricate(:member) }
+    let!(:banned_student) do
+      member = Fabricate(:banned_member)
+      Fabricate(:subscription, member: member, group: students_group)
+      member
+    end
+    let!(:student_without_toc) do
+      member = Fabricate(:member_without_toc)
+      Fabricate(:subscription, member: member, group: students_group)
+      member
+    end
+
+    let!(:student_with_very_old_attendance) do
+      member = Fabricate(:member)
+      Fabricate(:subscription, member: member, group: students_group)
+      Fabricate(
+        :workshop_invitation,
+        member: member,
+        workshop: Fabricate(:workshop, chapter: chapter, date_and_time: 14.months.ago),
+        role: "Student",
+        attended: true
+      )
+      member
+    end
+
+    it "emails only students who have not attended in the last 3 months and were not emailed before" do
+      expect { perform_enqueued_jobs { call } }.to change(MemberEmailDelivery, :count).by(2)
+
+      expect(MemberEmailDelivery.where(member: eligible_student)).to exist
+      expect(MemberEmailDelivery.where(member: student_with_old_attendance)).to exist
+    end
+
+    it "does not email a member already present in member_email_deliveries" do
+      expect { perform_enqueued_jobs { call } }
+        .not_to change { MemberEmailDelivery.where(member: already_emailed_student).count }
+    end
+
+    it "does not email students with a recent attended workshop" do
+      expect { perform_enqueued_jobs { call } }
+        .not_to change { MemberEmailDelivery.where(member: student_with_recent_attendance).count }
+    end
+
+    it "does not email members without a student subscription" do
+      perform_enqueued_jobs { call }
+
+      expect(MemberEmailDelivery.where(member: coach_member)).to be_empty
+      expect(MemberEmailDelivery.where(member: unsubscribed_member)).to be_empty
+    end
+
+    it "does not email banned students or students without accepted terms" do
+      perform_enqueued_jobs { call }
+
+      expect(MemberEmailDelivery.where(member: banned_student)).to be_empty
+      expect(MemberEmailDelivery.where(member: student_without_toc)).to be_empty
+    end
+
+    it "does not email students who have not attended in the past year" do
+      perform_enqueued_jobs { call }
+
+      expect(MemberEmailDelivery.where(member: student_with_very_old_attendance)).to be_empty
+    end
+
+    it "sends only one chaser for a member with multiple student subscriptions" do
+      member = Fabricate(:member)
+      other_chapter = Fabricate(:chapter)
+      other_students_group = Fabricate(:group, name: "Students", chapter: other_chapter)
+      Fabricate(:subscription, member: member, group: students_group)
+      Fabricate(:subscription, member: member, group: other_students_group)
+
+      perform_enqueued_jobs { call }
+
+      expect(MemberEmailDelivery.where(member: member).count).to eq(1)
+    end
+
+    it "sends only one chaser for a member with multiple qualifying old attendances" do
+      member = Fabricate(:member)
+      Fabricate(:subscription, member: member, group: students_group)
+      Fabricate(
+        :workshop_invitation,
+        member: member,
+        workshop: Fabricate(:workshop, chapter: chapter, date_and_time: 5.months.ago),
+        role: "Student",
+        attended: true
+      )
+      Fabricate(
+        :workshop_invitation,
+        member: member,
+        workshop: Fabricate(:workshop, chapter: chapter, date_and_time: 4.months.ago),
+        role: "Student",
+        attended: true
+      )
+
+      perform_enqueued_jobs { call }
+
+      expect(MemberEmailDelivery.where(member: member).count).to eq(1)
+    end
+
+    it "does not send chasers when there are no eligible members" do
+      Fabricate(
+        :workshop_invitation,
+        member: eligible_student,
+        workshop: Fabricate(:workshop, chapter: chapter, date_and_time: 1.month.ago),
+        role: "Student",
+        attended: true
+      )
+      Fabricate(
+        :workshop_invitation,
+        member: student_with_old_attendance,
+        workshop: Fabricate(:workshop, chapter: chapter, date_and_time: 1.month.ago),
+        role: "Student",
+        attended: true
+      )
+
+      expect { perform_enqueued_jobs { call } }.not_to change(MemberEmailDelivery, :count)
+    end
+
+    it "emails a student member who has recent attendance only as a coach" do
+      member = Fabricate(:member)
+      Fabricate(:subscription, member: member, group: students_group)
+      Fabricate(
+        :workshop_invitation,
+        member: member,
+        workshop: Fabricate(:workshop, chapter: chapter, date_and_time: 6.months.ago),
+        role: "Student",
+        attended: true
+      )
+      Fabricate(
+        :workshop_invitation,
+        member: member,
+        workshop: Fabricate(:workshop, chapter: chapter, date_and_time: 1.month.ago),
+        role: "Coach",
+        attended: true
+      )
+
+      perform_enqueued_jobs { call }
+
+      expect(MemberEmailDelivery.where(member: member)).to exist
+    end
+  end
+end
diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
index 3ee48ccc4..ce9f6ee41 100644
--- a/spec/spec_helper.rb
+++ b/spec/spec_helper.rb
@@ -57,6 +57,7 @@ def self.branch_coverage?
 ActiveRecord::Migration.check_all_pending! if defined?(ActiveRecord::Migration)
 
 RSpec.configure do |config|
+  config.include ActiveJob::TestHelper
   config.include ApplicationHelper
   config.include LoginHelpers
   config.include ActiveSupport::Testing::TimeHelpers
@@ -95,6 +96,9 @@ def self.branch_coverage?
       to_return(status: 200, body: '{"status":"active","segments":[]}', headers: { 'Content-Type' => 'application/json' })
 
     DatabaseCleaner.strategy = :transaction
+
+    clear_enqueued_jobs
+    clear_performed_jobs
   end
 
   # Driver is using an external browser with an app