diff --git a/app/models/article.rb b/app/models/article.rb
index 1c171e06b..a00eef547 100644
--- a/app/models/article.rb
+++ b/app/models/article.rb
@@ -97,6 +97,13 @@ class Article < ApplicationRecord
       tagged_with(tag_name)
   }
 
+  scope :user_published_with, lambda { |user_id, tag_name|
+    published.
+      where(user_id: user_id).
+      order(published_at: :desc).
+      tagged_with(tag_name)
+  }
+
   scope :cached_tagged_with, ->(tag) { where("cached_tag_list ~* ?", "^#{tag},| #{tag},|, #{tag}$|^#{tag}$") }
 
   scope :cached_tagged_by_approval_with, ->(tag) { cached_tagged_with(tag).where(approved: true) }
diff --git a/app/services/broadcasts/welcome_notification/generator.rb b/app/services/broadcasts/welcome_notification/generator.rb
index 6de98d020..f415d71d8 100644
--- a/app/services/broadcasts/welcome_notification/generator.rb
+++ b/app/services/broadcasts/welcome_notification/generator.rb
@@ -16,8 +16,9 @@ module Broadcasts
 
         send_welcome_notification unless notification_enqueued
         send_authentication_notification unless notification_enqueued
-        send_ux_customization_notification unless notification_enqueued
         send_feed_customization_notification unless notification_enqueued
+        send_ux_customization_notification unless notification_enqueued
+        send_discuss_and_ask_notification unless notification_enqueued
       end
 
       private
@@ -38,6 +39,12 @@ module Broadcasts
         @notification_enqueued = true
       end
 
+      def send_feed_customization_notification
+        return if user_is_following_tags? || received_notification?(customize_feed_broadcast) || user.created_at > 3.days.ago
+
+        Notification.send_welcome_notification(user.id, customize_feed_broadcast.id)
+      end
+
       def send_ux_customization_notification
         return if received_notification?(customize_ux_broadcast) || user.created_at > 5.days.ago
 
@@ -45,10 +52,11 @@ module Broadcasts
         @notification_enqueued = true
       end
 
-      def send_feed_customization_notification
-        return if user_is_following_tags? || received_notification?(customize_feed_broadcast) || user.created_at > 3.days.ago
+      def send_discuss_and_ask_notification
+        return if (asked_a_question && started_a_discussion) || received_notification?(discuss_and_ask_broadcast) || user.created_at > 6.days.ago
 
-        Notification.send_welcome_notification(user.id, customize_feed_broadcast.id)
+        Notification.send_welcome_notification(user.id, discuss_and_ask_broadcast.id)
+        @notification_enqueued = true
       end
 
       def received_notification?(broadcast)
@@ -80,20 +88,43 @@ module Broadcasts
         @customize_feed_broadcast ||= Broadcast.find_by(title: "Welcome Notification: customize_feed")
       end
 
-      def identities
-        @identities ||= user.identities.where(provider: SiteConfig.authentication_providers)
-      end
-
       def authentication_broadcast
         @authentication_broadcast ||= find_auth_broadcast
       end
 
+      def discuss_and_ask_broadcast
+        @discuss_and_ask_broadcast ||= find_discuss_ask_broadcast
+      end
+
+      def identities
+        @identities ||= user.identities.where(provider: SiteConfig.authentication_providers)
+      end
+
       def find_auth_broadcast
         missing_identities = SiteConfig.authentication_providers.map do |provider|
           identities.exists?(provider: provider) ? nil : "#{provider}_connect"
         end.compact
         Broadcast.find_by(title: "Welcome Notification: #{missing_identities.first}")
       end
+
+      def find_discuss_ask_broadcast
+        type = if !asked_a_question && started_a_discussion
+                 "ask_question"
+               elsif !started_a_discussion && asked_a_question
+                 "start_discussion"
+               else
+                 "discuss_and_ask"
+               end
+        Broadcast.find_by(title: "Welcome Notification: #{type}")
+      end
+
+      def asked_a_question
+        @asked_a_question ||= Article.user_published_with(user.id, "explainlikeimfive").any?
+      end
+
+      def started_a_discussion
+        @started_a_discussion ||= Article.user_published_with(user.id, "discuss").any?
+      end
     end
   end
 end
diff --git a/db/seeds.rb b/db/seeds.rb
index 9bc6f840c..b321ad678 100644
--- a/db/seeds.rb
+++ b/db/seeds.rb
@@ -251,7 +251,10 @@ broadcast_messages = {
   twitter_connect: "You're on a roll! 🎉 Let's connect your <a href='/settings'> Twitter account</a> to complete your identity so that we don't think you're a robot. 🤖",
   github_connect: "You're on a roll! 🎉 Let's connect your <a href='/settings'> GitHub account</a> to complete your identity so that we don't think you're a robot. 🤖",
   customize_feed: "Hi, it's me again! 👋 Now that you're a part of the DEV community, let's focus on personalizing your content. You can start by <a href='/tags'>following some tags</a> to help customize your feed! 🎉",
-  customize_experience: "Sloan here! 👋 Did you know that that you can customize your DEV experience? Try changing <a href='settings/ux'>your font and theme</a> and find the best style for you!"
+  customize_experience: "Sloan here! 👋 Did you know that that you can customize your DEV experience? Try changing <a href='settings/ux'>your font and theme</a> and find the best style for you!",
+  start_discussion: "Sloan here! 👋 I noticed that you haven't <a href='https://dev.to/t/discuss'>started a discussion</a> yet. Starting a discussion is easy to do; just click on 'Write a Post' in the sidebar of the tag page to get started!",
+  ask_question: "Sloan here! 👋 I noticed that you haven't <a href='https://dev.to/t/explainlikeimfive'>asked a question</a> yet. Asking a question is easy to do; just click on 'Write a Post' in the sidebar of the tag page to get started!",
+  discuss_and_ask: "Sloan here! 👋 I noticed that you haven't <a href='https://dev.to/t/explainlikeimfive'>asked a question</a> or <a href='https://dev.to/t/discuss'>started a discussion</a> yet. It's easy to do both of these; just click on 'Write a Post' in the sidebar of the tag page to get started!"
 }
 
 broadcast_messages.each do |type, message|
diff --git a/spec/factories/broadcasts.rb b/spec/factories/broadcasts.rb
index 7bb4557b0..6cb761ad6 100644
--- a/spec/factories/broadcasts.rb
+++ b/spec/factories/broadcasts.rb
@@ -32,6 +32,24 @@ FactoryBot.define do
       processed_html { "Hi, it's me again! 👋 Now that you're a part of the DEV community, let's focus on personalizing your content. You can start by <a href='/tags'>following some tags</a> to help customize your feed! 🎉" }
     end
 
+    factory :start_discussion_broadcast do
+      title          { "Welcome Notification: start_discussion" }
+      type_of        { "Welcome" }
+      processed_html { "Sloan here! 👋 I noticed that you haven't <a href='https://dev.to/t/discuss'>started a discussion</a> yet. Starting a discussion is easy to do; just click on 'Write a Post' in the sidebar of the tag page to get started!" }
+    end
+
+    factory :ask_question_broadcast do
+      title          { "Welcome Notification: ask_question" }
+      type_of        { "Welcome" }
+      processed_html { "Sloan here! 👋 I noticed that you haven't <a href='https://dev.to/t/explainlikeimfive'>asked a question</a> yet. Asking a question is easy to do; just click on 'Write a Post' in the sidebar of the tag page to get started!" }
+    end
+
+    factory :discuss_and_ask_broadcast do
+      title          { "Welcome Notification: discuss_and_ask" }
+      type_of        { "Welcome" }
+      processed_html { "Sloan here! 👋 I noticed that you haven't <a href='https://dev.to/t/explainlikeimfive'>asked a question</a> or <a href='https://dev.to/t/discuss'>started a discussion</a> yet. It's easy to do both of these; just click on 'Write a Post' in the sidebar of the tag page to get started!" }
+    end
+
     # TODO: [@thepracticaldev/delightful] Remove onboarding factory once welcome notifications are live.
     factory :onboarding_broadcast do
       title          { "Welcome Notification" }
diff --git a/spec/services/broadcasts/welcome_notification/generator_spec.rb b/spec/services/broadcasts/welcome_notification/generator_spec.rb
index af8529ab3..293699be2 100644
--- a/spec/services/broadcasts/welcome_notification/generator_spec.rb
+++ b/spec/services/broadcasts/welcome_notification/generator_spec.rb
@@ -4,10 +4,6 @@ RSpec.describe Broadcasts::WelcomeNotification::Generator, type: :service do
   let(:mascot_account)             { create(:user) }
   let!(:welcome_thread)            { create(:article, user: mascot_account, published: true, tags: "welcome") }
   let!(:welcome_broadcast)         { create(:welcome_broadcast) }
-  let!(:twitter_connect_broadcast) { create(:twitter_connect_broadcast) }
-  let!(:github_connect_broadcast)  { create(:github_connect_broadcast) }
-  let!(:customize_ux_broadcast)    { create(:customize_ux_broadcast) }
-  let!(:customize_feed_broadcast)  { create(:customize_feed_broadcast) }
 
   before do
     allow(Notification).to receive(:send_welcome_notification).and_call_original
@@ -68,6 +64,9 @@ RSpec.describe Broadcasts::WelcomeNotification::Generator, type: :service do
   end
 
   describe "#send_authentication_notification" do
+    let!(:twitter_connect_broadcast) { create(:twitter_connect_broadcast) }
+    let!(:github_connect_broadcast)  { create(:github_connect_broadcast) }
+
     it "does not send notification if user is created less than a day ago" do
       user = create(:user, :with_identity, identities: ["github"])
       sidekiq_perform_enqueued_jobs { described_class.new(user.id).send(:send_authentication_notification) }
@@ -109,37 +108,9 @@ RSpec.describe Broadcasts::WelcomeNotification::Generator, type: :service do
     end
   end
 
-  describe "#send_ux_customization_notification" do
-    # Ensure that the user is already authenticated with all providers and has commented on the
-    # welcome thread so that we can actually trigger just the customize notification only.
-    let(:user) { create(:user, :with_identity, identities: %w[twitter github], created_at: 5.days.ago) }
-
-    before do
-      create(:comment, commentable: welcome_thread, commentable_type: "Article", user: user)
-    end
-
-    it "does not send a notification to a newly-created user" do
-      user.update!(created_at: Time.zone.now)
-      sidekiq_perform_enqueued_jobs { described_class.new(user.id).send(:send_ux_customization_notification) }
-      expect(Notification).not_to have_received(:send_welcome_notification)
-    end
-
-    it "generates the correct broadcast type and sends the notification to the user" do
-      sidekiq_perform_enqueued_jobs { described_class.new(user.id).send(:send_ux_customization_notification) }
-      expect(user.notifications.count).to eq(1)
-      expect(user.notifications.first.notifiable).to eq(customize_ux_broadcast)
-    end
-
-    it "does not send duplicate notifications" do
-      2.times do
-        sidekiq_perform_enqueued_jobs { described_class.new(user.id).send(:send_ux_customization_notification) }
-      end
-      expect(user.notifications.count).to eq(1)
-    end
-  end
-
   describe "#send_feed_customization_notification" do
     let!(:user) { create(:user, :with_identity, identities: %w[twitter github], created_at: 3.days.ago) }
+    let!(:customize_feed_broadcast)  { create(:customize_feed_broadcast) }
 
     it "does not send a notification to a newly-created user" do
       user.update!(created_at: Time.zone.now)
@@ -167,10 +138,85 @@ RSpec.describe Broadcasts::WelcomeNotification::Generator, type: :service do
     end
   end
 
-  context "when sending a set_up_profile notification" do
-    xit "generates the appropriate broadcast to be sent to a user"
-    xit "it sends a welcome notification for that broadcast"
-    xit "it does not send duplicate welcome notification for that broadcast"
-    xit "does not send a notification to a user who has set up their profile"
+  describe "#send_ux_customization_notification" do
+    let!(:user) { create(:user, :with_identity, identities: %w[twitter github], created_at: 5.days.ago) }
+    let!(:customize_ux_broadcast) { create(:customize_ux_broadcast) }
+
+    it "does not send a notification to a newly-created user" do
+      user.update!(created_at: Time.zone.now)
+      sidekiq_perform_enqueued_jobs { described_class.new(user.id).send(:send_ux_customization_notification) }
+      expect(Notification).not_to have_received(:send_welcome_notification)
+    end
+
+    it "generates the correct broadcast type and sends the notification to the user" do
+      sidekiq_perform_enqueued_jobs { described_class.new(user.id).send(:send_ux_customization_notification) }
+      expect(user.notifications.count).to eq(1)
+      expect(user.notifications.first.notifiable).to eq(customize_ux_broadcast)
+    end
+
+    it "does not send duplicate notifications" do
+      2.times do
+        sidekiq_perform_enqueued_jobs { described_class.new(user.id).send(:send_ux_customization_notification) }
+      end
+      expect(user.notifications.count).to eq(1)
+    end
+  end
+
+  describe "#send_discuss_and_ask_notification" do
+    let!(:user) { create(:user, :with_identity, identities: %w[twitter github], created_at: 6.days.ago) }
+    let!(:ask_question_broadcast) { create(:ask_question_broadcast) }
+    let!(:start_discussion_broadcast) { create(:start_discussion_broadcast) }
+    let!(:discuss_and_ask_broadcast) { create(:discuss_and_ask_broadcast) }
+
+    context "with a user who has asked a question" do
+      it "generates the correct broadcast type and sends the notification to the user" do
+        create(:article, tags: "explainlikeimfive", user: user)
+
+        sidekiq_perform_enqueued_jobs { described_class.new(user.id).send(:send_discuss_and_ask_notification) }
+        expect(user.notifications.count).to eq(1)
+        expect(user.notifications.first.notifiable).to eq(start_discussion_broadcast)
+      end
+    end
+
+    context "with a user who has started a discussion" do
+      it "generates the correct broadcast type and sends the notification to the user" do
+        create(:article, tags: "discuss", user: user)
+
+        sidekiq_perform_enqueued_jobs { described_class.new(user.id).send(:send_discuss_and_ask_notification) }
+        expect(user.notifications.count).to eq(1)
+        expect(user.notifications.first.notifiable).to eq(ask_question_broadcast)
+      end
+    end
+
+    context "with a user who has neither asked a question and started a discussion" do
+      it "generates the correct broadcast type and sends the notification to the user" do
+        sidekiq_perform_enqueued_jobs { described_class.new(user.id).send(:send_discuss_and_ask_notification) }
+        expect(user.notifications.count).to eq(1)
+        expect(user.notifications.first.notifiable).to eq(discuss_and_ask_broadcast)
+      end
+    end
+
+    context "with a user who has asked a question and started a discussion" do
+      it "does not send a notification" do
+        create(:article, tags: "discuss", user: user)
+        create(:article, tags: "explainlikeimfive", user: user)
+
+        sidekiq_perform_enqueued_jobs { described_class.new(user.id).send(:send_discuss_and_ask_notification) }
+        expect(Notification).not_to have_received(:send_welcome_notification)
+      end
+    end
+
+    it "does not send a notification to a newly-created user" do
+      user.update!(created_at: Time.zone.now)
+      sidekiq_perform_enqueued_jobs { described_class.new(user.id).send(:send_discuss_and_ask_notification) }
+      expect(Notification).not_to have_received(:send_welcome_notification)
+    end
+
+    it "does not send duplicate notifications" do
+      2.times do
+        sidekiq_perform_enqueued_jobs { described_class.new(user.id).send(:send_discuss_and_ask_notification) }
+      end
+      expect(user.notifications.count).to eq(1)
+    end
   end
 end