diff --git a/app/mailers/group_smtp_mailer.rb b/app/mailers/group_smtp_mailer.rb
index 42a2c9a082f..5a72c1c92c7 100644
--- a/app/mailers/group_smtp_mailer.rb
+++ b/app/mailers/group_smtp_mailer.rb
@@ -16,7 +16,8 @@ class GroupSmtpMailer < ActionMailer::Base
       user_name: from_group.email_username,
       password: from_group.email_password,
       authentication: GlobalSetting.smtp_authentication,
-      enable_starttls_auto: from_group.smtp_ssl
+      enable_starttls_auto: from_group.smtp_ssl,
+      return_response: true
     }
 
     group_name = from_group.name_full_preferred
diff --git a/app/models/email_log.rb b/app/models/email_log.rb
index a75fc0764bb..8e3c7b163d3 100644
--- a/app/models/email_log.rb
+++ b/app/models/email_log.rb
@@ -127,22 +127,23 @@ end
 #
 # Table name: email_logs
 #
-#  id                :integer          not null, primary key
-#  to_address        :string           not null
-#  email_type        :string           not null
-#  user_id           :integer
-#  created_at        :datetime         not null
-#  updated_at        :datetime         not null
-#  post_id           :integer
-#  bounce_key        :uuid
-#  bounced           :boolean          default(FALSE), not null
-#  message_id        :string
-#  smtp_group_id     :integer
-#  cc_addresses      :text
-#  cc_user_ids       :integer          is an Array
-#  raw               :text
-#  topic_id          :integer
-#  bounce_error_code :string
+#  id                        :integer          not null, primary key
+#  to_address                :string           not null
+#  email_type                :string           not null
+#  user_id                   :integer
+#  created_at                :datetime         not null
+#  updated_at                :datetime         not null
+#  post_id                   :integer
+#  bounce_key                :uuid
+#  bounced                   :boolean          default(FALSE), not null
+#  message_id                :string
+#  smtp_group_id             :integer
+#  cc_addresses              :text
+#  cc_user_ids               :integer          is an Array
+#  raw                       :text
+#  topic_id                  :integer
+#  bounce_error_code         :string
+#  smtp_transaction_response :string(500)
 #
 # Indexes
 #
diff --git a/db/migrate/db/migrate/20220606061813_add_smtp_transaction_response_to_email_logs.rb b/db/migrate/db/migrate/20220606061813_add_smtp_transaction_response_to_email_logs.rb
new file mode 100644
index 00000000000..60a15a74d8c
--- /dev/null
+++ b/db/migrate/db/migrate/20220606061813_add_smtp_transaction_response_to_email_logs.rb
@@ -0,0 +1,7 @@
+# frozen_string_literal: true
+
+class AddSmtpTransactionResponseToEmailLogs < ActiveRecord::Migration[7.0]
+  def change
+    add_column :email_logs, :smtp_transaction_response, :string, null: true, limit: 500
+  end
+end
diff --git a/lib/email/message_builder.rb b/lib/email/message_builder.rb
index 187bfc364d4..62236252e0d 100644
--- a/lib/email/message_builder.rb
+++ b/lib/email/message_builder.rb
@@ -145,6 +145,7 @@ module Email
       }
 
       args[:delivery_method_options] = @opts[:delivery_method_options] if @opts[:delivery_method_options]
+      args[:delivery_method_options] = (args[:delivery_method_options] || {}).merge(return_response: true)
 
       args
     end
diff --git a/lib/email/sender.rb b/lib/email/sender.rb
index 7583c200d77..ce5ab66fc3a 100644
--- a/lib/email/sender.rb
+++ b/lib/email/sender.rb
@@ -315,7 +315,13 @@ module Email
       DiscourseEvent.trigger(:before_email_send, @message, @email_type)
 
       begin
-        @message.deliver_now
+        message_response = @message.deliver!
+
+        # TestMailer from the Mail gem does not return a real response, it
+        # returns an array containing @message, so we have to have this workaround.
+        if message_response.kind_of?(Net::SMTP::Response)
+          email_log.smtp_transaction_response = message_response.message&.chomp
+        end
       rescue *SMTP_CLIENT_ERRORS => e
         return skip(SkippedEmailLog.reason_types[:custom], custom_reason: e.message)
       end
diff --git a/spec/lib/email/sender_spec.rb b/spec/lib/email/sender_spec.rb
index 8045995edb9..f2615b96dab 100644
--- a/spec/lib/email/sender_spec.rb
+++ b/spec/lib/email/sender_spec.rb
@@ -7,6 +7,13 @@ describe Email::Sender do
     SiteSetting.secure_media_allow_embed_images_in_emails = false
   end
   fab!(:post) { Fabricate(:post) }
+  let(:mock_smtp_transaction_response) { "250 Ok: queued as 2l3Md07BObzB8kRyHZeoN0baSUAhzc7A-NviRioOr80=@mailhog.example" }
+
+  def stub_deliver_response(message)
+    message.stubs(:deliver!).returns(
+      Net::SMTP::Response.new("250", mock_smtp_transaction_response)
+    )
+  end
 
   context "disable_emails is enabled" do
     fab!(:user) { Fabricate(:user) }
@@ -41,19 +48,20 @@ describe Email::Sender do
       before { SiteSetting.disable_emails = "non-staff" }
 
       it "doesn't deliver mail to normal user" do
-        Mail::Message.any_instance.expects(:deliver_now).never
+        Mail::Message.any_instance.expects(:deliver!).never
         message = Mail::Message.new(to: user.email, body: "hello")
+        stub_deliver_response(message)
         expect(Email::Sender.new(message, :hello).send).to eq(nil)
       end
 
       it "delivers mail to staff user" do
-        Mail::Message.any_instance.expects(:deliver_now).once
+        Mail::Message.any_instance.expects(:deliver!).once
         message = Mail::Message.new(to: moderator.email, body: "hello")
         Email::Sender.new(message, :hello).send
       end
 
       it "delivers mail to staff user when confirming new email if user is provided" do
-        Mail::Message.any_instance.expects(:deliver_now).once
+        Mail::Message.any_instance.expects(:deliver!).once
         Fabricate(:email_change_request, {
           user: moderator,
           new_email: "newemail@testmoderator.com",
@@ -69,32 +77,32 @@ describe Email::Sender do
   end
 
   it "doesn't deliver mail when the message is of type NullMail" do
-    Mail::Message.any_instance.expects(:deliver_now).never
+    Mail::Message.any_instance.expects(:deliver!).never
     message = ActionMailer::Base::NullMail.new
     expect(Email::Sender.new(message, :hello).send).to eq(nil)
   end
 
   it "doesn't deliver mail when the message is nil" do
-    Mail::Message.any_instance.expects(:deliver_now).never
+    Mail::Message.any_instance.expects(:deliver!).never
     Email::Sender.new(nil, :hello).send
   end
 
   it "doesn't deliver when the to address is nil" do
     message = Mail::Message.new(body: 'hello')
-    message.expects(:deliver_now).never
+    message.expects(:deliver!).never
     Email::Sender.new(message, :hello).send
   end
 
   it "doesn't deliver when the to address uses the .invalid tld" do
     message = Mail::Message.new(body: 'hello', to: 'myemail@example.invalid')
-    message.expects(:deliver_now).never
+    message.expects(:deliver!).never
     expect { Email::Sender.new(message, :hello).send }.
       to change { SkippedEmailLog.where(reason_type: SkippedEmailLog.reason_types[:sender_message_to_invalid]).count }.by(1)
   end
 
   it "doesn't deliver when the body is nil" do
     message = Mail::Message.new(to: 'eviltrout@test.domain')
-    message.expects(:deliver_now).never
+    message.expects(:deliver!).never
     Email::Sender.new(message, :hello).send
   end
 
@@ -126,14 +134,14 @@ describe Email::Sender do
         to: 'eviltrout@test.domain',
         body: '**hello**'
       )
-      message.stubs(:deliver_now)
+      stub_deliver_response(message)
       message
     end
 
     let(:email_sender) { Email::Sender.new(message, :valid_type) }
 
     it 'calls deliver' do
-      message.expects(:deliver_now).once
+      message.expects(:deliver!).once
       email_sender.send
     end
 
@@ -414,6 +422,7 @@ describe Email::Sender do
 
         before do
           SiteSetting.enable_smtp = true
+          stub_deliver_response(message)
         end
 
         it 'adds the group id and raw content to the email log' do
@@ -684,7 +693,7 @@ describe Email::Sender do
       message = Mail::Message.new to: 'disc@ourse.org', body: 'some content'
       message.header['X-Discourse-Post-Id'] = post.id
       message.header['X-Discourse-Topic-Id'] = post.topic_id
-      message.expects(:deliver_now).never
+      message.expects(:deliver!).never
 
       email_sender = Email::Sender.new(message, :valid_type)
       expect { email_sender.send }.to change { SkippedEmailLog.count }
@@ -703,7 +712,7 @@ describe Email::Sender do
       message = Mail::Message.new to: 'disc@ourse.org', body: 'some content'
       message.header['X-Discourse-Post-Id'] = post.id
       message.header['X-Discourse-Topic-Id'] = post.topic_id
-      message.expects(:deliver_now).never
+      message.expects(:deliver!).never
 
       email_sender = Email::Sender.new(message, :valid_type)
       expect { email_sender.send }.to change { SkippedEmailLog.count }
@@ -717,7 +726,7 @@ describe Email::Sender do
   context 'with a user' do
     let(:message) do
       message = Mail::Message.new to: 'eviltrout@test.domain', body: 'test body'
-      message.stubs(:deliver_now)
+      stub_deliver_response(message)
       message
     end
 
@@ -733,6 +742,10 @@ describe Email::Sender do
       expect(@email_log.user_id).to eq(user.id)
     end
 
+    it 'should have the smtp_transaction_response message' do
+      expect(@email_log.smtp_transaction_response).to eq(mock_smtp_transaction_response)
+    end
+
     describe "post reply keys" do
       fab!(:post) { Fabricate(:post) }
 
@@ -782,7 +795,7 @@ describe Email::Sender do
   context "with cc addresses" do
     let(:message) do
       message = Mail::Message.new to: 'eviltrout@test.domain', body: 'test body', cc: 'someguy@test.com;otherguy@xyz.com'
-      message.stubs(:deliver_now)
+      stub_deliver_response(message)
       message
     end