diff --git a/Gemfile b/Gemfile
index e35e37c8104..f7271515eb0 100644
--- a/Gemfile
+++ b/Gemfile
@@ -41,7 +41,7 @@ gem 'actionview_precompiler', require: false
 
 gem 'seed-fu'
 
-gem 'mail', git: 'https://github.com/discourse/mail.git', require: false
+gem 'mail', git: 'https://github.com/discourse/mail.git'
 gem 'mini_mime'
 gem 'mini_suffix'
 
diff --git a/config/environments/production.rb b/config/environments/production.rb
index a523888a8d5..5f05f6e9b33 100644
--- a/config/environments/production.rb
+++ b/config/environments/production.rb
@@ -41,7 +41,7 @@ Discourse::Application.configure do
       settings[:tls] = true
     end
 
-    config.action_mailer.smtp_settings = settings.reject { |_, y| y.nil? }
+    config.action_mailer.smtp_settings = settings.compact
   else
     config.action_mailer.delivery_method = :sendmail
     config.action_mailer.sendmail_settings = { arguments: '-i' }
diff --git a/lib/freedom_patches/mail_disable_starttls.rb b/lib/freedom_patches/mail_disable_starttls.rb
new file mode 100644
index 00000000000..ccdd9116dd9
--- /dev/null
+++ b/lib/freedom_patches/mail_disable_starttls.rb
@@ -0,0 +1,21 @@
+# frozen_string_literal: true
+
+# Patch from
+# https://github.com/rails/rails/issues/44698#issuecomment-1069675285 to enable
+# previous behavior with Net::SMTP regarding TLS.
+#
+# This should be fixed in an upcoming release of the Mail gem (probably 2.8),
+# when this patch is merged: https://github.com/mikel/mail/pull/1435
+module FreedomPatches::MailDisableStarttls
+  def build_smtp_session
+    super.tap do |smtp|
+      unless settings[:enable_starttls_auto]
+        if smtp.respond_to?(:disable_starttls)
+          smtp.disable_starttls
+        end
+      end
+    end
+  end
+
+  ::Mail::SMTP.prepend(self)
+end
diff --git a/spec/lib/freedom_patches/mail_disable_starttls_spec.rb b/spec/lib/freedom_patches/mail_disable_starttls_spec.rb
new file mode 100644
index 00000000000..454c0372556
--- /dev/null
+++ b/spec/lib/freedom_patches/mail_disable_starttls_spec.rb
@@ -0,0 +1,23 @@
+# frozen_string_literal: true
+
+describe FreedomPatches::MailDisableStarttls do
+  subject(:smtp_session) { smtp.build_smtp_session }
+
+  let(:smtp) { Mail::SMTP.new(options) }
+
+  context "when the starttls option is not provided" do
+    let(:options) { {} }
+
+    it "doesn't disable starttls" do
+      expect(smtp_session).to be_starttls
+    end
+  end
+
+  context "when the starttls option is set to `false`" do
+    let(:options) { { enable_starttls_auto: false } }
+
+    it "properly disables starttls" do
+      expect(smtp_session).not_to be_starttls
+    end
+  end
+end