diff --git a/app/mailers/user_notifications.rb b/app/mailers/user_notifications.rb
index 724d9172afd..0f33c4021ab 100644
--- a/app/mailers/user_notifications.rb
+++ b/app/mailers/user_notifications.rb
@@ -224,7 +224,8 @@ class UserNotifications < ActionMailer::Base
     build_summary_for(user)
     @unsubscribe_key = UnsubscribeKey.create_key_for(@user, UnsubscribeKey::DIGEST_TYPE)
 
-    @since = opts[:since] || user.last_seen_at || user.user_stat&.digest_attempted_at || 1.month.ago
+    @since = opts[:since].presence
+    @since ||= [user.last_seen_at, user.user_stat&.digest_attempted_at, 1.month.ago].compact.max
 
     # Fetch some topics and posts to show
     digest_opts = {
diff --git a/spec/mailers/user_notifications_spec.rb b/spec/mailers/user_notifications_spec.rb
index adc4f2137b2..5ab50623a9c 100644
--- a/spec/mailers/user_notifications_spec.rb
+++ b/spec/mailers/user_notifications_spec.rb
@@ -450,6 +450,29 @@ RSpec.describe UserNotifications do
         expect(html).to match(' lang="pl-PL"')
         expect(html).to match(' xml:lang="pl-PL"')
       end
+
+      it "uses digest_attempted_at when user hasn't been seen in a while" do
+        user.update!(last_seen_at: 7.days.ago)
+        user.user_stat.update!(digest_attempted_at: 30.minutes.ago)
+        expect(email.to).to be_nil
+      end
+
+      it "uses last_seen_at when user has been sent a digest in a while" do
+        user.update!(last_seen_at: 30.minutes.ago)
+        user.user_stat.update!(digest_attempted_at: 7.days.ago)
+        expect(email.to).to be_nil
+      end
+
+      it "caps at 1 month when user has never been seen or sent a digest" do
+        old_topic = Fabricate(:topic, created_at: 2.months.ago)
+
+        user.update!(last_seen_at: nil)
+        user.user_stat.update!(digest_attempted_at: nil)
+        expect(email.to).to contain_exactly(user.email)
+
+        html = email.html_part.body.to_s
+        expect(html).not_to include(old_topic.title)
+      end
     end
   end