diff --git a/app/logical/approver_pruner.rb b/app/logical/approver_pruner.rb
index 7421eb4c3..67e7933b5 100644
--- a/app/logical/approver_pruner.rb
+++ b/app/logical/approver_pruner.rb
@@ -30,4 +30,19 @@ module ApproverPruner
       end
     end
   end
+
+  def dmail_inactive_approvers!
+    days_until_next_month = (Date.current.next_month.beginning_of_month - Date.current).to_i
+    return unless days_until_next_month <= 21
+
+    inactive_approvers.each do |user|
+      Dmail.create_automated(to: user, title: "You will lose approval privileges soon", body: <<~BODY)
+        You've approved fewer than #{MINIMUM_APPROVALS} posts in the past
+        #{APPROVAL_PERIOD.inspect}. You will lose your approval privileges in
+        #{days_until_next_month} #{"day".pluralize(days_until_next_month)}
+        unless you have approved at least #{MINIMUM_APPROVALS} posts by the end
+        of the month.
+      BODY
+    end
+  end
 end
diff --git a/app/logical/danbooru_maintenance.rb b/app/logical/danbooru_maintenance.rb
index ee9c56949..a76cfc9b1 100644
--- a/app/logical/danbooru_maintenance.rb
+++ b/app/logical/danbooru_maintenance.rb
@@ -21,6 +21,7 @@ module DanbooruMaintenance
   def weekly
     safely { UserPasswordResetNonce.prune! }
     safely { TagRelationshipRetirementService.find_and_retire! }
+    safely { ApproverPruner.dmail_inactive_approvers! }
   end
 
   def monthly
diff --git a/test/unit/approver_pruner_test.rb b/test/unit/approver_pruner_test.rb
index 444ae498e..b1f9b1952 100644
--- a/test/unit/approver_pruner_test.rb
+++ b/test/unit/approver_pruner_test.rb
@@ -27,5 +27,13 @@ class ApproverPrunerTest < ActiveSupport::TestCase
 
       assert_not_includes(ApproverPruner.inactive_approvers.map(&:id), @user.id)
     end
+
+    should "dmail inactive approvers" do
+      travel_to(Date.parse("2020-01-20")) do
+        ApproverPruner.dmail_inactive_approvers!
+      end
+
+      assert_equal("You will lose approval privileges soon", @approver.dmails.received.last.title)
+    end
   end
 end