diff --git a/app/controllers/legacy_tasks_controller.rb b/app/controllers/legacy_tasks_controller.rb
index 2f68f438334..96e91c7d542 100644
--- a/app/controllers/legacy_tasks_controller.rb
+++ b/app/controllers/legacy_tasks_controller.rb
@@ -96,6 +96,9 @@ def assign_to_judge
     # update the location to the assigned judge.
     QueueRepository.update_location_to_judge(appeal.vacols_id, assigned_to)
 
+    # Remove overtime status of an appeal when reassigning to a judge
+    appeal.overtime = false if appeal.overtime?
+
     render json: {
       task: json_task(AttorneyLegacyTask.from_vacols(
                         VACOLS::CaseAssignment.latest_task_for_appeal(appeal.vacols_id),
diff --git a/app/models/task.rb b/app/models/task.rb
index b137d902b01..eba4790cda3 100644
--- a/app/models/task.rb
+++ b/app/models/task.rb
@@ -517,6 +517,8 @@ def reassign(reassign_params, current_user)
 
     update_with_instructions(status: Constants.TASK_STATUSES.cancelled, instructions: reassign_params[:instructions])
 
+    appeal.overtime = false if appeal.overtime? && reassign_clears_overtime?
+
     [sibling, self, sibling.children].flatten
   end
 
@@ -593,6 +595,10 @@ def cancelled_by
     User.find_by_id(record.whodunnit)
   end
 
+  def reassign_clears_overtime?
+    false
+  end
+
   private
 
   def create_and_auto_assign_child_task(options = {})
diff --git a/app/models/tasks/attorney_task.rb b/app/models/tasks/attorney_task.rb
index 9e5c44cfa93..fb371b371dc 100644
--- a/app/models/tasks/attorney_task.rb
+++ b/app/models/tasks/attorney_task.rb
@@ -48,6 +48,10 @@ def stays_with_reassigned_parent?
     super || completed?
   end
 
+  def reassign_clears_overtime?
+    true
+  end
+
   def send_back_to_judge_assign!
     transaction do
       cancelled!
diff --git a/app/models/tasks/judge_task.rb b/app/models/tasks/judge_task.rb
index 455ec14c704..875138f0b67 100644
--- a/app/models/tasks/judge_task.rb
+++ b/app/models/tasks/judge_task.rb
@@ -41,4 +41,8 @@ def timeline_title
   def previous_task
     children_attorney_tasks.order(:assigned_at).last
   end
+
+  def reassign_clears_overtime?
+    true
+  end
 end
diff --git a/spec/controllers/legacy_tasks_controller_spec.rb b/spec/controllers/legacy_tasks_controller_spec.rb
index 13e7e0182c6..e382ffcf5b3 100644
--- a/spec/controllers/legacy_tasks_controller_spec.rb
+++ b/spec/controllers/legacy_tasks_controller_spec.rb
@@ -448,5 +448,30 @@
       end
       it_behaves_like "judge reassigns case"
     end
+
+    context "When the appeal has not been marked for overtime" do
+      before { FeatureToggle.enable!(:overtime_revamp) }
+      after { FeatureToggle.disable!(:overtime_revamp) }
+
+      it "does not create a new work mode for the appeal" do
+        expect(appeal.work_mode.nil?).to be true
+        patch :assign_to_judge, params: { tasks: params }
+        expect(appeal.work_mode.nil?).to be true
+      end
+    end
+
+    context "when the appeal has been marked for overtime" do
+      before do
+        FeatureToggle.enable!(:overtime_revamp)
+        appeal.overtime = true
+      end
+      after { FeatureToggle.disable!(:overtime_revamp) }
+
+      it "removes the overtime status of the appeal" do
+        expect(appeal.overtime?).to be true
+        patch :assign_to_judge, params: { tasks: params }
+        expect(appeal.reload.overtime?).to be false
+      end
+    end
   end
 end
diff --git a/spec/models/task_spec.rb b/spec/models/task_spec.rb
index c35577e418a..4737df2ed14 100644
--- a/spec/models/task_spec.rb
+++ b/spec/models/task_spec.rb
@@ -897,6 +897,64 @@
         end
       end
     end
+
+    context "When the appeal has not been marked for overtime" do
+      let!(:appeal) { create(:appeal) }
+      let(:task) { create(:ama_judge_assign_task, appeal: appeal) }
+
+      before { FeatureToggle.enable!(:overtime_revamp) }
+      after { FeatureToggle.disable!(:overtime_revamp) }
+
+      it "does not create a new work mode for the appeal" do
+        expect(appeal.work_mode.nil?).to be true
+        subject
+        expect(appeal.work_mode.nil?).to be true
+      end
+    end
+
+    context "When the appeal has been marked for overtime" do
+      shared_examples "clears overtime" do
+        it "sets overtime to false" do
+          expect(appeal.overtime?).to be true
+          subject
+          expect(appeal.overtime?).to be false
+        end
+      end
+
+      let!(:appeal) { create(:appeal) }
+      let(:task) { create(:ama_task, appeal: appeal.reload) }
+
+      before do
+        appeal.overtime = true
+        FeatureToggle.enable!(:overtime_revamp)
+      end
+      after { FeatureToggle.disable!(:overtime_revamp) }
+
+      context "when the task type is not a judge or attorney task" do
+        it "does not clear the overtime status" do
+          expect(appeal.overtime?).to be true
+          subject
+          expect(appeal.overtime?).to be true
+        end
+      end
+
+      context "when the task is a judge task" do
+        let(:task) { create(:ama_judge_assign_task, appeal: appeal) }
+
+        it_behaves_like "clears overtime"
+      end
+
+      context "when the task is an attorney task" do
+        let(:judge) { create(:user, :judge) }
+        let(:attorney) { create(:user, :attorney) }
+        let(:new_assignee) { create(:user, :attorney) }
+        let(:task) { create(:ama_attorney_rewrite_task, assigned_to: attorney, assigned_by: judge, appeal: appeal) }
+
+        subject { task.reassign(params, judge) }
+
+        it_behaves_like "clears overtime"
+      end
+    end
   end
 
   describe ".verify_org_task_unique" do