diff --git a/app/models/casa_case.rb b/app/models/casa_case.rb
index bc1e94a652..335f186897 100644
--- a/app/models/casa_case.rb
+++ b/app/models/casa_case.rb
@@ -158,6 +158,12 @@ def most_recent_past_court_date
     court_dates.where("date < ?", Date.today).order(:date).last
   end
 
+  def formatted_latest_court_date
+    most_recent = most_recent_past_court_date&.date&.in_time_zone || Time.zone.now
+
+    most_recent.strftime(::DateHelper::RUBY_MONTH_DAY_YEAR_FORMAT)
+  end
+
   def has_judge_name?
     judge_name
   end
diff --git a/app/views/casa_cases/_generate_report_modal.html.erb b/app/views/casa_cases/_generate_report_modal.html.erb
index 26f97f604c..b807383c38 100644
--- a/app/views/casa_cases/_generate_report_modal.html.erb
+++ b/app/views/casa_cases/_generate_report_modal.html.erb
@@ -22,7 +22,7 @@
         <div class="field form-group mb-20">
           <h6><label class="form-label" for="start_date">Starting From</label></h6>
           <%= form.text_field :start_date,
-            value: Time.zone.now.strftime(::DateHelper::RUBY_MONTH_DAY_YEAR_FORMAT),
+            value: @casa_case.formatted_latest_court_date,
             data: { provide: "datepicker",
                     date_format: ::DateHelper::JQUERY_MONTH_DAY_YEAR_FORMAT },
                     class: "form-control" %>
diff --git a/spec/models/casa_case_spec.rb b/spec/models/casa_case_spec.rb
index 4a4dbc96fc..2af5d61c9e 100644
--- a/spec/models/casa_case_spec.rb
+++ b/spec/models/casa_case_spec.rb
@@ -297,6 +297,34 @@
     end
   end
 
+  describe "#formatted_latest_court_date" do
+    let(:casa_case) { create(:casa_case) }
+
+    before do
+      travel_to Date.new(2021, 1, 1)
+    end
+
+    context "with a past court date" do
+      it "returns the latest past court date as a formatted string" do
+        most_recent_past_court_date = create(:court_date, date: 3.months.ago)
+
+        casa_case.court_dates << create(:court_date, date: 9.months.ago)
+        casa_case.court_dates << most_recent_past_court_date
+        casa_case.court_dates << create(:court_date, date: 15.months.ago)
+
+        expect(casa_case.formatted_latest_court_date).to eq("October 01, 2020") # 3 months before 1/1/21
+      end
+    end
+
+    context "without a past court date" do
+      it "returns the current day as a formatted string" do
+        allow(casa_case).to receive(:most_recent_past_court_date).and_return(nil)
+
+        expect(casa_case.formatted_latest_court_date).to eq("January 01, 2021")
+      end
+    end
+  end
+
   context "#remove_emancipation_category" do
     let(:casa_case) { create(:casa_case) }
     let(:emancipation_category) { build(:emancipation_category) }