diff --git a/app/models/admin_dashboard_data.rb b/app/models/admin_dashboard_data.rb
index a57b4d7c1b4..1e3c3c75356 100644
--- a/app/models/admin_dashboard_data.rb
+++ b/app/models/admin_dashboard_data.rb
@@ -207,7 +207,8 @@ class AdminDashboardData
                       :unreachable_themes,
                       :watched_words_check,
                       :google_analytics_version_check,
-                      :translation_overrides_check
+                      :translation_overrides_check,
+                      :legacy_navigation_menu_check
 
     register_default_scheduled_problem_checks
 
@@ -367,6 +368,12 @@ class AdminDashboardData
     end
   end
 
+  def legacy_navigation_menu_check
+    if SiteSetting.navigation_menu == "legacy"
+      I18n.t("dashboard.legacy_navigation_menu_deprecated", base_path: Discourse.base_path)
+    end
+  end
+
   def image_magick_check
     if SiteSetting.create_thumbnails && !system("command -v convert >/dev/null;")
       I18n.t("dashboard.image_magick_warning")
diff --git a/config/locales/server.en.yml b/config/locales/server.en.yml
index ce6f1bb5e8f..7e3831a69a3 100644
--- a/config/locales/server.en.yml
+++ b/config/locales/server.en.yml
@@ -1491,6 +1491,7 @@ en:
     unreachable_themes: "We were unable to check for updates on the following themes:"
     watched_word_regexp_error: "The regular expression for '%{action}' watched words is invalid. Please check your <a href='%{base_path}/admin/customize/watched_words'>Watched Word settings</a>, or disable the 'watched words regular expressions' site setting."
     v3_analytics_deprecated: "Your Discourse is currently using Google Analytics 3, which will no longer be supported after July 2023. <a href='https://meta.discourse.org/t/260498'>Upgrade to Google Analytics 4</a> now to continue receiving valuable insights and analytics for your website's performance."
+    legacy_navigation_menu_deprecated: "Your Discourse is currently using the 'legacy' navigation menu which <a href='https://meta.discourse.org/t/removing-the-legacy-hamburger-navigation-menu-option/265274'>will be removed in the first beta release of Discourse 3.2</a>. Migrate to the new 'sidebar' navigation menu by updating your <a href='%{base_path}/admin/site_settings/category/all_results?filter=navigation_menu'>navigation menu site setting</a>."
 
   site_settings:
     allow_bulk_invite: "Allow bulk invites by uploading a CSV file"
diff --git a/spec/models/admin_dashboard_data_spec.rb b/spec/models/admin_dashboard_data_spec.rb
index 4f93c786fd3..fec93548322 100644
--- a/spec/models/admin_dashboard_data_spec.rb
+++ b/spec/models/admin_dashboard_data_spec.rb
@@ -45,6 +45,18 @@ RSpec.describe AdminDashboardData do
         expect(problems.map(&:to_s)).to include("a problem was found")
       end
     end
+
+    describe "when `navigation_menu` site setting is `legacy`" do
+      it "should include the right problem message" do
+        SiteSetting.set(:navigation_menu, "legacy")
+
+        problem = AdminDashboardData.fetch_problems.last
+
+        expect(problem.message).to include(
+          I18n.t("dashboard.legacy_navigation_menu_deprecated", base_path: Discourse.base_path),
+        )
+      end
+    end
   end
 
   describe "adding scheduled checks" do