diff --git a/config/feature_flags/smart_search.yml b/config/feature_flags/smart_search.yml
index 30a454e6f6c..fbf81b6616b 100644
--- a/config/feature_flags/smart_search.yml
+++ b/config/feature_flags/smart_search.yml
@@ -4,4 +4,4 @@ smart_search:
   applies_to: RootAccount
   display_name: Smart Search
   description: AI driven smart search feature.
-
+  after_state_change_proc: smart_search_after_state_change_hook
diff --git a/lib/feature_flags/hooks.rb b/lib/feature_flags/hooks.rb
index 3e501254add..6f9cfae893a 100644
--- a/lib/feature_flags/hooks.rb
+++ b/lib/feature_flags/hooks.rb
@@ -107,5 +107,11 @@ module FeatureFlags
                                 )
       end
     end
+
+    def self.smart_search_after_state_change_hook(_user, context, old_state, new_state)
+      if %w[off allowed].include?(old_state) && %w[on allowed_on].include?(new_state) && !context.site_admin?
+        OpenAi.index_account(context)
+      end
+    end
   end
 end
diff --git a/lib/open_ai.rb b/lib/open_ai.rb
index 8927de87c92..2f353086a0c 100644
--- a/lib/open_ai.rb
+++ b/lib/open_ai.rb
@@ -66,5 +66,29 @@ module OpenAi
       vector_schema = ActiveRecord::Base.connection.extension("vector").schema
       ActiveRecord::Base.connection.add_schema_to_search_path(vector_schema, &)
     end
+
+    def index_account(root_account)
+      return unless smart_search_available?(root_account)
+
+      # by default, index all courses updated in the last year
+      date_cutoff = Setting.get("smart_search_index_days_ago", "365").to_i.days.ago
+      root_account.all_courses.active.where(updated_at: date_cutoff..).find_each do |course|
+        delay(priority: Delayed::LOW_PRIORITY,
+              singleton: "smart_search_index_course:#{course.global_id}",
+              n_strand: "smart_search_index_course").index_course(course)
+      end
+    end
+    handle_asynchronously :index_account, priority: Delayed::LOW_PRIORITY
+
+    def index_course(course)
+      return unless smart_search_available?(course.root_account)
+
+      # index non-deleted pages (that have not already been indexed)
+      course.wiki_pages.not_deleted
+            .where.missing(:wiki_page_embeddings)
+            .find_each do |page|
+        page.generate_embeddings(synchronous: true)
+      end
+    end
   end
 end