diff --git a/app/models/user/filtering.rb b/app/models/user/filtering.rb
index 1b4f3070e5..5558abe1fb 100644
--- a/app/models/user/filtering.rb
+++ b/app/models/user/filtering.rb
@@ -28,6 +28,21 @@ def users
     @users ||= account.users.active.alphabetically
   end
 
+  # Returns users sorted with selected assignees first
+  def users_for_assignee_filter
+    @users_for_assignee_filter ||= account.users.active.sorted_by_selection(filter.assignees.pluck(:id))
+  end
+
+  # Returns users sorted with selected creators first
+  def users_for_creator_filter
+    @users_for_creator_filter ||= account.users.active.sorted_by_selection(filter.creators.pluck(:id))
+  end
+
+  # Returns users sorted with selected closers first
+  def users_for_closer_filter
+    @users_for_closer_filter ||= account.users.active.sorted_by_selection(filter.closers.pluck(:id))
+  end
+
   def filters
     @filters ||= user.filters.all
   end
diff --git a/app/models/user/named.rb b/app/models/user/named.rb
index 804e516ee6..0d07f55a36 100644
--- a/app/models/user/named.rb
+++ b/app/models/user/named.rb
@@ -3,6 +3,23 @@ module User::Named
 
   included do
     scope :alphabetically, -> { order("lower(name)") }
+    
+    # Sort users with selected IDs first, then unselected, both alphabetically
+    # More efficient than in-memory sorting for large user lists
+    scope :sorted_by_selection, ->(selected_ids) {
+      return alphabetically if selected_ids.blank?
+      
+      # Convert string IDs to binary blobs for SQLite comparison
+      uuid_type = ActiveRecord::Type::Uuid.new
+      binary_ids = selected_ids.map { |id| uuid_type.serialize(id) }
+      quoted_ids = binary_ids.map { |blob| connection.quote(blob) }.join(',')
+      
+      # Order by selection status FIRST, then alphabetically
+      order(
+        Arel.sql("CASE WHEN users.id IN (#{quoted_ids}) THEN 0 ELSE 1 END"),
+        Arel.sql("LOWER(name)")
+      )
+    }
   end
 
   def first_name
diff --git a/app/views/filters/settings/_assignees.html.erb b/app/views/filters/settings/_assignees.html.erb
index ddff3f4fa8..71fac7d9b7 100644
--- a/app/views/filters/settings/_assignees.html.erb
+++ b/app/views/filters/settings/_assignees.html.erb
@@ -33,7 +33,7 @@
           </button>
         <% end %>
 
-        <% user_filtering.users.each do |user| %>
+        <% user_filtering.users_for_assignee_filter.each do |user| %>
           <%= tag.li class: "popup__item", data: {
                 filter_target: "item", navigable_list_target: "item", multi_selection_combobox_target: "item", multi_selection_combobox_value: user.id, multi_selection_combobox_label: user.familiar_name },
                 role: "checkbox", aria: { checked: filter.assignees.include?(user) } do %>
diff --git a/app/views/filters/settings/_closers.html.erb b/app/views/filters/settings/_closers.html.erb
index 057c99d405..ff7622f22c 100644
--- a/app/views/filters/settings/_closers.html.erb
+++ b/app/views/filters/settings/_closers.html.erb
@@ -24,7 +24,7 @@
       <% end %>
 
       <ul class="popup__list" data-filter-target="list" role="listbox">
-        <% user_filtering.users.each do |user| %>
+        <% user_filtering.users_for_closer_filter.each do |user| %>
           <%= tag.li class: "popup__item", data: {
                 filter_target: "item", navigable_list_target: "item", multi_selection_combobox_target: "item", multi_selection_combobox_value: user.id, multi_selection_combobox_label: user.familiar_name },
                 role: "checkbox", aria: { checked: filter.closers.include?(user) } do %>
diff --git a/app/views/filters/settings/_creators.html.erb b/app/views/filters/settings/_creators.html.erb
index 92831226a0..b18842c762 100644
--- a/app/views/filters/settings/_creators.html.erb
+++ b/app/views/filters/settings/_creators.html.erb
@@ -24,7 +24,7 @@
       <% end %>
 
       <ul class="popup__list" data-filter-target="list" role="listbox">
-        <% user_filtering.users.each do |user| %>
+        <% user_filtering.users_for_creator_filter.each do |user| %>
           <%= tag.li class: "popup__item", data: {
                 filter_target: "item", navigable_list_target: "item", multi_selection_combobox_target: "item", multi_selection_combobox_value: user.id, multi_selection_combobox_label: user.familiar_name },
                 role: "checkbox", aria: { checked: filter.creators.include?(user) } do %>
diff --git a/test/models/user/filtering_test.rb b/test/models/user/filtering_test.rb
new file mode 100644
index 0000000000..4bf3099e46
--- /dev/null
+++ b/test/models/user/filtering_test.rb
@@ -0,0 +1,77 @@
+require "test_helper"
+
+class User::FilteringTest < ActiveSupport::TestCase
+  setup do
+    @user = users(:david)
+    @filter = @user.filters.create!
+  end
+
+  test "users_for_assignee_filter sorts selected assignees first" do
+    # Create some test users with identities
+    alice_identity = Identity.find_or_create_by!(email_address: "alice@test.com")
+    alice = @user.account.users.create!(name: "Alice", identity: alice_identity)
+    
+    bob_identity = Identity.find_or_create_by!(email_address: "bob@test.com")
+    bob = @user.account.users.create!(name: "Bob", identity: bob_identity)
+    
+    charlie_identity = Identity.find_or_create_by!(email_address: "charlie@test.com")
+    charlie = @user.account.users.create!(name: "Charlie", identity: charlie_identity)
+    
+    # Select Bob and Charlie as assignees
+    @filter.assignees = [charlie, bob]
+    @filter.save!
+    
+    filtering = User::Filtering.new(@user, @filter)
+    result = filtering.users_for_assignee_filter
+    
+    # Selected users (Bob, Charlie) should appear first, both alphabetically sorted
+    assert_equal "Bob", result[0].name
+    assert_equal "Charlie", result[1].name
+    
+    # Alice (unselected) should appear after selected users
+    assert_equal "Alice", result.find { |u| u.name == "Alice" }.name
+    assert result.index { |u| u.name == "Alice" } > 1, "Unselected user should appear after selected users"
+  end
+
+  test "users_for_creator_filter sorts selected creators first" do
+    alice_identity = Identity.find_or_create_by!(email_address: "alice@test.com")
+    alice = @user.account.users.create!(name: "Alice", identity: alice_identity)
+    
+    bob_identity = Identity.find_or_create_by!(email_address: "bob@test.com")
+    bob = @user.account.users.create!(name: "Bob", identity: bob_identity)
+    
+    @filter.creators = [bob]
+    @filter.save!
+    
+    filtering = User::Filtering.new(@user, @filter)
+    result = filtering.users_for_creator_filter
+    
+    assert_equal "Bob", result.first.name
+  end
+
+  test "users_for_closer_filter sorts selected closers first" do
+    alice_identity = Identity.find_or_create_by!(email_address: "alice@test.com")
+    alice = @user.account.users.create!(name: "Alice", identity: alice_identity)
+    
+    bob_identity = Identity.find_or_create_by!(email_address: "bob@test.com")
+    bob = @user.account.users.create!(name: "Bob", identity: bob_identity)
+    
+    @filter.closers = [alice]
+    @filter.save!
+    
+    filtering = User::Filtering.new(@user, @filter)
+    result = filtering.users_for_closer_filter
+    
+    assert_equal "Alice", result.first.name
+  end
+
+  test "users method returns all users alphabetically without selection sorting" do
+    filtering = User::Filtering.new(@user, @filter)
+    result = filtering.users
+    
+    # Should just be alphabetical, no selection sorting
+    # User.alphabetically sorts case-insensitively, so we verify the order matches
+    assert result.count > 0, "Should have users"
+    assert_equal result, result.sort_by { |u| u.name.downcase }, "Users should be alphabetically sorted"
+  end
+end