diff --git a/app/controllers/assignments/toggles_controller.rb b/app/controllers/assignments/toggles_controller.rb
index bcf1616be..a2285b35e 100644
--- a/app/controllers/assignments/toggles_controller.rb
+++ b/app/controllers/assignments/toggles_controller.rb
@@ -2,12 +2,23 @@ class Assignments::TogglesController < ApplicationController
   include BubbleScoped, BucketScoped
 
   def create
-    @bubble.toggle_assignment assignee
+    new_assignee_ids = Array(params[:assignee_id])
+    current_assignees = @bubble.assignees
+
+    current_assignees.each do |assignee|
+      @bubble.toggle_assignment(assignee) unless new_assignee_ids.include?(assignee.id.to_s)
+    end
+
+    new_assignee_ids.each do |id|
+      assignee = @bucket.users.active.find(id)
+      @bubble.toggle_assignment(assignee) unless current_assignees.include?(assignee)
+    end
+
     redirect_to @bubble
   end
 
   private
     def assignee
-      @bucket.users.active.find params.expect(:assignee_id)
+      @bucket.users.active.find params[:assignee_id]
     end
 end
diff --git a/app/views/bubbles/sidebar/_assignment.html.erb b/app/views/bubbles/sidebar/_assignment.html.erb
index 215f0821f..59ce8d217 100644
--- a/app/views/bubbles/sidebar/_assignment.html.erb
+++ b/app/views/bubbles/sidebar/_assignment.html.erb
@@ -4,18 +4,22 @@
     <span>Assign</span>
   </button>
 
-  <dialog class="combox-popup panel align-center gap-half fill-white shadow" data-dialog-target="dialog">
-    <%= form_with url: bucket_bubble_assignment_toggles_path(bubble.bucket, bubble), data: { controller: "form" } do |form| %>
-      <%= form.combobox :assignee_id, users, required: true,
-            render_in: { partial: "bubbles/users/listbox_option", as: :user, locals: { bubble: bubble } },
-            data: { controller: "autofocus", action: "hw-combobox:selection->form#submit" } %>
-    <% end %>
+  <dialog class="combox-popup panel flex-column align-start gap-half fill-white shadow" style="--panel-border-radius: 1em;" data-dialog-target="dialog">
+    <strong>Assign this to…</strong>
 
-    <form method="dialog">
-      <button class="btn txt-small" title="Close (esc)">
-        <%= image_tag "remove.svg", aria: { hidden: true }, size: 24 %>
-        <span class="for-screen-reader">Close</span>
-      </button>
-    </form>
+    <%= form_with url: bucket_bubble_assignment_toggles_path(bubble.bucket, bubble), class: "flex flex-column gap-half full-width", data: { controller: "form" } do |form| %>
+      <% users.each do |user| %>
+        <div class="btn full-width borderless justify-start" style="--btn-border-radius: 0.3em;">
+          <%= form.check_box "assignee_id[]", { 
+            checked: bubble.assigned_to?(user),
+            data: { action: "change->form#submit" },
+            id: dom_id(user, :assign),
+            include_hidden: false,
+          }, user.id %>
+
+          <%= form.label "assignee_id[]", user.name, for: dom_id(user, :assign) %>
+        </div>
+      <% end %>
+    <% end %>
   </dialog>
 </div>
diff --git a/app/views/bubbles/users/_listbox_option.html.erb b/app/views/bubbles/users/_listbox_option.html.erb
deleted file mode 100644
index ec304a714..000000000
--- a/app/views/bubbles/users/_listbox_option.html.erb
+++ /dev/null
@@ -1,7 +0,0 @@
-<div class="flex gap-half justify-space-between align-center" style="--btn-icon-size: 1rem">
-  <%= user.name %>
-
-  <% if bubble.assigned_to?(user) %>
-    <%= image_tag "check.svg", aria: { hidden: "true" } %>
-  <% end %>
-</div>