diff --git a/src/DialogueEditor/components/Checkbox/init.luau b/src/DialogueEditor/components/Checkbox/init.luau
index fe09dd5b..bc088eac 100644
--- a/src/DialogueEditor/components/Checkbox/init.luau
+++ b/src/DialogueEditor/components/Checkbox/init.luau
@@ -4,6 +4,7 @@ local root = script.Parent.Parent.Parent;
 local React = require(root.roblox_packages.react);
 local useStudioColors = require(root.DialogueEditor.hooks.useStudioColors);
 local useStudioIcons = require(root.DialogueEditor.hooks.useStudioIcons);
+local VirtualService = require(root.VirtualService);
 
 export type CheckboxProperties = {
   text: string;
@@ -22,6 +23,34 @@ local function Checkbox(properties: CheckboxProperties)
   local onChanged = properties.onChanged;
   local colors = useStudioColors();
   local icons = useStudioIcons();
+  local buttonRef = React.useRef(nil :: TextButton?);
+  
+  React.useEffect(function()
+  
+    local button = buttonRef.current;
+    assert(button, "Button reference should not be nil.");
+
+    local activatedConnection = VirtualService.events.GuiButton.Activated:getSignal(button):Connect(function()
+
+      if not isDisabled then
+
+        onChanged(not isChecked);
+
+      end;
+
+    end);
+
+    return function()
+    
+      if activatedConnection then
+
+        activatedConnection:Disconnect();
+      
+      end;
+
+    end;
+
+  end, {onChanged});
 
   return React.createElement("Frame", {
     AutomaticSize = Enum.AutomaticSize.XY;
@@ -41,13 +70,10 @@ local function Checkbox(properties: CheckboxProperties)
       BackgroundTransparency = if isDisabled then 0.5 else 0;
       LayoutOrder = 1;
       Text = "";
-      [React.Event.Activated] = function()
-
-        if not isDisabled then
+      ref = buttonRef;
+      [React.Event.Activated] = function(self)
 
-          onChanged(not isChecked);
-        
-        end;
+        VirtualService.events.GuiButton.Activated:fireEvent(self);
 
       end;
     }, {
diff --git a/src/DialogueEditor/components/Explorer/components/Preview/components/AutoTriggerCheckbox/AutoTriggerCheckbox.test.luau b/src/DialogueEditor/components/Explorer/components/Preview/components/AutoTriggerCheckbox/AutoTriggerCheckbox.test.luau
new file mode 100644
index 00000000..3751510b
--- /dev/null
+++ b/src/DialogueEditor/components/Explorer/components/Preview/components/AutoTriggerCheckbox/AutoTriggerCheckbox.test.luau
@@ -0,0 +1,145 @@
+--!strict
+
+local root = script.Parent.Parent.Parent.Parent.Parent.Parent.Parent.Parent;
+local AutoTriggerCheckbox = require(script.Parent);
+local VirtualService = require(root.VirtualService);
+local React = require(root.roblox_packages.react);
+local ReactErrorBoundary = require(root.roblox_packages.ReactErrorBoundary);
+local ErrorBoundary = ReactErrorBoundary.ErrorBoundary;
+local ReactRoblox = require(root.roblox_packages["react-roblox"]);
+local IJW = require(root.roblox_packages.ijw);
+local expect = IJW.expect;
+local describe = IJW.describe;
+local it = IJW.it;
+
+local screenGui: ScreenGui?;
+local reactRoot: ReactRoblox.RootType?;
+local propagatedErrorMessage;
+
+return {
+
+  describe("DialogueGroupContainer", function()
+
+    local function MockComponent(properties: any)
+
+      local selectedScript = properties.selectedScript;
+      local onErrored = properties.onErrored or function() end;
+      local onRendered = properties.onRendered or function() end;
+
+      React.useEffect(function()
+
+        onRendered();
+
+      end, {onRendered});
+
+      return React.createElement(ErrorBoundary, {
+        FallbackComponent = React.Fragment;
+        onError = onErrored;
+      }, {
+        React.createElement(AutoTriggerCheckbox, {
+          selectedScript = selectedScript;
+          layoutOrder = 1;
+        })
+      });
+
+    end;
+
+    local function verifyReactStatus()
+
+      if propagatedErrorMessage then
+
+        error(propagatedErrorMessage);
+
+      end;
+
+    end;
+
+    local function createDialogueScript(name: string)
+
+      local dialogueScript = Instance.new("ModuleScript");
+      dialogueScript:AddTag("DialogueMakerConversationScript");
+      return dialogueScript;
+
+    end;
+
+    local function render(): ModuleScript
+
+      assert(reactRoot, "React root should be initialized before running tests.");
+
+      local selectedScript = createDialogueScript("TestDialogueScript");
+      local didRender = false;
+      local element = React.createElement(MockComponent, {
+        selectedScript = selectedScript;
+        onErrored = function(errorMessage)
+
+          propagatedErrorMessage = errorMessage;
+
+        end;
+        onRendered = function()
+          
+          didRender = true;
+
+        end;
+      });
+
+      reactRoot:render(element);
+      repeat task.wait() until didRender or propagatedErrorMessage;
+
+      return selectedScript;
+
+    end;
+
+    return {
+
+      it(`can add "ShouldAutoTriggerConversation" tag to selected script`, function()
+
+        expect(function()
+
+          -- Render the component and wait for it to finish rendering.
+          assert(screenGui, "ScreenGui should be initialized before running tests.");
+          local selectedScript = render();
+          verifyReactStatus();
+
+          -- Verify that the checkbox is unchecked.
+          local checkboxFrame = screenGui:FindFirstChildOfClass("Frame");
+          assert(checkboxFrame, "Frame should be present in the ScreenGui.");
+
+          local checkbox = checkboxFrame:FindFirstChild("Checkbox");
+          assert(checkbox and checkbox:IsA("TextButton"), "Checkbox should be present in the frame.");
+
+          VirtualService.events.GuiButton.Activated:fireEvent(checkbox);
+          expect(selectedScript:GetAttribute("ShouldAutoTriggerConversation")).toBe(true);
+
+        end).toFinishBeforeSeconds(1);
+
+      end);
+      
+    }
+
+  end, {
+    beforeEach = function()
+
+      local newScreenGui = Instance.new("ScreenGui");
+      screenGui = newScreenGui;
+      reactRoot = ReactRoblox.createRoot(newScreenGui);
+
+    end;
+    afterEach = function()
+
+      if reactRoot then
+
+        reactRoot:unmount();
+
+      end;
+
+      if screenGui then
+
+        screenGui:Destroy();
+
+      end;
+
+      propagatedErrorMessage = nil;
+
+    end;
+  })
+};
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