diff --git a/ui/src/ui/chat/grouped-render.test.ts b/ui/src/ui/chat/grouped-render.test.ts
index 24f0645b649..4dd75f0060b 100644
--- a/ui/src/ui/chat/grouped-render.test.ts
+++ b/ui/src/ui/chat/grouped-render.test.ts
@@ -303,6 +303,14 @@ function openDeleteConfirm(deleteButton: HTMLButtonElement) {
   deleteButton.dispatchEvent(new MouseEvent("click", { bubbles: true }));
 }
 
+function clickDeleteButtonIconPath(deleteButton: HTMLButtonElement) {
+  const icon = document.createElementNS("http://www.w3.org/2000/svg", "svg");
+  const path = document.createElementNS("http://www.w3.org/2000/svg", "path");
+  icon.appendChild(path);
+  deleteButton.appendChild(icon);
+  path.dispatchEvent(new MouseEvent("click", { bubbles: true }));
+}
+
 function setupArmedDeleteConfirm() {
   const flushAnimationFrames = stubAnimationFrameQueue();
   const addListenerSpy = vi.spyOn(document, "addEventListener");
@@ -455,6 +463,15 @@ describe("grouped chat rendering", () => {
     expect(fixture.onDelete).not.toHaveBeenCalled();
   });
 
+  it("removes the delete confirm outside-click listener when the delete button icon toggles it", () => {
+    const fixture = setupArmedDeleteConfirm();
+
+    clickDeleteButtonIconPath(fixture.deleteButton);
+
+    expectDeleteConfirmDismissed(fixture);
+    expect(fixture.onDelete).not.toHaveBeenCalled();
+  });
+
   it("does not attach the delete confirm outside-click listener after an immediate toggle", () => {
     const flushAnimationFrames = stubAnimationFrameQueue();
     const addListenerSpy = vi.spyOn(document, "addEventListener");
diff --git a/ui/src/ui/chat/grouped-render.ts b/ui/src/ui/chat/grouped-render.ts
index 87f59f0cabd..53fe34d903a 100644
--- a/ui/src/ui/chat/grouped-render.ts
+++ b/ui/src/ui/chat/grouped-render.ts
@@ -676,7 +676,7 @@ function renderDeleteButton(onDelete: () => void, side: DeleteConfirmSide) {
           }
           function closeOnOutside(evt: MouseEvent) {
             const target = evt.target;
-            if (target instanceof Node && !popover.contains(target) && target !== btn) {
+            if (target instanceof Node && !popover.contains(target) && !btn.contains(target)) {
               dismissPopover();
             }
           }