diff --git a/.changeset/tidy-popovers-float.md b/.changeset/tidy-popovers-float.md
new file mode 100644
index 000000000..70cb170bf
--- /dev/null
+++ b/.changeset/tidy-popovers-float.md
@@ -0,0 +1,5 @@
+---
+"@cloudflare/kumo": patch
+---
+
+Keep Popover arrows visible during opening and closing transitions when content uses overflow clipping or scrolling.
diff --git a/packages/kumo/src/components/popover/popover.tsx b/packages/kumo/src/components/popover/popover.tsx
index bdaab3c3e..7e575760d 100644
--- a/packages/kumo/src/components/popover/popover.tsx
+++ b/packages/kumo/src/components/popover/popover.tsx
@@ -206,31 +206,40 @@ function PopoverContent({
         sideOffset={sideOffset}
         positionMethod={positionMethod}
       >
-        <PopoverBase.Popup
+        <div
           className={cn(
-            "flex origin-(--transform-origin) flex-col rounded-lg bg-kumo-base px-4 py-3 text-sm text-kumo-default",
-            "shadow-md outline outline-kumo-line",
-            "transition-[transform,scale,opacity] duration-150",
-            "data-starting-style:scale-90 data-starting-style:opacity-0",
-            "data-ending-style:scale-90 data-ending-style:opacity-0",
-            "data-instant:duration-0",
-            "kumo-popover-popup",
-            className,
+            "relative origin-(--transform-origin) overflow-visible transition-[scale] duration-150",
+            "[&:has(>.kumo-popover-popup[data-starting-style])]:scale-90",
+            "[&:has(>.kumo-popover-popup[data-ending-style])]:scale-90",
+            "[&:has(>.kumo-popover-popup[data-instant])]:duration-0",
           )}
         >
-          <PopoverBase.Arrow
+          <PopoverBase.Popup
             className={cn(
-              "flex",
-              "data-[side=bottom]:-top-2",
-              "data-[side=left]:right-[-13px] data-[side=left]:rotate-90",
-              "data-[side=right]:left-[-13px] data-[side=right]:-rotate-90",
-              "data-[side=top]:-bottom-2 data-[side=top]:rotate-180",
+              "flex flex-col rounded-lg bg-kumo-base px-4 py-3 text-sm text-kumo-default",
+              "shadow-md outline outline-kumo-line",
+              "transition-opacity duration-150",
+              "data-starting-style:opacity-0",
+              "data-ending-style:opacity-0",
+              "data-instant:duration-0",
+              "kumo-popover-popup",
+              className,
             )}
           >
-            <ArrowSvg />
-          </PopoverBase.Arrow>
-          {children}
-        </PopoverBase.Popup>
+            <PopoverBase.Arrow
+              className={cn(
+                "flex",
+                "data-[side=bottom]:-top-2",
+                "data-[side=left]:right-[-13px] data-[side=left]:rotate-90",
+                "data-[side=right]:left-[-13px] data-[side=right]:-rotate-90",
+                "data-[side=top]:-bottom-2 data-[side=top]:rotate-180",
+              )}
+            >
+              <ArrowSvg />
+            </PopoverBase.Arrow>
+            {children}
+          </PopoverBase.Popup>
+        </div>
       </PopoverBase.Positioner>
     </PopoverBase.Portal>
   );
diff --git a/packages/kumo/src/components/popover/popover.visual.browser.test.tsx b/packages/kumo/src/components/popover/popover.visual.browser.test.tsx
new file mode 100644
index 000000000..8a9da8c46
--- /dev/null
+++ b/packages/kumo/src/components/popover/popover.visual.browser.test.tsx
@@ -0,0 +1,93 @@
+import { describe, expect, test } from "vite-plus/test";
+import { userEvent } from "vite-plus/test/browser";
+import { render } from "vitest-browser-react";
+import { Popover } from "./popover";
+
+describe("Popover", () => {
+  test("keeps the arrow outside scrollable content during the opening scale transition", async () => {
+    const { getByRole } = await render(
+      <>
+        <style>{`
+          .kumo-popover-popup {
+            transition-duration: 50ms !important;
+          }
+
+          *:has(> .kumo-popover-popup:not([data-ending-style]):not([data-instant])) {
+            transition-duration: 10s !important;
+          }
+
+          *:has(> .kumo-popover-popup[data-ending-style]) {
+            transition-duration: 0s !important;
+          }
+        `}</style>
+        <Popover>
+          <Popover.Trigger>Open popover</Popover.Trigger>
+          <Popover.Content className="h-24 w-56 overflow-auto">
+            <div className="h-96 shrink-0">Scrollable content</div>
+          </Popover.Content>
+        </Popover>
+      </>,
+    );
+
+    const trigger = getByRole("button", { name: "Open popover" });
+    await trigger.click();
+
+    const popup = getByRole("dialog").element();
+    await expect.poll(() => getComputedStyle(popup).opacity).toBe("1");
+
+    const motionWrapper = popup.parentElement;
+    const arrow = popup.querySelector<HTMLElement>("[aria-hidden='true']");
+
+    expect(motionWrapper).not.toBeNull();
+    expect(arrow).not.toBeNull();
+    expect(getComputedStyle(popup).scale).toBe("none");
+    expect(getComputedStyle(popup).transitionProperty).toBe("opacity");
+
+    const wrapperScale = Number.parseFloat(
+      getComputedStyle(motionWrapper!).scale,
+    );
+    expect(wrapperScale).toBeGreaterThanOrEqual(0.9);
+    expect(wrapperScale).toBeLessThan(1);
+
+    expect(popup.scrollHeight).toBeGreaterThan(popup.clientHeight);
+    const arrowTopBeforeScroll = arrow!.getBoundingClientRect().top;
+
+    popup.scrollTop = 64;
+    await new Promise<void>((resolve) =>
+      requestAnimationFrame(() => resolve()),
+    );
+
+    expect(popup.scrollTop).toBe(64);
+    expect(
+      Math.abs(arrow!.getBoundingClientRect().top - arrowTopBeforeScroll),
+    ).toBeLessThan(1);
+
+    const arrowRect = arrow!.getBoundingClientRect();
+    const popupRect = popup.getBoundingClientRect();
+    const hitTarget = document.elementFromPoint(
+      arrowRect.left + arrowRect.width / 2,
+      arrowRect.top + arrowRect.height / 4,
+    );
+
+    expect(arrowRect.top).toBeLessThan(popupRect.top);
+    expect(hitTarget === arrow || arrow!.contains(hitTarget)).toBe(true);
+
+    await trigger.click();
+    await expect.poll(() => popup.hasAttribute("data-ending-style")).toBe(true);
+    expect(document.body.contains(popup)).toBe(true);
+    expect(getComputedStyle(motionWrapper!).scale).toBe("0.9");
+    await expect.element(getByRole("dialog")).not.toBeInTheDocument();
+
+    trigger.element().focus();
+    await userEvent.keyboard("{Enter}");
+    await expect.element(getByRole("dialog")).toBeInTheDocument();
+
+    const instantPopup = getByRole("dialog").element();
+    await expect
+      .poll(() => instantPopup.hasAttribute("data-instant"))
+      .toBe(true);
+    expect(
+      getComputedStyle(instantPopup.parentElement!).transitionDuration,
+    ).toBe("0s");
+  });
+});