diff --git a/.changeset/fix-checkbox-onchange-target.md b/.changeset/fix-checkbox-onchange-target.md
new file mode 100644
index 0000000000..94c13e0aa4
--- /dev/null
+++ b/.changeset/fix-checkbox-onchange-target.md
@@ -0,0 +1,12 @@
+---
+"@cloudflare/kumo": patch
+---
+
+fix(Checkbox): use Proxy instead of Object.assign to avoid crashing on read-only Event.target
+
+The deprecated `onChange` handler used `Object.assign(event, { target: ... })` which throws
+`TypeError: Cannot set property target of #<Event> which has only a getter` because `Event.target`
+is a read-only getter property. Replaced with `Object.create` to create a new object that shadows
+the prototype getter with an own `target` property.
+
+Fixes #409
diff --git a/packages/kumo/src/components/checkbox/checkbox.test.tsx b/packages/kumo/src/components/checkbox/checkbox.test.tsx
new file mode 100644
index 0000000000..aa2e4ee95e
--- /dev/null
+++ b/packages/kumo/src/components/checkbox/checkbox.test.tsx
@@ -0,0 +1,32 @@
+import { fireEvent, render, screen } from "@testing-library/react";
+import { describe, expect, it } from "vitest";
+import { Checkbox } from "./checkbox";
+
+describe("Checkbox", () => {
+  it("preserves native event APIs on deprecated onChange callbacks", () => {
+    const events: Array<React.ChangeEvent<HTMLInputElement>> = [];
+
+    render(
+      <Checkbox
+        label="Accept terms"
+        onChange={(event) => {
+          events.push(event);
+        }}
+      />,
+    );
+
+    expect(() => fireEvent.click(screen.getByRole("checkbox"))).not.toThrow();
+    expect(events.length).toBeGreaterThan(0);
+
+    const event = events[0];
+
+    expect(event).toBeDefined();
+    expect(event.target.checked).toBe(true);
+    expect(event.currentTarget.checked).toBe(true);
+    expect(event instanceof Event).toBe(true);
+
+    expect(() => event.preventDefault()).not.toThrow();
+    expect(event.defaultPrevented).toBe(true);
+    expect(typeof event.timeStamp).toBe("number");
+  });
+});
diff --git a/packages/kumo/src/components/checkbox/checkbox.tsx b/packages/kumo/src/components/checkbox/checkbox.tsx
index 27838c08c7..bd685418d2 100644
--- a/packages/kumo/src/components/checkbox/checkbox.tsx
+++ b/packages/kumo/src/components/checkbox/checkbox.tsx
@@ -56,6 +56,41 @@ const CheckboxGroupContext = createContext<{ controlFirst: boolean }>({
   controlFirst: true,
 });
 
+function brandSafeProxy<T extends object>(
+  source: T,
+  overrides: Record<PropertyKey, unknown>,
+): T {
+  return new Proxy(source, {
+    get(target, property) {
+      if (Object.hasOwn(overrides, property)) {
+        return overrides[property];
+      }
+
+      const value = Reflect.get(target, property, target);
+      return typeof value === "function" ? value.bind(target) : value;
+    },
+  });
+}
+
+function createLegacyCheckboxChangeEvent(
+  event: Event,
+  checked: boolean,
+): React.ChangeEvent<HTMLInputElement> {
+  const target = brandSafeProxy(
+    (event.target ?? {}) as EventTarget & HTMLInputElement,
+    { checked },
+  );
+  const currentTarget = brandSafeProxy(
+    (event.currentTarget ?? {}) as EventTarget & HTMLInputElement,
+    { checked },
+  );
+
+  return brandSafeProxy(event, {
+    target,
+    currentTarget,
+  }) as unknown as React.ChangeEvent<HTMLInputElement>;
+}
+
 /**
  * Single checkbox component props with accessibility guidance.
  *
@@ -245,9 +280,10 @@ const CheckboxBase = forwardRef<HTMLButtonElement, CheckboxProps>(
       if (onChange) {
         // Backwards compatibility: extend native event with target.checked
         // so existing code using `e.target.checked` continues to work
-        const event = Object.assign(eventDetails.event, {
-          target: { checked: newChecked },
-        });
+        const event = createLegacyCheckboxChangeEvent(
+          eventDetails.event,
+          newChecked,
+        );
         onChange(event as never);
       }
     };