diff --git a/Lib/test/test_free_threading/test_io.py b/Lib/test/test_free_threading/test_io.py
@@ -191,3 +191,23 @@ def reset_worker():
                 decoder.reset()
 
         run_concurrently([decode_worker] * 2 + [reset_worker] * 2)
+
+
+class TextIOWrapperTest(TestCase):
+    def test_buffer_detach_race(self):
+        make = lambda: io.TextIOWrapper(io.BytesIO())
+        slot = [make()]
+
+        def reader():
+            for _ in range(1000):
+                try:
+                    slot[0].buffer
+                except ValueError:
+                    pass
+
+        def detacher():
+            for _ in range(1000):
+                slot[0] = make()
+                slot[0].detach()
+
+        run_concurrently([reader, detacher])
diff --git a/Lib/test/test_io.py b/Lib/test/test_io.py
@@ -4276,6 +4276,86 @@ def closed(self):
         wrapper = self.TextIOWrapper(raw)
         wrapper.close()  # should not crash
 
+    def test_reentrant_detach_during_flush(self):
+        # gh-143008: Reentrant detach() during flush should not crash.
+
+        class DetachOnce(self.BufferedRandom):
+            wrapper = None
+
+            def detach_once(self):
+                original = self.wrapper
+                self.wrapper = None
+                if original is not None:
+                    original.detach()
+                    original.flush()
+
+        class DetachOnFlush(DetachOnce):
+            def flush(self):
+                self.detach_once()
+
+        class DetachOnWrite(DetachOnce):
+            def write(self, b):
+                self.detach_once()
+                return len(b)
+
+        # Separate reference for after detach_once.
+        wrapper = None
+
+        def make_text(buffer):
+            nonlocal wrapper
+            buffer.wrapper = self.TextIOWrapper(buffer, encoding='utf-8')
+            wrapper = buffer.wrapper
+
+        # Many calls could result in the same null self->buffer crash.
+        tests = [
+            ('truncate', lambda: wrapper.truncate(0)),
+            ('close', lambda: wrapper.close()),
+            ('detach', lambda: wrapper.detach()),
+            ('seek', lambda: wrapper.seek(0)),
+            ('tell', lambda: wrapper.tell()),
+            ('reconfigure', lambda: wrapper.reconfigure(line_buffering=True)),
+        ]
+        for name, method in tests:
+            with self.subTest(name):
+                make_text(DetachOnFlush(self.MockRawIO()))
+                self.assertRaisesRegex(ValueError, "detached", method)
+
+        # Should not crash.
+        with self.subTest('read via writeflush'):
+            make_text(DetachOnWrite(self.MockRawIO()))
+            wrapper.write('x')
+            self.assertRaisesRegex(ValueError, "detached", wrapper.read)
+
+    def test_reentrant_detach_during_read(self):
+        # gh-157363, gh-157364: The buffer must stay alive until its active
+        # read operation returns.
+        wrapper = None
+
+        class DetachOnRead(self.RawIOBase):
+            detached = False
+
+            def readable(self):
+                return True
+
+            def readinto(self, b):
+                if self.detached:
+                    return 0
+                self.detached = True
+                wrapper.detach()
+                b[:3] = b"ab\n"
+                return 3
+
+        for method_name in ("read", "readline"):
+            with self.subTest(method_name):
+                raw = DetachOnRead()
+                wrapper = self.TextIOWrapper(
+                    self.BufferedReader(raw), encoding="utf-8")
+                method = getattr(wrapper, method_name)
+                self.assertEqual(method(), "ab\n")
+                with self.assertRaisesRegex(ValueError,
+                                            "underlying buffer has been detached"):
+                    getattr(wrapper, 'buffer')
+
 
 class PyTextIOWrapperTest(TextIOWrapperTest):
     io = pyio

diff --git a/Misc/NEWS.d/next/Library/2025-12-21-17-56-37.gh-issue-143008.aakErJ.rst b/Misc/NEWS.d/next/Library/2025-12-21-17-56-37.gh-issue-143008.aakErJ.rst
@@ -0,0 +1,2 @@
+Fix crash in :class:`io.TextIOWrapper` when reentrant
+:meth:`io.TextIOBase.detach` is called reentrantly from the underlying buffer.
diff --git a/Misc/NEWS.d/next/Library/2026-06-04-18-22-56.gh-issue-143008.z5tw-J.rst b/Misc/NEWS.d/next/Library/2026-06-04-18-22-56.gh-issue-143008.z5tw-J.rst
@@ -0,0 +1 @@
+Fix race conditions when re-initializing a :class:`io.TextIOWrapper` object.
diff --git a/Misc/NEWS.d/next/Library/2026-07-23-18-53-48.gh-issue-154523.XUSRBO.rst b/Misc/NEWS.d/next/Library/2026-07-23-18-53-48.gh-issue-154523.XUSRBO.rst
@@ -0,0 +1,2 @@
+Fixed data-race when calling :meth:`io.TextIOBase.detach` in
+:term:`free-threaded build`.
diff --git a/Misc/NEWS.d/next/Library/2026-09-12-18-03-15.gh-issue-157364.Qd7mKs.rst b/Misc/NEWS.d/next/Library/2026-09-12-18-03-15.gh-issue-157364.Qd7mKs.rst
@@ -0,0 +1,2 @@
+Fix a use-after-free in :class:`io.TextIOWrapper` when a call to the
+underlying buffer reentrantly detaches it. Patched by Shamil Abdulaev.
diff --git a/Modules/_io/clinic/textio.c.h b/Modules/_io/clinic/textio.c.h
Original file line number	Diff line number	Diff line change
		@@ -0,0 +1,2 @@
		Fix crash in :class:`io.TextIOWrapper` when reentrant
		:meth:`io.TextIOBase.detach` is called reentrantly from the underlying buffer.
Original file line number	Diff line number	Diff line change
		@@ -0,0 +1 @@
		Fix race conditions when re-initializing a :class:`io.TextIOWrapper` object.
Original file line number	Diff line number	Diff line change
		@@ -0,0 +1,2 @@
		Fixed data-race when calling :meth:`io.TextIOBase.detach` in
		:term:`free-threaded build`.
Original file line number	Diff line number	Diff line change
		@@ -0,0 +1,2 @@
		Fix a use-after-free in :class:`io.TextIOWrapper` when a call to the
		underlying buffer reentrantly detaches it. Patched by Shamil Abdulaev.