diff --git a/Lib/asyncio/proactor_events.py b/Lib/asyncio/proactor_events.py
index 7adb09f3fce5de..1be0a8f777974b 100644
--- a/Lib/asyncio/proactor_events.py
+++ b/Lib/asyncio/proactor_events.py
@@ -534,6 +534,18 @@ def _loop_writing(self, fut=None):
                                                               addr=addr)
         except OSError as exc:
             self._protocol.error_received(exc)
+            if self._buffer:
+                # Reschedule the write loop so buffered data isn't stranded and
+                # a paused protocol is eventually resumed (gh-156698).
+                def resume_writing():
+                    # a sendto() may have armed a write in the meantime;
+                    # its own callback will drain the rest of the buffer.
+                    if self._write_fut is None:
+                        self._loop_writing()
+
+                self._loop.call_soon(resume_writing)
+            else:
+                self._maybe_resume_protocol()
         except Exception as exc:
             self._fatal_error(exc, 'Fatal write error on datagram transport')
         else:
diff --git a/Lib/test/test_asyncio/test_events.py b/Lib/test/test_asyncio/test_events.py
index 06f538bceea167..c52af810f56ed3 100644
--- a/Lib/test/test_asyncio/test_events.py
+++ b/Lib/test/test_asyncio/test_events.py
@@ -1583,6 +1583,135 @@ def create_socket():
         transport_1.close()
         transport_2.close()
 
+    def _test_datagram_write_error_resumes_paused_protocol(self, first, second):
+        # See https://github.com/python/cpython/issues/156698: a
+        # datagram write error must not strand data left in the write
+        # buffer, nor leave a paused protocol paused forever.
+        loop = self.loop
+
+        class Protocol(asyncio.DatagramProtocol):
+            def connection_made(self, transport):
+                self.transport = transport
+                self.paused = False
+                self.resumed = False
+                self.errors = []
+                self.error_received_event = loop.create_future()
+
+            def pause_writing(self):
+                self.paused = True
+
+            def resume_writing(self):
+                self.resumed = True
+
+            def error_received(self, exc):
+                self.errors.append(exc)
+                if not self.error_received_event.done():
+                    self.error_received_event.set_result(None)
+
+        sock = socket.socket(socket.AF_INET, socket.SOCK_DGRAM)
+        sock.setblocking(False)
+        sock.bind(('127.0.0.1', 0))
+        transport, protocol = loop.run_until_complete(
+            loop.create_datagram_endpoint(Protocol, sock=sock))
+        addr = sock.getsockname()
+
+        # A high water mark of 0 makes pausing deterministic whenever
+        # anything is left in the write buffer.
+        transport.set_write_buffer_limits(0)
+
+        # The first sendto() may arm an in-flight write, so the second
+        # one can end up queued behind it; queuing is what trips
+        # pause_writing() at a high water mark of 0.
+        transport.sendto(first, addr)
+        transport.sendto(second, addr)
+
+        loop.run_until_complete(
+            asyncio.wait_for(protocol.error_received_event, 10))
+        self.assertTrue(protocol.errors)
+        self.assertIsInstance(protocol.errors[0], OSError)
+
+        # The write buffer must not be left stranded.
+        test_utils.run_until(
+            loop, lambda: transport.get_write_buffer_size() == 0)
+
+        # A protocol that got paused must eventually be resumed too --
+        # without requiring an unsolicited extra sendto() to un-stick it.
+        if protocol.paused:
+            test_utils.run_until(loop, lambda: protocol.resumed)
+
+        transport.close()
+        test_utils.run_briefly(loop)
+
+    def test_datagram_write_error_resumes_paused_protocol_in_flight(self):
+        # oversized datagram fails while in flight; a normal datagram
+        # queued right behind it must not be stranded.
+        oversized = b'\x00' * 70000
+        self._test_datagram_write_error_resumes_paused_protocol(
+            oversized, b'queued')
+
+    def test_datagram_write_error_resumes_paused_protocol_from_callback(self):
+        # oversized datagram fails once it reaches the front of the
+        # buffer; the protocol must not stay paused forever.
+        oversized = b'\x00' * 70000
+        self._test_datagram_write_error_resumes_paused_protocol(
+            b'ok', oversized)
+
+    def test_datagram_write_error_reentrant_sendto(self):
+        # See https://github.com/python/cpython/issues/156698: an
+        # error_received() callback that sends more data synchronously
+        # can itself arm a new write. The write-loop restart scheduled
+        # for the failed write must notice that and not try to start a
+        # second, conflicting one.
+        loop = self.loop
+        unhandled = []
+        loop.set_exception_handler(lambda loop, context: unhandled.append(context))
+
+        class Protocol(asyncio.DatagramProtocol):
+            def connection_made(self, transport):
+                self.transport = transport
+                self.sent_extra = False
+                self.errors = []
+                self.done = loop.create_future()
+
+            def datagram_received(self, data, addr):
+                if not self.done.done():
+                    self.done.set_result(None)
+
+            def error_received(self, exc):
+                self.errors.append(exc)
+                if not self.sent_extra:
+                    # Reentrantly kicks off another write while the
+                    # failing one is still unwinding on the stack.
+                    self.sent_extra = True
+                    self.transport.sendto(b'extra', self.addr)
+
+        sock = socket.socket(socket.AF_INET, socket.SOCK_DGRAM)
+        sock.setblocking(False)
+        sock.bind(('127.0.0.1', 0))
+        transport, protocol = loop.run_until_complete(
+            loop.create_datagram_endpoint(Protocol, sock=sock))
+        protocol.addr = addr = sock.getsockname()
+
+        oversized = b'\x00' * 70000
+        transport.sendto(oversized, addr)
+        transport.sendto(b'queued', addr)
+
+        # The 'extra' datagram sent from error_received() is delivered
+        # back to the same socket; waiting for it proves the write loop
+        # kept running instead of wedging or crashing.
+        loop.run_until_complete(asyncio.wait_for(protocol.done, 10))
+
+        test_utils.run_until(
+            loop, lambda: transport.get_write_buffer_size() == 0)
+
+        transport.close()
+        test_utils.run_briefly(loop)
+
+        self.assertTrue(protocol.errors)
+        self.assertFalse(
+            unhandled,
+            f'unhandled exception in the write loop: {unhandled}')
+
     def test_datagram_recvfrom_connection_reset_recovers(self):
         # gh-127057: a UDP socket that sent a datagram to an address that
         # wasn't listening can raise ConnectionResetError on a later
diff --git a/Misc/NEWS.d/next/Library/2026-08-31-00-00-00.gh-issue-156698.gyDxUe.rst b/Misc/NEWS.d/next/Library/2026-08-31-00-00-00.gh-issue-156698.gyDxUe.rst
new file mode 100644
index 00000000000000..4e3a292ce9b821
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2026-08-31-00-00-00.gh-issue-156698.gyDxUe.rst
@@ -0,0 +1,4 @@
+Fix :class:`asyncio.ProactorEventLoop` UDP transports so that a write
+error no longer strands a paused protocol: the write loop is now
+rescheduled when data remains buffered, and the protocol is resumed
+when the buffer has drained.