diff --git a/src/python/grpcio/grpc/_server.py b/src/python/grpcio/grpc/_server.py
index d48c4a2a717..3b5a7e69f6c 100644
--- a/src/python/grpcio/grpc/_server.py
+++ b/src/python/grpcio/grpc/_server.py
@@ -958,11 +958,27 @@ class _Server(grpc.Server):
         _add_generic_handlers(self._state, generic_rpc_handlers)
 
     def add_insecure_port(self, address):
-        return _add_insecure_port(self._state, _common.encode(address))
+        port = _add_insecure_port(self._state, _common.encode(address))
+        if port == 0:
+            # The Core API doesn't return a failure message. The best we can do
+            # is raising an exception to prevent further confusion.
+            raise RuntimeError('Failed to bind to address %s; set '
+                               'GRPC_VERBOSITY=debug env to see detailed error '
+                               'message.' % address)
+        else:
+            return port
 
     def add_secure_port(self, address, server_credentials):
-        return _add_secure_port(self._state, _common.encode(address),
+        port = _add_secure_port(self._state, _common.encode(address),
                                 server_credentials)
+        if port == 0:
+            # The Core API doesn't return a failure message. The best we can do
+            # is raising an exception to prevent further confusion.
+            raise RuntimeError('Failed to bind to address %s; set '
+                               'GRPC_VERBOSITY=debug env to see detailed error '
+                               'message.' % address)
+        else:
+            return port
 
     def start(self):
         _start(self._state)
diff --git a/src/python/grpcio/grpc/experimental/aio/_server.py b/src/python/grpcio/grpc/experimental/aio/_server.py
index 00c53490c5d..78eadfa3074 100644
--- a/src/python/grpcio/grpc/experimental/aio/_server.py
+++ b/src/python/grpcio/grpc/experimental/aio/_server.py
@@ -80,7 +80,15 @@ class Server(_base_server.Server):
         Returns:
           An integer port on which the server will accept RPC requests.
         """
-        return self._server.add_insecure_port(_common.encode(address))
+        port = self._server.add_insecure_port(_common.encode(address))
+        if port == 0:
+            # The Core API doesn't return a failure message. The best we can do
+            # is raising an exception to prevent further confusion.
+            raise RuntimeError('Failed to bind to address %s; set '
+                               'GRPC_VERBOSITY=debug env to see detailed error '
+                               'message.' % address)
+        else:
+            return port
 
     def add_secure_port(self, address: str,
                         server_credentials: grpc.ServerCredentials) -> int:
@@ -97,8 +105,16 @@ class Server(_base_server.Server):
         Returns:
           An integer port on which the server will accept RPC requests.
         """
-        return self._server.add_secure_port(_common.encode(address),
+        port = self._server.add_secure_port(_common.encode(address),
                                             server_credentials)
+        if port == 0:
+            # The Core API doesn't return a failure message. The best we can do
+            # is raising an exception to prevent further confusion.
+            raise RuntimeError('Failed to bind to address %s; set '
+                               'GRPC_VERBOSITY=debug env to see detailed error '
+                               'message.' % address)
+        else:
+            return port
 
     async def start(self) -> None:
         """Starts this Server.
diff --git a/src/python/grpcio_tests/tests/unit/_server_test.py b/src/python/grpcio_tests/tests/unit/_server_test.py
index bf00158ecdf..0ade8877b13 100644
--- a/src/python/grpcio_tests/tests/unit/_server_test.py
+++ b/src/python/grpcio_tests/tests/unit/_server_test.py
@@ -18,6 +18,8 @@ import logging
 
 import grpc
 
+from tests.unit.framework.common import get_socket
+
 
 class _ActualGenericRpcHandler(grpc.GenericRpcHandler):
 
@@ -47,6 +49,17 @@ class ServerTest(unittest.TestCase):
         self.assertIn('grpc.GenericRpcHandler',
                       str(exception_context.exception))
 
+    def test_failed_port_binding_exception(self):
+        address, _, __ = get_socket()
+        server = grpc.server(None)
+
+        with self.assertRaises(RuntimeError):
+            server.add_insecure_port(address)
+
+        with self.assertRaises(RuntimeError):
+            server.add_secure_port(address,
+                                   grpc.ssl_server_credentials(((b'', b''),)))
+
 
 if __name__ == '__main__':
     logging.basicConfig()
diff --git a/src/python/grpcio_tests/tests_aio/unit/server_test.py b/src/python/grpcio_tests/tests_aio/unit/server_test.py
index 43c90dc823e..73c28ef2557 100644
--- a/src/python/grpcio_tests/tests_aio/unit/server_test.py
+++ b/src/python/grpcio_tests/tests_aio/unit/server_test.py
@@ -21,7 +21,7 @@ import unittest
 import grpc
 from grpc.experimental import aio
 
-from tests.unit.framework.common import test_constants
+from tests.unit.framework.common import get_socket, test_constants
 from tests_aio.unit._test_base import AioTestBase
 
 _SIMPLE_UNARY_UNARY = '/test/SimpleUnaryUnary'
@@ -464,6 +464,17 @@ class TestServer(AioTestBase):
 
         self.assertEqual(grpc.StatusCode.INTERNAL, await call.code())
 
+    async def test_port_binding_exception(self):
+        address, _, __ = get_socket()
+        server = aio.server()
+
+        with self.assertRaises(RuntimeError):
+            server.add_insecure_port(address)
+
+        with self.assertRaises(RuntimeError):
+            server.add_secure_port(address,
+                                   grpc.ssl_server_credentials(((b'', b''),)))
+
 
 if __name__ == '__main__':
     logging.basicConfig(level=logging.DEBUG)