diff --git a/tests/test_ssl.py b/tests/test_ssl.py
index 6fe1c1ac2..4145b08c2 100644
--- a/tests/test_ssl.py
+++ b/tests/test_ssl.py
@@ -321,7 +321,7 @@ def loopback_server_factory(socket, version=SSLv23_METHOD):
     return server
 
 
-def loopback(server_factory=None, client_factory=None):
+def loopback(server_factory=None, client_factory=None, blocking=True):
     """
     Create a connected socket pair and force two connected SSL sockets
     to talk to each other via memory BIOs.
@@ -337,8 +337,8 @@ def loopback(server_factory=None, client_factory=None):
 
     handshake(client, server)
 
-    server.setblocking(True)
-    client.setblocking(True)
+    server.setblocking(blocking)
+    client.setblocking(blocking)
     return server, client
 
 
@@ -3292,11 +3292,131 @@ def test_memoryview_really_doesnt_overfill(self):
         self._doesnt_overfill_test(_make_memoryview)
 
 
+@pytest.fixture
+def nonblocking_tls_connections_pair():
+    """Return a non-blocking TLS loopback connections pair."""
+    return loopback(blocking=False)
+
+
+@pytest.fixture
+def nonblocking_tls_server_connection(nonblocking_tls_connections_pair):
+    """Return a non-blocking TLS server socket connected to loopback."""
+    return nonblocking_tls_connections_pair[0]
+
+
+@pytest.fixture
+def nonblocking_tls_client_connection(nonblocking_tls_connections_pair):
+    """Return a non-blocking TLS client socket connected to loopback."""
+    return nonblocking_tls_connections_pair[1]
+
+
 class TestConnectionSendall:
     """
     Tests for `Connection.sendall`.
     """
 
+    def test_want_write(
+            self,
+            monkeypatch,
+            nonblocking_tls_server_connection,
+            nonblocking_tls_client_connection,
+    ):
+        msg = b"x"
+        garbage_size = 1024 * 1024 * 64
+        large_payload = b"p" * garbage_size * 2
+        payload_size = len(large_payload)
+
+        sent_garbage_size = 0
+        try:
+            sent_garbage_size += nonblocking_tls_client_connection.send(
+                msg * garbage_size,
+            )
+        except WantWriteError:
+            pass
+        for i in range(garbage_size):
+            try:
+                sent_garbage_size += nonblocking_tls_client_connection.send(
+                    msg,
+                )
+            except WantWriteError:
+                break
+        else:
+            pytest.fail(
+                "Failed to fill socket buffer, cannot test "
+                "'want write' in `sendall()`"
+            )
+        garbage_payload = sent_garbage_size * msg
+
+
+        def consume_garbage(conn):
+            assert patched_ssl_write.want_write_counter >= 1
+            assert not consume_garbage.garbage_consumed
+
+            while len(consume_garbage.consumed) < sent_garbage_size:
+                try:
+                    consume_garbage.consumed += conn.recv(
+                        sent_garbage_size - len(consume_garbage.consumed),
+                    )
+                except WantReadError:
+                    pass
+
+            assert consume_garbage.consumed == garbage_payload
+
+            consume_garbage.garbage_consumed = True
+
+        consume_garbage.garbage_consumed = False
+        consume_garbage.consumed = b""
+
+        def consume_payload(conn):
+            try:
+                consume_payload.consumed += conn.recv(payload_size)
+            except WantReadError:
+                pass
+        consume_payload.consumed = b""
+
+        original_ssl_write = _lib.SSL_write
+        def patched_ssl_write(ctx, data, size):
+            write_result = original_ssl_write(ctx, data, size)
+            try:
+                nonblocking_tls_client_connection._raise_ssl_error(
+                    ctx, write_result,
+                )
+            except WantWriteError:
+                patched_ssl_write.want_write_counter += 1
+                consume_data_on_server = (
+                    consume_payload if consume_garbage.garbage_consumed
+                    else consume_garbage
+                )
+
+                consume_data_on_server(nonblocking_tls_server_connection)
+                # NOTE: We don't re-raise it as the calling code will do
+                # NOTE: the same after the call.
+            return write_result
+
+        patched_ssl_write.want_write_counter = 0
+
+        # NOTE: Make the client think it needs a handshake so that it'll
+        # NOTE: attempt to `do_handshake()` on the next `SSL_write()`
+        # NOTE: that originates from `sendall()`:
+        nonblocking_tls_client_connection.set_connect_state()
+        try:
+            nonblocking_tls_client_connection.do_handshake()
+        except WantWriteError:
+            assert True  # Sanity check
+        except:
+            assert False  # This should never happen (see the note above)
+
+        with monkeypatch.context() as mp_ctx:
+            mp_ctx.setattr(_lib, "SSL_write", patched_ssl_write)
+            nonblocking_tls_client_connection.sendall(large_payload)
+
+        assert consume_garbage.garbage_consumed
+
+        # NOTE: Read the leftover data from the very last `SSL_write()`
+        consume_payload(nonblocking_tls_server_connection)
+
+        assert consume_payload.consumed == large_payload
+
     def test_wrong_args(self):
         """
         When called with arguments other than a string argument for its first