diff --git a/mitmproxy/proxy/protocol/rawtcp.py b/mitmproxy/proxy/protocol/rawtcp.py
index 0ec505945..00bba04c5 100644
--- a/mitmproxy/proxy/protocol/rawtcp.py
+++ b/mitmproxy/proxy/protocol/rawtcp.py
@@ -29,13 +29,20 @@ class RawTCPLayer(base.Layer):
         server = self.server_conn.connection
         conns = [client, server]
 
+        # https://github.com/openssl/openssl/issues/6234
+        for conn in conns:
+            if isinstance(conn, SSL.Connection) and hasattr(SSL._lib, "SSL_clear_mode"):
+                SSL._lib.SSL_clear_mode(conn._ssl, SSL._lib.SSL_MODE_AUTO_RETRY)
+
         try:
             while not self.channel.should_exit.is_set():
                 r = mitmproxy.net.tcp.ssl_read_select(conns, 10)
                 for conn in r:
                     dst = server if conn == client else client
-
-                    size = conn.recv_into(buf, self.chunk_size)
+                    try:
+                        size = conn.recv_into(buf, self.chunk_size)
+                    except (SSL.WantReadError, SSL.WantWriteError):
+                        continue
                     if not size:
                         conns.remove(conn)
                         # Shutdown connection to the other peer
diff --git a/setup.py b/setup.py
index c5837b823..4172c46f7 100644
--- a/setup.py
+++ b/setup.py
@@ -67,7 +67,7 @@ setup(
         "Brotli>=1.0,<1.1",
         "certifi>=2019.9.11",  # no semver here - this should always be on the last release!
         "click>=7.0,<8",
-        "cryptography>=2.1.4,<2.5",
+        "cryptography>=2.1.4,<3.0",
         "flask>=1.1.1,<1.2",
         "h2>=3.0.1,<4",
         "hyperframe>=5.1.0,<6",
@@ -76,7 +76,7 @@ setup(
         "passlib>=1.6.5, <1.8",
         "protobuf>=3.6.0, <3.11",
         "pyasn1>=0.3.1,<0.5",
-        "pyOpenSSL==19.0.0",
+        "pyOpenSSL>=19.1.0,<19.2",
         "pyparsing>=2.4.2,<2.5",
         "pyperclip>=1.6.0,<1.8",
         "ruamel.yaml>=0.16,<0.17",
diff --git a/test/mitmproxy/net/test_tcp.py b/test/mitmproxy/net/test_tcp.py
index 22a306dc9..f204b8b9c 100644
--- a/test/mitmproxy/net/test_tcp.py
+++ b/test/mitmproxy/net/test_tcp.py
@@ -37,7 +37,7 @@ class ClientCipherListHandler(tcp.BaseHandler):
     sni = None
 
     def handle(self):
-        self.wfile.write(str(self.connection.get_cipher_list()).encode())
+        self.wfile.write(f"{self.connection.get_cipher_list()}\n".encode())
         self.wfile.flush()
 
 
@@ -421,16 +421,18 @@ class TestServerCipherList(tservers.ServerTestBase):
         cipher_list='AES256-GCM-SHA384'
     )
 
+    @pytest.mark.xfail
     def test_echo(self):
+        # Not working for OpenSSL 1.1.1, see
+        # https://github.com/pyca/pyopenssl/blob/fc802df5c10f0d1cd9749c94887d652fa26db6fb/src/OpenSSL/SSL.py#L1192-L1196
         c = tcp.TCPClient(("127.0.0.1", self.port))
         with c.connect():
             c.convert_to_tls(sni="foo.com")
-            expected = b"['AES256-GCM-SHA384']"
-            assert c.rfile.read(len(expected) + 2) == expected
+            expected = b"['TLS_AES_256_GCM_SHA384']"
+            assert c.rfile.readline() == expected
 
 
 class TestServerCurrentCipher(tservers.ServerTestBase):
-
     class handler(tcp.BaseHandler):
         sni = None
 
@@ -442,7 +444,10 @@ class TestServerCurrentCipher(tservers.ServerTestBase):
         cipher_list='AES256-GCM-SHA384'
     )
 
+    @pytest.mark.xfail
     def test_echo(self):
+        # Not working for OpenSSL 1.1.1, see
+        # https://github.com/pyca/pyopenssl/blob/fc802df5c10f0d1cd9749c94887d652fa26db6fb/src/OpenSSL/SSL.py#L1192-L1196
         c = tcp.TCPClient(("127.0.0.1", self.port))
         with c.connect():
             c.convert_to_tls(sni="foo.com")
@@ -608,7 +613,7 @@ class TestDHParams(tservers.ServerTestBase):
     def test_dhparams(self):
         c = tcp.TCPClient(("127.0.0.1", self.port))
         with c.connect():
-            c.convert_to_tls()
+            c.convert_to_tls(method=SSL.TLSv1_2_METHOD)
             ret = c.get_current_cipher()
             assert ret[0] == "DHE-RSA-AES256-SHA"
 
diff --git a/test/mitmproxy/net/test_tls.py b/test/mitmproxy/net/test_tls.py
index c4e76bc6e..e78564c7b 100644
--- a/test/mitmproxy/net/test_tls.py
+++ b/test/mitmproxy/net/test_tls.py
@@ -43,7 +43,7 @@ class TestMasterSecretLogger(tservers.ServerTestBase):
 
             tls.log_master_secret.close()
             with open(logfile, "rb") as f:
-                assert f.read().count(b"CLIENT_RANDOM") == 2
+                assert f.read().count(b"CLIENT_RANDOM") >= 2
 
         tls.log_master_secret = _logfun