diff --git a/libmproxy/exceptions.py b/libmproxy/exceptions.py
index 6b997041e..7d80ce31b 100644
--- a/libmproxy/exceptions.py
+++ b/libmproxy/exceptions.py
@@ -33,6 +33,11 @@ class TlsException(ProtocolException):
     pass
 
 
+class ClientHandshakeException(TlsException):
+    # This subclass is quite useful to give hints about cert errors.
+    pass
+
+
 class Socks5Exception(ProtocolException):
     pass
 
diff --git a/libmproxy/protocol/base.py b/libmproxy/protocol/base.py
index 9d8c8bfe4..6793d3df3 100644
--- a/libmproxy/protocol/base.py
+++ b/libmproxy/protocol/base.py
@@ -1,4 +1,6 @@
 from __future__ import (absolute_import, print_function, division)
+import six
+import sys
 from netlib import tcp
 from ..models import ServerConnection
 from ..exceptions import ProtocolException
@@ -172,8 +174,12 @@ class ServerConnectionMixin(object):
         try:
             self.server_conn.connect()
         except tcp.NetLibError as e:
-            raise ProtocolException(
-                "Server connection to %s failed: %s" % (repr(self.server_conn.address), e), e)
+            six.reraise(
+                ProtocolException,
+                ProtocolException("Server connection to %s failed: %s" %
+                                  (repr(self.server_conn.address), e), e),
+                sys.exc_info()[2]
+            )
 
 
 class Kill(Exception):
diff --git a/libmproxy/protocol/rawtcp.py b/libmproxy/protocol/rawtcp.py
index 6ab0196ad..8a597a15a 100644
--- a/libmproxy/protocol/rawtcp.py
+++ b/libmproxy/protocol/rawtcp.py
@@ -1,6 +1,8 @@
 from __future__ import (absolute_import, print_function, division)
 import socket
 import select
+import six
+import sys
 
 from OpenSSL import SSL
 
@@ -63,4 +65,8 @@ class RawTCPLayer(Layer):
                         )
 
         except (socket.error, NetLibError, SSL.Error) as e:
-            raise ProtocolException("TCP connection closed unexpectedly: {}".format(repr(e)), e)
+            six.reraise(
+                ProtocolException,
+                ProtocolException("TCP connection closed unexpectedly: {}".format(repr(e)), e),
+                sys.exc_info()[2]
+            )
diff --git a/libmproxy/protocol/tls.py b/libmproxy/protocol/tls.py
index 2cddb1dd4..6f6c2c789 100644
--- a/libmproxy/protocol/tls.py
+++ b/libmproxy/protocol/tls.py
@@ -1,18 +1,19 @@
 from __future__ import (absolute_import, print_function, division)
 
 import struct
+import sys
 
 from construct import ConstructError
 import six
-import sys
 
 from netlib.tcp import NetLibError, NetLibInvalidCertificateError
 from netlib.http.http1 import HTTP1Protocol
 from ..contrib.tls._constructs import ClientHello
-from ..exceptions import ProtocolException, TlsException
+from ..exceptions import ProtocolException, TlsException, ClientHandshakeException
 from .base import Layer
 
 
+
 # taken from https://testssl.sh/openssl-rfc.mappping.html
 CIPHER_ID_NAME_MAP = {
     0x00: 'NULL-MD5',
@@ -407,8 +408,17 @@ class TlsLayer(Layer):
                 chain_file=chain_file,
                 alpn_select_callback=self.__alpn_select_callback,
             )
+            # Some TLS clients will not fail the handshake,
+            # but will immediately throw an "unexpected eof" error on the first read.
+            # The reason for this might be difficult to find, so we try to peek here to see if it
+            # raises ann error.
+            self.client_conn.rfile.peek(0)
         except NetLibError as e:
-            raise TlsException("Cannot establish TLS with client: %s" % repr(e), e)
+            six.reraise(
+                ClientHandshakeException,
+                ClientHandshakeException("Cannot establish TLS with client: %s" % repr(e), e),
+                sys.exc_info()[2]
+            )
 
     def _establish_tls_with_server(self):
         self.log("Establish TLS with server", "debug")
@@ -457,17 +467,25 @@ class TlsLayer(Layer):
                 (tls_cert_err['depth'], tls_cert_err['errno']),
                 "error")
             self.log("Aborting connection attempt", "error")
-            raise TlsException("Cannot establish TLS with {address} (sni: {sni}): {e}".format(
-                address=repr(self.server_conn.address),
-                sni=self.sni_for_server_connection,
-                e=repr(e),
-            ), e)
+            six.reraise(
+                TlsException,
+                TlsException("Cannot establish TLS with {address} (sni: {sni}): {e}".format(
+                    address=repr(self.server_conn.address),
+                    sni=self.sni_for_server_connection,
+                    e=repr(e),
+                ), e),
+                sys.exc_info()[2]
+            )
         except NetLibError as e:
-            raise TlsException("Cannot establish TLS with {address} (sni: {sni}): {e}".format(
-                address=repr(self.server_conn.address),
-                sni=self.sni_for_server_connection,
-                e=repr(e),
-            ), e)
+            six.reraise(
+                TlsException,
+                TlsException("Cannot establish TLS with {address} (sni: {sni}): {e}".format(
+                    address=repr(self.server_conn.address),
+                    sni=self.sni_for_server_connection,
+                    e=repr(e),
+                ), e),
+                sys.exc_info()[2]
+            )
 
         self.log("ALPN selected by server: %s" % self.alpn_for_client_connection, "debug")
 
diff --git a/libmproxy/proxy/server.py b/libmproxy/proxy/server.py
index 91a12df9d..c00bb815a 100644
--- a/libmproxy/proxy/server.py
+++ b/libmproxy/proxy/server.py
@@ -3,6 +3,7 @@ from __future__ import (absolute_import, print_function, division)
 import traceback
 import sys
 import socket
+import six
 
 from netlib import tcp
 from netlib.http.http1 import HTTP1Protocol
@@ -39,7 +40,11 @@ class ProxyServer(tcp.TCPServer):
         try:
             super(ProxyServer, self).__init__((config.host, config.port))
         except socket.error as e:
-            raise ServerException('Error starting proxy server: ' + repr(e), e)
+            six.reraise(
+                ServerException,
+                ServerException('Error starting proxy server: ' + repr(e), e),
+                sys.exc_info()[2]
+            )
         self.channel = None
 
     def start_slave(self, klass, channel):
@@ -117,6 +122,7 @@ class ConnectionHandler(object):
             self.log("Connection killed", "info")
         except ProtocolException as e:
             self.log(repr(e), "info")
+            self.log(traceback.format_exc(), "debug")
             # If an error propagates to the topmost level,
             # we send an HTTP error response, which is both
             # understandable by HTTP clients and humans.