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README.md
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# SSLsplit - transparent SSL/TLS interception [![Build Status](https://travis-ci.org/droe/sslsplit.svg?branch=master)](https://travis-ci.org/droe/sslsplit)
# SSLproxy - transparent SSL/TLS proxy for diverting packets to other programs
Copyright (C) 2017, [Soner Tari](https://github.com/sonertari).
https://github.com/sonertari/SSLproxy
Copyright (C) 2009-2016, [Daniel Roethlisberger](//daniel.roe.ch/).
http://www.roe.ch/SSLsplit
The modifications for SSLproxy are copyrighted to [Soner Tari](https://github.com/sonertari),
and licensed under the same terms as SSLsplit.
## Overview
SSLproxy is based on SSLsplit.
SSLsplit is a tool for man-in-the-middle attacks against SSL/TLS encrypted
network connections. It is intended to be useful for network forensics,
application security analysis and penetration testing.
SSLsplit is designed to transparently terminate connections that are redirected
to it using a network address translation engine. SSLsplit then terminates
SSL/TLS and initiates a new SSL/TLS connection to the original destination
address, while logging all data transmitted. Besides NAT based operation,
SSLsplit also supports static destinations and using the server name indicated
by SNI as upstream destination. SSLsplit is purely a transparent proxy and
cannot act as a HTTP or SOCKS proxy configured in a browser.
SSLsplit supports plain TCP, plain SSL, HTTP and HTTPS connections over both
IPv4 and IPv6. SSLsplit fully supports Server Name Indication (SNI) and is
able to work with RSA, DSA and ECDSA keys and DHE and ECDHE cipher suites.
Depending on the version of OpenSSL built against, SSLsplit supports SSL 3.0,
TLS 1.0, TLS 1.1 and TLS 1.2, and optionally SSL 2.0 as well.
For SSL and HTTPS connections, SSLsplit generates and signs forged X509v3
certificates on-the-fly, mimicking the original server certificate's subject
DN, subjectAltName extension and other characteristics. SSLsplit has the
ability to use existing certificates of which the private key is available,
instead of generating forged ones. SSLsplit supports NULL-prefix CN
certificates but otherwise does not implement exploits against specific
SSLproxy is a proxy for SSL/TLS encrypted network connections. It is intended
to be used for diverting network traffic to other programs, such as UTM
services.
SSLproxy is designed to transparently terminate connections that are redirected
to it using a network address translation engine. SSLproxy then terminates
SSL/TLS and initiates a new SSL/TLS connection to the original destination
address. Packets received on the client side are decrypted and sent to the
program listening on a port given in the proxy specification. SSLproxy inserts
in the first packet the address and port it is expecting to receive the packets
back from the program. Upon receiving the packets back, SSLproxy re-encrypts
and sends them to their original destination. The return traffic follows the
same path back to the client.
For example, given the following proxy specification:
https 127.0.0.1 8443 up:8080
The SSLproxy listens for HTTPS connections on 127.0.0.1:8443. Upon receiving a
connection from the Client, it decrypts and diverts the packets to a Program
listening on 127.0.0.1:8080. After processing the packets, the Program gives
them back to the SSLproxy listening on a dynamically assigned address, which
the Program obtains from the first packet in the connection. Then the SSLproxy
re-encrypts and sends the packets to the Server. The response from the Server
follows the same path to the Client in reverse order:
Program
^^
/ \
v v
Client <-> SSLproxy <-> Server
The program that packets are diverted to should support this mode of operation.
Specifically, it should be able to recognize the SSLproxy address in the first
packet, and give the first and subsequent packets back to SSLproxy listening on
that address, instead of sending them to the original destination as it
normally would.
SSLproxy supports plain TCP, plain SSL, HTTP, HTTPS, POP3, POP3S, SMTP, and
SMTPS connections over both IPv4 and IPv6. SSLproxy fully supports Server Name
Indication (SNI) and is able to work with RSA, DSA and ECDSA keys and DHE and
ECDHE cipher suites. Depending on the version of OpenSSL, SSLproxy supports
SSL 3.0, TLS 1.0, TLS 1.1 and TLS 1.2, and optionally SSL 2.0 as well.
For SSL/TLS connections, SSLproxy generates and signs forged X509v3
certificates on-the-fly, mimicking the original server certificate's subject
DN, subjectAltName extension and other characteristics. SSLproxy has the
ability to use existing certificates of which the private key is available,
instead of generating forged ones. SSLproxy supports NULL-prefix CN
certificates but otherwise does not implement exploits against specific
certificate verification vulnerabilities in SSL/TLS stacks.
SSLsplit implements a number of defences against mechanisms which would
normally prevent MitM attacks or make them more difficult. SSLsplit can deny
OCSP requests in a generic way. For HTTP and HTTPS connections, SSLsplit
removes response headers for HPKP in order to prevent server-instructed public
key pinning, for HSTS to avoid the strict transport security restrictions, and
Alternate Protocols to prevent switching to QUIC/SPDY. HTTP compression,
SSLproxy implements a number of defences against mechanisms which would
normally prevent MitM attacks or make them more difficult. SSLproxy can deny
OCSP requests in a generic way. For HTTP and HTTPS connections, SSLproxy
removes response headers for HPKP in order to prevent server-instructed public
key pinning, for HSTS to avoid the strict transport security restrictions, and
Alternate Protocols to prevent switching to QUIC/SPDY. HTTP compression,
encodings and keep-alive are disabled to make the logs more readable.
As an experimental feature, SSLsplit supports STARTTLS and similar mechanisms,
where a protocol starts on a plain text TCP connection and is later upgraded to
SSL/TLS through protocol-specific means, such as the STARTTLS command in SMTP.
SSLsplit supports generic upgrading of TCP connections to SSL.
See the manual page sslsplit(1) for details on using SSLsplit and setting up
Another reason to disable persistent connections is to reduce file descriptor
usage. Accordingly, connections are closed if they remain idle for a certain
period of time. The default timeout is 120 seconds, which can be changed in a
configuration file.
In order to maximize the chances that a connection can be successfully split,
SSLproxy does not verify upstream server certificates. Instead, all
certificates including self-signed are accepted and if the expected hostname
signalled in SNI is missing from the server certificate, it will be added to
dynamically forged certificates.
SSLproxy does not automagically redirect any network traffic. To actually
implement a proxy, you also need to redirect the traffic to the system
running \fBsslproxy\fP. Your options include running \fBsslproxy\fP on a
legitimate router, ARP spoofing, ND spoofing, DNS poisoning, deploying a rogue
access point (e.g. using hostap mode), physical recabling, malicious VLAN
reconfiguration or route injection, /etc/hosts modification and so on.
As SSLproxy is based on SSLsplit, this is a modified SSLsplit README file.
See the manual page sslproxy(1) for details on using SSLproxy and setting up
the various NAT engines.
## Requirements
SSLsplit depends on the OpenSSL and libevent 2.x libraries.
SSLproxy depends on the OpenSSL and libevent 2.x libraries.
The build depends on GNU make and a POSIX.2 environment in `PATH`.
If available, pkg-config is used to locate and configure the dependencies.
The optional unit tests depend on the check library.
SSLsplit currently supports the following operating systems and NAT mechanisms:
SSLproxy currently supports the following operating systems and NAT mechanisms:
- FreeBSD: pf rdr and divert-to, ipfw fwd, ipfilter rdr
- OpenBSD: pf rdr-to and divert-to
@ -70,7 +110,7 @@ and FreeBSD.
SSL/TLS features and compatibility greatly depend on the version of OpenSSL
linked against; for optimal results, use a recent release of OpenSSL proper.
OpenSSL forks like LibreSSL and BoringSSL may or may not work.
OpenSSL forks like BoringSSL may or may not work.
## Installation
@ -102,11 +142,5 @@ See `AUTHORS.md` for the list of contributors.
SSLsplit is provided under a 2-clause BSD license.
SSLsplit contains components licensed under the MIT and APSL licenses.
See `LICENSE.md` and the respective source file headers for details.
## Credits
SSLsplit was inspired by `mitm-ssl` by Claes M. Nyberg and `sslsniff` by Moxie
Marlinspike, but shares no source code with them.
The modifications for SSLproxy are licensed under the same terms as SSLsplit.

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sslproxy.1
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.\" SSLproxy - transparent SSL/TLS proxy
.\" Copyright (c) 2017, Soner Tari <sonertari@gmail.com>
.\" Copyright (c) 2009-2016, Daniel Roethlisberger <daniel@roe.ch>
.\" All rights reserved.
.\" https://github.com/sonertari/SSLproxy
.\" http://www.roe.ch/SSLsplit
.\"
.\" The modifications for SSLproxy are copyrighted to
.\" Soner Tari <sonertari@gmail.com>
.\" The modifications for SSLproxy are licensed under the same terms as
.\" SSLsplit.
.\"
.\" Redistribution and use in source and binary forms, with or without
.\" modification, are permitted provided that the following conditions
@ -55,57 +57,57 @@ sslproxy \-\- transparent SSL/TLS proxy for diverting packets to programs
.SH DESCRIPTION
As SSLproxy is based on SSLsplit, this is a modified SSLsplit man page.
.LP
SSLproxy is a proxy for SSL/TLS encrypted network connections. It is intended t
o be used for diverting network traffic to other programs, such as UTM services.
SSLproxy is a proxy for SSL/TLS encrypted network connections. It is intended
to be used for diverting network traffic to other programs, such as UTM
services.
.LP
SSLproxy is designed to transparently terminate connections that are redirected
to it using a network address translation engine. SSLproxy then terminates SSL/
TLS and initiates a new SSL/TLS connection to the original destination address.
Packets received on the client side are decrypted and sent to the program liste
ning on a port given in the proxy specification. SSLproxy inserts in the first p
acket the address and port it is expecting to receive the packets back from the
program. Upon receiving the packets back, SSLproxy re-encrypts and sends them to
their original destination. The return traffic follows the same path back to th
e client.
to it using a network address translation engine. SSLproxy then terminates
SSL/TLS and initiates a new SSL/TLS connection to the original destination
address. Packets received on the client side are decrypted and sent to the
program listening on a port given in the proxy specification. SSLproxy inserts
in the first packet the address and port it is expecting to receive the packets
back from the program. Upon receiving the packets back, SSLproxy re-encrypts
and sends them to their original destination. The return traffic follows the
same path back to the client.
.LP
The program that packets are diverted to should support this mode of operation.
Specifically, it should be able to recognize the SSLproxy address in the first p
acket, and give the first and subsequent packets back to SSLproxy listening on t
hat address, instead of sending them to the original destination as it normally
would.
Specifically, it should be able to recognize the SSLproxy address in the first
packet, and give the first and subsequent packets back to SSLproxy listening on
that address, instead of sending them to the original destination as it
normally would.
.LP
SSLproxy supports plain TCP, plain SSL, HTTP, HTTPS, POP3, POP3S, SMTP, and SMTP
S connections over both
IPv4 and IPv6. SSLproxy fully supports Server Name Indication (SNI) and is able
to work with RSA, DSA and ECDSA keys and DHE and ECDHE cipher suites. Dependin
g on the version of OpenSSL, SSLproxy supports SSL 3.0, TLS 1.0, TLS 1.1 and TLS
1.2, and optionally SSL 2.0 as well.
SSLproxy supports plain TCP, plain SSL, HTTP, HTTPS, POP3, POP3S, SMTP, and
SMTPS connections over both IPv4 and IPv6. SSLproxy fully supports Server Name
Indication (SNI) and is able to work with RSA, DSA and ECDSA keys and DHE and
ECDHE cipher suites. Depending on the version of OpenSSL, SSLproxy supports
SSL 3.0, TLS 1.0, TLS 1.1 and TLS 1.2, and optionally SSL 2.0 as well.
.LP
For SSL/TLS connections, SSLproxy generates and signs forged X509v3 certificates
on-the-fly, mimicking the original server certificate's subject DN, subjectAltN
ame extension and other characteristics. SSLproxy has the ability to use existi
ng certificates of which the private key is available, instead of generating for
ged ones. SSLproxy supports NULL-prefix CN certificates but otherwise does not
implement exploits against specific certificate verification vulnerabilities in
SSL/TLS stacks.
For SSL/TLS connections, SSLproxy generates and signs forged X509v3
certificates on-the-fly, mimicking the original server certificate's subject
DN, subjectAltName extension and other characteristics. SSLproxy has the
ability to use existing certificates of which the private key is available,
instead of generating forged ones. SSLproxy supports NULL-prefix CN
certificates but otherwise does not implement exploits against specific
certificate verification vulnerabilities in SSL/TLS stacks.
.LP
SSLproxy implements a number of defences against mechanisms which would normally
prevent MitM attacks or make them more difficult. SSLproxy can deny OCSP reque
sts in a generic way. For HTTP and HTTPS connections, SSLproxy removes response
headers for HPKP in order to prevent server-instructed public key pinning, for
HSTS to avoid the strict transport security restrictions, and Alternate Protocol
s to prevent switching to QUIC/SPDY. HTTP compression, encodings and keep-alive
are disabled to make the logs more readable.
SSLproxy implements a number of defences against mechanisms which would
normally prevent MitM attacks or make them more difficult. SSLproxy can deny
OCSP requests in a generic way. For HTTP and HTTPS connections, SSLproxy
removes response headers for HPKP in order to prevent server-instructed public
key pinning, for HSTS to avoid the strict transport security restrictions, and
Alternate Protocols to prevent switching to QUIC/SPDY. HTTP compression,
encodings and keep-alive are disabled to make the logs more readable.
.LP
Another reason to disable persistent connections is to reduce file descriptor us
age. Accordingly, connections are closed if they remain idle for a certain perio
d of time. The default timeout is 120 seconds, which can be changed in a configu
ration file.
Another reason to disable persistent connections is to reduce file descriptor
usage. Accordingly, connections are closed if they remain idle for a certain
period of time. The default timeout is 120 seconds, which can be changed in a
configuration file.
.LP
In order to maximize the chances that a connection can be successfully split,
SSLproxy does not verify upstream server certificates. Instead, all
certificates including self-signed are accepted and if the expected hostname
signalled in SNI is missing from the server certificate, it will be added to
In order to maximize the chances that a connection can be successfully split,
SSLproxy does not verify upstream server certificates. Instead, all
certificates including self-signed are accepted and if the expected hostname
signalled in SNI is missing from the server certificate, it will be added to
dynamically forged certificates.
.LP
SSLproxy does not automagically redirect any network traffic. To actually
@ -152,8 +154,8 @@ List all supported NAT engines available on the system and exit. See
NAT ENGINES for a list of NAT engines currently supported by SSLproxy.
.TP
.B \-f \fIconffile\fP
Read configuraion from \fIconffile\fP. Only certain configuration options can be
loaded from file.
Read configuraion from \fIconffile\fP. Only certain configuration options can
be loaded from file.
.TP
.B \-F \fIlogspec\fP
Log connection content to separate log files with the given path specification
@ -591,15 +593,14 @@ Note that return path filtering (rp_filter) also needs to be disabled on
interfaces which handle TPROXY redirected traffic.
.RE
.SH EXAMPLES
With configuraion similar to the above NAT engine samples, intercept HTTPS and P
OP3S
over IPv4 using forged certificates with CA private key \fBca.key\fP
and certificate \fBca.crt\fP, logging connections to \fBconnect.log\fP and
connection data into separate files under \fB/tmp\fP (add \fB-e\fP
\fInat-engine\fP to select the appropriate engine if multiple engines are
With configuraion similar to the above NAT engine samples, intercept HTTPS and
POP3S over IPv4 using forged certificates with CA private key \fBca.key\fP and
certificate \fBca.crt\fP, logging connections to \fBconnect.log\fP and
connection data into separate files under \fB/tmp\fP (add \fB-e\fP
\fInat-engine\fP to select the appropriate engine if multiple engines are
available on your system) and diverting packets to a program running on address
127.0.0.1 and port 8080 for HTTPS and to another program running on address 127.
0.0.1 and port 8110 for POP3S:
127.0.0.1 and port 8080 for HTTPS and to another program running on address
127.0.0.1 and port 8110 for POP3S:
.LP
.nf
\fBsslproxy -k ca.key -c ca.crt -l connect.log -L /tmp \\
@ -657,8 +658,8 @@ SSLsplit was written by Daniel Roethlisberger <daniel@roe.ch>.
.LP
SSLproxy has been developed by Soner Tari <sonertari@gmail.com>.
.LP
The following individuals have contributed code or documentation to the SSLsplit
project, in chronological order of their first contribution:
The following individuals have contributed code or documentation to the
SSLsplit project, in chronological order of their first contribution:
Steve Wills, Landon Fuller, Wayne Jensen, Rory McNamara, Alexander Neumann,
Adam Jacob Muller, Richard Poole, Maciej Kotowicz, Eun Soo Park and Christian
Groschupp.

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