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+TIP: WatchGuard has
+[responded](https://www.reddit.com/r/netsec/comments/5tg0f9/reverseengineering_watchguard_mobile_vpn/dds6knx/)
+to this post on Reddit. If you haven\'t read the post yet I\'d recommend
+doing that first before reading the response to have the proper context.
+
+------------------------------------------------------------------------
+
+One of my current client makes use of
+[WatchGuard](http://www.watchguard.com/help/docs/fireware/11/en-US/Content/en-US/mvpn/ssl/mvpn_ssl_client-install_c.html)
+Mobile VPN software to provide access to the internal network.
+
+Currently WatchGuard only provides clients for OS X and Windows, neither
+of which I am very fond of. In addition an OpenVPN configuration file is
+provided, but it quickly turned out that this was only a piece of the
+puzzle.
+
+The problem is that this VPN setup is secured using 2-factor
+authentication (good!), but it does not use OpenVPN\'s default
+[challenge/response](https://openvpn.net/index.php/open-source/documentation/miscellaneous/79-management-interface.html)
+functionality to negotiate the credentials.
+
+Connecting with the OpenVPN config that the website supplied caused the
+VPN server to send me a token to my phone, but I simply couldn\'t figure
+out how to supply it back to the server. In a normal challenge/response
+setting the token would be supplied as the password on the second
+authentication round, but the VPN server kept rejecting that.
+
+Other possibilities were various combinations of username&password
+(I\'ve seen a lot of those around) so I tried a whole bunch, for example
+`$password:$token` or even a `sha1(password, token)` - to no avail.
+
+At this point it was time to crank out
+[Hopper](https://www.hopperapp.com/) and see what\'s actually going on
+in the official OS X client - which uses OpenVPN under the hood!
+
+Diving into the client
+----------------------
+
+The first surprise came up right after opening the executable: It had
+debug symbols in it - and was written in Objective-C!
+
+![Debug symbols](/static/img/watchblob_1.webp)
+
+A good first step when looking at an application binary is going through
+the strings that are included in it, and the WatchGuard client had a lot
+to offer. Among the most interesting were a bunch of URIs that looked
+important:
+
+![Some URIs](/static/img/watchblob_2.webp)
+
+I started with the first one
+
+    %@?action=sslvpn_download&filename=%@&fw_password=%@&fw_username=%@
+
+and just curled it on the VPN host, replacing the username and
+password fields with bogus data and the filename field with
+`client.wgssl` - another string in the executable that looked like a
+filename.
+
+To my surprise this endpoint immediately responded with a GZIPed file
+containing the OpenVPN config, CA certificate, and the client
+*certificate and key*, which I previously thought was only accessible
+after logging in to the web UI - oh well.
+
+The next endpoint I tried ended up being a bit more interesting still:
+
+    /?action=sslvpn_logon&fw_username=%@&fw_password=%@&style=fw_logon_progress.xsl&fw_logon_type=logon&fw_domain=Firebox-DB
+
+Inserting the correct username and password into the query parameters
+actually triggered the process that sent a token to my phone. The
+response was a simple XML blob:
+
+```xml
+<?xml version="1.0" encoding="UTF-8"?>
+<resp>
+  <action>sslvpn_logon</action>
+  <logon_status>4</logon_status>
+  <auth-domain-list>
+    <auth-domain>
+      <name>RADIUS</name>
+    </auth-domain>
+  </auth-domain-list>
+  <logon_id>441</logon_id>
+  <chaStr>Enter Your 6 Digit Passcode </chaStr>
+</resp>
+```
+
+Somewhat unsurprisingly that `chaStr` field is actually the challenge
+string displayed in the client when logging in.
+
+This was obviously going in the right direction so I proceeded to the
+procedures making use of this string. The first step was a relatively
+uninteresting function called `-[VPNController sslvpnLogon]` which
+formatted the URL, opened it and checked whether the `logon_status` was
+`4` before proceeding with the `logon_id` and `chaStr` contained in the
+response.
+
+*(Code snippets from here on are Hopper\'s pseudo-Objective-C)*
+
+![sslvpnLogon](/static/img/watchblob_3.webp)
+
+It proceeded to the function `-[VPNController processTokenPrompt]` which
+showed the dialog window into which the user enters the token, sent it
+off to the next URL and checked the `logon_status` again:
+
+(`r12` is the reference to the `VPNController` instance, i.e. `self`).
+
+![processTokenPrompt](/static/img/watchblob_4.webp)
+
+If the `logon_status` was `1` (apparently \"success\" here) it proceeded
+to do something quite interesting:
+
+![processTokenPrompt2](/static/img/watchblob_5.webp)
+
+The user\'s password was overwritten with the (verified) OTP token -
+before OpenVPN had even been started!
+
+Reading a bit more of the code in the subsequent
+`-[VPNController doLogin]` method revealed that it shelled out to
+`openvpn` and enabled the management socket, which makes it possible to
+remotely control an `openvpn` process by sending it commands over TCP.
+
+It then simply sent the username and the OTP token as the credentials
+after configuring OpenVPN with the correct config file:
+
+![doLogin](/static/img/watchblob_6.webp)
+
+... and the OpenVPN connection then succeeds.
+
+TL;DR
+-----
+
+Rather than using OpenVPN\'s built-in challenge/response mechanism, the
+WatchGuard client validates user credentials *outside* of the VPN
+connection protocol and then passes on the OTP token, which seems to be
+temporarily in a \'blessed\' state after verification, as the user\'s
+password.
+
+I didn\'t check to see how much verification of this token is performed
+(does it check the source IP against the IP that performed the challenge
+validation?), but this certainly seems like a bit of a security issue -
+considering that an attacker on the same network would, if they time the
+attack right, only need your username and 6-digit OTP token to
+authenticate.
+
+Don\'t roll your own security, folks!
+
+Bonus
+-----
+
+The whole reason why I set out to do this is so I could connect to this
+VPN from Linux, so this blog post wouldn\'t be complete without a
+solution for that.
+
+To make this process really easy I\'ve written a [little
+tool](https://github.com/tazjin/watchblob) that performs the steps
+mentioned above from the CLI and lets users know when they can
+authenticate using their OTP token.