Remote Weaponization of WSUS MITM


Let’s take a step back and learn the different components of a WSUS MITM attack first. Web Proxy Auto-Discovery (WPAD) is a protocol used by Microsoft Windows clients to automatically configure local proxy settings. Enterprises use the protocol to allow clients to automatically locate and use the proper proxy settings to egress the enterprise network. The discovery process and configuration is as follows:

  1. Did I get a proxy configuration during DHCP negation?
  2. If not, resolve “” and get the configuration from that server.
  3. If we did not get a result, broadcast using NetBIOS (NBT-NS) to resolve the name “WPAD”
  4. If a server has been found, request the resource from that server with the uri “/wpad.dat (http://<SERVER>/wpad.dat) which will contain the settings for the proxy
  • HTTP MITM with an iframe (HTA, Exploit, Java Applet, etc.)
  • HTTP Auth Prompt / Social Engineering
  • WSUS Injection
  • …and many many more


Windows Server Update Services (WSUS) is a system that allows for companies to manage and deploy updates or hotfixes from a centralized intranet location. At Blackhat USA 2015, a group of security researchers, Paul Stone () and Alex Chapman from Context, presented on the obvious problems with allowing enterprise updates to occur unencrypted over the network. They made the obvious point that without SSL, anyone can conduct a man-in-the-middle attack on the updates to serve a malicious update package. Oh by the way, HTTP is the default for WSUS. One problem: the update binary must be signed by Microsoft. One solution: PsExec from SysInternals allows an attacker to execute arbitrary Windows commands from a signed Windows binary. This attack was demoed at the conference and had me intrigued. Throughout the majority of the engagements I have been on, it is slight misconfigurations like these that have allowed our red team to get access to the key terrain we needed.

Putting It Together

Okay okay… All I have done at this point is regurgitate well-known vulnerabilities and attack strategies. The power is introduced when you put the tools together and weaponize it in a platform like Cobalt Strike enabling a MiTM attack outside the bounds of the local intranet. For this section, I will assume we have gained initial access from an external perspective to a domain joined host.

1. Identify the Possibilities

The first step is to identify any WSUS misconfigurations. In most RATs, we can do this by querying the registry to determine the system’s WSUS settings. Next we can query the current proxy configuration of Internet Explorer. If the URL for WSUS is “HTTP://<SERVER>” and the browser is set to automatically configure the proxy, we can continue!

  • HKLM\Software\Policies\Microsoft\Windows\WindowsUpdate\WUServer
  • HKLM\Software\Policies\Microsoft\Windows\WindowsUpdate\AU\UseWUServer
  • HKCU\Software\Microsoft\Windows\CurrentVersion\Internet Settings\Connections\DefaultConnectionSettings (Note: If the 5th byte is even, automatic detection of the proxy is likely set in internet explorer which enabled WPAD)

2. Network Bending Kung-fu

The obvious problem arose during exploitation of how we use our agent as the WSUS Proxy. Luckily with Cobalt Strike’s Beacon, we have reverse port forward capabilities. During the WPAD poison, we can point the victim’s browser at our “proxy” which is simply a reverse tunnel out of the network to our C2 server. Then, using the SOCKS forward tunnels, we can push the browsing traffic back into the environment to receive the action WSUS updates in addition to the tampered package.

3. Poison

Once the tunnels are ready, it is finally time for the attack. First, I to configure my malicious payload and start WSUSpectProxy. WSUSpectProxy takes in a custom payload defined in their payload.ini file (example shown below). Like the researchers recommend in their white paper, I use PsExec.exe with a command line parameter. In my case, I made the parameter launch powershell.exe to run “net user” and “net localgroup” to add a backdoor user “bob”.

  • -IP <IP OF POISON VICTIM> : Set the IP to bind the raw socket to
  • -NBNS Y : Set NBNS spoofing to be enabled
  • -LLMNR Y : Set LLMNR spoofing to be enabled
  • -HTTP Y : Turn on the HTTP server for serving up WPAD.dat files
  • -SMB N : Do not do any sort of SMB relay kind of stuff
  • -StatusOutput Y : Print status outputs
  • -Tool 2 : Configure the settings to run this in a certain tool. The Empire setting works well for Cobalt Strike
  • -SpooferIPsReply <TARGET IP> : IP of the target or CSV list of targets
  • -WPADAuth Anonymous : Do not pop a creds box for the WPAD
  • -WPADIp <ProxyHost> : IP of poison host where the rportfwd command is run
  • -WPADPort 8080 : port of the rportfwd command

4. MITM Updates

Once the MITM condition is met, the update request is intercepted and my malicious package is passed to the client. Since the update is critical, it will likely get executed, adding a local user and allowing us to laterally spread.

Fixing the Vulnerabilities

There are numerous flaws that allow for this attack chain to be successful and they should be fixed in any network. These issues have been identified for a long time but I continue to see a lack of awareness and controls surrounding the misconfigurations abused in this chain. In addition to controls to prevent the vulnerabilities, there are many ways that SOCs and CIRTs can detect malicious activity like this occurring on their network and with sophisticated attackers, a heavy focus on detection is healthy.

WPAD Controls / Fixes

To remediate the WPAD misconfiguration, DNS A or CNAME records should be added in the internal DNS server with the name “wpad” to prevent the host from getting to the step where it performs the MDNS/LLMNR broadcast. Further, it helps to uncheck the automatic settings via a GPO if that feature is not needed.

WSUS Fixes

Any update packages or software should ALWAYS be deployed over secure connections (at least SSL). There are many projects that focus on backdooring software and applications in transit across networks… many bad guys used this technique to gain initial access and laterally spread. For WSUS specifically, I found this site helpful for configuration of a proper setup:


Prevention controls are a bare minimum expectation but as an organization grows in maturity and works through the hierarchy of security controls, auditing and forensic capabilities are a must. As organizations shift to an assume breach mentality, they maintain their focus on prevention but also introduce the heavy demand of detection and response. There are a couple themes that can be abstracted from the attack chain above to alert on suspicious activity.

PowerShell v5

PowerShell v4 and v5 have introduced many features that the blue folks should appreciate. I mention them here specifically because I used Inveigh.ps1 in my attack chain but is not directly relevant to detection of the underlying techniques, only the weaponization vector. There is an article out that sums up most of the features that will be helpful. Anyone who is working on improving network detection should look for and introduce features to combat PowerShell attacks. PowerShell attacks are on the rise and are not going anywhere any time soon.

Event Logs

Event Log forwarding in a large enterprise can be difficult. The value earned from centralized collection and monitoring and collection of these logs cannot be understated and in my opinion, is totally worth it. In the case of this attack chain, it seems like the best log to add to collection is the c:\windows\windowsupdate.log file. If you are not collecting that, the System event log with a source of “WindowsUpdateClient” and ID of 17 or 19 will show you the names of the updates downloaded/installed. Comparing thees logs across the hosts will allow you to pick out edge events (rogue updates) which have only happened on selected hosts.

WMI Event Subscription

Our team is a huge proponent of WMI’s uses offensively and defensively. You might have seen Matt Graeber’s recent tweets such as this one where he provides WMI signatures that would provide alerts surrounding events worth monitoring. Jared Atkinson, ATD’s Hunt capability lead, has developed a tool called Uproot which is, in effect, an agent-less host-based IDS using that uses WMI event subscriptions.


While I did not introduce any new tools in this post, my goal was to stitch together several awesome tools to show an interesting attack chain and encourage creative techniques. Further, I hoped to bring light to several misconfigurations I still commonly see in large enterprise environments.



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