Proxy-Aware Payload Testing

TL;DR - I get told that I am too wordy, so if you want the summary, here are some steps to setup a virtual testing environment to test payloads to see if they can handle HTTP(S) proxies and if so, can they authenticate properly through them as well. This post will cover the proxy setup without authentication since that is the easier part, and I will do a second post shortly to hack together the authentication portion of it.

Skip down to the actual setup here if you wanted to skip the fluff.


There have been times in my red teaming and pentesting experience that I have run into networks where direct outbound traffic to the internet (or in some cases out of the subnet) is completely restricted. When I say direct, I mean that all DNS traffic first goes to an internal DNS server, all web traffic goes through an internal proxy, email to an internal SMTP/IMAP server, etc. From the client workstation to any internet IP address is dropped for TCP, UDP, and ICMP. For the blue teamers reading this post, this is something I highly recommend pushing for in your environment if it is not already the case. This not only allows for better monitoring but also breaks a large amount of commodity malware (and some red team tools) from working. It is one of my favorite incidental preventative controls.

In these cases, we need tools that can communicate out in an indirect manner. The choice of a TCP reverse shell or meterpreter payload are gone. Even default settings for meterpreter HTTP(S) payloads will be blocked since they don’t try to use a proxy by default.

There are times where I might consider C2 over DNS or SMTP, but these can be loud or somewhat complicated respectively. For this purpose, I often look to C2 tools that can use HTTP to communicate and either handle proxies by default or provide configuration options to allow you to set proxy settings for the payload.

I don’t plan to go through all of the C2 tools out there and talk about how they handle or can be made to handle HTTP proxies, but I will quickly highlight some of the different scenarios to show why having an environment test all parts of a proxy connection may be useful to C2 developers and the users of those tools.


By default, payload/windows/meterpreter/reverse_http and similar payloads are not proxy aware. These payloads will attempt to go directly to the IP address set for RHOST or resolve the hostname for RHOST then try to go directly to that IP address. Once a connection is established (SYN/ACK), then the traffic sent over that connection will be HTTP.

If traffic for direct outbound connections for your target is blocked, the initial TCP connection will fail and you will not get your shell. Sad day…

All is not lost though if you really want to use meterpreter over HTTP in this environment and you already have gained access to some information. The payload/windows/meterpreter/reverse_http and similar Windows payloads have the following advanced options available:
-       HttpProxyHost
-       HttpProxyPass
-       HttpProxyPort
-       HttpProxyUser

By setting these options, we can get meterpreter to connect out through an internal web proxy. But how do we get this information? We would have to have already compromised a system, phished a user, exposed in code or config files on public sources, or through some other information disclosure. Times where I have used this is for simulating a knowledgeable insider. Metasploit is one of the most popular public “hacking” tools, so to simulate someone who wants to “hack” their own company, I have assumed insider knowledge of their own credentials and the proxy configuration and set those in the payload then used meterpreter to get an external shell. Another situation that I have used has been finding proxy settings in code posted to public GitHub repositories. Developers love to create configuration files that set the proxy settings so that their applications can get out through the proxies like they can.

So, although meterpreter supports proxies and authentication, it does not handle those by default and requires some prior knowledge of the environment to use. I have seen similar results with many C2s that work on Mac OS or Linux such as EmPyre.

Some other tools or payloads currently do not support proxying HTTP payloads. One example would be the meterpreter payloads for Mac OS. The HttpProxy* options metioned for the Windows meterpreter payloads are not accepted by the Mac OS payloads.

PowerShell Empire and Cobalt Strike:

PowerShell Empire and Cobalt Strike work a little bit differently. They use libraries such as .NET’s System.Net.CredentialCache to ask the system to apply the processes current proxy settings and net credentials to the HTTP request. This allows the HTTP connection to be properly proxied the same way the current process would normally proxy web traffic. I continue to say process rather than user, because that can be a pretty important distinction in certain situations. If your process is running as SYSTEM (and you haven’t impersonated a user), then your net credentials will be the credentials of the host computer and not an AD user. Unless the computer accounts are allowed to authenticate through the proxy, this traffic will be denied, and your payload won’t get out. There have been many times where I have used privilege escalations or PSExec to spawn new beacons or agents and struggled to figure out why I wasn’t getting the callbacks. Most of the time, this has been due to being denied at the proxy.

In these situations, there are a few options. Assuming we have already compromised the host, we can do what we did with meterpreter and just hard-code these settings and override the defaults. This way, we have a SYSTEM level shell, but are using a user’s credentials and proxy settings to send traffic out. The other option is to use something like Cobalt Strike’s SMB beacon to create an internal C2 channel and link to those beacons from your HTTP beacon.

How Do We Test This:

How would we test this? Do we need to build a full domain-configured network? Do we need a complex proxy setup? I thought so at first and heavily put this project off but eventually dove in and tried it. What I learned was that just setting up a network with a proxy that didn’t check authentication was extremely easy and served as a good test environment for most of the situations I came across. When I decided that I needed to test authentication as well, things became a bit trickier. I will write a second post on that soon to cover the configuration for that part.

Building the Network:

Note: I was using VMware Fusion for my setup, but the steps should be very similar for something else such as VirtualBox.

For this setup to work, we need to ensure that our test host cannot call directly out to the internet. This could be done with host-based firewalls or IPTables but I decided that I didn’t want to make a bunch of configuration changes on each host that I wanted to test on. I wanted to build a network that I could attach a virtual machine to and it would just work (kind of… I’ll talk about the specifics in the authentication part of the proxy setup).

Here is a diagram of the network we are building:

To accomplish the port restrictions and web proxy, I built two virtual machines:
-       pfSense Firewall
o   Hardware
§  1 core
§  256 MB RAM
§  8 GB Disk (probably excessive)
§  2 network adapters
·      WAN – ‘Share with my Mac’
·      LAN – ‘SimpleProxyNet’ (see below)
o   Software
§  Nothing additional, no addons
-       Ubuntu Server
o   Hardware
§  2 cores
§  1 GB RAM
§  16 GB Disk (again, probably excessive)
§  1 network adapter – ‘SimpleProxyNet’ (see below)
o   Software
§  Added Squid Proxy software

For the networking setup, I created a network in VMware and unchecked the box that allows the network to connect to external networks. I wanted this network to be internal only. This will be the network that I attach my test VM and the proxy to.

Before starting either VM, I attached the network interfaces to the appropriate networks.

Setting Up pfSense:

I am not going to go into too many details on this one but rather include a screenshot of a couple of settings and a couple of tips that I learned along the way. There are many guides for setting up pfSense and I didn’t stray off the beaten path for this. For more info on getting started with pfSense, check out this link:

Some tips:
-       On the LAN interface, I did not set VMware to handle DHCP in anticipation of using pfSense for that purpose.
-       Keeping track of which interface is which can be a little tricky, but usually “Network Adapter” will be em0 or the WAN and “Network Adapter 2” will be em1 or the LAN.
-       Once you add a LAN interface, the management web portal will default to the internal network. I used my victim VM to browse to this management interface once I attached it to the network. You can also use your host OS if you have it also able to communicate on this network.
-       Since pfSense is handling DHCP, I tend to start this VM first and make sure it is fully booted before starting up the proxy or attaching any victim VMs.

Setting Up Squid Proxy:

Before adding any firewall rules, we want to setup our Squid proxy. We do this first because we want to create firewall rules that allow the proxy to call out to the internet, but we don’t want any other hosts on the SimpleProxyNet to be able to do so.

Setting up the Squid proxy without forcing user authentication was actually much easier than I expected, so I am not going to go into too many details on this setup either. I just setup a vanilla Ubuntu Server 18.04 and used apt to install Squid and set a static IP address on the OS (in my case I used I followed a guide all the way up to where they add authentication. A guide such as this could be useful:

Finally, I set up the ACLs to allow the SimpleProxyNet subnet to connect to the proxy and moved on to setting up the firewall rules on the pfSense.

Firewall Rules:

With the proxy and firewall built, we need to connect a system to this network and configure the firewall rules. I created a Windows VM that would serve as my victim and attached it to the SimpleProxyNet network.

To access the pfSense web UI, I used my victim Windows VM by attaching the network interface for my Windows VM to the SimpleProxyNet network and opening a web browser and going to http(s)[:]//[IP of pfSense]/ and logging in with the credentials that I set when first configuring the pfSense (default is admin:pfsense). Once logged in, I went to the firewall settings and configured the LAN settings to allow the IP address of the Squid proxy to communicate outbound on 53/DNS, 80/HTTP, and 443/HTTPS:

These settings prevent the victim VM from being able to connect directly out to the internet as only the Squid proxy traffic is allowed.

Note: The ports from the proxy have been limited to 80, 443, and 53. This is a common situation but not necessarily the way all proxies are setup. In this case, your C2 channels would be limited to calling back on one of these three ports. Some proxies at client environments are allowed out on any port to accommodate web services that run on other ports such as 8080. If you wanted to test in this fashion, you could alter your rules to allow for this and see how your tools work in this situation (proxying SSH can be a fun one if you can figure it out).

Once you have the firewall rules set, your proxy setup, and your victim VM connected, we just need to go to the victim VM and configure it to know about the proxy. Once this is one, we should have an unauthenticated proxied network setup and ready to start testing payloads.

Setting the Proxy Settings on the Victim VM:

For this section, I am only going to go into the setup for modern Windows hosts and not worry about *nix hosts. This is something that is quickly and easily searchable on the internet.

Open the Start Menu and find the Internet Options settings menu. Once opened, go to the Connections tab and click on the LAN settings button. Uncheck the Automatically detect settings checkbox (this is for WPAD, something beyond the scope of this post) and check the Use a proxy server for your LAN checkbox. Enter the IP address of your Squid proxy server (in my case and port (default for Squid is 3128).

Click the OK button on each menu to save the settings. Pop open a web browser and try to browse the internet to confirm that the proxy is working. You should be all setup and ready to test your payloads for proxy-awareness.


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