This One Time on a Pen Test: Outwitting the Vexing VPN

This One Time on a Pen Test: Outwitting the Vexing VPN

Each year, Rapid7 penetration testers complete hundreds of internally and externally based penetration testing service engagements. This post is part of an ongoing series featuring testimonials of what goes on beneath the hoodie. For more insights, check out our 2020 Under the Hoodie report.


Just as we do with the vast majority of our engagements, I started by digging around the internet looking for information about my target’s employees. One thing I had a hard time figuring out was what their username format was. I scraped the metadata from documents they hosted, used resources like hunter.io, and also used the Harvester to dig up what I could. But, I was still not positive on the format. Most companies use common formats like FLast, or First.Last. To validate the username formats, I was using a tool called lyncsmash, which leverages a timing vulnerability in the Lync service used by on-premises Skype servers. Testing FLast, and First.Last turned up nothing for me, but on my third try, I thought to use LastF, and that turned out to be the ticket. I start seeing a fair amount of valid usernames scroll by.


I parsed my list of usernames for valid accounts and found that out of 482, I ended up with 230 valid accounts. This was still a good number, so I kept rolling with a password spray using lyncsmash. After about my fourth try, I hit some gold: Eleven accounts came back, all using the same weak and guessable password.


You can’t hate on having 11 accounts to validate external access with, am I right?!


While doing my OSINT, I found several exte ..

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