HTB: Outbound

Recently, I completed the Seasonal HTB machine "Outbound" and wanted to document my journey and methodology — without spoiling anything for others who want to take on the challenge themselves.

So let’s start:
As always, I began with a full port scan and noted down services running on the box. This allowed me to understand what surface I had to work with.

Enumeration

This was the most critical part of the entire challenge. I kept a detailed note of each step I took, tracked responses, and tested potential vectors. The enumeration was tricky but rewarding, and it slowly revealed what I needed to move forward.

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Tools I Used

I tried to stick to my usual methodology and tools. Here’s a small, non-spoiler list of what I used:

• nmap + rustscan for recon

• Custom payload generation via msfvenom

• Linux CLI tools (curl, nc, openssl, etc.)

• Various Impacket scripts

• Local privilege escalation via behavior analysis

For analysis, I worked from a Dockerized Kali setup and sometimes cross-tested with my main Arch Linux machine.

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Obstacles Faced

This machine was one of the more creative ones I’ve tackled recently. I had to chain multiple small misconfiguration and features to progress. A few times I hit a dead end, but going back to the fundamentals helped me reset and refocus.

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Privilege Escalation

Let’s just say... it was beautiful. It taught me a unique way to think about local file manipulation and service behavior abuse without being too obvious.

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Lessons Learned

• Always recheck every configuration, even after getting user access.

• Automation is helpful, but manual validation is king.

• Write everything down — screenshots, commands, hashes, and all observations. It helps immensely when reviewing.

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Final Thoughts

"Outbound" is a masterpiece of subtlety and depth. I highly recommend it to anyone looking for a serious challenge. This write-up doesn’t contain spoilers, but feel free to connect with me privately if you want to discuss techniques or general strategies.

Happy hacking!

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