Back On Track

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2 min read

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Updated May 24, 2026

While going through Advent of Cyber this year I decided to pay closer attention to the YouTubers that have taken on the Walk Throughs for each challenge.

I discovered TylerRamsbey‘s channel and was inspired!

He’s got a path laid out that he says worked for him to get to Pentesting. I am going to give it a try. Step one complete, I am currently working through the PEH course. After that I’ll revisit the HTB Academy Academy and take the Pentester Track, I completed the Bug Bounty Hunter track last year. For what these all offer, the cost is really, really reasonable.

Tyler says the OSCP should be doable at that point, so I will go after that. This is the “Pass HR Cert” that I guess you need. I hate certs. I used to have the CCNA, VCP, RHCP, blah blah certs and I can tell you that I learned on the job and struggling, not in those courses. I really don’t like certs, but I get they are needed.

Tyler also says that what he think will make someone stand out are things like having CVE’s in your name. I don’t believe that will ever be me, but I love the idea. I will of course go for it eventually. Check out his video here.

I’ve joined his Discord Server (HackSmarter) but have not had time to explore.

Finger’s crossed! I finally broke down and got a Pineapple. It’s easy peasy to use, way easier than struggling with the drivers for an ALFA, though there is something to just using the CLI and not a fancy UI.

What interests me the most about Penetration Testing is Social Engineering, Physical Security and WiFi Hacking.

Onward!

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