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7MS #353: Tales of Internal Pentest Pwnage - Part 1

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Manage episode 229816202 series 1288763
Content provided by Brian Johnson. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Brian Johnson or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://player.fm/legal.

Buckle up! This is one of my favorite episodes.

Today I'm kicking off a two-part series that walks you through a narrative of a recent internal pentest I worked on. I was able to get to Domain Admin status and see the "crown jewels" data, so I thought this would be a fun and informative narrative to share. Below are some highlights of topics/tools/techniques discussed:

Building a pentest dropbox

The timing is perfect - my pal Paul (from Project7) and Dan (from PlexTrac) have a two-part Webinar series on building your own $500 DIY Pentest Lab, but the skills learned in the Webinars translate perfectly into making a pentest dropbox. Head to our webinars page for more info.

Securing a pentest dropbox

What I did with my Intel NUC pentest dropbox is build a few VMs as follows:

  • Win 10 pro management box with Bitlocker drive encryption and Splashtop (not a sponsor) which I like because it offers 2FA and an additional per-machine password/PIN. I think I spent $100/year for it.

  • Kali attack box with an encrypted drive (Kali makes this easy by offering you this option when you first install the OS).

Scoping/approaching a pentest

From what I can gather, there are (at least) two popular schools of thought as it relates to approaching a pentest:

  • From the perimeter - where you do a lot of OSINT, phish key users, gain initial access, and then find a path to privilege from there.

  • Assume compromise - assume that eventually someone will click a phishing link and give bad guys a foothold on the network, so you have the pentester bring in a Kali box, plug it into the network, and the test begins from that point.

Pentest narrative

For one of the tests I worked on, here were some successes and challenges I had along the way:

Check out the show notes at 7MS.us as there's lots more good info there!

  continue reading

641 episodes

Artwork
iconShare
 
Manage episode 229816202 series 1288763
Content provided by Brian Johnson. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Brian Johnson or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://player.fm/legal.

Buckle up! This is one of my favorite episodes.

Today I'm kicking off a two-part series that walks you through a narrative of a recent internal pentest I worked on. I was able to get to Domain Admin status and see the "crown jewels" data, so I thought this would be a fun and informative narrative to share. Below are some highlights of topics/tools/techniques discussed:

Building a pentest dropbox

The timing is perfect - my pal Paul (from Project7) and Dan (from PlexTrac) have a two-part Webinar series on building your own $500 DIY Pentest Lab, but the skills learned in the Webinars translate perfectly into making a pentest dropbox. Head to our webinars page for more info.

Securing a pentest dropbox

What I did with my Intel NUC pentest dropbox is build a few VMs as follows:

  • Win 10 pro management box with Bitlocker drive encryption and Splashtop (not a sponsor) which I like because it offers 2FA and an additional per-machine password/PIN. I think I spent $100/year for it.

  • Kali attack box with an encrypted drive (Kali makes this easy by offering you this option when you first install the OS).

Scoping/approaching a pentest

From what I can gather, there are (at least) two popular schools of thought as it relates to approaching a pentest:

  • From the perimeter - where you do a lot of OSINT, phish key users, gain initial access, and then find a path to privilege from there.

  • Assume compromise - assume that eventually someone will click a phishing link and give bad guys a foothold on the network, so you have the pentester bring in a Kali box, plug it into the network, and the test begins from that point.

Pentest narrative

For one of the tests I worked on, here were some successes and challenges I had along the way:

Check out the show notes at 7MS.us as there's lots more good info there!

  continue reading

641 episodes

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