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Penetration testing using AI bots

Did I just see an OpenAI example?

         

SumGuy

1:43 am on Aug 2, 2026 (gmt 0)

5+ Year Member Top Contributors Of The Month



You've heard recently about penetration testing using AI's in sand boxes that somehow escape? Read on and tell me that's not what I've just seen from OpenAI.

Today, twice, I got a few dozen hits from 172.213.2.180. User-agent is:

Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/120.0.0.0 Safari/537.36

My server flags "Chrome/120" as unwanted bot or residential VPN/proxy and serves "you are a bot" file. In most cases I don't know what file was being requested, but for a few of them I know the target path:

/contact-form-7/includes/js/jquery-ui/themes/smoothness/
/content-management/
/core-plugin/
/core-stab/
/core/

None of which I have on my server.

I have seen, just within the past few days, instances from other IP ranges that to me are clearly bot-originated penetration attempts. These IP ranges are not associated to the other main-line AI bots (or regular search bots) - they are IP's associated with crack-pot hosters I have never had hits from before (and as usual I block them when I see them).

The entire 172.213.0.0/16 has been a clean CIDR since I started to see hits from it last year in June and they've all been OpenAI on a few specific /24's.

But the hits I'm seeing today from 172.213.2.180 are far too close to the openai bot's Microsoft IP range (172.213.21.0/24) to be a coincidence.

Also today, the first openai hit from 9.anything (9.129.58.94 - also microsoft). Hits from 9.anything are super rare (5) with 1 in 2025 and 4 this year. I wonder what's going on recently with 9.0.0.0/8.