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Hacking/attack experiences...
I'm, for obvious reasons, only going to talk about the attacks I went through and the *legal* ones I did 😅 😜

Let's first get some things clear/funny facts:
I've been doing offensive security since I was 14-15. Defensive since the age of 16-17. I'm getting close to 23 now, for the record.

First system ever hacked (metasploit exploit): Windows XP.
(To be clear, at home through a pentesting environment, all legal)
Easiest system ever hacked: Windows XP yet again.

Time it took me to crack/hack into today's OS's (remote + local exploits, don't remember which ones I used by the way):
Windows: XP - five seconds (damn, those metasploit exploits are powerful)
Windows Vista: Few minutes.
Windows 7: Few minutes.
Windows 10: Few minutes.
OSX (in general): 1 Hour (finding a good exploit took some time, got to root level easily aftewards. No, I do not remember how/what exactly, it's years and years ago)
Linux (Ubuntu): A month approx. Ended up using a Java applet through Firefox when that was still a thing. Literally had to click it manually xD
Linux: (RHEL based systems): Still not exploited, SELinux is powerful, motherfucker.

Keep in mind that I had a great pentesting setup back then 😊. I don't have nor do that anymore since I love defensive security more nowadays and simply don't have the time anymore.

Dealing with attacks and getting hacked.

Keep in mind that I manage around 20 servers (including vps's and dedi's) so I get the usual amount of ssh brute force attacks (thanks for keeping me safe, CSF!) which is about 40-50K every hour. Those ip's automatically get blocked after three failed attempts within 5 minutes. No root login allowed + rsa key login with freaking strong passwords/passphrases.

linu.xxx/much-security.nl - All kinds of attacks, application attacks, brute force, DDoS sometimes but that is also mostly mitigated at provider level, to name a few. So, except for my own tests and a few ddos's on both those domains, nothing really threatening. (as in, nothing seems to have fucked anything up yet)

How did I discover that two of my servers were hacked through brute forcers while no brute force protection was in place yet? installed a barebones ubuntu server onto both. They only come with system-default applications. Tried installing Nginx next day, port 80 was already in use. I always run 'pidof apache2' to make sure it isn't running and thought I'd run that for fun while I knew I didn't install it and it didn't come with the distro. It was actually running. Checked the auth logs and saw succesful root logins - fuck me - reinstalled the servers and installed Fail2Ban. It bans any ip address which had three failed ssh logins within 5 minutes:
Enabled Fail2Ban -> checked iptables (iptables -L) literally two seconds later: 100+ banned ip addresses - holy fuck, no wonder I got hacked!

One other kind/type of attack I get regularly but if it doesn't get much worse, I'll deal with that :)

Dealing with different kinds of attacks:

Web app attacks: extensively testing everything for security vulns before releasing it into the open.
Network attacks: Nginx rate limiting/CSF rate limiting against SYN DDoS attacks for example.
System attacks: Anti brute force software (Fail2Ban or CSF), anti rootkit software, AppArmor or (which I prefer) SELinux which actually catches quite some web app attacks as well and REGULARLY UPDATING THE SERVERS/SOFTWARE.

So yah, hereby :P