Let’s get this community popping with some useful information. Reddit’s sysadmin subreddit seemed like a place of complainers, I look forward to having actual productive conversation in this community.
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Big fan of the IODD. I love having a ton of bootable images ready to go on a single drive. I mostly use it to boot disk wiping software, disk imaging software, and malware removal tools but it also serves as my main flash drive with common software and scripts I use a lot.
I’m a big fan of RoyalTS for managing my RDP / SSH access to servers. Keepass for password storage.
Notepad++ is one of the best applications ever made