I don't recall a more annoying install package than Bitdefender IS 2016. I had the 2015 version but kept getting annoying "Upgrade to 2016 at a Discount" notices so I had some time to spare and did that.

Once I paid ($30) and downloaded the upgrade I tried to install it and was told it was in violation of group policies. I knew that this was the Cryptolocker settings I had set but not which one. Since it was most likely a self extracting zip, I changed the EXE to ZIP and opened it up and extracted it myself. But the Install.exe it contained proceeded to download more files which once again were blocked by security policies.

So, I removed the security policies and reran the original install. Once again it downloaded files then told me I had to first uninstall the prior version. WTF? It can't do that itself? So I uninstalled the prior version and then had to rerun the installer whereupon it proceeded to download files, yet again!

Then, it told me I had to reboot before it could install. WTF? It couldn't have told me that before? So I rebooted and this time it actually installed. But I'm not sure if it kept my old profiles or not since when I uninstalled the prior version it kept asking why I was removing it and what my intentions were - rather reminded me of HAL talking to Dave, "Why are you doing this Dave?..."

I've now got to put the security policies back and check to see if the AV kept my old settings of if I'm going to have to do those all over again. I'm not a happy camper.