Updating my Sony Xperia phone (via PC) still tops my regrets chart. The phone just refused to work after the Software Update and there was just nothing I could do about it. It is always on my table to remind me that I'm no software guru and therefore should always consult the experts just in case I must update a device.
Something always stops working properly when you update, it's inevitable! Mind you, Sony Xperia devices seem to be the worst for this, both me and my OH have had numerous issues with updating these phones. These days, I leave updates to the last possible point and will even do without the latest features on my apps if it means I can avoid doing this.
Yes. Very much so. When I was forced to update my drivers for my graphics tablet, at first, it seemed fine--but then, it was not to be. The new drivers were far glitchier, and I sometimes needed to reboot my laptop when they ceased to function and pressure sensitivity was no more. However, the drivers I have now (as that was a while ago) for the same tablet do function properly, and seem to work well--so I think whatever was going wrong got fixed. I avoided upgrading my computer to Windows 8 after I saw the interface, and tried to navigate it--multiple times!--on laptops that belonged to my friends. I found the interface to be terrible; while I suppose that you would get used to it after a while, I'm fond of my actual start menu and taskbar, so I'm not going to be updating to Windows 8 any time soon.
Not a device but a program. I recently updated uTorrent and it installed the program named EpicScale. It was a program that used your computer resources to generate bitcoins to third-party firms. It was overall a big scam. Since then I deleted uTorrent and installed another software - and I'm never going back.