14.04, Dell Vostro 3546
I went to Settings - Displays and set Rotation to Counterclockwise. That worked great, but after rebooting my system and logging in, nothing loaded. I got the normal mouse cursor on a black background, then the cursor rotated to Counterclockwise, but nothing else happened (for however long i waited.) There was just the rotated cursor on a black background. No launcher, no wallpaper, no keyboard shortcuts working, no panel. Forcing shutdown with the hardware button and booting into recovery let me boot without Counterclockwise (or the resulting bug) kicking in, but in that recovery mode it's not possible to disable Counterclockwise again, because that setting is not adjustable in recovery mode. So when I then reboot normally again, the same lonely, rotated cursor appears again.
Eventually I just overwrote my whole Ubuntu partition with a Clonezilla image from a few days back. Now, if I want to continue using Counterclockwise view (which I do,) I have to switch it back to Normal every time I want to power down or reboot, and then switch it back to Counterclockwise again upon boot. I also have to keep regular Timeshift/Clonezilla backups in case my computer crashes or inadvertently powers down while in Counterclockwise mode. This is actually what I am doing at the moment, but it's hardly handy for a native function in the standard build.