I've tried most of the solutions I've found so far still to no avail. I have a 29" widescreen Dell monitor running Ubuntu 18.04.4. First I went into display settings and attempted to switch to portrait mode, it logged me out, I logged back in, nothing changed. I tried landscape flipped and it worked just fine.
Next, I tried using various
xrandr commands (see below)
xrandr --output HDMI-1 --rotate right xrandr -o right
If needed I can get any output log, I just don't know which one's you all may need to see. I think the weirdest part of the problem is that landscape works in both ways, but portrait doesn't work in either direction. Thanks in advance for any help :)