Shuffle Mode Won't Turn Off

Just a brief update on this situation. The problem in principle is still present but every once in a while shuffle mode does turn off. The UI is quite confusing in this area. At the top of my song list I see the "shuffle" icon (two arrows crossing over each other), the label "Shuffle all" is next to it along with a song counter. This is obviously a command link because it highlights when my mouse hovers over it.

On the bottom where my playback controls are located, there is the same "shuffle" icon. It also highlights when I hover over it but it also gives me a tooltip saying "Shuffle on" or "Shuffle off". This is clearly a toggle command, but this does not ever seem to control whether or not shuffling on. Clicking on this toggle just randomizes my playlist again and start to play in the new shuffle order.