Step Backward Not Always Working with Brush Tool

I'm usually painting in photoshop and I undo a lot using the Opt+Cmd+Z shortcut. It works about 4/5 times I do it, but sometimes it just stops working. I either need to switch to a different tool, so just make a random brush stroke on the canvas and then it will start working again. Does anyone have a fix for this?

I'm using Photoshop CC on Mac OSX. The problem I'm having is not the inability to step backwards--I can get it to work by making a random brush stroke and then it will work again--but since it happens after every four or five "step backwards" commands it is really slowing my workflow. I'm constantly redoing lines multiple times in a few seconds when I'm drawing and it's really getting annoying.

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