I've run into the exact same issue with identical system specs.

I have Due and Flagged buttons in the toolbar. When in Planning mode, I expect both of these to provide a filtered view of only due or flagged items, staying in Planning mode. Instead it switches to what appears to be the last selected context in Context mode.

whpalmer4: You think that's the intended behavior? Doesn't make much sense to me. I guess I could just create a new perspective, but is there any way to add them to the toolbar?