It should be updated after each step - it is for me. Can you try restarting Devkit and trying again? There is a bug where if you select 10khz mode with the vector display plugin loaded, things go very wrong from that point, which might explain it. Let me know? :)

To be clear : the stack is properly updated on push, pop & jsr. It is not however (confirmed on three win7 installs, including one vm) with this code :
set x, 4
set a, 7
set push, x
shr peek, 1 ; <= stack view not updated
mul x, a
add x, pop ; x=ax x/2

yeah, I read my first message again : it was not clear at all, sorry. The problem is when you change the content of already pushed values (that is the temporary working variables or non-static function local variables).