I was shocked to see "letter of the law" enforcement at PDX in the Horizon A gate area (E-75 flight). Right before boarding the gate agent looked at people waiting to get on - and the "trap" was set. She'd walk up to people and say "let's make sure you won't have any problems with your carry on size" Then the bag would be placed into the sizer (and typically flunk) - next step was to demand $25 dollars to check it. People who were very close to fitting complained - demanding a re-measure, warning notice, etc. But the gate agent judge would hear none of it - $25 please.
I understand the complaints about big overhead bags slowing down boarding. Given the reaction and blow back I think Alaska would have been better served by announcing strict enforcement of current size rules rather than shrinking the maximum size (and somehow saying it was for the benefit of passengers). They look like a legacy airline at its worst with this move.