Just throwing this out there as a discovered solution ( to my problem ) as it may help others.  I can't specifically say if its an Alexa or Kasa issue.

Alexa will not turn on my plugs unless they are the first actions of a routine.

My "good morning" routine initially consisted, of and was working fine with, my prior brand of plugs:

   playing an iheart radio station

   setting my Echo Dot's volume

   turning on plug #1

   turning on plug #2

My "good night" routine consisted of:

  stopping playback

  turning off plug #1

  turning off plug #2

My "good morning" fails to turn on either plug ( or both when tried as a group ) as listed above.  If I rearrange the action order so that the plugs are first, the routine works fine.  After verifying correct function, moving them back down the order will fail to turn them on yet again.  The failure happens when told to toggle them on, or explicitly to turn them on.  Toggling them off works without regard to action order.

The "good night" works without regard to action order.