Shouldn't I get the contact in a segment in this situation?

Your software
My Mautic version is: v4.1.0

  1. I have a user with tag “catching-up”:

image

  1. I have a segment with a filter sayin to “include” cathing-up as a tag:

  1. But the segment does not get the user in:

Am I doing something wrong?

Often, when a segment misbehaves, its usually because

  • U have removed that contact from the segment before manually, meaning they cant be added back by a filter (look at the contact history for clues)
  • There is an automation somewhere that is removing the person from the segment.
  • Something is wrong with how you have set up filters for the segment. (they look correct in your screen grab)