Hello @BrianJ557 ,
Since contact engagement is under the "Contact Activity" type for segmentation, and Tags are their own separate type, they will only be able to exist in a segmentation with an AND relationship. OR relationships only work within the same type (i.e. Contact Activity > most engaged OR least engaged).
For more info on creating segments
A potential workaround would be to add the separate segments (one for most engaged, the other for your tag), and add them to a singular list. You can also accomplish this by simply searching for all contacts with the tag, select-all, then add those to the applicable list, if you don't want to make a separate segment for them with that sole criteria.
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William A
Community & Social Media Support
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