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Text messages connect to existing contacts no matter if they are in a team or agent account and regardless of how long ago they were last texted.

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Jorge Martinez commented
We were told by the Help Desk to request help here.
The reason for that is due to the replies from the contacts being 30 days or older from the last text they were sent, in cases where they reply to old texts like that, the contact is created in the personal account instead of having the text added to the team contact. Apologies for the inconvenience on this! As this is intended behavior, this isn't something we can fix or adjust on the tech support side, instead the best place for this would be to submit this over at our ideas.kw.com site, as that will get the request in front of our product team. They decide on new features, changes and updates to make to Command, so they'd be able to look into changing that behavior moving forward, but once that request is filed, we'll do everything we can to try to help push that along on our side for you as well! I'm sorry we can't do more for this request on our side here but hopefully they make that change so things are easier for you and your team here.