Can't send photo to one person sometimes

alex86

    Hello after updating to Android 9 sometimes I can not send a photo in a text to one person only without restarting phone. It starts sending and then says message not sent try again. Trying again produced same result. I can however send the same image to anyone else without doing anything.  But to get it to send to this person I have to restart my device. They are also on tmo with a galaxy note9.

     

    Lg v40

    Lg messenger

    Gboard

    Purchased from tmo

    Full signal 4g lte

     

    Have tried deleting the conversation, restoring apn to default, and clearing cache. The only thing that seems to work is restarting my device. This however is a poor solution and never use to happen. Any ideas?

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