So I have all my settings "on" in my conversations section (attached) - Conversekit allows me to select a file to share but it is not sent to the other chat user...thoughts?
Actually that was known issue, if the system detected message content is empty, it will not allow to send out even you have upload 1 of the attachment file.
In next version, we will populate a warning message "Please type a message" if that is empty message.