Why does my messaging app fail to send in reply to a MMS message?

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When an MMS message arrives (ex.: from "+[phone no]@tmomail.net"), as soon as I send a reply I see the message "switching to MMS", after which anything I send fails to go through, displaying a red caution triangle and shows "Retry" message. The other party does Not receive the message.

If I send a message to the same phone number by itself - i.e., 10-digit number - that Will go through. Also, when I start typing that phone number in, the contact is recognized and it automatically switches to the MMS "tmomail.net" address, which then fails to go through.
 

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