Help Having very odd problems texting a certain contact, looking for advice please.

[sequel]

Hey folks,

I'm a newcomer here. Done a lot of Googling around but my problem is pretty rare and specific so finding similar resolved issues was nearly impossible. I decided to come here and give a shot at asking the pros.

Here's my problem:

I have one contact in my list that I text often. For some reason, I can only send him a new text. When he replies, and I try to reply back, I get a "message unable to send" notification. I then have to delete our conversation thread, and send him a brand new text, which goes through fine every time. Every once in a while, a reply will go through, but it happens so rarely that I don't even bother to try anymore. I've tried completely deleting his contact, adding a +1 before the area code, typing in his number, etc, etc. Here are the specs on my phone:

Motorola Milestone XT270
Android 2.1
Using stock messaging app
His contact is identical to all my others, except his number of course
Never have issues texting anyone else but him
He said no one else has ever complained about this to him and he really doubts it's his phone

Does my phone need flashed back to stock or something?

 

[Frisco]

Hello sequel, and welcome to the forums.

I'd first try just removing him as a contact (from the device as well as your Google/Gmail account online, it that's what you sync with), rebooting the device, then re-entering him as a new contact, to see if that washes out the issue.

 

[sequel]

Hello sequel, and welcome to the forums.

I'd first try just removing him as a contact (from the device as well as your Google/Gmail account online, it that's what you sync with), rebooting the device, then re-entering him as a new contact, to see if that washes out the issue.

I had previously tried deleting his contact and rebooting, but I had not tried removing him from my Gmail. I only had his email address on my Gmail though, not his phone number, but I deleted him anyway. Still no luck. Every time I reply it says "Message not sent" in my notification bar up top, and a little envelope with an exclamation point appears next to the message text. I can click the envelope, and when I do, it pastes the text I typed back into the input field. I then hit send again, and get the same result -- message not sent.

Edit - I also removed Gmail sync entirely so it doesn't interfere with my contacts at all.