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As far as I know, with the stock messaging app (or handcent, or Go), you are always using your cellular data to send/receive. That is why I asked about the app. So the delays/failures are probably related to the network, not your phone. I have had problems sending picture messages sometimes.

The only way to send over WiFi only is to use an app like Tango, as far as I know.

good luck
 
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I watch my signal bar when they are sent and it never switches out of WiFi and they get sent. ???

That is arbitrary information. A text message takes a split second. A pic message takes longer, but still seeing the phone switch out of WiFi usually doesn't happen. I've watched also to see what's going on as well. Sometimes with a pic message, you will see flashes of activity over the cell signal without switching off wifi.

And like I said a regular text message takes but a split second. Ever notice that you can get texts in fringe areas where you can't really make a call?

But basically I don't have the answer for you, I'm just saying it has nothing to do with your WiFi connection as they do not go over your WiFi.
 
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