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Text messages send pictures via data connection. Make sure your data is on also. I use Handcent for texting and you can see the data being used to send pictures.
My does same thing on WiFi too. But as soon as I send an attachment to any text message the data signal lights up and sends the message. I'm thinking it might be in the settings of message app. I'll see what I can find. Check yours out too.
Like aarong03 stated, the phone needs a data connection to send MMS messages, even when on WiFi. When you are connected to WiFi, is your Mobile Data toggle set to "Off"? Do you have a Smart Action in place that turns Mobile Data to Off when connected to WiFi?
Glad to hear that! The only silly question is one that is not asked. There are plenty of great people on here that will help you! Don't be afraid to ask questions.