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Actually, the answer is no, technically, an iPhone does not have to be jailbroken to work with T-Mobile. It has to be unlocked. You can unlock it via jailbroken apps, or by means of hardware, as in a piggyback SIM. You do not need to jailbreak a phone to unlock it with a piggyback SIM.
 
The answer is no. I have an iPhone 3G, never been jailbroken, and I am using T-mobile. It's an unlocked phone from overseas (updates as per usual).
 
does every t-mobile phone have a sim card? So if i signed up for t-mobile service i could just get the cheapest phone and take the sim out of it and put it into my iphone?
 
does every t-mobile phone have a sim card? So if i signed up for t-mobile service i could just get the cheapest phone and take the sim out of it and put it into my iphone?
You could, or you might be able to just get a new SIM card with activation without buying a phone.
 
you don't need to buy a phone to get the sim card. I switched from sprint to Tmobile to use an iphone and I have never had a sim card before. Tmobile sold me a new sim and set up my phone. You don't have to be sneaky about using the iphone on Tmobile. They will set you up. They even provide technical support even though it isn't one of their phones.
 
Depends

1.1.4 and below no 2.0 above yes use ziphone and just select unlock on 1.x.x on 2.0 upgrade to 2.2.1 jailbreak downgrade baseband in cydia then use yellowsnow also in cydia. You can always downgrade to 1.1.4!
 
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