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Monitoring data usage
Most users will not be lucky enough to have a grandfathered unlimited data plan and therefore will want to monitor their data usage. Luckily there are a number of ways to do this. One is to dial *DATA# (*3282#) then [Send]. You'll get a text message back from AT&T with your current stats. Don't worry: these text messages are free.
Another option is the useful AT&T myWireless app. Search for it in the Marketplace. Once you've got it set up, you can click on the [Usage] button, then the Data tab. You'll find lots of other good info and tools with this app, so it's highly-recommended.
For automatic moment-to-moment tracking of your usage, the free app 3G Watchdog is recommended. This app takes some configuring but has lots of handy features. You set it to what kind of plan you have, and it can provide warnings when you get too close to your limit. It also has a really useful widget you can put right on your home screen that will show you your current stats.
While it'd be immensely useful to be able to track usage by application, currently there are no programs that will do this on the Captivate. The two apps that provide this feature, TrafficInfo and TrafficStats, are both for Android 2.2 only, so if you haven't installed the 2.2 update yet you will need to do so.
Why does my phone do huge data transfers at night? I have wifi at home!
The default configuration for the Captivate is to disable the wifi when the phone goes to "sleep" in order to save battery power. An unfortunate side-effect of this is that when you're in an area with wifi (like at home), any background apps doing data transfers will be forced to switch to EDGE/3G which will then count against your data plan. A common time for this to happen is at night.
All users are advised to make the following settings change: Menu -> Settings -> Wireless and network -> Wifi settings -> Menu -> Advanced -> Wi-Fi sleep policy -> Never.