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Follow the ESRI Tutorial on Getting Data for Arcpad

Important Options to Use

1. In the Select Output Options dialog box, under "Where do you want this folder to be stored?", be sure to save the folder to the ActiveSync folder in MyDocuments.  It will look something like this: "I:\kwhite2\My Documents\Geo4939435713 My Documents"
2.  
3. In the Select Deployment Options dialog box, check the box next to the "Create ready to deploy .CAB file containing the ArcPad data."  If the GPS unit is connected to the computer and turned on, checking this box will result in the immediate deployment of the Map Project and its data to the GPS unit.
4. If the operation is successful (no errors detected during the Validation process), and  the GPS unit is on and attached to the computer you will be asked if you want to deploy the data immediately.  Click yes.

Here's the actual tutorial:

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