Always program drag brake through the ESC, if it's an option (some ESCs don't have such option).

Also, when possible, always program an ESC though an app on a phone/tablet or computer. While the hardware programming "boxes" agree good for on-the-fly/at-the-track programming, they don't provide the finer options that software provides. A perfect example would be drag brake - with a "box", you're typically limited to 10% increases/decreases, whereas you'll have 1% increase/decrease from the software.