If you are using a TBDML with the 908JB8 and a 6MHz crystal, you are limited to debugging a device with a target crystal frequency of around 16MHz (has worked up to 19.5MHz).
If you use the 908JB16 with a 12MHz crytal, you will be able to debug devices with a target crystal freq of about 33Mhz.
Above those freqs you will loose communication with the hardware, therefore no programming or debugging.