Yes, I've not tried it myself, but a couple of ideas;
use the UART to check the current firmware version before you upload a new one; see the ATI command for V1.02 or later or the AT+CGMR command for V1.24 or later,
make sure you are powering the shield before you plug in the USB cable and try the update; this is based on the Wiki photograph with the red text never power through it,
check your computer operating system's list of detected USB devices, before and after plugging in, to make sure the shield is detected.
@Azmat wrote about the same product last year if that might help. @Azmat, any ideas?