Hi,
Sorry about the confusion. In order to troubleshoot this please open Device Manager, locate the Olimex device and locate its Hardware ID (via Properties window). Then please check the USB VID and PID shown in the Hardware ID against the IDs specified in the .cfg file. Can you confirm that the IDs match?
If yes, which driver is installed for the Olimex interface?
In order to use automatic connection testing, please update to VisualGDB 5.3 and install the latest ESP8266 toolchain. It includes an updated debug mechanism that detects and fixes most of the driver problems automatically.