Hmmm,
1. Virus scanner might be stopping cigar box. In your virus scanner settings add an exception rule for that folder or at least the kaCars*.exe file.)
2. Confirm that your FSUIPC is installed working. (Cigar Box requires FSUIPC active to be able to connect to your sim.)
3. Run cigar box as admin.
If this doesn't work, uninstall Cigar Box, then turn off your antivirus first, then reinstall cigar box.(And in your virus scanner settings add an exception rule for that folder or at least the kaCars*.exe file.)