Sounds weird, Cigar Box rarely crashes in that regard. But it does take time for the cigar box initial connectivity to the site and sim. If you don't wait for the ding that it is fully connected then it might have an issue.
You can try to re-file. (That is if you saved your pirep). Go to the Main tab > File Saved Pirep then a saved pireps folder will open - select the pirep for that flight. If not saved, then no. It's a re-fly or Manual pirep.
Will manually put in a pirep for Tour MFC0011, leg 6: HWI TO OOH (which will have no pirep record), but it will set you up to fly leg 7- From PAOH Hoonah to PEC Pelican.
So when you get Cigar Box started up, wait for it to fully connect before trying to select it's functions.
Norm