it has the quirk that I can't make a good .bat file. I have to run cgminer alone then enter a pool. pretty sure that is something to do with vmware fusion shell.
This might be VM performance lag; I would suggest adding:
timeout 5
between each step in the bat file. This will cause a pause of 5 seconds between each step. If its VM performance lag thats the problem this should solve it. Maybe if your mac is old you will need 10 seconds.
cgminer.exe -o stratum+tcp://solo.ckpool.org:3333 -u 1JiWuyX94wrCr7JhkAn7x5qNMCEef1KhqX.philipma1957sticks