I am seeing a problem with custom context commands in our custom connector that is also reproducible with the sample FTP connector shipped with the SDK. I am using Adobe Drive 220.127.116.11 on Mac OS X 10.8.2
For my test I am connecting to a FTP server and attempting to run the "File Properties" command from a file's Adobe Drive menu in Finder. When I first start Drive and connect, the command works and the "File Properties" dialog appears as expected. However, if I disconnect, reconnect, then browse back to the file and attempt the command again, the File Properties dialog does not appear. The Finder window does kind of "grey out" as if another dialog is about to be shown, but it never is. I don't see any kind of error messages in the CS5ServiceManager logs.
If I disconnect, close Drive, kill the AdobeDriveCS5 and CS5ServiceManager processes with Activity Monitor, and then restart Drive and reconnect, the custom commands work again.
Has anyone else experienced these kinds of problems with custom commands on Mac OS after a disconnect/reconnect cycle?