I tried to deploy to a remote debian (etch/testing) server running dropbear instead of openssh. Rake blew up (Vlad impaled it?) with an error such as this:

Writing configuration file to /***/mongrel_cluster.conf.
rake aborted!
execution failed with status 255: ssh www.****.com mongrel_rails cluster::configure -N 2 -p 8000 -e production</pre>

-a 127.0.0.1 -c /****/current -C ****/shared/mongrel_cluster.conf

This was strange because when I checked on the server, all of the tasks were being executed correctly, and dirs and files were created.

I switched to OpenSSH and the problem went away.

It looks like, even if the command executed is successful, dropbear sometimes ignores the return code and exits with 255, which confuses rake. This doesn’t happen with OpenSSH.

It looks as if the problem is with dropbear, as I had the same issue when trying to deploy with capistrano (crapistrano?). So I guess I’m back to plain old openssh…