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Would seem like an environment problem.
Windows services are started in a threaded manner. Thus if if service A depends on service B then service A might be started before B. That is normally solved with a dependency list as part of the service (part of the install.)
Other than that maybe a permissions problem whch impacts how soon something is ready to be used.
Thanks jschell and I would keep on digging the problem. One clarification: the exception "no printer connection...." was our customized handler message and not from java.