Hi Oliver,
The 'Max number of backup' setting has nothing to do with archive older backups. Archives will be created if the the feature is enabled and more than one FULL backup is done. The older FULL backups will be archived, the last one will be not archived because this will simplifying the mechanism with DIFF backups.

I tried to reproduce your issue on Windows 7 and Kubuntu 12.04, but everything works as expected. In both cases I started jenkins with the build-in winstone servlet container, but on my productive server (Ubuntu Server 12.04) it works also as expected on a Tomcat 7.
So please double check your access rights for the backup directory. The user whose running jenkins need write access for the backup directory and of course for al the backups. If you have older backups, done with an different user it midge be that you are not able to access it for archiving or deleting it.

Please reopen this issue if you feel this is still a problem, and more information about your settings and environment.

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