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I have existing Jenkins (2.90) jobs that are taking up disk space. When I enable the "Discard Old Builds" option I don't see any cleanup going on in the folder on the builds older than 7 days.

When does Jenkins do this cleanup? Or does it only apply for new builds after I apply the setting?

Jenkins discard build option

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Per the Jenkins documentation:

Cleanup per project/job is performed after that job runs.

As of v2.221, cleanup will also periodically run using the new Global Build Discarders (even if a job has not recently been run).

Source.

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