Copied from this post: http://ithinksharepoint.blogspot.com/2009/03/expiration-policy-timer-job-does-not.html
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The policy is run once a day, however fortunately you can start it manually. Using Central Admin->Operations->Information Management Policy Configuration, I clicked on the Expiration policy link. Then within there clicked "Process Expired Items Now". Looked at the Timer Job Status (Central Admin->Operations->Timer Job Status) and there was no reference of the Expiration Policy.
Looked within Timer Job Definitions (just under the Timer Job Status link) and a timer job had been created called "Expiration Policy (manually initiated)" but it had never been run. Actually neither had the daily "Expiration Policy". I went back to the Information Management Policy Configuration and into the Expiration policy. The "Process Expired Items Now" button was greyed out, to clear this I ended up deleting the "Expiration Policy (manual initiated)" timer job. This enabled the "Process Expired Items Now" button... however nothing.
Other things that I tried included stsadm -o execadmsvcjobs - though nanda.
Then I thought about the fact that the job had never been run and I found this article
http://www.sharepointblogs.com/teameli/archive/2008/10/13/record-center-information-management-policy-jobs-not-running.aspx
Following the instructions sorted the problem...
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