Saw a previous post on this by Chad, but there was no solution listed.In Managed Default Folders I created a new Managed Content Setting for Deleted Items. Name : Remove messages older than 30 daysLength of retention : 30Retention period starts - When item is moved to folder:Action to take at the end of the retention period : permanently deleteIn Managed Folder Mailbox Policies I created a policy Name : Trash Deletion PolicyManaged folders that are associated with this policy : Deleted ItemsOn 2 mailboxes, Managed folder mailbox policy is enabled and set to 'Trash Deletion Policy'In Outlook the oldest message in the Deleted Items folder is dated March 21, 2008. (More than 6 months old)I scheduled the task to run 10:00 PM every nightIn the Application Event Log I see : "Service MSExchangeMailboxAssistants. Managed Folder Mailbox Assistant for database First Storage Group/Mailbox Database (629ca542-bba8-447a-815a-270726034819) is entering a scheduled time window. There are 70 mailboxes to process.Later in the log I see: "Service MSExchangeMailboxAssistants. Managed Folder Mailbox Assistant for database First Storage Group/Mailbox Database (629ca542-bba8-447a-815a-270726034819) is exiting a scheduled time window. 70 out of 70 mailboxes were successfully processed. 0 mailboxes were skipped due to errors. 0 mailboxes were processed separately. 0 mailboxes were not processed due to insufficient time."I check the Deleted Items folder in Outlook but the oldest message is still March 21, 2008.Any Ideas on what could be wrong?Thanks

Clarify: Messaging Records Management (MRM) not works When When item is moved to the folder is chosen, which means the retention will start after users items being moved to Deleted items folder, does user moved oldest mail to Deleted items folder before 30 days? In order to test the function of MRM, could you set the retention time to 1 day? 1. Remove the policy from users 2. Change the day setting 3. Apply policy to a test user 4. Then delete a testing mail to Deleted items folder, and check the result after 24 hours Notes: We can manually start Mailbox Assistant after 24 hours, run "Start-ManagedFolderAssistant mailbox testuser@domain.com" in the EMS

Hi, Net Admin, I assume your question has been answered, and I'd like to change the status to "Marked as answer", please feel free to post here if you have any update

I had to finish up some testing, but it appears to be working now. I had found something on Microsoft's site that said if I applied a policy to 'Entire Mailbox' it would apply to all folders unless specified differently on a folder. I had a 6 month deletion policy set on 'Entire Mailbox' that never worked, but when I removed that policy and applied a new 6 month deletion policy on the 'inbox' default folder, both the 30 trash and 180 day inbox deletion policies began working. Go figure....