Retention Tags - expired items not deleted from Deleted Items

I created a simple Retention Policy Tag to apply to Deleted Items folder, which should "Delete and Allow Recovery" anything that's older than 21 days. I created new Retention Policy and added the Policy Tag I just created. I applied this policy to my mailbox to see how it works, before I roll it out for other users. I ran Start-ManagedFolderAssistance on my mailbox to speed it up.

When I open my Outlook 2010, and look at items inside my Deleted Items folder, I still see all the items that were there going back to early 2010. I know the Retention Policy is being applied to all items, since on any email inside the Deleted Items, I can see "Retention Policy: Deleted Items removed after 21 days (3 weeks)  Expires 11/4/2010 (for an email that was moved there on 10/14/2010). So, the policy is applied, but all the "expired" items are still sitting inside the Deleted Items folder. I click on old emails, and I can see "i" blue circle in the top left and line "This item is expired", but when it's actually going to be deleted?

Any ideas?
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Svet PaperovConnect With a Mentor IT ManagerCommented:
I dont beleive that retention policy pertains to teh actual emails in a Users Physical Deleted Items folder in the Mialbox

But to the Recover Deleted Items Option

To see this locatoin this refferes to select your deleted items folder
Then Select Folder in the Ribbon
Now select Recover Deleted Items

This location is where that retention policy will be getting applied to
Svet PaperovIT ManagerCommented:
I had the same exact behaviour when I first enabled Retention Policy Tags on the Deleted Items folder: the old items (that were there before applying the policy) stayed even if they were far behind the deletion period.

I was never able to find a good explanation of how the retention tags are applied on existing items but I believe the retention count starts from the moment when the tag is applied. That means they will disappear after 21 days, even if it says that they have already expired. At least, that was the case when I configured our server for testing purposes. However, all newly deleted items will be correctly tagged.
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