We are having a problem with a retention policy being applied.  We have a (2) server Exchange 2013 environment, both machines CAS/Mailbox roles with all DBs set up in single DAG between them.  It is a single forest, single domain, single AD site with approximately 200 mailboxes.

The retention policy contains (1) tag.  All mailboxes are configured to use this policy.

The retention policy tag settings are as follows:

PS C:\Windows\system32> Get-RetentionPolicytag "our deleted items"|fl

MessageClassDisplayName               : All Mailbox Content
MessageClass                          : *
Description                           : Managed Content Settings
RetentionEnabled                      : True
RetentionAction                       : PermanentlyDelete
AgeLimitForRetention                  : 1.00:00:00
MoveToDestinationFolder               : 
TriggerForRetention                   : WhenDelivered
MessageFormatForJournaling            : UseTnef
JournalingEnabled                     : False
AddressForJournaling                  : 
LabelForJournaling                    : 
Type                                  : DeletedItems
IsDefaultAutoGroupPolicyTag           : False
IsDefaultModeratedRecipientsPolicyTag : False
SystemTag                             : False
LocalizedRetentionPolicyTagName       : {}
Comment                               : 
RetentionId                           : f8aaef16-e1f0-436a-8e55-e83676e4792e
LocalizedComment                      : {}
MustDisplayCommentEnabled             : False
LegacyManagedFolder                   : 
AdminDisplayName                      : 
ExchangeVersion                       : 1.0 (14.0.100.0)
Name                                  : Our Deleted Items
Identity                              : Our Deleted Items
Guid                                  : f8aaef16-e1f0-436a-8e55-e83676e4792e
ObjectCategory                        : OURNAME.ORG/Configuration/Schema/ms-Exch-ELC-Folder
ObjectClass                           : {top, msExchELCFolder}
WhenChanged                           : 10/29/2014 1:47:45 PM
WhenCreated                           : 12/16/2011 10:06:35 AM
WhenChangedUTC                        : 10/29/2014 8:47:45 PM
WhenCreatedUTC                        : 12/16/2011 6:06:35 PM
OrganizationId                        : 
OriginatingServer                     : DC02.OURNAME.ORG
IsValid                               : True
ObjectState                           : Unchanged

The problem is that our policy runs once a day by default, but does not permanently delete the DELETED ITEMS content.

There are no holds.  When I run "Get-Mailboxsearch" nothing is returned.

If I run "Get-MailboxServer | Format-List *WorkCycle*" it shows for both servers

CalendarRepairWorkCycle                                : 1.00:00:00
CalendarRepairWorkCycleCheckpoint                      : 1.00:00:00
SharingPolicyWorkCycle                                 : 1.00:00:00
SharingPolicyWorkCycleCheckpoint                       : 1.00:00:00
SharingSyncWorkCycle                                   : 03:00:00
SharingSyncWorkCycleCheckpoint                         : 03:00:00
PublicFolderWorkCycle                                  : 1.00:00:00
PublicFolderWorkCycleCheckpoint                        : 1.00:00:00
SiteMailboxWorkCycle                                   : 06:00:00
SiteMailboxWorkCycleCheckpoint                         : 06:00:00
ManagedFolderWorkCycle                                 : 1.00:00:00
ManagedFolderWorkCycleCheckpoint                       : 1.00:00:00
MailboxAssociationReplicationWorkCycle                 : 1.00:00:00
MailboxAssociationReplicationWorkCycleCheckpoint       : 1.00:00:00
GroupMailboxWorkCycle                                  : 1.00:00:00
GroupMailboxWorkCycleCheckpoint                        : 1.00:00:00
TopNWorkCycle                                          : 7.00:00:00
TopNWorkCycleCheckpoint                                : 1.00:00:00
UMReportingWorkCycle                                   : 1.00:00:00
UMReportingWorkCycleCheckpoint                         : 1.00:00:00
InferenceTrainingWorkCycle                             : 
InferenceTrainingWorkCycleCheckpoint                   : 
DirectoryProcessorWorkCycle                            : 1.00:00:00
DirectoryProcessorWorkCycleCheckpoint                  : 1.00:00:00
OABGeneratorWorkCycle                                  : 08:00:00
OABGeneratorWorkCycleCheckpoint                        : 01:00:00
InferenceDataCollectionWorkCycle                       : 
InferenceDataCollectionWorkCycleCheckpoint             : 
PeopleRelevanceWorkCycle                               : 1.00:00:00
PeopleRelevanceWorkCycleCheckpoint                     : 1.00:00:00
SharePointSignalStoreWorkCycle                         : 7.00:00:00
SharePointSignalStoreWorkCycleCheckpoint               : 1.00:00:00
PeopleCentricTriageWorkCycle                           : 1.00:00:00
PeopleCentricTriageWorkCycleCheckpoint                 : 12:00:00
MailboxProcessorWorkCycle                              : 1.00:00:00
StoreDsMaintenanceWorkCycle                            : 00:15:00
StoreDsMaintenanceWorkCycleCheckpoint                  : 00:05:00
StoreIntegrityCheckWorkCycle                           : 00:15:00
StoreIntegrityCheckWorkCycleCheckpoint                 : 00:05:00
StoreMaintenanceWorkCycle                              : 00:15:00
StoreMaintenanceWorkCycleCheckpoint                    : 00:05:00
StoreScheduledIntegrityCheckWorkCycle                  : 00:15:00
StoreScheduledIntegrityCheckWorkCycleCheckpoint        : 00:05:00
StoreUrgentMaintenanceWorkCycle                        : 00:15:00
StoreUrgentMaintenanceWorkCycleCheckpoint              : 00:05:00
JunkEmailOptionsCommitterWorkCycle                     : 00:15:00
ProbeTimeBasedAssistantWorkCycle                       : 00:15:00
ProbeTimeBasedAssistantWorkCycleCheckpoint             : 00:05:00
SearchIndexRepairTimeBasedAssistantWorkCycle           : 30.00:00:00
SearchIndexRepairTimeBasedAssistantWorkCycleCheckpoint : 1.00:00:00
DarTaskStoreTimeBasedAssistantWorkCycle                : 00:30:00
DarTaskStoreTimeBasedAssistantWorkCycleCheckpoint      : 00:30:00

If I force the mailbox assistant to run for a single mailbox, e.g. "Get-Mailbox username| Start-ManagedFolderAssistant" I see

Information 9/8/2015 3:23:29 PM MSExchange Assistants 9021 Assistants
Service MSExchangeMailboxAssistants. Managed Folder Mailbox Assistant for database DBLS (0c2cfa96-3e00-4404-aee4-a8984db9fb05) is processing an on-demand request. There are 1 mailboxes to process.

Information 9/8/2015 3:23:29 PM MSExchange Assistants 9022 Assistants
Service MSExchangeMailboxAssistants. Managed Folder Mailbox Assistant for database DBLS (0c2cfa96-3e00-4404-aee4-a8984db9fb05) has finished an on-demand request. 1 out of 1 mailboxes were successfully processed.  0 mailboxes were skipped due to errors. 0 mailboxes were skipped due to failure to open a store session.

If I force it for all mailboxes I get the 9021 and 9022 informational messages I am expecting.  But no one's email is purged.

There seem to be no other errors and the various exchange services are all running correctly.  We have also tried various reboots, etc over several weeks.

Any thoughts/direction?

We added a retention policy tag that deletes the items from the Junk Mail folder after 1 day and it appears to work.

We also deleted the old retention policy and tag and created a new retention tag and policy to delete from the Deleted Items and it does not work.  It seems to be limited to just the Deleted Items folder.

Hi,

The retention tag calculated in Deleted Items folder is different from other default folder. The start date for items in the Deleted Items folder are handled differently. Please confirm whether the item in Deleted Items folder was deleted from a folder that does not have an inherited or implicit retention tag.

https://technet.microsoft.com/en-us/library/bb430780.aspx

Please run the following command to check the retention policy applied to this mailbox:

Get-Mailbox Test1 | fl Identity,*retention*

Additionally, please check the items in OWA or Outlook Online mode and confirm whether the items is expired.

Regards,