Office 365: Retention Policies: Why would an email show both "expired" and that it will expire tomorrow?

Have you set Retention Policy Tag for that sub-folder?

Can you post the screen on how did you set your Retention Policy Tag?

What do you see in OWA?

please see below article for info regarding the retention age calculation.

https://technet.microsoft.com/en-us/library/bb430780(v=exchg.160).aspx

The items are moved only after the MFA (re)processes the mailbox, thus they can stay in a "expired" configuration for a while. In the case of O365, it's a 7-day workload cycle!

Usually you can give it a push via Start-ManagedFolderAssistant. You cannot abuse this cmdlet however, as you will get throttled eventually.

If your idea is to delete items every day (judging by the other threads), EWS remains the best option. Here's a detailed post on the subject: http://samspoerle.com/exchange-online-managed-folder-assistant-and-the-7-day-limit/

Vasil they have chosen to delete every 90 days.  I am just testing with "1-day" to expedite the testing process.

Here is the code I used to create the RPTs and DPT

<#
CSV should look like this:

DefaultFolder
Clutter
DeletedItems
Drafts
Inbox
JunkEmail
Journal
Outbox
SentItems
RssSubscriptions
SyncIssues
ConversationHistory

#>

$TheCSV             = Import-Csv ./defaultfolders.csv
$RetentionPolicy    = "DeleteAllONEDay"
$DefaultPolicyTag   = "DPT_ALL"
$prefix             = "RPT_"
New-RetentionPolicy -name $RetentionPolicy
New-RetentionPolicyTag -Name $DefaultPolicyTag -Type "all" -AgeLimitForRetention 1 -RetentionAction 'PermanentlyDelete' -RetentionEnabled $True
$TagList = (Get-RetentionPolicy $RetentionPolicy).RetentionPolicyTagLinks
$TagList.Add((Get-RetentionPolicyTag $DefaultPolicyTag).DistinguishedName)
Set-RetentionPolicy $RetentionPolicy -RetentionPolicyTagLinks $TagList

foreach ($row in $TheCSV)
    {
    $df      = $row.defaultfolder
    $tag     = $prefix + $df
    New-RetentionPolicyTag -Name $tag -Type $df -AgeLimitForRetention 1 -RetentionAction 'PermanentlyDelete' -RetentionEnabled $True
    $TagList = (Get-RetentionPolicy $RetentionPolicy).RetentionPolicyTagLinks
    $TagList.Add((Get-RetentionPolicyTag $tag).DistinguishedName)
    Set-RetentionPolicy $RetentionPolicy -RetentionPolicyTagLinks $TagList
    }

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I planned on having a script run Start-ManagedFolderAssistant -Identity TestUser01 once a day through this testing process (and recommended for production)

Since the request is a bit more "normal", this time (90 days), I was going to suggest Retention Policies.  Thoughts?

Here is what I see this morning.  I just ran Start-ManagedFolderAssistant this morning (how can I tell if I am being throttled?). I did run it numerous times 6 hours ago but will refrain from running it again today.

Vasil, I read that article and what you are saying makes even more sense now.  So, do i need to use the EWS script if they want retention policies to delete all email older than 90 days?  It seems the main problem they were having was with throttling .. as it was regarding them wanting to delete everyday.
In my case the user wants to delete every email older than 90 days.  will the original script you reference do that in every single folder? Will it ignore calendar, contacts, notes and tasks as this client is requesting?

Are retention policies just not reliable for legal requirements?

I suppose to bring it back to my original question (and the last image I posted above).... Why do I have an email (that I moved from the inbox) that says "This item is expired" AND it says "Expires 2/28/2017" which is today?


Update: okay I sent an email to the mailbox and then moved it to the subfolder and this is what I see... is this normal?

Okay I need to research why my DPT is not being applied to non default folders.  

Default policy tag (DPT)
Automatically to entire mailbox
A DPT applies to untagged items, which are mailbox items that don’t have a retention tag applied directly or by inheritance from the folder.