Office 365 Mailbox User Cannot Delete Mail

One of our users is unable to delete mail from the Deleted items on their 365 mailbox.

In Outlook 2016 it appears to delete the mail, but if you click on to another folder and then back in to deleted it is there again. I have tried this in safe mode, disabled all add ins, .old the OST file and let the profile rebuild, a new email profile on a different machine, and also it will not delete from the OWA. When deleting in the OWA you get the message to say this will be permanently deleted, are you sure? When you click yes the selected mail just stays in deleted.

My guess is it is an issue in the background of the mailbox as we cannot remove from the OWA but I thought I would see if anyone had this before whilst we wait for our host to come back.
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Vasil Michev (MVP)Commented:
Outlook might take some time to perform the operation, especially for large mailboxes, and will also need time to reflect the changes. OWA should perform better in this regard, but might need the occasional refresh. One thing to check for though is the size of the recoverable items subtree, if it's too big it will cause you trouble with deleting messages as detailed for example here:
ryank85Author Commented:

I checked the TotalDeletedItemSize and it shows as 30GB. Also checked the litigation and in-place holds which I had not previously, but these came back as false.

The mailbox is 43GB in total out of 50GB. Originally the user was trying to delete a big chunk of emails, which I would expect to take a fair ammount of time to sync up. However trying to delete 1 x test email from OWA should be instant, shouldn't it?
Vasil Michev (MVP)Commented:
30 GB is the default quota for the RecoverableItems subtree, and you have reached that, thus the issue. You can either place the mailbox on hold to automatically increase the quota, or contact O365 support to have it increased for you.
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Jason CrawfordTransport NinjaCommented:
The 30 GB limit for RecoverableItems works by removing items on a first in first out basis once the quota is reached.  I would focus your troubleshooting elsewhere.
ryank85Author Commented:
Any other suggestions on this?

I purged the recover deleted items around 7pm last night. Left it over night to sync up, this section now shows empty. Still getting the same issue.

The TotalDeletedItems on powershell stills shows as 30GB. I was under the impression that the 30GB was the mail from the recover section, is this not correct?
Vasil Michev (MVP)Commented:
@Jason, no it does not automatically remove items on first in first out basis, the whole idea of the RecoverableItems subtree is to prevent accidental item loss.

@Ryan, what exactly did you try? Hard-deleting the items from the client does not get rid of them completely, they will still be stored in the Purges folder. If you have tried to clean the Purges folder via EWS or the Search-Mailbox cmdlet, you need to make sure that the Single Item Recovery is disabled. In any case, run the following to better understand what's happening.

Get-MailboxFolderStatistics mailboxname -FolderScope recoverableitems | ft Name,Folder*Size,Items*

Open in new window

Jason CrawfordTransport NinjaCommented:
@Vasil, yes it does


Additionally, the Purges folder is only a factor when SingleItemRecovery is enabled on the mailbox level.
Jason CrawfordTransport NinjaCommented:
So on that note, is the mailbox in question on a litigation hold?
ryank85Author Commented:
I checked the TotalDeletedItemSize and it shows as 30GB. Also checked the litigation and in-place holds which I had not previously, but these came back as false.
Vasil Michev (MVP)Commented:
@Jason Right, I assumed a bit to much I guess, apologies.

@Ryan, can you post the output of the cmdlet above? In addition to generic item deletion, the folder can become bloated due to versioning issues and so on. And check the status of SingleItemRecovery, it's on by default in O365, which means you cannot immediately purge items.
Jason CrawfordTransport NinjaCommented:
Happens to all of us at one time or another.  I just can't believe I knew something you didn't :)
ryank85Author Commented:
Thanks for all the suggestions on this, we ended up adding an exchange plan 2 licence and adding litigation hold on the mailbox, then ran the following command:

Search-Mailbox -Identity  -SearchDumpsterOnly -DeleteContent –donotincludearchive

This then cleared the deleted items overnight and then user was then again able to delete as normal.

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Seth SimmonsSr. Systems AdministratorCommented:
No comment has been added to this question in more than 21 days, so it is now classified as abandoned.

I have recommended this question be closed as follows:

Accept: ryank85 (https:#a42403765)

If you feel this question should be closed differently, post an objection and the moderators will review all objections and close it as they feel fit. If no one objects, this question will be closed automatically the way described above.

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