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HOW TO RECOVER DELETED EMAILS IN MICROSOFT 365

Brett Hill
January 30, 2022

Save to My DOJO




TABLE OF CONTENTS



 1.  Deleted Email Recovery in Microsoft And Office 365
 2.  Items vs. Email
 3.  Policy
 4.  ‘Deleted Items’ Email
 5.  But I Didn’t Delete It!
 6.  ‘Soft-Deleted’ Email
 7.  How items become soft-deleted
 8.  Recovering soft-deleted mail
 9.  Hard-Deleted Email
 10. How items become Hard-Deleted
 11. Recovering Hard-Deleted Mail
 12. Last Chance Recovery
 13. What about using Outlook to backup email?
 14. Alternative Strategies
 15. Summary

When the CEO realizes they deleted a vital email thread three weeks ago, email
recovery becomes suddenly becomes an urgent task. Sure, you can look in the
Deleted Items folder in Outlook, but beyond that, how can you recover what has
undergone “permanent” deletion? In this article, we review how you can save the
day by bringing supposedly unrecoverable email back from the great beyond.


DELETED EMAIL RECOVERY IN MICROSOFT AND OFFICE 365

Email Recovery for Outlook in Exchange Online through Microsoft and Office can
be as simple as dragging and dropping the wayward email from the Deleted Items
folder to your Inbox. But what do you do when you can’t find the email you want
to recover?

First, let’s look at how email recovery is structured in Microsoft 365. There
are few more layers here than you might think! In Microsoft 365, deleted email
can be in one of three states: Deleted, Soft-Deleted, or Hard-Deleted. The way
you recover email and how long you have to do so depends on the email’s delete
status and the applicable retention policy.



Let’s walk through the following graphic and talk about how email gets from one
state to another, the default policies, how to recover deleted email in each
state, and a few tips along the way.


ITEMS VS. EMAIL

Outlook is all about email yet also has tasks, contacts, calendar events, and
other types of information. For example, you can delete calendar entries and may
be called on to recover them, just like email. For this reason, the folder for
deleted content is called “Deleted Items.” Also, when discussing deletions and
recovery, it is common to refer to “items” rather than limiting the discussion
to just email.


POLICY

Various rules control the retention period for items in the different states of
deletion. A policy is an automatically applied action that enforces a rule
related to services. Microsoft 365 has hundreds of policies you can tweak to
suit your requirements. See Overview of Retention policies for more information.


‘DELETED ITEMS’ EMAIL

When you press the Delete key on an email in Outlook, it’s moved to the Deleted
Items folder. That email is now in the “Deleted” state, which simply means it
moved to the Deleted Items folder. How long does Outlook retain deleted email?
By default – forever! You can recover your deleted mail with just a drag and
drop to your Inbox. Done!

If you can’t locate the email in the Deleted Items folder, double-check that you
have the Deleted Items folder selected, then scroll to the bottom of the email
list. Look for the following message:



If you see the above message, your cache settings may be keeping only part of
the content in Outlook and rest in the cloud. The cache helps to keep mailbox
sizes lower on your hard drive, which in turn speeds up search and load times.
Click on the link to download the missing messages.


BUT I DIDN’T DELETE IT!

If you find content in the Deleted Items and are sure you did not delete it, you
may be right! Administrators can set Microsoft 365 policy to delete old Inbox
content automatically.

Mail can ‘disappear’ another way. Some companies enable a personal archive
mailbox for users. When enabled, by default, any mail two years or older will
“disappear” from your Inbox and the Deleted Items folder. However, there is no
need to worry. While apparently missing, the email has simply moved to the
Archives Inbox. A personal Archives Inbox shows up as a stand-alone mailbox in
Outlook, as shown below.



 

As a result, it’s a good idea to search the Archives Inbox, if it is present
when searching for older messages.

Another setting to check is one that deletes email when Outlook is closed.
Access this setting in Outlook by clicking “File,” then “Options,” and finally
“Advanced” to display this window:



If enabled, Outlook empties the Deleted Items when closed. The deleted email
then moves to the ‘soft-delete’ state, which is covered next. Keep in mind that
with this setting, all emails will be permanently deleted after 28 days


‘SOFT-DELETED’ EMAIL

The next stage in the process is Soft-Deleted. Soft-Deleted email is in the
Deleted-Items folder but is still easily recovered. At a technical level, the
mail is deleted locally from Outlook and placed in the Exchange Online folder
named Deletions, which is a sub-folder of Recoverable Items. Any content in the
Recoverable Items folder in Exchange Online is, by definition, considered
soft-deleted.

You have, by default, 14 days to recover soft-deleted mail. The service
administrator can change the retention period to a maximum of 30 days. Be aware
that this can consume some of the storage capacity assigned to each user account
and you could get charged for overages.


HOW ITEMS BECOME SOFT-DELETED

There are three ways to soft-delete mail or other Outlook items.

 1. Delete an item already in the Deleted Items folder. When you manually delete
    something that is already in the Deleted Items folder, the item is
    soft-deleted. Any process, manual or otherwise that deletes content from
    this folder results in a ‘soft-delete’

 2. Pressing Shift + Delete on an email in your Outlook Inbox will bring up a
    dialog box asking if you wish to “permanently” delete the email. Clicking
    Yes will remove the email from the Deleted-Items folder but only perform a
    soft delete. You can still recover the item if you do so within the 14 day
    retention period.

 



 

 3. The final way items can be soft-deleted is by using Outlook policies or
    rules. By default, there are no policies that will automatically remove mail
    from the Deleted-Items folder in Outlook. However, users can create rules
    that ‘permanently’ (soft-delete) email. If you’re troubleshooting missing
    emails, have the user check for such rules as shown below. You can click
    Rules on the Home menu and examine any created rules in the Rules Wizard
    shown below.



Note that the caution is a bit misleading as the rule’s action will soft-delete
the email, which, as already stated, is not an immediate permanent deletion.


RECOVERING SOFT-DELETED MAIL

You can recover soft-deleted mail directly in Outlook. Be sure the Deleted Items
folder is selected, then look for “Recover items recently removed from this
folder“ at the top of the mail column, or the “Recover Deleted Items from
Server” action on the Home menu bar.



Clicking on the recover items link opens the Recover Deleted Items window.



Click on the items you want to recover or Select All, and click OK.

NOTE: The recovered email returns to your Deleted Items folder. Be sure to move
it into your Inbox.

If the email you’re looking for is not listed, it could have moved to the next
stage: ‘Hard-Deleted.’

While users can recover soft-deleted emails, Administrators can also recover
soft-deleted emails on their behalf using the ‘Hard-Deleted’ email recovery
process described next (which works for both hard and soft deletions). Also,
Microsoft has created two PowerShell commands very useful in this process for
those who would rather script the tasks. You can use the Get-RecoverableItems
and Restore-RecoverableItems cmdlets to search and restore soft-deleted emails.


HARD-DELETED EMAIL

The next stage for deletion is ‘Hard Delete.’ Technically, items are
hard-deleted when items are moved from the Recoverable folder to the Purges
folder in Exchange online. Administrators can still recover items in the folder
with the recovery period set by policy which ranges from 14 (the default) to 30
(the maximum). You can extend the retention beyond 30 days by placing legal or
litigation hold on the item or mailbox.


HOW ITEMS BECOME HARD-DELETED

There are two ways content becomes hard-deleted.

 1. By policy, soft-deleted email is moved to the hard-deleted stage when the
    retention period expires.
 2. Users can hard-delete mail manually by selecting the Purge option in the
    Recover Deleted Items window shown above. (Again, choosing to ‘permanently
    delete’ mail with Shift + Del, results in a soft-delete, not a hard-delete.)


RECOVERING HARD-DELETED MAIL

Once email enters the hard-delete stage, users can no longer recover the
content. Only service administrators with the proper privileges can initiate
recovery, and no administrators have those privileges by default, not even the
global admin. The global admin does have the right to assign privileges so that
they can give themselves (or others) the necessary rights. Privacy is a concern
here since administrators with these privileges can search and export a user’s
email.

Microsoft’s online documentation Recover deleted items in a user’s mailbox
details the step-by-step instructions for recovering hard-deleted content. The
process is a bit messy compared to other administrative tasks. As an overview,
the administrator will:

 1. Assign the required permissions
 2. Search the Inbox for the missing email
 3. Copy the results to a Discovery mailbox where you can view mail in the
    Purged folder (optional).
 4. Export the results to a PST file.
 5. Import the PST to Outlook on the user’s system and locate the missing email
    in the Purged folder


LAST CHANCE RECOVERY

Once hard-deleted items are purged, they are no longer discoverable by any
method by users or administrators. You should consider the recovery of such
content as unlikely. That said, if the email you are looking for is not
recoverable by any of the above methods, you can open a ticket with Microsoft
365 Support. In some circumstances, they may be able to find the email that has
been purged but not yet overwritten. They may or may not be willing to look for
the email, but it can’t hurt to ask, and it has happened.


WHAT ABOUT USING OUTLOOK TO BACKUP EMAIL?

Outlook does allow a user to export an email to a PST file. To do this, click
“File” in the Outlook main menu, then “Import & Export” as shown below.



You can specify what you want to export and even protect the file with a
password.

While useful from time to time, a backup plan that depends on users manually
exporting content to a local file doesn’t scale and isn’t reliable.
Consequently, don’t rely on this as a possible backup and recovery solution.


ALTERNATIVE STRATEGIES

After reading this, you may be thinking, “isn’t there an easier way?” A service
like Altaro Office 365 Backup allows you to recover from point-in-time snapshots
of an inbox or other Microsoft 365 content. Having a service like this when you
get that urgent call to recover a mail from a month ago can be a lifesaver.


SUMMARY

Users can recover most deleted emails without administrator intervention. Often,
deleted email simply sits in the Deleted folder until manually cleared. When
that occurs, email enters the ‘soft-deleted stage,’ and is easily restored by a
user within 14-days. After this period, the item enters the ‘hard-deleted’
state. A service administrator can recover hard-deleted items within the
recovery window. After the hard-deleted state, email should be considered
uncoverable. Policies can be applied to extend the retention times of deleted
mail in any state. While administrators can go far with the web-based
administration tools, the entire recovery process can be scripted with
PowerShell to customize and scale larger projects or provide granular discovery.
It is always a great idea to use a backup solution designed for Microsoft 365,
such as Altaro Office 365 Backup.

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