How to process a leaver in Office 365

Mark GalvinHead Of Projects
This article will describe some of the best ways to process an ex-employee from an Office 365 subscription. I will describe the methods I would recommend when the data needs to be kept for the ex-employee as well as how to manage any new email as well as the license assigned to them.
Here's the scenario. Within your Office 365 subscription you have someone who has left the organization and now you need to assign that license to another user.

First step is to decide on what will happen to:
  1. The ex-employee's mailbox data
  2. Any new email that comes in for leaver1
There may already be a policy that dictates the answers to these questions, so make sure you check'. Some companies will want to have Out Of Office/Auto Replies for any one that has left, for a set period of time, advising the sender of what to do (keep in mind this will require the license to stay assigned). Some companies will have strict policies in place to state that the above never happens and that email gets to a live mailbox. Either way make sure you plan out what will happen.

For this article we are going to say that:
  1. The ex-employee's mailbox data needs to be saved
  2. Any new email for the ex-employee is going to be forwarded onto their manager plus one other person
First step - forwarding any new emails
For me, I know that the mailbox data needs to be saved. The manager of the person that left hasn't yet decided where to put the data so best to have it stored in a PST file for now. But, I don't want to export the mailbox to PST only for new emails to come in during this process and be missed by the export process.

So what I'm going to do is redirect incoming mail to the Manager. To do that you need to edit the Exchange settings of the ex-employee in the Office 365 Web GUI. Open the Exchange Admin Center from the left hand Admin menu:
1.PNGLocate the ex-employee and open their properties. Then go to the 'mailbox feature' settings and scroll to the bottom. You're looking for the 'Mail Flow' section:
2.PNGClick the 'View details' link which will open a new window:
3.PNGCheck the 'Enable Forwarding' box, click 'Browse' and select the name of the person that should receive new emails sent to the ex-employee. Don't check the 'Deliver message to both forwarding address and mailbox' box. Then click 'OK' to save the changes. Now any new email that comes in for the ex-employee will go to the nominated person.

Second step - export mailbox to PST
Now I'm ready to connect Outlook (I'm using Outlook 2013) to the ex-employee's mailbox and export that data to PST. Using my article here I will connect Outlook to the mailbox. I make sure not to use 'Cached Exchange Mode'. Once Outlook is open I go into File, Open & Export, Import/Export. Then run through the wizard:
4.PNG5.PNG6.PNG7.PNGOnce the PST file has been created, I can now move onto the next step, which is to delete the Office 365 account of the ex-employee completely.

Third step - delete the user from Office 365
This step is simple. The Office 365 Admin page provides an easy method for the deletion of Users. Before I do that though I need to document the ex-employee's SMTP address/es so that incoming emails will still come work as per the decision to have 'Any new email for the ex-employee is going to be forwarded onto their manager plus one other person', which is one of the requirements set out at the beginning of this article. It’s important to do this, as once we delete the user, and the Office 365 stack processes that request, the Mail Flow setting we set above will be deleted alongside the user and we will need to create a new method for any incoming emails (I will detail that in Step 4 below).

From within the Exchange Admin Center, open the users properties once more and open the 'email address' settings:
7.1.PNGYou only need the Primary SMTP address which is the one with SMTP in CAPITALS. Once documented you can move onto the deletion of the user.

From the main Office 365 Admin page, select Users, then Active Users from the left hand menu:
8.PNGSelect the check box next to the user and then click 'Delete' from the right hand menu:
9.PNGOffice 365 will ask you to confirm.

Depending on how busy the Office 365 system is, it can take up to 15 minutes for this request to be completed. Once it is the Mail Flow change we made in Step 1 will stop working so next I need to setup a new path for incoming emails to flow.

Step four - dealing with incoming emails now the leaver's user account (and mailbox) have been deleted
There are a number of ways to achieve this.

If new email needs to go to one particular user, then all you need to do is add the ex-employee's Primary SMPT address as a secondary SMTP address to the user that will receive new emails. From the Exchange Admin Center open the properties of the resource that is going to receive new emails sent to the ex-employee:
7.1.PNGClick the '+' icon and add the SMTP address and click OK. That's it.

However, I prefer to set up a Distribution Group using the ex-employee's Primary SMTP address. This allows new emails to go to multiple recipients and is easily tracked for future changes. To do that, from the Exchange Admin Page, go To 'groups' and click the '+' icon:
11.PNGSelect the 'Distribution Group' option:
11.1.PNGFill out the relevant details:
12.PNG12.1.PNGAnd save the new Distribution Group. Go back into the group again as there are some more settings that you need to change.

First change who can email the group, under 'delivery management':
14.PNGThis allows senders external to your system to be able to email the group.

Next add the Primary SMTP address of the ex-employee:
15.PNGSame as before, using the '+' icon, add the address and click 'OK'.

And that's it!

Thank you for reading my article, feel free to leave me some feedback - always appriecated!  If you liked this article please click the big green 'Vote this article as helpful' button at the bottom of this article.
I look forward to hearing from you -  Mark Galvin  (LinkedIn)
Mark GalvinHead Of Projects

Comments (7)

Thanks for that, especially the last step, which is one way for freeing up the license and organizing the ex-employee emails in a sensible way. But it seems that you would create a separate distribution list for each manager who would be responsible for a set of ex-employees and then the emails end up in the manager's mailbox -- which puts off the problem: what is the procedure when that manager becomes an ex-employee.

Instead of a distribution list, what about using a Shared Mailbox?

One way we do for some clients rather than creating a PST is to convert the users mailbox into a shared mailbox which doesn't require a license, and then just grant the required users access, and sent forwarding from their.

Great article!  Thanks for sharing.

Any thoughts or suggestions on how best to handle data recovery for deleted accounts?  For instance, say the leaver deletes a bunch of emails prior to leaving...but we have a 7 year data retention policy.  I may be asked to recover emails from a year ago...but if I delete their email account, I lose that capability, correct?

Does that mean it's best that I keep the account for that 7 years in case I have to hunt down an old deleted email?

Also, great comments regarding a shared mailbox not needing a license.  Does anyone know if RackSpace offers shared mailboxes for their Hosted Exchange service?
Mark GalvinHead Of Projects



Thanks for the feedback.

For a Manager that becomes an ex-employee then, I would create a Distribution Group for the Manager's SMTP address, and then add the ex-employees SMTPs as secondary email addresses to that new Managers DG. And so on. Whilst it may seem over kill I feel its the best way to stay on top of ex-employees

For me, Shared Mailboxes have their uses but as they are limited in the mailbox storage you might find that they fill up in a short space of time. Personally, I feel there could also be an operational issue of who is taking care of those inbound emails.

I prefer the 'simplest is the best' method.

Hope that helps!


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