A bit later than expected, here’s finally the successor to the first article about Exchange Online Archiving which I wrote a while ago.

Exchange Online Archives and Outlook

How does Outlook connect to the online archive? Essentially, it’s the same process as with an on-premises archive. The client will receive the archive information during the initial Autodiscover process. If you take a look at the response, you will see something similar in the ouput:


Based on the SMTP address, the Outlook client will now make a second Autodiscover call to retrieve the connection settings for the archive after which it will try connecting to it. What happens then is exactly the same as how Outlook would connect to a regular mailbox in Office 365. Because Exchange Online is configured to use basic authentication for Outlook, the user will be prompted to enter their credentials. It’s particularly important to point this out to your users as the credential window will have no reference to what it’s used for. If you have deployed SSO, users will have to use their UPN (and not domain\username !) in the user field.


So far we have covered what Exchange Online Archiving is all about, what the prerequisites are to make it work and how things come together in e.g. Outlook. Now, it’s time to stir things up a little and talk about how things are actually perceived in real life.

First, let me start by pointing out that this feature actually works great, IF you are willing to accept some of the particularities inherent to the solution. What I mean with particularities?


Unlike on-premises archives, your archives are now stored ‘in the cloud’. Which means that the only way to access them is over the internet. Depending on where you are connecting from, this could be an advantage or a disadvantage. I’ve noticed that connectivity to the archive and therefore the user-experience is highly dependent on the internet access you have. Rule of thumb: the more bandwidth/lower latency the better it gets. This shouldn’t be a surprise, but can be easily forgotten. I have found on-premises archives to be more responsive in terms of initial connectivity and retrieval of content. This brings me to the second point: speed.


As you are connecting over the internet, the speed of fetching content is highly dependent on the speed of your internet connection (you see a similarity here?). The bigger the message/attachment you want to download is, the longer it will take. Truth be told, you’ll have the same experience while accessing your on-premises archive from a remote location, so it’s not something exclusive to Office 365.


To be honest, Outlook does a relative good job of working with the archive – at least when you deal with it the way it was designed. If you let Exchange sync expired items to your archive using the Managed Folder Assistant, your life will be great! However, if you dare to manually drag & drop messages from your primary mailbox into the archive, you’ll be in for a surprise. Outlook treats such an operation as a “foreground” action, which means that you will have to wait for this action to complete before you can do anything else in Outlook. The problem here is that if you choose to manually move a 4Mb message to the archive, it could take as long as 20 – 30 seconds (depending on your internet connection) before the action completes. To make things worse: during this operation Outlook freezes and if you try clicking something it’ll (temporarily) go into a “Not Responding…” state until the operation completes. According to Microsoft’s support, this is by design. So, as a measure of precaution: advise your users to NOT drag & drop messages, just let Exchange take care of it; something it does marvelously by the way.

I have found that proper end-user educations is also key here. If they are well informed about the how the archive works and have had some training on how to use retention tags, they’ll be on their way in no time!


As part of the problem I described above, the initial provisioning process can be a problem. When you first enable an archive, chances are that a lot of items will be moved to the archive. Although this process is handled by the MFA, if you mailbox is open whilst the MFA processes the mailbox, Outlook might become unresponsive or extremely slow at the least – this because the changes are happening and Outlook needs to sync those changes to the client’s OST file (when running in cached mode at least). Instead, it’s better to provision the archive on-premises, let the MFA do it’s work and then move the archive to Office 365. The latter approach works as a charm and doesn’t burden the user with an unresponsive Outlook client. If you are going to provision archives on-premises first, you might find it useful to estimate the size of an archive before diving in, heads first.


This is a short one. Search is great. Because Outlook and Exchange can do cross-premises searches, you will be able to search both your primary mailbox and archive mailbox at once. Didn’t have much issues here. So: thumbs up!

Other Tips & Tricks

General (best) practices

Other than the particularities above, you shouldn’t do anything else compared to ‘regular’ on-premises archives. Try not to overwhelm your users with a ginormous amount of retention tags. Instead offer them a few tags they can used and – if necessary – adapt based on user feedback.


Given the dependency from both Outlook and Exchange to make the online archive work, you should make sure that Autodiscover is working for your Exchange deployment AND that your Exchange servers are able to query Office 365’s Autodiscover service successfully as well.

This is especially important if you are using Outlook Web App (OWA) to access your online archive. In this case, it’s not Outlook but Exchange that will perform an Autodiscover lookup and connect to the archive. If your internet connection isn’t working properly or you have some sort forward authenticating proxy server in between, things could not (or intermittently) work.

Implement it gradually

As described above, it’s a bad idea to grant everyone with a new cloud-based archive at once. It will not only put a heavy load on your internet connection, but it will also affect your users. Instead, try to gradually implement the solution and request feedback from your users. Start with on-premises archives and move them to the cloud in batches, for instance.

DirSync is utterly important!

As described in the prerequisites sections, DirSync is very important to online archives. So make sure that you closely monitor how it’s doing. If you have issues with DirSync, you will inadvertently also have issues with creating archives. Issues with DirSync won’t interfere with archives that have already been provisioned though.


Is Exchange Online Archiving going to solve all your issues? Probably not. Is it a good solution. Yes, absolutely! I have been using Exchange Online Archiving for quite a while and I’m quite happy with it. I rarely encounter any issues, but I also have learnt to live with some of the particularities I mentioned earlier. Also, I treat my archive as a real archive. The stuff that’s in there are usually things I don’t need all that often. So the little latency-overhead that I experience whilst browsing/searching my archives is something I’m not bothered with. However, if I’d had to work with items from my archive day in, day out in; I’d probably have a lot more issues with adjusting to the fact that it’s less snappier than an on-premises archive.

So remember, set your (or your customer’s) experiences straight and you’ll enjoy the ride. If not, there might be some bumpy roads ahead!