Things to Consider when Moving to Office 365

Here is Mark’s list of Top Ten things to consider before subscribing to Office 365. I hope you find it useful!

1. Migrating is not a simple process

If you have an on-premise Active Directory environment and you want to perform a migration, it won’t be an easy process. Exchange Server 2010 SP2 includes a wizard that reduces the number of steps from roughly 50 down to six, but the migration process is still tedious and requires a lot of advanced planning.

2. You may have to start over with spam filtering

One of the biggest things that surprised me was that spam filtering suddenly became an issue.. Office 365 uses Microsoft Forefront Online Protection for Exchange. Although Forefront is a decent spam filter, I had to take the time to configure it.

3. Outbound email addresses might change

When you subscribe to Office 365, all user accounts have a default email address that ends in While it is possible to use your own domain, simply accepting mail for your domain name isn’t enough. Outbound messages will continue to use the domain unless you make some configuration changes, which are far from intuitive.

4. You can say goodbye to third-party utilities

ImageMany organizations use third-party utilities to manage Exchange Server. If you are using any such utilities and they’re designed to be installed directly on an Exchange Server, you won’t be able to use them with Office 365 (unless you keep an Exchange Server on premise). Microsoft does not allow you to install software onto the Office 365 servers.

5. You might have DNS issues

When you add a domain to your Office 365 account, you will receive a list of DNS entries that you must be make for the domain to function correctly. Although most of these DNS entries are relatively straightforward, Microsoft Lync requires some SRV records to be created.

This shouldn’t be a problem for those who have Microsoft DNS servers, but it can be problematic for non-Microsoft DNS servers. For example, my ISP manages my DNS entries. The ISP had no idea how to create the SRV records because it uses a Linux DNS server. That isn’t to say that the DNS entries won’t work with a Linux DNS server — but if someone else manages your DNS, you might have trouble getting the necessary DNS records created.

6. You may have to use different management tools

Because I didn’t keep any on-premise servers, managing Exchange through the Exchange Management Console was no longer an option. Office 365 uses the Exchange Control Panel as the primary Exchange Server management tool. Likewise, user accounts are created through a proprietary interface rather than through the Active Directory Users And Computers console.

7. You might have to reset file server permissions

Just remember that if you are outsourcing everything except for your file servers, you probably won’t be able to use Active Directory accounts for managing file access.

8. Prepare to be bombarded with phone calls and email messages

One aspect of the transition that really surprised me was that I was bombarded with phone calls and email messages from Microsoft. While I appreciate having the opportunity to ask questions about the transition, there is such a thing as too much of a good thing.

9. You might not be able to immediately connect users’ mobile devices

One of the issues I ran into during my transition was that even though I was able to bring my mailbox online quickly, the logistics of the transition kept me from connecting my Windows Phone to my mailbox for several days.

The reason for this is that prior to the transition I had an on-premise domain and an on-premise Exchange Server. Rather than working through a co-existence scenario and migrating everything, I decided that it would be easier to start fresh. This meant that if I had immediately connected my phone to my new Exchange mailbox, my contacts, calendar entries, and old messages would have disappeared from my phone (which would have been a big deal).

So I had to create a PST file on my PC and move all my mail, contacts, and calendar entries from Outlook to my PST. Once that was done, I disjoined my PC from the on-premise domain and then connected Outlook to my new Office 365 mailbox. Then I copied all my PST data to the new mailbox. At that point, I was able to connect my phone to my mailbox without having to worry about losing access to my contacts and other data.

Obviously, this won’t be a concern for organizations that work through the “real” migration process. But smaller organizations that choose to abandon their on-premise domain will have to consider this.

10. Expect a loss of control

Finally, moving to Office 365 means giving up some level of control. For example, you won’t have any control over the patch management process, software upgrades, and other similar administrative tasks you may be used to performing on-premise.

If you are thinking about moving to Office 365, Waterford Technologies can help you get prepared.

2 thoughts on “Things to Consider when Moving to Office 365”

  1. A lot of misinformation here.

    1 – I'll give you. It's really not painful, but we use a third party utility (that most people aren't going to default to) that makes it exceptionally simple. However, the tools provided by Microsoft are really not that bad if you take the time to use them, our tool (MigrationWiz) just makes it that much simpler.

    2 – Valid point, but only from the aspect that your existing spam filter has been 'learning' this whole time and now you get to start at square 1 again. I've never had to configure forefront for our customers, it just works.

    3 – This is only true if you've misconfigured your instance. If you load the domain first (which is the step they just about force you to do first), the user accounts you create will default to your domain, not the

    4 – Also not true. Anything worth its salt is going to work with Exchange via PowerShell, and if it supports Exchange 2013 but not Office 365, the developers of the tool were simply lazy. I've not run into any application that manages one and not the other and wasn't replaceable by something equivalent.

    5 – This one isn't Microsoft's fault. If you are worried about your DNS, you can move it away from your ISP and into 365.

    6 – This is true for Exchange 2013 as well as Office 365.

    7 – Not really sure where this one came from. No matter how you integrate Office 365 with your infrastructure, it interfaces with user accounts only, not file server permissions.

    8 – Again, doesn't line up with my nor my customers' experiences. If I may be snarky for a moment, if you've have taken them up on one of those phone calls, they may have put you in touch with someone to help you avoid a lot of your issues.

    9 – There's no reason for the items to have disappeared from your phone unless you migrated the data improperly. Even when you're 100% functional on 365, your existing Exchange server is still plenty capable of sending mail, and retaining a copy of all of your data while you're making the move. DNS propagation would explain why it took your mobile device a day or so to marry up to 365, but even then most devices allow you to provide specifics in regards to server address, expediting the process.

    10 – But isn't that kind of the point?

    I'd love to know specifics in regards to what your migration process was.

  2. This Article is nothing but FUD, written to propagate traffic to his IT consulting firm.

    What the commenter above (jon) has specified is spot on.

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