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Top 9 Things to Know Before Moving to Exchange Online

It’s quite simple really – if you can’t swim, don’t jump in the deep end.

If you haven’t done your research, don’t go running into an Exchange Online migration (or any migration for that matter). There are certain things you need to be aware of before making the switch. In this case, there are in fact 9 things you need to know.

1. Email is not a stand-alone product

It is imperative that prior to migrating a single mailbox you understand which other core business applications integrate with your current email system. Chances are, your email system is tied to several specific workflows, involving a variety of additional applications.

Let’s say, for example, you work for a healthcare organization. That means you have very strict HIPAA compliance standards, including in your email, like automated workflows to black out certain keywords or data when a message goes out. In order to stay in compliance you need to consider how to maintain that workflow upon migrating to the new system.

And since you can’t put the security of your organization within the end users’ hands, you (hopefully) have back end data loss prevention processes to encrypt certain messages and keep sensitive data from leaving internal communications. These policies need to be included in your migration plan.

You may be tempted to try and deploy only Exchange Online to get you started, but if you want users to continue using email for more than just text, you need to consider additional programs. For example, if you expect users to send email attachments, that’s going to require OneDrive for Business and SharePoint Online licensing. Assuming you’re deploying Exchange Online through Office 365, you’ll have access to these applications, but you need to think about that when determining the right license for each user.

These workflows need to be documented, accounted for, and planned for prior to beginning any migration. Not only could it turn into a huge security risk otherwise, but a headache for you and a hassle for the end user (which just adds to your headache).

2. Schedule your cutover wisely

Let’s set the scene: your cut-over is complete, you shut down for the night and arrive in the office the next day. You now have 100 end users calling you for workstation configuration. You keep your cool as you totally planned for this. What you didn’t plan for is the 75 end users begging for help as you work with the others, followed by 100 end users knocking at your door because your network is too slow to do much of anything and they’ve lost valuable working time, followed by you hiding under your desk and crossing your fingers it’ll all be over soon.

Ok, so you’re likely much more confident than that, but the point is, you have to plan your migration times very carefully. There’s more to a migration than the cut-over phase and you need to consider how to handle the workstation updates and lengthy mailbox downloads, otherwise you may be in danger of impacting revenue and productivity levels for the day.

Pro tip:

Working nights and weekends is never fun, but if you plan your cut-over for Friday night, your workstation configurations for Saturday and your mailbox downloads for Sunday, you’ll be much happier on Monday!
( P.S. this is much easier with a partner)

3. Manage end user experiences

Nobody really likes change. Some people are better than others at accepting and adapting to change, but it’s still complicated and messy and not fun to deal with. Enter: change management. Remember that vision of you hiding under your desk? Don’t be that guy. Take the time to manage end user expectations – document all of the upcoming changes, why they’re changing, how much better they’ll be, and what they need to know and do prior to those changes occurring. Once done, set a reminder to yourself to send out those same communications several more times before the migration takes place, and likely once or twice more post-migration. Here are some things to include in your change management efforts:

    1. Workstation updates – Exchange Online and OWA maintain a support level for web browsers of current versions, minus one. This is a much bigger deal than most people originally realize. If you have an old ERP system that only runs on IE7 and that’s the browser you mandate within your organization, your users will not be able to access OWA. Of course there are ways to get around this, like pushing out a secondary browser or deploying virtual desktops – either way, you need to have a plan for this and be very clear on how it will impact your users’ day-to-day.
    2. Signatures – Seems like such a small detail, but if you have required confidentiality notices within your signature and those signatures don’t carry over to Exchange Online, you’ll definitely need a plan to reinstate them ASAP.
    3. Plugins – Everyone has a plugin for something these days. Let’s consider your Sales team for a moment. Not only do they have a CRM integration, but they may even have a Starbucks integration for sending gift cards on the fly (so smart, am I right?). Those plugins are like a way of life for your Sales team and if you take them away, it completely disrupts how they do business. Figure out what’s being used and how to deploy it in the new environment.
    4. Mobile devices – Fact is, most people check email on their phones these days and in many migration scenarios mobile devices will not be updated automatically. Make sure you have a well-documented how-to for DIY end user updates.
    5. Email access – Again, sounds simple, but if your users constantly access email from a specific URL and you go and change that without notice…I think you know how this story ends.

4. PowerShell is your new BFF

If you are in fact migrating to Exchange Online via Office 365, PowerShell is going to be your new best friend. The funny thing about the Office 365 Admin Center is that it’s constantly evolving. There have honestly been times in the middle of our own client trainings when we realize something has moved, disappeared or been added. As an administrator, you really must be nimble. It may seem frustrating to deal with constant change, but that’s where PowerShell comes in to save the day.

Anything you want to accomplish that is not built into the UI of the Admin Center can be accomplished with PowerShell.

What you have to understand is that, as an on-prem organization, there are certain features you may expect to be built into the UI that will inevitably be missing. With an on-prem infrastructure you have decoupled systems with individual admins making their own updates. With Exchange Online, all systems are now tied together and a simple change impacts other applications. So again, the day-to-day limitations may sound frustrating, but PowerShell is always there when you need it.

5. Black and White Listing

When you move to Exchange Online, your IP address will be updated. May not sound like a big deal, but it could end up getting you blacklisted if not handled appropriately. Because email addresses are so easily faked, many of your customers likely rely on IP addresses rather than domain names to determine safe senders.

When your IP address changes, your customers and vendors need to be updated immediately to make sure your emails don’t bounce, end up in junk, or worse, get blacklisted.

6. Archiving

Typically, when an organization is running email on-prem or through a third party provider, archives of emails are stored locally after so many days. Not a big deal until you get ready for your Exchange Online migration.

During your migration you’re only going to pull emails from your server, which means all of those emails that have been stored on users’ devices won’t be pulled over, potentially ending in a massive loss of data.

The good news is that there are ways to grab those emails, but it definitely requires a level of support or additional applications. If you need to retain those archived emails for any reason, you absolutely need to plan a way to incorporate them into your migration strategy.


Pro Tip!

Locally stored data is a huge security risk – it can easily be lost if not backed up, or stolen by malicious employees (not to mention external threats). Move to Exchange Online for better control of your data.

7. Usage Limits

What platform are you using to run Exchange Online? Outlook? That’s certainly the most common answer, but you need to be aware of usage limits regardless of platform and be prepared to notify users of changes and train them on best practices for working around them.

Let’s say your CEO needs to send out email updates to all 50 of your subsidiaries. The catch is that the message to each group is different and he wants to exclude a certain department from each message. You may be thinking that this could be solved with a simple distribution list, but as soon as the CEO expands that list to exclude a certain group, he risks going over the 500 addresses per email limit. If he does that several times a day, he’ll risk hitting the 10,000 addresses per day limit and be locked out of sending email for 24 hours. I do not want to be the one my angry CEO comes to when he can’t work in email for the rest of the day.

Think that scenario is too ridiculous to worry about it? Let’s think about Sales and Marketing for a second – how many users blast hundreds or thousands of contacts in a day in hopes of a white paper download or a meeting request? Now imagine an entire salesforce unable to send emails for an entire day – not just the meeting invites, but an update on SOWs and following up on hot leads. Not a pretty picture.

Now let’s say that same CEO has a file to send out that happens to surpass Outlook’s attachment size limits. There are other ways to share out information, like shared folders, OneNote, Teams, etc., but if your users don’t know of these tools or how to use them they’ll either A) put in a support request every time they need to send a large file or B) find some crazy workaround that’s not only ridiculous but could pose a potential security threat.

Knowing email limitations isn’t just for your sake – it’s a company-wide requirement. Understand what you’re getting into, share the changes internally, and offer several rounds of training.

8. Compliance

Compliance is easily one of the top concerns we face with Exchange Online migrations.

We all know that mailboxes can easily turn into a wasteland of junk and clutter emails. When you’re performing a migration it simply doesn’t make sense to lift and shift all of that clutter (just because you have the space doesn’t mean you have to fill it!).

Pro Tip!

Prior to migrating, delete items in the junk and deleted items folder that are older than 30 days.

You may run into the classic issue of end users using the deleted items folder as document storage, but now is the time to put an end to their silly ways and help mandate a safer, more compliant, and frankly easier storage system.

It’s also important to know that, unlike on-prem email systems, Exchange Online comes with a default policy of permanently deleting deleted items after 30 days and archiving emails older than 2 years. For organizations in legal, healthcare and education, this may not fit internal requirements and needs to be addressed from the start.

9. Get to Know the End Users

Scheduling a migration isn’t just about timing, it’s knowing who works with whom and how. This is very important if you plan to do a staged or hybrid migration.

Typically, an Admin may think ‘I’ll just move the entire Marketing team at the same time and there won’t be any downtime for the group.’ Good thought, but the Marketing team also works heavily with Sales and Product Management and they all rely on shared access of different documents, folders and calendars to push out new collateral, plan for product updates and so on.

If you don’t move the right people at the right time, you risk major downtime and revenue loss.

Feeling overwhelmed?

It’s a lot to think about and this honestly doesn’t cover everything, but moving to Exchange Online doesn’t have to be scary and it doesn’t have to be hard.

Check out How to Move to Exchange Online

If you’re ready to make the move, click here. If you need some clarity on the above, fill out the form below and one of our experts will happily reach out.


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