Thursday, July 27, 2017

Migrating to Exchange Online: It's Really about the Journey and not the Destination

By: Mike Cavasin   Categories:Cloud Services

Migrating to Exchange Online: It's Really about the Journey and not the Destination
I recently returned from Microsoft’s “Inspire” Conference, formerly known as the Worldwide Partner Conference.

I recently returned from Microsoft “Inspire”, formerly known as the Worldwide Partner Conference. This 3-day event for partners that resell, integrate, build upon and otherwise utilize Microsoft solutions as an integral aspect of their business and/or product(s) was filled with stories about how MS Partners like Sentia about how they have utilized the myriad of MS offerings to provide value through innovation for their clients. These exposes of the triumph of innovation in technology over complex modern problems ranged from the truly heart-warming to the just plain cool.

Of course, the focus of much of the event - and I’m sure many of the conversations you're having with your management and colleagues - was “the cloud”. Not just the mere migration of on-premise workloads to IaaS offerings such as Azure or more structured SaaS offerings such as the Office365 services and suites, but on the “Digital Transformation” that can be enabled for businesses once they make the move.

This enablement can range from the almost instant value add that comes from the personal awareness of Delve/MyAnalytics and business-spanning real-time reporting capabilities of Power BI, to the relative ease of leveraging advanced Machine Learning capabilities - without the requirement to build-out an on-premise platform - once your data is “in the cloud”.

For most of you the move to “the cloud” is a foregone conclusion - something that WILL happen – even if you haven’t had time to put together the what, when or how of your move yet.

So where do you start?

If you’re reading this I’m guessing you’re already very familiar with Sentia as a valued partner in architecting, deploying and managing your traditional business-critical systems. 

However, you may not have thought of us as experts in Microsoft solutions like, Exchange, Windows Server, and Hyper-V - let alone the cloud-based, Azure-driven offerings.

The fact is we have been deploying, upgrading, migrating and managing Microsoft solutions for as long as we’ve been in business (in fact much longer than that for most of our senior staff) and have been right there beside our clients to guide them on their “journey to the cloud”. Emphasizing the importance of understanding the gravity and complexity of that journey is the purpose of this blog and the key value Sentia can add to any of your current or future “cloud initiatives”.

Now as a “tech guy” I could go on about the various cloud offerings available just under the MS/Azure/Office365 umbrella, and those of you who have invited me to speak to you about what we can offer may have experienced this first-hand.

For the purposes of this blog post, I will focus on the most commonly requested “cloud migration” and the “gateway drug” of choice to organizations that are just starting their “cloud journey” – moving to Exchange Online.

Phase 1: Office365 Plan Selection

The first step is to decide on the Office365 package that’s right for you. In case you didn’t know, just like the traditional Office Suite, Office365 is a package of many smaller parts (Exchange/SharePoint/Office Online, OneDrive/Skype for Business) which can be purchased in Suite offerings for Home/Small/Medium Business or Enterprise, or in a-la-carte form – all at set prices for monthly or annual commit.

Each one of these usually having at least two tiers of plan and plethora of sub-components, options, features and limitations to evaluate in making your first of many decisions. At this point in your journey you are just determining what your destination end-state will be for the first of likely many cloud migration journeys. 

A few questions you’ll have to ask yourself are:

1) Will I need to upgrade the Office suite for my on-premise users? If so, should I purchase a package or a-la-carte offering that includes this?

2) Do my current mailbox sizes, retention/compliance requirements and other key configurations require I purchase a particular plan level?

3) What is my plan for anti-malware, filtering and data-loss prevention? Am I going to continue to use my existing on-premise/cloud solution? Leverage the included Exchange Online Protection? Deploy advanced solutions like Advanced Threat Protection and Azure Rights Management?

Suggested links to some high-level offerings and specifics for Exchange Online to help you in responding to these questions.

Office 365 Service Descriptions

Exchange Online Service Description

Exchange Online Limits

Exchange Online Protection Service Description

Exchange Online Protection Limits

Exchange Online Advanced Threat Protection Service Description  

If you took the time to open the links and look over the articles, you likely are already wishing you had someone to point you in the right direction (and maybe a shoulder to cry on). I’ll take this moment to remind you that is one of the first benefits Sentia can offer you in evaluating your options and it just gets more complex from there. 

We can also advise and help procure licensing not just for traditional Commercial businesses, but for Academic, Government and Non-Profit/Charitable organizations – each with its own unique process and requirements to follow.

migration diagram
Phase 2: Assessing, Planning and Executing your Migration

Once you’ve figured out the package and options that will work for you, then the real fun starts – assessing, planning and executing your migration. 

If you’ve already looked into it a bit then you’ve likely been made aware of the fact that there are many tools offered to accelerate your migration that are marketed as “fire and forget” solutions to your migration problems – BitTitan, SkyKick and the like. I know the partner booths at Inspire had no lack of enthusiastic representatives espousing the benefits of their products.

The unfortunate part about this is that these tools tend to focus just on the end-user management/wrangling part of the migration problem such as tracking down and re-integrating rouge PSTs, transferring mail-management rules and patching Office installations.

While these are all important aspects of your move they are only a small portion of the whole picture and will only really be a one-stop shop solution for those blessed with a small and pristinely maintained Exchange environment – or those moving from a non-Exchange solution.

They also almost always involve a cut-over migration strategy that requires significant end-user interaction (i.e. installing client agents to execute Office updates and input of credentials for mailbox access), cause downtime/disruption of access (especially if you’re not prepared to move everyone in a single shot) and don’t do anything to migrate the customizations, scripts and configurations you’re applied over the years to your on-premise Exchange environment (many of which may have been forgotten over time).

Third-party tool limitations
By far the biggest issue, especially for larger organizations, that isn’t spoken of when these tools are marketed, is that they almost always involve the recreation of the local mail profile for Outlook. 

If you are a small organization or don’t use mail-caching, this may not be a big deal. If you’re like the other 99%, then this migration strategy will require every user to download their mail again, which can clog your network, blow-up your bandwidth bill and leave everyone in the company pulling their hair out for the better part of a day. Also, while these tools may help point out some issues in user and server configurations which need to be corrected pre-migration, we’ve found they are rarely a replacement for having a technical specialist with 10+ years of Exchange experience on hand to aid in making those changes.

Here are some of the common challenges we’ve helped clients with in previous migrations, that had little to no impact to the end-user, contrary to third-party tools lacking in this area.

Automated Updates to Office Suite Installations
Without getting into the complexities involved if you must move from a traditional MSI-based deployment and management strategy for your workstation Office installations to the modern Click-to-Run (C2R) - and most of you will - having to move from older Office Suite installations to current versions is a pre-requisite for most migrations. The Office Deployment Tool (ODT) makes this relatively straight-forward to push out to your endpoints with minimal effort using start-up scripts, GPO, SCCM or most 3rd-party deployment management tools you might already be using. We can show you how to use this to painlessly update hundreds of workstations in a single evening.

Maintaining Delegate Access during
Staged Migration
Most organizations above 50 users will want to move in multiple phases, if for nothing more than test/pilot before making the leap. Don’t let anyone tell you that doing this with any 3rd-party tool will be easy and painless. The only way to pull this off is with a properly set up Exchange Hybrid/Federation between your on-premise and cloud environments. Without this you will only have email communication between those moved to the cloud and those remaining on-premise (no shared calendars, delegated access, shared mailbox access, or common address book). We understand all the complexities involved in deploying and maintaining this hybrid before, during and after your migration is completed so that your end-users may never even notice that they’ve been migrated.

Modernizing Shared/Resource Mailboxes and Public Folders
If your organization has been upgrading since Exchange 2000 or earlier and don’t remember specifically doing this when you moved to Exchange 2010/2013 or aren’t already on Exchange 2016, then trust me you will HAVE to deal with this during your migration. This can be a relatively simple process if you can just PowerShell an update to the Mailbox Type on your Shared/Resources mailboxes, or it can be almost an entire separate project in itself if you have 35,000 mail-enabled Public Folders – half of which no one remembers what they are for anymore - and almost all have issues with their names and hierarchy. Sentia can help you untangle these messes which a minimum of stress to both you and your user-base.

Third-Party Mobile Device Management (MDM)
If you currently just use the built-in MDM capabilities of Exchange (which are good enough for most when used properly), are migrating via Hybrid and all your end-user mobile devices are less than 5 years old then your end-users won’t notice a thing has changed on their mobile devices when their mailboxes are migrated. If not, then you might have to have them all re-create their mobile accounts (and approve all the new adds if this is a manual process for you) or at least make updates and coordinated changes to the application of ActiveSync profile policies in your MDM of choice. This high-end-user-impact aspect of your migration can vary greatly depending on your individual setup and function of your MDM, and again is something that Sentia’s wealth of experience can become invaluable for when addressing.

Assuming you get through the gauntlet I’ve already described and manage to move all your users and their mailboxes to the cloud without a RGA (resume generating event), it's now cleanup time. You still have your on-premise Exchange environment to take-down if it’s no longer required, not an easy task for most. Your mailflow and internal/external DNS records need to be updated. Don’t forget as well about all the on-premise devices and applications that have been relying on that infrastructure to reliably send emails for everything from daily reports to mission-critical service failure/error alerts. How do all of those get discovered and updated to continue to send their important missives in a server-free world?

This is another area where the experts at Sentia can help you plan and execute this important post-migration work for which there is absolutely no easy 3rd-party solution as well as many other challenges which could be unique to your environment. This is because years of experience have taught us that no two business, systems or even users are exactly the same and every business and person deserves a solution tailored to their unique needs.

I appreciate you taking the time to read this and I invite you to reach out and see what we can do to help. Whether it’s just assisting with the planning and identification of pre-migration issues or handling the entire project as a turn-key engagement, we are here to be your companion on your journey to the cloud.

We hope to be hearing from you soon. Feel free to connect with me via LinkedIn or send me an email.

Mike Cavasin
Support Operations - Team Lead, Sentia
1-866-610-8489 x349


Mike Cavasin
Mike Cavasin

Mike Cavasin

Michael Cavasin has spent over 15 years in progressive IT positions developing hands-on experience from end-user application support to enterprise systems deployment and project management on a wide variety of platforms

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Full biography

Michael Cavasin has spent over 15 years in progressive IT positions developing hands-on experience from end-user application support to enterprise systems deployment and project management on a wide variety of platforms. His detailed knowledge of the entire infrastructure stack and complex interdependencies of these systems allows him to look beyond point solutions and consider the way each customer’s unique historical development and business processes influence their IT needs. Michael takes a holistic approach to ensure solutions not only address the needs of today, but are ready to scale and adjust to fit your long-term direction. Michael enjoys hiking, camping, portaging, hunting, swimming, skiing, cooking, gardening, movies, TV and video games.


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