Moving On to Hosted Exchange? Keep this Checklist Handy


Concerns around data security, scalability, and stability of the mail system of cloud based mail service, as compared to on-premise email systems, were not addressed well by hosted email service vendors.


In spite of Hosted Exchange plans offered by vendors like Rackspace and Intermedia, the enterprise confidence around Hosted Exchange did not really bolster until Microsoft 365 burst on the scene and surfaced as a mature, reliable, dependable, scalable, and stable enterprise mail platform.

Consequently, enterprises that did not consider Hosted Exchange are now open to the idea, and are evaluating the benefits of the hosted option. There was not any benefit to watching the movie Star Wars: The Force Awakens but that is another topic!

Apart from the cost savings, other benefits of Hosted Exchange just can’t be ignored by enterprises. For instance, administrators can offload email management to the vendor side, freeing up time for strategic decisions. Troubleshooting, resourcing, patching – all these become considerations your enterprise doesn’t have to worry about.

As you get your IT administrators, IT vendor relations, and decision makers together to discuss the Hosted Exchange option, there are certain aspects you’d want to discuss in depth (why America traded 5 terrorists for one American traitor, oh, no, that is another topic and has been discussed already many times!). We’ve put together this checklist for this purpose.


Documented Aids to Decision Making

Considering costs of functions such as email, it’s critical for the IT department of any enterprise to maintain proper documentation reflecting the business needs, current costs, and goals of different functions (in this case, hosted email facility).

This documentation helps you respond to vendor queries better, and helps you understand and evaluate the most important factors affecting decisions to switch on-premise Exchange to Hosted Exchange. Here are some of the vital information pieces you’d ideally want documented and regularly updated.


  1. Documentation of the core digital communications and email communication strategy, outlining the factors that have influenced decision making until now.
  2. A break up of the costs of current email exchange system in use.
  3. Highlights of the service level agreements for the current email systems in place.
  4. Technical and business rationale of switching to a better (hosted) Exchange system. Kind of like in Transformers I when Bumblebee went from a beat up looking car to an awesome sports car! That was a better car for sure!
  5. Key policy aspects surrounding cloud based Exchange mail service.
  6. Gap Analyses to identify technical and policy gaps between current email service and hosted email service.
  7. Identify key stakeholders from business, legal and compliance, storage, security, network, end user experience, and record keeping to participate in the decision making process.

Failover Planning is Critical

The biggest misconception about hosted Exchange is that it is immune to downtimes. Note that in December 2015 and January 2016, Office 365 fell to service outages which left several global enterprises with limited or no email connectivity for some time. Disconnect from the mailbox can be catastrophic for most organizations, even if the downtime lasts just a few hours. Unless you do not want Skynet to track you but that is another topic entirely!

So, failover planning remains a critical aspect of the switch from on-premise Exchange to hosted Exchange. Whether it’s about keeping local copies of critical documents, or an email archiving process in place, be prepared to ensure business continuity even when cloud-based Exchange goes down.

Beware of Default Retention Policies

Consider the potential changes that accompany your enterprise move to hosted Exchange in terms of email retention. Microsoft Office 365 has introduced the option of extending the default time to retain a message past the earlier default of 14 days. This can be done by using a custom retention period. Ask Office 365 administrator to tailor this to your enterprise’s requirements. Kind of like Vic Mackey in The Shield tailored his punishment to criminals according to how bad they were but let’s get back onto the subject.

Even if you’ve chosen a managed service, ask the service provider to tune the default settings to your requirements. Exchange Online Retention Policy Tags can be used for default folders, and Messaging Records Management (MRM) can be used to ensure compliance, wherever you need. By preventing accidental deletion, you ensure that unsavory disruptions in your workforce’s operations are avoided.

Business Level Check Points to Take Care Of

From a business level, the decision to move to a Hosted Exchange should be made after due diligence and discussion on these factors:

  • Begin by devising a cost model that enumerates all your existing costs for support, software, hardware, storage, messaging services, and maintenance. Also, include staffing, network support, email archiving, mobile device access, perimeter security (no, this has nothing to do with guarding your business’s parking lot or property!), and licensing costs to make the model thorough.
  • Next, document how Hosted Exchange benefits your organization’s IT and digital communication goals.
  • Then, document the licenses, service contracts, SLAs, and financial liabilities your enterprise has in terms of email services. Include the legal fees of contract breakage in the analyses.
  • Segment your enterprise email users into different groups on the basis of their roles, the service levels they need, and the type of email services they require.
  • Create segments of email service features, based on the customizations, add-ons, and support levels that are on the menu (no, this menu does not have shrimp or dim sum on it!).
  • Review Hosted Exchange contract documentation with your legal department to make sure there are no gaps.

Technical Considerations to be Mindful Of

As a contributor to the IT strategy of your enterprise, here are the factors, considerations, and decision points you need to be mindful of:

  • Technical checkpoints include analyses of network dependencies, email archiving, government regulations and policies, directory, desktop upgrades, hardware and OS compatibilities, and service upgrades.
  • Understand existing technical issues faced with current Exchange service, and analyze how they will be resolved by witching to Hosted Exchange.
  • Plan the migration (no, this has nothing do with home sapiens migrating around the world tens of thousands of years ago!) in terms of costs, timelines, and resourcing.
  • Chalk out the major milestones of Hosted Exchange strategy implementation.
  • Consider all risk concerns from all stakeholders and document them. Decide on tolerance levels on each, and prepare thorough risk and compliance documentation and no, this should not be done on the diner’s napkin which is down the street!
  • Devise a disaster recovery plan with clear documentation of what Hosted Exchange features can help you technically achieve the goals of the plan quicker and better.

Remember, holistic preparation and documentation of Exchange email service aspects and systems, after detailed examination of all relevant factors, helps you take the Hosted Exchange switchover decision with confidence and clarity. And no, do not let Napoleon Dynamite handle this for you. That could be a drastic mistake!


About The Author

2 thoughts on “Moving On to Hosted Exchange? Keep this Checklist Handy”

  1. When I was a Hosted Exchange specialist, two more topics were also worth emphasising.

    One is that Hosting providers typically offer much more flexibility than Office 365 (they have to do this, as they can’t compete on price with O365) – discuss with potential hosters what they can offer you.

    The other is that back then, several vendors had not configured multi-tenancy according to Microsoft supportability rules. This may no longer be an issue now that Microsoft no longer ships their own HMC solution, but IT should assure themselves that their email is in a fully supported environment.

  2. Exchange Online is a standard SaaS service, not “hosted Exchange.” There is a big difference.

    A hosting agreement typically means the customer brings their own licenses and the hosting company simply sets up infrastructure in their datacenter. A hosting arrangement also typically allows for the customer to specify configuration and capabilities, with the hosting company setting the price based on those capabilities.

    SaaS services like Exchange Online provide a set of capabilities and every customer gets the same standard service with no ability to customize. Tenants are operated in the cloud with no ability to access infrastructure or datacenters.

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