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4 scary stories of failed Office 365 migrations that will give you chills!

In theory, moving from on-premise Exchange to the cloud-based Office 365 should be a straightforward process. But this assumes that you are going about in the right way. The fact is that all migration processes – whether they involve Office 365 or not – require planning, familiarity, a methodical approach (not to mention a cool head).

So what can possibly go wrong – and what wider headaches can this cause for a business? Here are some of the problems we have come across…

Incomplete migration of email

Let’s say that for whatever reason, you’ve retained large quantities of emails. Quite understandably, these have been archived methodically in various folders. Yet here’s the thing: you move the mailbox to the cloud and the stubs are broken. At some point after the migration, your staff realise that they are unable to access archived emails. From customer service right through to HR, if your business is heavily dependent on email communication, the blowback from this can be a real headache.

This happens where your legacy archiving method isn’t compatible with Office 365. There are ways around it, however – although the way around it depends on the export capabilities of your archive solution. A word of warning however: it’s a far more straightforward process to pre-empt the problem, by understanding what the situation is in terms of native export tools and data extraction within your current infrastructure – rather than trying to fix it later.

OneDrive sync issues

Once it is up and running in the right way, OneDrive provides the ideal tool for accessing business files remotely and for multi-user collaboration on shared documents. Yet for many clients who approach us for advice after they have already undergone an Office 365 migration, problems with OneDrive feature prominently.

Files can fail to sync properly due to a various reasons. It might, for instance be down to a specific problem with the version of Office you are migrating from, or it could be that you’ve failed to deploy the Next Generation Sync Client correctly. It’s fixable, but the best way of resolving it is via a full diagnostic check: where, exactly, does the problem lie and what needs to be done to remove it?

Sharepoint permissions incorrectly configured

This is a good example of a simple oversight that can have unfortunate repercussions for a business. It happens when entire document libraries are moved over to Office 365. The transferral occurs successfully; it’s just that the job of setting access permissions has been overlooked. At some point, the omission is realised and access permissions are reinstated – but not before members of staff have been able to access sensitive files that ought to have been kept out of bounds (to do with HR, for instance).

Some more potential stumbling blocks…

Let’s say that your pre-migration infrastructure was never really all that reliable; it tended to be unstable and occasionally prone to corruption issues. It’s good practice to identify those problems and take them into account before the migration process takes place – to avoid any unwelcome surprises.

Likewise, there’s the issue of downtime while migration is happening. The smoothest migrations happen after a realistic assessment of what’s going to be required. It’s only then that a business can work from a reliable time estimate on how long critical systems are going to be down. The decision can then be made on when to migrate to minimise disruption.

Microsoft bills the migration process as being relatively easy; but when you realise the potential problems that can arise, you see that expert input can save a lot of hassle.

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Tom Finnis

Tom Finnis is responsible for the delivery of IT support services and projects to help4IT's clients, as well as the development of the company's cloud infrastructure and related products. Tom has overseen the growth of the Help4IT technical department from 3 to 12 full-time staff, with additional contract workers, creating the systems and procedures to enable the efficient provision of the company's high level of support. More recently he has led the design and deployment of help4IT's multi-site cloud infrastructure.


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