There are plenty of misconceptions about migration to Office 365 from Live Exchange Server. One such misconception is that it is rather hard to accomplish migration from legacy on-premise Exchange deployments to Exchange Online. While it is not easy by any means to carry out large-scale migration projects, if you are well prepared and have the right tools for the task, the migration process can be as straightforward as it gets.

Let’s have a look at some quirks that can come in the way of seamless Office 365 migration for any organization. If you try to find and fix these issues in the planning phase itself, it is then easy to accomplish your goals.
Organizational requirements:
The requirements of an organization will vary from one organization to another. And you will have to deal with each on a case-by-case basis. For example, some organizations may have a strict policy of “zero downtime”. This means that the employees of such organizations cannot afford to have any breaks in their workflow at all. Hence, the migration projects should be planned so as to avoid any downtime whatsoever.
Regulatory issues:
There are also certain legal and regulatory compliance issues, depending on the geographic location of the organization, that one needs to be mindful of when moving data to the cloud. For example, the Health Insurance Portability and Accountability Act (or HIPAA) in the United States or the General Data Protection Regulation (GDPR) in the European Union.
Exchange corruption issues:
If your Exchange database EDB file is in a dirty shutdown state or is corrupted by any other means, then it can create problems during the migration process, as the information contained in the Exchange database may be affected.
Slow Migration:
An important factor, often overlooked, is the speed and bandwidth of the network connection. While Office 365 may have its own data throttling policies, the migration performance is directly dependent on how good the end-to-end network connection between the source and target server is. However, slow migration cannot always be attributed to network issues alone. There can be instances where the security practices adopted by the organization itself are so complex and strict that these policies hamper migration projects. Firewall configurations and proxies can also play a role in such scenarios.
Third-party apps:
If you are facing any migration issues, then it is also worth noting that some add-ons or server apps installed to get certain additional functionalities could be messing up your migration project. Once you have figured out which software is the culprit, it can be easily fixed.
Tenant naming:
Sometimes it so happens that someone has already used your organization’s name with Office 365 trial offers. When the time to set up a real tenant comes, your preferred tenancy name, as in, organization-name.onmicrosoft.com may not be available anymore.
Legacy Outlook clients:
Believe it or not, there are still plenty of organizations clinging to Office 2003. This can be a roadblock as far as direct migrations are concerned, as the Office 365-supported Outlook version starts from Outlook 2007 SP3. It is best that in such a case, the clients are first upgraded to Outlook 2010/2013 before migration. Also note that to take advantage of features like Office 365 groups, the users will need to upgrade to Outlook 2016. If a license upgrade for Office is not an option, then using OWA is the best alternative.
To conclude
Summing up, there are quite a few quirks to take care of when attempting migrations to Office 365 as discussed above. However, a utility that can make things easier for you is the EdbMails Office 365 migration tool, which enables secure, direct mailbox transfers between tenants or from on-premises Exchange to Office 365. It ensures zero downtime, preserves folder hierarchy, and automatically manages throttling and large mailboxes. With its intuitive interface and advanced reporting, EdbMails helps administrators overcome migration challenges and complete projects successfully with minimal disruption.
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