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Address the Office 365 Migration Challenges Via Expert Insights

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Published By Siddharth Sharma
Anuraag Singh
Approved By Anuraag Singh
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Published On December 7th, 2023

Moving to a new cloud-based environment like Microsoft 365 is a critical task for any organization, big or small. So there is always a need to be proactive and identify the Office 365 migration challenges ahead of time. We have prepared this guide and filled it with the top 10 most common issues that users may encounter. Without further ado, let’s get straight to the topic. 

First of the Office 365 Migration Challenges is Planning and Strategy

Any complicated task requires pre-planning and a refined strategy; this is especially true for migrations as well. As discussed in the guide on service selection for cloud-based migration platforms like Microsoft 365 involves many variables. The list goes like like users, their mailboxes, calendar events, and contacts, to name a few. To make sure that all these items get to their destination, we need a foolproof plan. Furthermore, as organizational needs vary from industry to industry, the plan needs to be changed accordingly. For those who want to export offline Exchange database to Office 365 mailboxes planning will be different when compared to the strategy to migrate Yahoo Mail to Office 365 environment.

Resolution: Prepare an Organization Specific Plan

To make sure the planning goes smoothly, admins should have a thorough understanding of the organization’s needs and expectations. Moreover, the plan should include checks at key phases to avoid unnecessary errors. It needs to have a timeline that gives stakeholders an idea of the cloud transition duration. 

A strategy should be made by asking each member about their workflow on the current system. This simple task helps to make sure no critical tasks are interrupted due to the migration.

Challenge Number 2 is the Issue of User Adoption

Updating the local infrastructure is part of staying competitive with our peers. However, during this transition, one of the biggest Office 365 migration challenges is informing the average user. This problem is industry-wide as people get used to their old setup and are reluctant to change. Not to mention the extra cost the company has to bear in the form of maintaining two separate systems.

Resolution: Inform and Train the Users

Everyone on the team must have adequate training before the new system rolls out. This prevents user-level errors and allows for a smooth transition. Failure to provide training to the members leads to issues like permission errors and accidental deletions. Moreover, some of the user concerts can provide key insights on how to progress with the migration itself. Therefore, it is in the best interest of the company to provide training and address all user-level queries. Make them understand the benefits of the change by highlighting some real-life examples.

The Third Challenge is Navigating Legacy Software Hurdles

Most users hesitate to change because they fear that they will lose access to the system they are familiar with. There lies the problem of extending the lifecycle of legacy systems beyond their certified years. Although sometimes backward compatibility is preferred, knowing when to stop using old infrastructure is also important. Custom-built solutions are also difficult to migrate in one go.

Resolution: Update Apps to the Latest Version

This simple tip goes a long way toward reducing the workload of admins. Even if apps can’t be updated, in most cases, the cloud can adjust the data type automatically. It all comes down to the migration method of choice. For custom solutions, admins may have no other option but to build a skeletal structure on the cloud itself and then move the data manually. 

Office 365 Migration Challenges Include Managing Data Security

Migration scenarios put organizations in a vulnerable position. This is because they have to manually switch off security settings like firewalls and disable antivirus. Although this is temporary, this small window is enough for cybercriminals to wreak havoc on the system. That is why security should be at the top of the Office 365 migration checklist for all admins.

Resolution for this Office 365 migration Issue: Deploy Alternate Data Security Tactics

As the primary means of data security are unavailable, administrators need to get creative. Some ideas that we suggest that have helped other organizations are as follows.

  • Create a data backup.
  • Migrate the data in an isolated environment.
  • Provide migration information on a need-to-know basis.
  • Avoid delays and interruptions by using a professional utility for data transfer.

These are the tips with which organizations can prevent hackers from deploying malicious files in the system.

Fifth Challenge is to Ensure Network Bandwidth

As the local bandwidth is one of the factors responsible for determining the speed of the migration, no compromises can be made here. Moving thousands of user accounts from on-premises to the cloud means transferring terabytes of data. So any disruption can cause major data loss. Moreover, finding out exactly which packet of data went missing is another issue on its own.  

Resolution for this Office 365 migration Issue: Keep the Network Clear 

Although the bandwidth comes under the network engineer’s control, the admin must be in constant communication with them. This is to make sure that no other demanding task is scheduled on the network while the migration is taking place. Apart from the network, the local hardware must also be prepared for decommissioning once the migration ends.

Office 365 Migration Issue of Breaching the Budget

Another one of the challenges is the overall cost of the migration operations. As migration to the cloud is a way of cutting down on hardware maintenance costs, if migration itself goes out of the budget, the organization may rethink its need entirely. So it is the job of the admins to perform the migration within the allocated budget. 

Resolution: Use Procedures that Minimize Costs

First, only migrate the data that is required. In other words, perform a thorough cleanup operation to weed out the redundant data. One way to speed up the cleanup operation is to put the users themselves in charge of their data. It helps reduce both the time and the cost involved. Moreover, this has the added advantage of reducing accidental deletions. There have been many instances where data that is important to someone is deemed trash and removed. All manual tasks should be performed in-house to keep the cost as low as possible.

7th Challenge of How to Minimize Downtime

Migration of large amounts of data is not possible without severing connections between other linked services. This downtime is often inevitable, so the only possible option is to minimize it to a more manageable degree. If, for any reason, the downtime exceeds its preplanned time, the business workload can have a negative effect. Problems like failure to reply to business emails, not being able to attend online events, etc.

Resolution for this Office 365 Migration Issue: Careful Planning and Implementation

Small organizations can get away with a downtime-less migration as their data set is limited. However, for large businesses, this is not an option, so they must plan accordingly. One way is to anticipate it and thus plan the migration during holidays or non-working hours(for a staged migration). This ensures that even if we have to close other systems business is not affected as a whole.

Office 365 Migration Challenge 8: Issue of License Procurement

Sometimes failing to account for the correct number of users can lead to insufficient licenses. Furthermore, all those accounts that don’t receive the license cannot start their work on the new cloud platform. Admins have to reschedule the migration of remaining users, leading to unnecessary burdens and productivity issues.

Resolution: Count Users Correctly and Buy Accordingly

It is a good idea to purchase some additional licenses to avoid migration hiccups entirely. Moreover, Microsoft gives the option to either add the license to the other active accounts or get a monetary refund. So organizations can proceed with whatever option suits them the best.

Challenge 9: Struggle with DNS Setup

The domain name system is the mechanism responsible for delivering the mail to its correct address. Whenever there is a change in mailbox location from an on-premise setup to the cloud or even two different cloud providers, admins must also change this setup. Without this change, no email communication can take place.

Resolution for this Office 365 Migration Issue: Go to the DNS Provider Site

For this, administrators have to visit their domain service provider and perform the configuration there. These changes can only be made via the admin credentials. Also, the MX record and TXT configuration must be changed. 

Office 365 Migration Challenge 10:- Choosing a Proper Method

None of the other settings matter if the organization uses an inferior method for data transfer. Moreover, selecting a bad method can amplify the negative aspects of migration or even fail to migrate the data entirely. Apart from the obvious problems like delays, lack of support, and data loss, manual methods may allow cybercriminals to attack the system. As manual methods are generally for large-scale organizations, small businesses may fail to handle the complexity present in them. 

Resolution: Select a Trusted Migration Partner 

In the end, it is better to trust the automated SysTools Office 365 migration tool instead of the manual alternatives for this critical task.

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The tool has an intelligent design and includes industry-leading features like: 

  • Inbuilt filtering capability (based on date, workload, and users).
  • A variety of user mapping options to choose from. 
  • Single purchase with no additional subscription fees.
  • 24×7 support worldwide for any and all issues.
Conclusion

Here we learned how to deal with various Office 365 migration challenges that organizations may encounter in their cloud transition. Moreover, by combining expert insights with real-life scenarios, we were able to simplify the complex process of issue resolution.

As we have guided many organizations previously, we are happy to share these tips with you as well. Furthermore, a successful migration can take place only after dealing with these obstacles first.