Key Office 365 Migration Challenges And How We Overcome Them

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Futurism Technologies

April 9, 2019 - 3.2K
5 Min Read

Key Office 365 Migration Challenges And How We Overcome Them

The success of the Office 365 migration challenges revolves around the right selection of the partner. This claim stems from the fact that though Office 365 does offer several efficiency-boosting benefits, migrating to it is a multi-pronged process. It requires the readiness of numerous factors that constitute the core of the operational efficiency.

Thus, despite Microsoft’s allotting more responsibility to partners for ensuring a smooth transition, a migration of this magnitude can present substantial roadblocks that hinder an otherwise smooth transition process. These roadblocks are Office 365 migration challenges.

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However, this should not be the reason to leave on the table the wonderful advantages that Office 365 offers. After churning a lot, which is based on still observations, we have come up with remedies to overcome some of the fiercest challenges that Office 365 migration throws. 

A) Structuring Hybrid Solutions:

Structuring Hybrid Solutions for office 365 migration

For organizations that wish to move all employees from on-premises applications to Office 365, the migration process is usually straightforward and simple. The same process becomes more complicated for organizations that want to retain some aspects of their on-premises environments while moving the rest to Office 365.

The latter is the common case scenario for organizations that require Office 365 for their mobile workforce but also want to keep on-premises solutions for employees working behind a desk. A hybrid structure appears more sensible approach for organizations who cannot function without maintaining data stores for thousands of users.


We propose the implementation of a single sign-on with Active Directory Federation Services to harness the benefits of Office 365 and the familiar on-premises solutions.   

B) Active Directory Quality:

Active Directory Quality

For a smooth migration to Office 365, the synchronization of Active Directory between on-premises Active Directory and Office is key. This is particularly true if you are opting in for the hybrid solution. Moreover, Active Directory quality is needed when setting up Single Sign-on (SSO) using Active Directory Federation Services (ADFS) or Microsoft Azure Active Directory Connect. Despite this, the state of the Active Directory in your company is the most overlooked component in the whole migration process. 

Your Active Directory may be ailing with a surprisingly high number of old or inactive user accounts, bad data quality, inconsistency in UPNs. It usually happens when Active Directory properties haven’t been exposed like here especially when using Skype for Business and SharePoint Online.

Image to Download office 365 migration checklist


We thoroughly inspect your Active Directory before making the switch to Office 365. If we find any issues, we perform Directory cleanup tasks to remove any duplicate values in the proxyAddresses attribute. To negate these kind of Office 365 migration challenges, we also ensure that each user who will be assigned service offerings has a valid and unique email address along with focusing on making optimal use of the global address list (GAL) by ensuring that the information in the attributes is correct.

C) Transition Difficulty:

Transition Difficulty

The truth is some areas of organizational tasks are complex to migrate. Migrating SharePoint Online, for example, it macreate discomfort to users. A linked Excel spreadsheet is a case in point here. Links directed to legacy environments that are not SharePoint will fail to update automatically.  Similarly, as legacy ECM systems do not use concepts such as inheritance, they will differ from permission models on SharePoint Online.


We present very realistic expectations for our clients. To minimize user confusion, we provide reports with details such as file source location, file name or SharePoint Online location.

D) Bad Quality of Network:

Bad Quality of Network while migration

Migration from on-premises to Office 365 can become a lengthy and daunting process for organizations that use limited bandwidth and have a huge chunk of data to migrate. And even after migration, poor internet connectivity can prove detrimental to the customer experience – giving rise to myriad Office 365 migration challenges. 

Note that unlike more forgiving Exchange Online where only a few users will notice that e-mails arrive a few seconds late, in OneDrive and SharePoint, low bandwidth will result in an endless loading of files and pages. Similarly, in Skype for Business, the effectiveness of online meetings will be afflicted by the rather poor quality of sound and video performance.


We use migration tools to help overcome this problem. These tools bypass mailbox data multiple times before making the actual cut-over. It ensures that your data is imported multiple times before finally moving into a mail. After making the final switch, your mail is Office 365 ready. 

E) User Adoption:

User Adoption of office 365

A man is wired to feel comfortable in the zone of known terrain.  Having used Outlook and the rest of the Office applications since the inception of their careers, use of Skype for Business, SharePoint, OneDrive for Business or Microsoft Teams will come across as a cultural shock to your clients as well as their employees.

There will be resistance to its use, as you cannot expect them to embrace the new technology in a flash when being left to their own resources.  Moreover, it takes time to figure out what to communicate, what to implement, and when.


To create the feel of familiarity, we reach out to the right stakeholders regarding user adoption as early as possible in the migration process. We do it by creating touch bases with internal communications, HR, and the Marketing department. The aim is to curtail these Office 365 migration challenges by educating and prepare them for the migration process along with the clear statement of office 365 benefits.Also, we make sure to feed them with the right info at the right stage of the migration process.  

F) Security Concerns:

Security Concerns in office 365 migration

The idea of sharing the same multi-tenant server with what looks like a million other small companies still send a ripple of worries among CIOs. Despite cloud providers efforts to calm the security concerns, CIOs still hesitate to share business information in something as seemingly vaporous as the cloud. The question of data safety has hindered many switches from corporate-owned mail servers.  The cloud providers need to address the burning question that almost all the organizations ask: how safe is my data?


We preemptively approach these sort of Office 365 migration challenges by involving stakeholders as early in the migration process as possible.  If they have resentments regarding the security concerned with physical access to Microsoft data centers, we tell them that Microsoft takes the full responsibility of data security. With the help of Office Trust Center, we try to answer all the security questions that our clients may have.

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