IT Tips & Tricks

The Pros & Cons of Moving to SharePoint Online — and 7 Headaches to be Prepared For

Published 26 September 2018

Updated 2 May 2022

Updated 29 January 2024

No one really likes moving. It’s one of those times that friends regret owning a truck. However, while the process can be full of headaches, hard decisions and a lot of work, the end result is usually an improved situation.

This is especially true when moving from your crowded apartment, with little to no storage for all your stuff, to a spacious new home in the suburbs. There are still transition issues to deal with, but at least you’ll have a place for your growing collection of Star
Trek memorabilia.

... but at least you’ll have a place for your growing collection of Star Trek memorabilia.

The same is true for most organizations looking to migrate to SharePoint Online from SharePoint On-Premises (or from anything, for that matter). Migrating from on-premises SharePoint to SharePoint in Microsoft 365, like anything else, has its fair share of pros and cons that can make the process frustrating but the long-term rewards worth it.

Due to its many benefits, especially its seamless integration with other Microsoft 365 applications, many organizations are moving their server-based SharePoint to SharePoint Online. Is SharePoint Online the right choice for your organization? Wondering about SharePoint’s advantages and disadvantages in the Cloud? We’ll break it down for you and provide both pros and cons.


With over 200 million monthly users, Microsoft got it right with
SharePoint Online.

Incidentally, since mainstream support for SharePoint 2019 (on-prem) ended in January 2024 and end of life (EOL) is set for mid-2026, the current on-prem alternative is SharePoint Server Subscription Edition (SPSE), which, according to Microsoft, is the equivalent of SharePoint 2021 had there been such a thing.

It’s important to understand what’s in store ahead of time. It could save hours of otherwise avoidable downtime while helping you make the most of the benefits.

Advantages of Migrating to SharePoint Online

1. Rolling Releases

Users who migrate to SharePoint Online get to enjoy a rolling release model of new updates, improvements, and features. With SharePoint 2019 On-Premises, organizations are stuck with the point-release model — which may entail the uninstallation of previous versions and installation of the newer version. Even SharePoint Server Subscription Edition only updates once a month. Since new features are automatically pushed to SharePoint Online, users get to enjoy newly released upgrades much earlier.

Whether you intend to utilize Microsoft’s SharePoint Migration Tool (SPMT) or some other software to perform your migration, it’s important to understand their limitations when it comes to protecting your linked data.

2. Microsoft 365 Included

A Microsoft 365 subscription provides users with access to an awesome variety of useful tools, including options such as the Office suite, SharePoint, Teams and so on. Your choice of Microsoft 365 subscription level will determine which apps are available to you, as well as which features and levels of functionality. Bear in mind that various apps and features can be added, a la carte, to lower subscription levels.

3. 99.9% Uptime

When you migrate to SharePoint online, you’re investing in an excellent uptime-to-downtime ratio. This frees you up to focus on your own company’s performance instead of worrying about whether or not services will be reliable. With a 99.9% service-level–agreement reliability, SharePoint Online is truly phenomenal. One important aspect of this uptime is the issue of “availability from anywhere.” Users are no longer tied to the physical office, meaning they can work from anywhere, which supports increased remote positions. Combined with an outstanding support team (handling tickets within one business day), migrating to SharePoint Online sure seems worth the trouble.

4. Reduced Cost

Broadly speaking, SharePoint Online is cheaper for most companies, starting at around $5 per user per month, compared to SPSE which starts at around $15 per user per month. (Prices accurate at time of publication.) Although your total cost of ownership for SharePoint Server Subscription Edition may vary, migrating to SharePoint Online reduces heavy upfront hardware and licensing costs, the need for onsite backup software, electricity consumption, hardware maintenance costs and other associated costs of running SharePoint’s on-prem version.

... all underlying hardware and platform problems, as well as server upgrades and patches, are covered by Microsoft.

5. Improved Storage Capacity

There’s a huge emphasis on digital data management in businesses today, so the more storage space you have, the better your potential for growth. In addition to new features that help boost its already robust performance, SharePoint Online allows users access to 1 TB plus 10 GB per user license and file upload sizes of up to 250 GB. In terms of SharePoint Online’s pros and cons, this is a major pro if you value scalability.

6. Zero Maintenance

Unlike SPSE which requires in-house teams or external support from managed service providers or other consults for maintenance and technical support, all technical assistance for back-end processes in SharePoint Online is handled by the Microsoft team. This means that all underlying hardware and platform problems, as well as server upgrades and patches, are covered by Microsoft.

99% Uptime...

This is a major advantage since large organizations that want to maintain healthy on-premises SharePoint servers will need to hire dedicated IT staff to support end users, stay on top of the latest updates and patches, review hardware resources and handle all repairs and replacements. Even small and medium-sized organizations still need at least one SharePoint expert on their payroll.

7. Hybrid Deployment

Although SharePoint Online comes with a host of Microsoft’s top-notch security features, some users still have fears about data security. Notwithstanding Microsoft’s wealth of knowledge, experience and resources (which may facilitate a very secure and stable environment), some users may be reluctant to move their financial data, customer and employee data, trade secrets, innovations, research data and other sensitive information out of their network. However, they can still enjoy the benefits of SharePoint Online via a third option — hybrid deployment. Keep the most sensitive files on-premise and move the rest to the Cloud.

The Disadvantages of Migrating to SharePoint Online

Migrating to the SharePoint Cloud version does have its downsides and associated risks including loss of metadata, security issues, storage challenges and the difficulty in keeping data organized during the migration process. It’s critical that you keep these in mind while planning the transition from one database to another. This will help you take action to prevent serious financial losses.


Don’t let the inevitable speed bumps deter you from the benefits of the open road. SharePoint Online may be the best option for your organization.

We’ve already looked at the pros, and to keep this overview balanced, we also address the cons. Let’s take a look at some of the challenges associated with migrating to SharePoint Online — especially at the enterprise level.

1. Associated Costs

Migrating to SharePoint Online (or Microsoft 365) can be complicated and may require the expertise of SharePoint developers. Aside from the costs of hiring such professionals, other costs often come with migrating to SharePoint Online. These costs depend on a variety of factors including the size of your organization, the amount of data to be migrated, whether you need to transition your legacy systems, the level of customization used (if you are currently in SharePoint On-Premise) as well as the cost of upgrading the underlying infrastructure. The good news is that the higher such costs are for you, the more likely it is that you will experience greater ongoing savings over the years after making the switch to online. Although expenses could initially be more challenging, you may find that the migration to SharePoint Online is a better long-term investment.

2. Increased Bandwidth

Some new SharePoint Online users noticed some slowness in using the platform. They screwed up. They weren’t aware that SharePoint Online uses more bandwidth than its on-premise cousin. While the increased bandwidth is hardly a catastrophic issue, it can seem like one for those who are unaware. This “disadvantage” is preventable by simply increasing your bandwidth before migrating. This could be as simple and straightforward as increasing your overall connection to the internet, or you could adjust settings on your router to prioritize SharePoint bandwidth. That being said, with the current trend of remote work, the Cloud may be faster and reduce the company’s need for internal internet bandwidth.

Some new SharePoint Online users noticed some slowness in using the platform. They screwed up.

3. Loss of Back-End Control

There is no doubt that the redevelopment of existing apps can be costly, but the way that SharePoint Online works — versus SharePoint On-Premise — may not really produce a loss of back-end control, but more an evolution of control. There will most likely be newer, different ways to achieve the same outcome that are designed to favor the way the Cloud works as opposed to using older, local server controls and bending them to work in the Cloud. Either way, making the change is challenging and gets to the heart of migrating SharePoint-based apps to
the Cloud.

4. Disruption of Customization Settings

If you’ve been using the same software or operating system for a long time, you probably like to keep the settings a certain way. The rolling out of new updates/releases by Microsoft might affect users’ customization settings, which may make the migration from On-Premise SharePoint to Microsoft 365 seem like a hassle. But you can minimize this issue by keeping tabs on upcoming updates and considering their impact on your customization settings. Just add this to your checklist of something to be ahead of the game on, and you’ll be fine here.

5. User Adoption

Changing how we think about things and do our “work” always creates challenges. Often, these SharePoint Cloud migrations are part of an overall move by the company to a more modern network, managed by Cloud services versus locally installed and controlled network servers. Depending on the organization and how it works, this can add a lot of tasks to the to-do list and additional info to the learning curve. Again, you can overcome this issue —with a little pre-migration training for all the staff.

6. Data Security

Many companies that decide on Cloud migration still worry about the security of their data. Users are sometimes reluctant to move sensitive data to a Cloud environment and prefer to keep it on their on-premises data servers. The availability of SharePoint mobile apps is also adding to data security concerns since organizations are unsure of the relevant degree of protection available for corporate data exchanged via mobile devices. There are ways to mitigate this concern. Consider, for example, Microsoft’s In-Tune. This is an MDM (Mobile Device Management) software that allows companies to control users’ access to company data from mobile devices like phones, tablets, and laptops. You can even install it on PCs.

Depending on the volume of data involved, migrating to SharePoint Online can result in thousands (possibly even millions) of broken links.

This supports users in a BYOD (Bring Your Own Device) scenario as well. They can use their personal phone or laptop if they allow the company to manage it with In-Tune. This partitions the user’s system into work and personal areas and controls what happens in the work area. When a user is separated from the company, the company can wipe the remote partition and remove all company data from
that device.

7. Broken Links

Migrating from SharePoint On-premises to SharePoint Online requires moving all the data as well, and this can lead to a few problems.

Broken links are one of those problems.

Whether you intend to utilize Microsoft’s SharePoint Migration Tool (SPMT) or some other software to perform your migration, it’s important to understand their limitations when it comes to protecting your linked data.

Depending on the volume of data involved, migrating to SharePoint Online can result in thousands (possibly even millions) of broken links. These links can be found anywhere from within Microsoft Word, Access, Excel, OneNote, PowerPoint, and Visio, to Windows shortcuts, ASPX pages, Adobe Acrobat, Autodesk AutoCAD, InDesign and more.

Although fixing broken file links after migrating to SharePoint Online may seem plausible, manually scanning the thousands of files to test for broken links and fix each one of them is a daunting to near-impossible task — one which will require a lot of financial resources and time to execute. Using some sort of replace tool is faster, but still slow compared with the modern solution (mentioned below) and subject to many errors. Failing to preserve or fix broken links often results in the loss of crucial data, as well as the loss of major company profits. Even the most experienced IT professionals can be vulnerable to this issue.


Protecting links — pre-migration — is your most efficient option.

There is an effective way to handle this. You can use LinkFixer Advanced™ to prevent this common cause of data loss before it ever becomes a concern. When migrating to SharePoint Online, LinkFixer Advanced automates the management of file links, safeguards them during the migration process, and automatically repairs them. This software makes SharePoint Online migration easier by handling all the file links so they stay intact.

Note: If you have already migrated and are experiencing thousands or even millions of broken links, LinkFixer Advanced even offers a “Modify Links” option that can help you fix them — surprisingly fast.


Although there are speed bumps to migrating to SharePoint Online, its pros, in terms of speed, reliability, security, user-friendliness and reduced cost, far outweigh its cons.

However, before you make the move to SharePoint’s Cloud version, you should take a look at our checklist of things to keep in mind when moving your data to the Cloud. This list is a great preparation tool, and it may help you use both the pros and cons of Microsoft 365 SharePoint to your advantage.

One More Thing

The success of a SharePoint Online migration is measured not only by the smoothness and seamlessness of the migration process itself but also by the successful adoption by employees and end-users. It is important that your organization’s SharePoint consultants (or IT department) organize dedicated training sessions to present the migrated solution to employees and show them how to use
it effectively.

Now that you understand SharePoint Online’s key pros and cons, you’re ready to get started on your Microsoft 365 migration. For more information about LinkFixer Advanced, visit us at Feel free to send us a message or give us a call at 727-442-1822 if you have any questions about SharePoint Online or other data migration concerns.