Top 5 Reasons to Migrate from Dropbox to Office 365

If you ask anyone what cloud storage service they use, it’s a good bet that Dropbox and OneDrive are the top replies. It’s easy to understand: Dropbox is the cloud storage service that really popularized the concept, and Microsoft Office 365 is the biggest player in workforce productivity. If you’re comparing cloud storage applications, the battle between Dropbox vs OneDrive would rival Godzilla vs King Kong. Let’s explore the details of the best-known cloud storage solutions. While they are toe-to-toe on many features, which we’ll explain first, the Microsoft Office 365 product, One Drive, is the clear winner.  We set the stage for the debate, and then give you the top 5 reasons to migrate from Dropbox to Office 365.

Storage, Pricing, Syncing, and File Sharing are a Level Playing Field

The basic functions of cloud storage have been in place for many years.  Dropbox was the pioneer in making it quick and easy for consumers and SMB’s to grab and share files, and that is why they led the market for many years.  However, the largest companies in the world, Microsoft and Google, quickly followed suit with their own versions of cloud storage platforms.  As a small business owner, you may have been using Dropbox for years.  It was free to get started and offered a simple solution for storing and sending files between your fellow employees.  Its simplicity was the reason it become so popular but that simple DNA is the reason why migrating to Office 365 is the better long term solution, as we will explain in detail shortly.

First, let’s set the table with the functions where Dropbox and One Drive are equals:

  • Storage Capabilities

Both cloud storage providers offer a version of “unlimited storage,” but that isn’t necessarily the full picture. With the Dropbox Business Advanced plan, for instance, you start off with 3TB. Accessing the full unlimited amount requires you to contact Dropbox support for assistance. OneDrive works in a similar way. For subscriptions with more than five users, each user will initially be given 1TB of storage, which admins can increase up to 5TB per user. Anything above this has to be requested through OneDrive support, who will then increase the available space to up to 25TB per user. Beyond this, you’ll need to look at SharePoint team plans and other enterprise or non-profit plans that require Microsoft approval. Basically, storage capabilities are a commodity and a tie.

  • Pricing

Like Dropbox, OneDrive comes with three business plans. The imaginatively named OneDrive for Business Plan 1 is $5 per month per user and gives 1TB of storage each. The OneDrive for Business Plan 2 comes with unlimited storage at $10 per month per user. Both plans require an annual commitment and don’t come with access to any Office apps. The Office 365 Business Premium plan is the plan you’ll need if you want Office access, at $15 per month per user for unlimited storage. You can take this down to $12.50 per month if you subscribe annually. If you’re not looking to store a huge amount of data, then there are well-priced cloud storage options from both companies.

  • File Syncing

Dropbox is the company that first popularized the sync folder model that is used in the industry. Dropbox sets up a sync folder on your computer for you to use, with any files or folders placed in that folder synced to the cloud. Both companies also offer what Dropbox calls “selective sync.” It allows you to choose which folders sync to your hard drive and which remain solely in the cloud to save space on your drive. Folders that are not synced will not be visible on your computer. OneDrive has a similar system called Files On-Demand. If you download an online-only file, it will remain on your hard drive after you close it. You’ll need to right-click and choose “free up space” to return it to being online-only. Both Dropbox and OneDrive use block-level sync, matching other big-name providers. Both Dropbox and OneDrive offer smart syncing and rewind features. Again in this category the battle ends in a tie.

  • File Sharing

Both of these software programs make file sharing simple by creating shareable links. Each service gives you the option to determine whether the recipient can edit or view a file. Dropbox and OneDrive also allow you to password-protect your links and set expiration dates to provide temporary access.

Top 5 Reasons to Migrate from Dropbox to Office 365

We’ve reviewed the areas where an individual or small business would be indifferent between using Dropbox or OneDrive. However, here is the rub. As your SMB scales up, the quick and easy solution is not the best way to run your operations. Graduating from a group of 10-15 colleagues who have a nice little business going to a professional organization of 25-200 employees with growth goals, work from home issues, remote salespeople, and the need for streamlined processes, requires investing in scalable technology.  This is where migrating from Dropbox to Office 365 pays off for C-Suite executives.

  • Security

Both platforms offer the typical industry-standard levels of security in their basic features. Dropbox offers two-factor authentication using SMS or an authenticator app. With OneDrive, you can use a text message or an authentication app to sign in, or as a Windows user, you can use Windows Hello to access your account via facial recognition or fingerprint, depending on your hardware.


OneDrive has also recently introduced a new feature called “personal vault,” which forces you to use two-factor authentication to access anything held within. It will also automatically lock after 20 minutes of inactivity. However, there’s no option to upgrade your account to zero-knowledge encryption, like you can with a service such as pCloud. Within the OneDrive program, as well as requiring two-factor authentication, personal vault files on Windows 10 are synced to a BitLocker encrypted area of your hard drive. There’s no similar protection for Mac, however, so if you’re an Apple fan, you might want to explore alternatives for encryption software.


You can use the OneDrive app to upload scanned documents directly into the vault without saving them on your phone first. The app even detects 3rd-party keyboards installed on the phone and encouraged users to use the default keyboard when entering the password. In terms of security, neither of the providers offer zero-knowledge encryption, so they’re never going to be the best cloud storage for encryption in our eyes. OneDrive does offer a little more protection, however, by having a personal vault that forces you to use two-factor authentication and will automatically lock during inactivity. OneDrive also offers block-level sync for files, with a personal vault for your most sensitive documents.  The sum of all these attributes tils in favor of Office 365, which is why we believe that OneDrive is a safer, more secure options for SMB and middle market companies.

  • Privacy

OneDrive is a little less obtrusive. The Microsoft privacy policy states that it doesn’t “use what you say in email, chat, video calls or voicemail, or your documents, photos or other personal files to target ads to you.” Despite this, with no zero-knowledge encryption and files that are based in the U.S., Microsoft engineers can access your files if required to do so.


Dropbox’s privacy policy states that it collects your data for a number of reasons. It also admits that the data that is analyzed includes “your stuff,” which is “what you decide to store in your Dropbox account” — meaning your files. Not only that, but your data is also disclosed to “trusted” third parties that include Amazon Web Services, Google and Zendesk.  Dropbox was also famously hacked in 2012, with a leak of nearly 70 million user passwords, although it has upped its game since then.


  • Collaboration Features for Employees

OneDrive is a Microsoft product, so it plays very nicely with other Microsoft apps. If you receive an attachment in Outlook, for example, you can right-click and save it directly to any OneDrive folder of your choice. As part of an Office 365 subscription, you also access to the full suite of business productivity tools that are the worldwide standard for office management. You can share OneDrive files, photos or folders directly through other O365 applications like Skype. OneDrive does have some unique features and options that might make it stand out from the competition, but the biggest selling point is its integration with the Office suite. OneDrive is completely integrated with other Microsoft services, including Office, Skype, OneNote and Outlook, making document sharing and collaboration a convenient and streamlined process.

  • Ease of Use / Mobile App

Both of these cloud storage platforms use the same tried-and-tested method to sync folders, with an accessible system tray or menu bar icon that allows you to quickly change settings. The experience is pretty similar across all three platforms. For Mac users, an issue with the Dropbox web app is that it doesn’t list folders first. The default is to list every file and folder alphabetically, regardless of type. If you have a large folder full of photos and subfolders, you may have to wade through thousands of image files before you find the folder you’re looking for. Dropbox and OneDrive offer mobile apps for Android and iOS. On the whole, these all appear fairly similar, although the Dropbox app has a serious flaw in the iOS version. Frustratingly, on Dropbox’s iOS app, the same problem occurs as with the web app on Mac: files and folders are listed alphabetically, and there’s no way to force the app to list folders first. If you’re locked into the Apple ecosystem, you’re getting a far worse user experience on both web and mobile. With a near-flawless interface, OneDrive is simply better, and OneDrive takes the trophy for its Windows integration. OneDrive is also includes a “photos” page that allows you to search your photos by places, tags and more.

  • Customer Support

Dropbox offer email, phone and 24/7 live chat support.  These are standard levels of support that would expect to get from any software application today. However, service levels are tailored to individuals.  As a growing corporation, you expect higher levels of service. You can’t rely on service quality from a call center rep who could be 1,000’s of miles or a world away. By migrating off the basic Dropbox program to the more sophisticated OneDrive application, it is customary to employ a Managed Service Provider (MSP) to assist your organization with the migration. With an MSP, the level of customer support is best-in-class. Companies like Concertium are able to provide both real-time support online, but they have the added benefit of providing service in-person and on-site. An MSP can send a help desk or Level 2 engineer directly to your office. Face-to-face assistance is the gold standard for customer service, and with a migration to Office 365, you’ll enjoy this benefit from Concertium as your MSP.


You may have started your business by yourself or with some close friends.  Budget was zero. Speed was critical. So it is possible you grabbed the quick and easy option for storing and sharing files. Or maybe you had been a Dropbox user for years, since the early days of its existence. You are not alone.  This is a common and understandable situation to be in.

But now your business is growing. Employees are scattered. There are people who work for you that you don’t see everyday or don’t know well at all. You need a full-scale solution for cloud storage that will meet the needs of your business, and security, privacy, collaboration, mobility and customer support at the key factors in your decision-making for any software you purchase. Given those criteria, the best choice for your business is to adopt OneDrive as your cloud storage solution, and we have provided the top 5 reasons to migrate from Dropbox to Office 365.

Concertium can provide a free IT assessment

Concertium can help with the migration to OneDrive. Contact us today, and our CEO and CTO will provide you with a free IT assessment. Our senior leadership is well versed in the top 5 reasons to migrate from Dropbox to Office 365.  We have completed this process for dozens of small and middle market businesses. We provide strategic technology solutions that businesses can afford.

If you would like to hear more about how Concertium can support your business and its technology infrastructure, let’s schedule a free IT assessment call with our CEO and CTO to learn more about your business and current technology needs.