After a conversation with Barron at Affinity Consulting Group, I was inspired to write a blog comparing Dropbox for Business and OneDrive for Business.

I enjoy comparisons, but I was disappointed by what I found. The comparisons were very “techy”, cost centric, or filled with useless feature charts. I have nothing against charts, but the feature set for each vendor should be standardized for this to be effective. For instance, I found Dropbox had “any device accessibility” and OneDrive had “mobile application”. These sound the same to me and without explanation how am I to know if they are different?

Also, a comparison does not have to be about which product is better. We all know a square peg does not go in a round hole, but does it mean the square peg is bad? No. Instead, it means that the square peg does not go “there”. The same can be said for software, one size does not fit all. I realize this makes the selection of a “winner” subjective, but comparisons of this type need no winner.

In this comparison, I have focused on those items that seem to interest most law firms and broken them into two main categories. Those categories are:

User Features

  • Save locally and sync to cloud/offline access
  • Sharing files (internally and externally) and controlling access
  • Co-authoring
  • Versioning
  • Apps

Administrative Features

  • Remote wipe
  • General security

Here is where I will save you some time. Yes, both products do all the above. BUT what matters is understanding how they accomplish each task and what, if any, are the notable differences.

User Features

Save Locally and Sync to Cloud /Offline Access

Here, there is little difference other that graphical user interface (GUI, or icons and pictures) and workflow. They both allow you to choose what to sync. Anything accessed from that synced location will be opened locally. Once saved in the synced folders, those changes will be synced back to the cloud. I’ve read that Dropbox works better with many file types, but I have no evidence that supports this claim, nor have I tried to test this. Also, those articles were usually 3-4 years old. Considering that cloud products are updated frequently, numerous updates would have been released by now.

Regarding offline access, again both are very similar. If the file is synced locally, you have access to that file on your computer. If that file is updated by someone else while you are offline, you will not receive those updates until you are reconnected.

What is an upload conflict and how does each product handle them?

An upload conflict is when one person works on a document offline, and another person works on the same document online. Then, when the offline person reconnects, you have two different versions of that document.

Microsoft – Resolve Conflicts in Upload Center

Dropbox – Conflicted Copy

Sharing Files (Internally and Externally) and Controlling Access

Since the workflow and options available are somewhat different, I’ll be addressing each program separately.

OneDrive for Business

To share a document (or folder) internally, simply right click on that document and choose share. You will be prompted to enter a name or email address and a message. If that person is inside your organization, they will receive a link to that document. Alternatively, you can just send a link to that document.  Both options provide the recipient access to that exact document, not a copy of the document. Finally, you can attach the document to an email as a link, or as a full copy. The latter will provide the recipient with their own version of that document.

Sharing externally follows that same process, but this must be enabled by the organization. Otherwise sharing externally will not work.

Now what about permissions for shared files? You have several different options when controlling access for sharing documents

Options for who can access this link (options vary based on admin settings):

  • Anyone with this link gives access to anyone who receives this link, whether they receive it directly from you or from someone else. This may include people outside of your organization.
  • Only people in <Your Organization>gives everyone in your organization access to the link, whether they receive it directly from you or from someone else.
  • Only specific people gives access only to the people you specify, although other people may already have access. If people forward the link, only people who already have access to the item will be able to use the link.

By default, allow editing is turned on. If you want people to only view your files, uncheck the box.

Dropbox for Business

The workflow for sharing is a little different. Hover over the document (or folder) that you want to share and click the share button. Enter the user’s name and choose share. This will provide them a direct link to that document, NOT a copy of the document. This is where things get a bit different. Sharing a link will provide the recipient a COPY of the file. So, if you share a link internally, you have given someone in your organization a copy of the file, not the actual file. Meaning, if they make changes, those changes only affect their copy, and not the file you initially shared.

It is important to understand the difference here. In OneDrive, sharing and providing a link are the same thing. Both provide the recipient access to the original file.

In Dropbox, each action is very different. Sharing is sharing the original copy. Providing someone with a link is giving them their own copy.

While this may sound like a problem for Dropbox, it’s NOT! This demonstrates the importance of training and proper use of a tool. A hammer is good at driving nails, but using it to polish your Audi would be tragic. Everyone still thinks the hammer, when used properly, is a good tool.

Now that I have made that important disclaimer, let’s look at permissions in Dropbox. First access can only be controlled at the folder level. Meaning If I share a document with someone, I cannot control their access. There are two access options when sharing (to share a file with someone they must have a Dropbox account). Additionally, you can share links with expiration dates, so your firm’s information does not remain out there for eternity.

People with edit access can:

  • Edit files
  • Comment on files
  • View Files

People with view access can:

  • View files
  • Download Files
  • Comment on files

When giving someone a link they can:

  • View files
  • Comment on files
  • Download copies of files

*Note: people who receive a shared link/file won’t be able to edit the original file in any way*


Both tools allow users multiple people to access a document simultaneously and make changes collaboratively. Both programs will re-direct you to the necessary office application (Word, Excel, etc). The best experience occurs when using the online versions of Word or Excel because changes happen instantly.

However, if you coauthor from Dropbox, all co-authors must access the file from, not the local synced folder. This places some limitations when attempting to co-author from a mobile device. Another thing to note, is that the file must be in a folder that is accessible to all parties that may want to co-author.

In OneDrive, the documents must be in a location that is accessible to everyone who may want to edit that document. This works better with Word Online, but you can use the desktop app. You must make sure automatically share changes is setup in your preferences. Depending on what is selected, your experience could be drastically affected.

Microsoft Real Time Co-Authoring

Dropbox Co-Authoring


Dropbox and OneDrive track and store versions of a document automatically. The way you access each is different, but the outcome is largely the same. You can also restore previous versions.

Depending on your version of Dropbox, your file’s versions are retained for 30 days or 120 days (Dropbox Business). More information about Dropbox’s Extended version can be found here. Information about plans and what is offered can be found here.

OneDrive will retain versions as well. The settings can be adjusted by site. But by default, versioning is enabled (yes, it can be disabled), and will retain 500 versions of a document. However, I found this setting very difficult to locate within the OneDrive interface. Also, this was not listed anywhere on Microsoft’s website that I or Google could find. Even the instructions providing by Microsoft, found here at the bottom, to access this information were not helpful. (Never mind the misleading title).


As far as I tell both Dropbox and OneDrive are available on Windows, Mac, iOS, and Android. While I have not tested the applications on each platform, nor do I intend too, they are out there. How well the apps work, their features or lack thereof, are not in the scope of this blog. If the apps do not work on your device you can always access the documents though a web browser if needed.


Administrative Features

The benefits for the admin team will differ greatly from those for other firm members. In almost every software category, the main concern for the management team is control. “Can I control users, groups, features, access etc?” Yes, you can.

Remote Wipe

Remote wipe is the ability to remove all documents or data from a mobile device if it is lost or stolen. For this to work with any software, the device must connect to the internet. Both Dropbox and OneDrive have mobile device management (remote wipe) capabilities.

General Security

Both programs use encryption at rest and in transit. Both programs allow dual factor authentication and allow the administrators to require everyone in the firm to secure passwords. Administrators in both programs can control access to files/folders and create/remove users.

But what I find most interesting is the ability to place controls on how firm members use the programs. For example, in both programs you can prevent firm members from sharing externally (sharing with people outside your domain/firm). Other editing features can be disabled or enabled. Both Dropbox and OneDrive (besides the document versions information noted above) have intuitive admin consoles that allow you to control various features within the program.


Finally, integration. Both products integrate with a lot of the major practice management solutions. The specifics and functionality of the integration change depending on the program, so make sure to get a demo or thorough review before deploying firm wide. While most links are simple, some have weird functionality.

Final Thoughts

I will say this, OneDrive is already part of the O365 suite. So why pay for another service when you have one with all the major functionality already?

Now, to be clear, if you have a specific need for a feature that does not exist in OneDrive, or you don’t have O365 then the field is even.

As I stated initially, there is no winner. Know your specific needs and choose accordingly.