Dropbox Review - 2021 Content Service Provider Roundup

October 29, 2021

This is part of the 2021 Content Service Provider Roundup series.

Founded in 2007, Dropbox has been in the personal cloud storage space from the beginning. Viewing them in a business context, Dropbox has a lot to offer when it comes to team plans with 5TB and Unlimited storage offerings. Why choose Dropbox over the similarly named Box, OneDrive, or other storage providers? Dropbox claims to have one of the best in class streaming sync technology that we’ll put to the test. Furthermore their free trial doesn’t require a credit card making the signup experience frictionless.

User Experience

General Impressions

Installing Dropbox on a mac is fairly straightforward with a single click installer, though unlike other sync agents it requires accessibility controls to be enabled. The installer itself is a <1 MB file that downloads the application itself during install. The fully installed application is around 422 MB at the time of writing. Unlike the old single user Dropbox app, the team oriented Dropbox app (which mirrors the WebUI) is collaboration focused. The comments I add in a word document show up in the desktop app for Dropbox. Activity is shown right next to the file in the app and online, making it hard to miss and easy to see changes as they happen. Dropbox is very proactive about trying to sync your folders, and even screenshots as they happen, replacing them with dropbox links if you want.

Tracking File Changes

Like all other cloud storage platforms we looked at, Dropbox offers file versioning as a means of tracking changes. Unlike OneDrive or Box, Dropbox limits the number of file versions by days (180 across all plans). This can be really advantageous if you’re looking for a solution for frequently changing files. Especially in combination with their best in class syncing technology makes them a strong choice for the frequently changing file use case. Dropbox offers file and folder level reversion in the case of malware or ransomware infection. One difficulty we encountered when using Dropbox’s activity stream is that file updates and comments are not versioned in the UI and therefore difficult to corroborate.

It’s difficult to see what comments are associated with what version of the file, and when they were made in comparison to the file edits. The differential syncing works well, even with a large 1GB text file, I noticed that the difference syncing was significantly faster (on the order of 10 seconds) than the initial upload (which took a few minutes), which was very promising. In addition to files not being versioned in the UI, differentiating and communicating file versions is difficult as file’s don’t have corresponding version numbers and instead changes are displayed by date. Reverting to a file is easy enough through the UI and clicking on a file version luckily brings up the file preview.

Documentation and Ownership

Dropbox features a prominent activity stream that provides comments alongside the file, including comments from within office documents. The most recent activity is also viewable on the file list itself which makes finding who made the last edit even easier, though you’ll still probably want to know the entirety of the edits since you last opened the file. Dropbox also features Dropbox Paper which is their real time collaborative text editing option (as shown above in Tracking File Changes). One of the best features for documentation I’ve seen for collaborative documentation in a cloud storage tool is Dropbox Spaces which lets you add rich text descriptions to folders, tag users, include todo items, right at the folder level. 

Internal Collaboration

Internal collaboration seems super easy. Membership to a folder is easily viewable in the sidebar. By default everything in the team space is accessible to everyone, and everything in your member folder is accessible to yourself. This split seems very convenient and likely what you’ll want for a small team. As the team gets larger you can configure subteams (called Groups) and after creating a folder can scope the permissions down to the specific Groups or users via the Share… settings.

Whether or not you like it, sharing a link by default will allow anyone with the link to view it. This can be remedied from an admin perspective by simply changing the default link sharing settings in the admin panel as pictured below.

Dropbox offers a slew of integrations that make it easy to integrate into your existing workflows or tooling such as Office 365, Google Docs, Salesforce, etc. Finally Dropbox does allow you to enable file locking as a collaboration mechanism to prevent you from overwriting other’s file changes, and vice versa.

Client Collaboration

Dropbox features a few tools which make client collaboration nice, including link sharing. We found the link sharing UI slightly unintuitive. Sharing a link was very easily done from the sidebar or by right clicking on a file. Clicking to copy a shared link immediately shares the file with the default settings. Seeing the permissions and scoping of the link was slightly hidden out of the way, only showing up when you went into the share settings for the particular file.

Link expiration is a nice feature. Password protection is available by scoping down the people the link is accessible to.

Furthermore because of the rich web preview capabilities, you can restrict the link to be preview only and prevent file downloads. Dropbox features a built-in integration with HelloSign. A DocuSign integration was previously available but has since been retired, so a seamless integration with DocuSign is no longer available. Shared items can be audited via a report in the Dropbox admin console. Simple metrics for what’s been shared and where are also available.

Sharing reports are prepared asynchronously (as they are in most platforms) and then uploaded to a specified folder. Dropbox features email notifications for when the reports have finished generating. An example sharing report is available below.

However on top of the CSV output sharing report, you can also get a richer view into sharing via the new (at the time of writing) External sharing admin tab as pictured below.

Dropbox Transfer is Dropbox’s anonymous file sharing service, that allows you to easily request files from clients up to 100MB without granting access to your Dropbox account. Moving the file from Dropbox Transfer to your account is as simple as clicking “Save to Dropbox” and selecting the destination folder. Using Dropbox Transfer to send outgoing files seems to have less utility, though it adds a bit more transparency and auditability into seeing who downloaded what links since you can have email notifications and logging for downloads and views.

Beyond just Dropbox transfer, dropbox also offers a File request that lets you request files from clients that make their way directly into your Dropbox folder without granting access. You can do this by right clicking on a folder and then clicking Request files…


Search works inside office documents and standard text files as well as within the file path. Searching within a large text file (~1GB) did not work. On reducing the file size the file then becomes searchable and previewable. Arbitrary text based files are limited to 8MB for these features. Search shows the first instance of the term in context, making it easy to see how the term is used in the document.



The trickiest aspect of any cloud storage solution is the migration (and adoption) story. The Dropbox data migration add-on is just that, an add-on that is available to business advanced or enterprise plan users. The add-on is powered by Cloud FastPath, which has been acquired and rolled up into Box Shuttle. In general Cloud FastPath seems somewhat complicated to use, their new user guide is 44 printed pages long, though we haven’t tried it and users seem to love it and claim it works great. Cloud FastPath supports a wide range of data sources including Sharepoint on premise or online, OneDrive, Box, Google, S3, and more. Pricing information on Cloud FastPath is scarce and it’s not clear how much longer they will support migrating to Dropbox after being rolled up into Box. Other options include movebot.io ($0.04/GB for simple block storage transfer to $0.39/GB for organizational features), Tzunami cloudsfer (pricing not published, but old data shows this is somewhere around $1.25/GB). All in all Dropbox is probably one of the weaker choices for enterprises requiring large data migrations into the platform.

IT Administration

In terms of administration Dropbox offers a wide range of functionality on the admin dashboard. Dropbox provides auditing (see Tracking File Changes and Security) both from a link sharing and user action perspective. Insights make it easy to see file activity as it happens over time. Member management and SSO integrations are available (though SSO integrations are only available with the Business Advanced or Enterprise plan). Two factor authentication and password requirements can be set at the account level and administrators can also reset individual user or entire team passwords.

Device restrictions per use can be enforced. Dropbox features the ability to delegate control and management of group administration. Extensively Dropbox allows configuring the following controls on the settings panel


Oddly enough throughout Dropbox’s terms there is no mention of a service level agreement. Further research indicates that Dropbox does not offer an SLA that is common among most enterprise SaaS agreements, usually promising 99.9% or greater uptime. Also interesting enough Dropbox has scheduled maintenance windows, something not seen at any of the other cloud storage providers we’ve reviewed. Like Box.com, Dropbox does use Atlassian statuspage and therefore their incidents are publicly available. We’ve looked through the incidents for 2021 so far and have documented them as below up to the time of writing (October 28th 2021).

Of the 30 incidents for the first 10 months of 2021, 15 (50%) were scheduled maintenance. All scheduled outages are only 30 minutes long. The average duration of a non-scheduled event was 63 minutes, excepting one multi day event. Only one event is critical (red). Overall, although Dropbox does not offer a service SLA we find that it’s availability is much stronger than competitors such as Box (see our Box comparison under Stability here).


The Dropbox App Center provides tons of applications that integrate with Dropbox. Contextual suggestions for file type actions show up in the file sidebar.

HelloSign is the preferred/integrated signing platform as Dropbox has acquired them in 2019. As I mentioned earlier in the review, DocuSign integration no longer works. Overall there are around 150 applications available for integration in the App Center, most notably Zoom, Slack, Trello, G Suite, Office and Teams.


Dropbox uses standard AES256 encryption on the server, and SSL/TLS at the transport layer to secure your files. This is pretty standard across service providers online. From a password perspective, Dropbox offers features around setting password strength and two factor authentication. Furthermore administrators can reset individual user passwords, or everyone’s passwords at any time. Dropbox provides great link sharing auditability (see Client Collaboration), and settings (expiration, password protection) as well as user activity auditing as pictured below.

Overall dropbox features strong content level security controls though perhaps not as fine grained as Box.com.



Team plans offer 5TB (for standard) or Unlimited (for Advanced) storage options. Version history is kept for 180 days. Note that they do offer extended file versioning as an add-on up to 10 years for compliance applications. Unlike OneDrive, old versions of a file are not counted towards your storage quota. Storage quotas can be set so that all users have the same amount of storage (in the case of the 5TB plan). Dropbox limits downloads to 1TB of bandwidth per day for Business Standard, and 4TB for Business Advanced and Enterprise. Note that accounts on trial have lower limits (20GB or 100,000 downloads). This is explicitly noted for shared links, it’s possible that private data transfer limits are larger. Dropbox limits are based on the method of upload. For the website, limits are 50GB, for the API 350GB, and for the desktop and mobile applications 2TB. Dropbox notes that accounts with more than 300,000 files may experience performance issues. File and folder paths must be less than 260 characters, making them friendly on all platforms.


Comparative analysis of Dropbox pricing will be available once we have finished reviewing all platforms. Team oriented plans of Dropbox start at $15/User for the Business Standard and $20/User for the Business Advanced. See https://www.dropbox.com/plans for more details.


In summary Dropbox is a great cloud storage offering. It’s collaborative features within the Dropbox app provide almost every feature available when it comes to cloud storage. From an end user perspective the app is easy to use and set up. File activity is easy to understand and clearly visible. One downside is that versioning is not entirely clear from a UX perspective and comments and versioning are not clearly tied together, making using comments to document or discuss specific changes difficult. On the note of downsides the lack of diverse tools for data migration is a sore one, as well as the lack of an SLA. Despite this lack of SLA, we find Dropbox to be more reliable than most of their competitor’s. Dropbox spaces, while simple, is one of my favorite approaches to storing folder level documentations. From an administrative point of view, Dropbox is easy to audit and administer. File limits are generous compared to other platforms (2TB), the intelligent difference syncing actually works, and in combination with the 180 day version history mean that Dropbox is by far the strongest platform out there for large file sharing and collaboration.