A Guerilla Usability Test on Dropbox Photos

Part 1 in a series on reimagining the Dropbox Photos experience

Francine Lee
Design Insights from Designer Fund
4 min readFeb 11, 2014


Dropbox is a great product, but a quick usability test reveals that people run into two critical issues with Dropbox’s Photos feature.


Identify the pain points of Dropbox’s current “Photos” interface:

Current dropbox.com/photos UI

Test Parameters

  • What: Dropbox web app platform.
  • Who: Existing Dropbox users who own photos.
  • Where: Screen passerbys outside of a coffee shop, SF.

Test tasks

  1. Upload a photo(s)
  2. View a photo(s)
  3. Share a photo(s)

(Tasks were determined based on essential needs of a photo storage app. Tasks were phrased as open-ended scenarios to avoid leading the user to solve their problem in a predetermined way. Example in notes.)


Reviewing notes, identifying the usability issues and prioritizing them:

notes on each session. identifying each issue with a post-it
bucketing issues by similarity, then naming the buckets. ordering buckets by frequency.

Findings: 2 Key Issues


Users expect 1-clicking on a thumbnail -> enlarge a thumbnail

“My god. How do I look at this?”

Every single user’s first interaction in trying to enlarge a photo was to (single) click on a thumbnail. Half of the users never attempted to double-click a thumbnail (the current way to enlarge a photo), and instead went back to the Files page to enlarge a photo file from there.

Interactions when attempting to enlarge a photo

The single-click seems to be a valid expectation considering a single-click on items in the “Files” page = enlarges the photo.

RECOMMENDATION: Allow users to enlarge a thumbnail in the way they expect to. Redesign the [single-click] action to an [enlarge thumbnail] outcome, and replace the action for the [selection] outcome. Selection via transparent checkboxes is a prevalent design pattern within photo apps.


Users think “Photos” is a directory within their Dropbox (but it isn’t)

“Where the heck is the upload button?”
“It’s terrible. I don’t even know where the album is that I just created.”

There’s a few issues in onboarding:
Users expect an “Upload” function in the Photos page. In attempting to upload photos, users scan the top nav for an upload button, then click other areas for a resolution (account, settings, and Files directory). It’s not clear to users that “Photos” is not actual Dropbox directory (it’s a visual feed of their photos), and that items therefore can’t be uploaded into it.

Interactions when attempting to upload a photo

As a result of failing to upload and enlarge photos, some users were unsure of the benefits of the “Photos” page .

Some users also didn’t understand how albums worked. Upon creating one, they checked for that album back in their Files directory—only to find it didn’t exist.

“Why are ‘albums’ not actually real!?”

RECOMMENDATION: Users need to know that “Photos” is not a real directory, and that albums are not real subdirectories. Tooltips, onboarding modals, or making the correct file structure explicit are possible solutions here.

A Design Suggestion

Users want to enlarge a photo with a single click. Users need to know that “Photos” and albums are not real directories. Potential solution?:

See below for the anatomy

1. Enlarge a thumbnail with a single click

2. Select via checkboxes

3. Understand that the Photo feed and albums are not real

Up Next

Part 1 of this series on reimagining the Dropbox Photos experience is user research. The goal of user research is to understand the target user’s needs and motivations. I’ll be using these needs and motivations to drive the development of the product at each subsequent step of my design process.

Here’s my process:

We’ve covered Part 1: usability testing

I want to make sure I design a system that people need.
Personas and job stories to follow in the next post.

*I don’t work for or represent Dropbox. I’m a mere mortal shipping UX projects at 2 design programs until the end of March. I study under Laura Klein & Kate Rutter @Tradecraft and Megan O’Rorke @GA_SF. Dropbox is one of the few products I use daily and love; I’m exploring how I might make it better ☺