Search for the elusive, perfect file & screenshot sharing tool

In my daily work, as well as the maintenance of three blogs, I frequently need a tool that allows me to conveniently share files and screenshots. This article discusses my search for that elusive perfect app.

Use cases

Following are my typical use cases:

• I need to send someone a file that’s too large for email.
• I need to quickly post an annotated screenshot to a work colleague in chat.
• I need a fast and efficient way to get an image into a blog article.

Droplr—a great service

Although I started with CloudApp, I later moved to its main competitor, Droplr. The reason? The $10 monthly fee for CloudApp just felt a bit too high for such a service, while the $5 monthly fee for Droplr didn’t.

Droplr runs on both the desktop and iOS devices, and provides a wealth of features:

• Via keystrokes, you can snap and upload a screenshot, an area of the screen, an annotated screenshot, a screencast recording, a Markdown note, the contents on the clipboard or whatever’s selected in the Finder.
• For those times you need some security, you can optionally password-protect your uploads, and set them to auto-delete after certain periods of times.
• If you send someone the Droplr link to a file that hasn’t finished uploading, the recipient will see a nicely designed landing page with a progress indicator.

It’s really a great product and service (and its developer Dustin Driver is fast and friendly in providing support!)

Droplr shortcomings

There’s one use case for which I’m uncomfortable using Droplr, and that’s uploading images and files to be used in my blog articles. Here’s why:

1. While I can control whether my blogs will still be around in five years, I have no control over whether Droplr will, and I would hate for the day to come when Droplr shuts down and suddenly all my historical blog references break. Therefore, I want all my blog media to reside in storage that I control—namely, three Amazon S3 buckets. And, unfortunately, Droplr doesn’t support upload to any endpoints other than its own service.
2. To get around this limitation, I used to use Droplr to snap and upload images, and then would drag those images from Safari to Dropzone, in order to upload them to S3. Unfortunately, though, Droplr only supports the PNG image format, and for 95% of these types of images the smaller JPG format would be more appropriate.

So as good as Droplr is, it’s still not quite the perfect tool for me.

The candidate alternatives

A search for alternatives (or complements) led me to the discovery of Dropshare, Monosnap and TinyGrab.

I discounted TinyGrab quickly as they require you to create an account with their hosting service, support only one Amazon S3 endpoint, and seems to use the OS X system utilities for creating screenshots (since there’s a preference about what to do with the screenshot file after uploading.) I also found the user interface confusing, as it seems that some settings are configured in the app, while others are configured at their website.

That left Dropshare and Monosnap.

At first glance, Dropshare looked quite promising—it seemed to be modeled after Droplr—supporting the capture and upload of screenshots, screen recordings, notes and files—but to a set of user-configurable endpoints, including Amazon S3, rather than to a proprietary service. And to get really close to Droplr-like feature coverage, they implemented a mechanism to auto-create a “landing page,” and even went so far as to implement their own proxy service to support password-protection and availability expiration.

Dropshare’s another great product. In fact, it would almost be a complete replacement for Droplr, except for the following:

1. Like Droplr, it only supports uploading PNG file formats, and doesn’t provide an option for JPG.
2. It doesn’t provide an image editing & annotation environment, instead relying on clunky integration with Preview, Skitch or Napkin via OS X 10.10 Sharing.

Which leaves us with Monosnap.

Monosnap is free in the App Store, and requires in-app purchases to enable certain endpoints, like Evernote and Dropbox. Fortunately, the free version includes Amazon S3 as an endpoint! Unfortunately, however, you can only configure one Amazon S3 endpoint, and since I need to keep the assets associated with my three blogs separated, I need to be able to configure three S3 endpoints—which is a bit of a showstopper in terms of the app’s potential for replacing Droplr.

Although Monosnap is missing some key features, it does provide a reasonably nice image editing & annotation environment, and unlike all other tools, it actually allow you to specify via preference to use JPG instead of PNG!

So where does all this leave us?

Current situation—a bit of a mess

The current situation is that there doesn’t appear to exist the perfect file and screenshot sharing tool for me, and so, as ridiculous as it sounds, I’m actually running all three apps:

• For all image and file sharing not destined for my blogs, I use Droplr.
• When I need an image for a blog article, I’ll snap, and optionally annotate or resize it, using Monosnap. I’ll then copy the image as JPG to the clipboard, and do a command-shift-8 to upload it to Amazon S3 with Dropshare.

My hope is that one of two things will happen in the future: Either Droplr evolves to support JPG upload and user-configurable endpoints (including S3), or Dropshare evolves to support JPG upload, and adds an editing/annotation environment.

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