Sharing is Caring

Secure File Sharing is Harder than it Should Be

by Michael Delcour

As always, I receive no compensation or benefit from any of the products or services mentioned in this article.

Sharing sensitive, confidential, or privileged material is surprisingly difficult to accomplish. I have yet to find one service that can handle every scenario. You see, the problem is not really how to send the information; the real complications arise in receiving and accessing the information. The simplest options (like Dropbox, Google Drive, etc.) are increasingly being blocked by corporate and legal IT departments for their perceived "lack of security." You can always send encrypted email through a service (Virtru, Hightail, etc.), but recipients unfamiliar with these services often have problems accessing the message. So, what to do?

With a client-driven business, the client always comes first. In this case, this means providing secure file sharing in as many different formats as possible. Hopefully the client will be familiar with at least one of the options that can make it through their corporate firewalls. My system can be broken down into three general components: (1) the file sharing services, (2) the product that synchronizes the file sharing services, and (3) a program that allows me to directly upload files from a computer.

There are so many reliable and secure file sharing services out there. My favorites include Dropbox, Google Drive, OneDrive, and Box. Between these four services, usually any given client has access and familiarity to at least one. To keep things as simple as possible, I register with each service using an obvious address like "".

Next, I need a product that will connect all of these file sharing services together so that if I upload a file to Dropbox to share, that file will also be available on the other three services. Again, there are many cloud products out there that accomplish this task. My current pick is CloudHQ, which synchronizes file sharing services reliably and cheaply.

Finally, I need a good way to get files up to the file sharing services from my computer. Of course, I can use the web-based interface to directly upload files, but for monster-sized video files, for example, this might be impractical. Instead, I want to find a desktop application that will synchronize a folder with the file sharing service. All of the services I have referenced have their own desktop applications, but in my case, I already use those applications for my own personal files. This is a problem because these applications do not allow multiple accounts to be used on the same computer at the same time.

This problem can be overcome by creating a second user account on the computer, but this becomes as hassle as you need to log out of your regular account and into your second account every time you want to upload a shared file. A better option is a service called insync, which allows for multiple Google Drive accounts to be active at the same time. In this way the Google Drive shared account becomes my anchor, and with CloudHQ, the other file sharing services are updated shortly after a file is uploaded.

All of the services I have mentioned here are not free. In fact, I don't think I would trust a free solution for secure file sharing, regardless. Ultimately, this setup allows me to share files securely with pretty much any client in any security situation without having to spend too much time on training them how to access the files. This alone justifies the expense for me. Share safely!

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