Files too big for email? Large file cloud services to the rescue. Caution first!

As a small business owner or employee, have you ever tried to send a large presentation or big files through email? Did you find that sometimes the email didn't make it and you received a message that read the attachment was too big?

Do you ever consider the security of your content? Perhaps you are emailing trade secrets or other private information you don’t want unauthorized people to view. Unless you are using an encrypted email service, most likely your email could be at risk of being intercepted and read.

Well, fortunately, there are a number of great services available online which can help solve your issues but you have to be a little careful with the service you choose. Security used by the service is the most important thing for you to consider. You will want to do at least a little investigation into the security of the service you choose to use. Later in this post I provide some tips on how to investigate the security of the service without having to be a programmer.


How most large file transfer services work

Most large file transfer services offer some type of free service with additional functionality and services available for a premium. Most of these services work through you favourite website browser (Internet Explorer, Safari, Chrome, Firefox, etc…) and don’t require you to download any application to make the transfer work.

Here are the steps which occur to make the transfer happen:

Step 1. You enter your email address as the FROM and you enter the address you are sending to the TO.
Step 2. You click a file upload button or browse button and locate the file on your computer
Step 3. You click send and the file is first uploaded to the services’ website server and then a link to the uploaded file is emailed to the TO address
Step 4. The recipient of your file receives an email with a download link in the body of the email
Step 5. The recipient clicks on the download link and their internet browser will open with either another download link or will start downloading the file
Step 6. The internet browser will ask the recipient where they would like to download the fill or may just put the file in the download directory of their computer
Step 7. The service should delete your file from their server after some allotment of time.

The process is now done.


Security and what to look for

The majority of large file transfer services provide good security, however, some don’t. Following are some tips to look for when determining which service to use.

Tip 1. The easiest thing to check for is that the address bar in your internet browser window should start with https:// and not http://. The https:// indicates the communication between your internet browser and the website is encrypted. The encryption makes it more difficult for hackers to see your transfer or steal your stuff.

Tip 2. If the site requires you to create a login, you can run some tests to see if they encrypt your password. One test it to try the “forget your password” link on the site. If the site simply emails your password to you then you know that they don’t encrypt your password. Not encrypting passwords means that the organization most likely doesn’t hold security in the highest regard. A password reset is the better option, however, they should also do this with a challenge response question. The challenge response question will be something like “where did you attend primary school” and would be asked when you create your account and again when you are retrieving your forgotten password.

Tip 3. Create a simple text file with a few lines of text and send this file to yourself through the service. In most cases the service will send you a link to the content which you should click on. Again, once your browser window opens for the download, notice if the address bar contains the https:// as noted above. If it does contain the https://, it means that your download will be encrypted as well as when it was uploaded which is good!

Tip 4. Okay this is the hardest tip, however, you should read the site’s terms of service. Yes, everyone knows that this is usually legal jargon and tough to get through, but you should know what terms you are accepting. As well, the terms may also indicate a little more about how the service operates.

NOTE: it is possible for the service to program their site to encrypt the transfer of files without the URL showing the https://, however, as you may be new to this process you may want to stay with the service providers who provide the obvious https://.


Review of some large file transfer services

Through a quick search using “large files”, the following is a closer look at the top 5 sites which the search results returned.

Just off the top, notice the https://, you know that this site looks like it takes security seriously because the main site is presented through encryption to your browser. As their file transfer service is from the main page of the site most likely you file upload to their server will be encrypted which is good.

The free service offers upto 2GB file size which is good and they keep the file active for download for 1 week on their website servers. They do offer premium services as well. - terms of service

Okay, so no https:// on their main site which is not a good indication of good security. Now, when testing the functionality a new window popped up to process the file and send the email with the link. This pop-up window did indeed have the https:// encryption indicated with is a good sign that the site has uploaded the file using an encryption which is good.

Again, the email link they sent to the recipient for the file download doesn’t have the https://, however, when you click on the link the web page in the browser does have the https:// which means the download will be encrypted.

Although this service at first seemed a little light on security they do appear to have the security in order. Too bad they don’t simply follow the encryption on all pages as this would make it easier for everyone to know easily if they take security seriously.

The free service is reported to allow 4GB file transfers. The service also offers premium options. - terms of service

The main site of this service is using encryption indicated by the https://. The use of the https:// again is a good sign that this service takes security seriously. As with the others above this service is easy to use, however, it doesn’t enable you to add a message without an account.

The email link was clearly encrypted with the https:// which again means the download would be encrypted from the website servers to the recipient’s computer. The security looks good on this site.

The free service is reported to allow 20GB file transfers, however, it only keeps the files on the server for 5 days. The service also offers premium options and a downloadable application which they claim will make the transfers easier. - terms of service

The main site doesn’t provide an https:// so we will have to dig a little deeper into their security. They do upload the file in the background so they could be using encryption to do that but it is still not clear. The send email did offer an option to place a password on the recipients download page, but I was unable to set the password because it is a premium service. With the password option it does appear that they do at least think about security.

Unfortunately the download link in the email was only http:// which means the link was not encrypted and the web page to download the file from was not encrypted. Too bad as they look like they provide a good service with good programming but it looks a little shy on security.

A little more digging does show that their site could be secured with https:// as they have the proper technology on their server to do this, however, they don’t force the browsers to us https:// which is a problem.

Unfortunately, the terms of service could not be found, which is not a great sign.

The main site doesn't provide the https:// so where is their security? They could be providing the security within the background programming, however, we just don’t know.

Unfortunately, the download link is not encrypted. After the recipient clicks the link the browser webpage for the download is also not encrypted, which means this is not good. It seems the company doesn’t care that much about security.

The free service allows 2GB file transfers and the file is available on the website server for 10 days. There are also premium services available. - terms of service


Other options for large file management

Other than just sending files in a one way blast there are services and technology to assist in much more functional file management. These services usually require a download of some software or provide a website interface to a folder structure where your files will be managed. This type of file storage on the internet is commonly referred to as “cloud storage” and is offered by many companies.

Apple, Microsoft and Google all offer cloud storage. Many other companies as well offer cloud storage of files. The tools each company offers to manage and share files varies greatly and is a topic for another posting.

One service I have used which seems to work well is which provide file sending capabilities as well as file management. Once their desktop application is installed on your computer, sharing files with others is as easy as drag and drop into folders just like you would when moving other files around on your computer.


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