Sending Large Email Files via Dropbox and Outlook 2011 for Mac

With the introduction of Cloud services, sending large files via email has become a thing of the past.

Before the introduction of cloud services like Dropbox, you had to send large file attachments via email which was problematic or impossible. Depending on the size of the file, sending could take a very long time or timeout. Furthermore, in most organizations, attachment size is often locked down and limited.

In this tutorial, we are going to show you how to bypass email attachments and send large files by taking advantage of Dropbox.

Installing Dropbox

Dropbox is one of my favorite tools to use on the Internet. Not only does it back up your specified files to the cloud (encrypted of course), but it also synchronizes your files to any other computer where you have Dropbox installed. In the event that one of your computers become unstable or stolen, simply install Dropbox on a new computer and all your files download and synchronize.

Let’s Begin by browsing to and signing up for a free account. If you already have an account, please skip this step.

After you signup, you are prompted to install Dropbox on your Mac Computer. Once Dropbox is installed, look for a Dropbox icon on the top-right corner of your screen.

Note: Dropbox provides 2 GB of free space. You can upgrade to different storage levels for additional cost.

Uploading Files to Dropbox

Next, upload documents to Dropbox by simply dragging files into the Dropbox folder.

Single-Click the Dropbox icon at the top right-corner of your screen and choose Dropbox folder.


You can setup your folder structure in Dropbox any way you like. A green check next to the folder means the file is being synchronized to the cloud and any other computer you may have.

Drobox Legend

Icon Descriptions
1 Green check mark means
files are uploaded to the
1 Turning circle means files
are uploading to the cloud.
Icon Descriptions
1 You can hover over the
Dropbox icon to see how
much time is remaining to

Now that you understand the basics of Dropbox, simply drag any large files into a Dropbox folder and wait for it to upload.

Create Dropbox Link to Share in Outlook

Once the file(s) are uploaded to Dropbox, you are now ready to create a shared link that you can use to send large files via email.

    • Open your Dropbox folder by clicking the Dropbox icon at the top right-corner and selecting Dropbox Folder. For example, we are going to share a 60 MB install folder in an email to an associate.
    • Right-click on the file or folder and choose Share Dropbox Link.


  • A copy of this link will be stored on your clipboard. Next, open Outlook and compose a new email. When you are ready, paste your link in the email as shown below.


When the recipient receives the email, they will click the link and download the file.

That is all there is to it. You can now save all of your large email attachments to the cloud via Dropbox instead of attaching them to email.1

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