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Send Large Files In Outlook For Free Using YouSendIt [How-To]

image Sending someone a really large file (5 megs or larger) can really be a pain sometimes for both home and corporate users.  Most email servers cap attachment size at 5 megs so that leaves the options fairly limited for the “non-techy”.  And no… FTP is not an option for most as it’s both complex and not always available to everyone. 😉

Fortunately, several online FREE services are available to help solve the problem of large file transfers.  I and today I’m going to talk about one of my other favorites is a great online service with several different service options depending on what you need.  The Lite or Free service is limited in features however it allows you to send files up to 100 Megs in size (vs. 2 gigs for the paid service levels) which for most should be good enough.

YouSendit Service OptionsYouSendIt Application PluginsAlthough you can use YouSendIt through their web interface, they also provide several applications to make sending large files even easier.  The one I’m focusing on with this Tutorial however is the Outlook Plugin.

The Outlook Plugin works really well with Outlook 2003 and 2007 (I’ve not tested it with Outlook 2010 yet).  Once installed, the plugin integrates nicely with Outlook.  Let’s take a look.

To start out, you’ll need to visit and sign yourself up for a youSENDit trial account.  The trial account will give you 14 days of paid features, including the ability to send files that are up to 2GB in size.  When the 14 day period ends your account will revert into a free Lite account.  As mentioned earlier, the Lite accounts can only send files up to 100MB,  If you like the service you can subscribe for a paid account at any time.

YouSendIt Signup Process

Once your account is setup it’s time to grab the Outlook Plugin.

How To Send Large Attachments in Microsoft Outlook For Free Using

1. In your web browser, go to down to the middle of the page and Click the Download For Windows link.  Save the file and run it.

YouSendIt Download Link

2. Once you run the setup file, the Installation wizard will appear.  Installation is very simple and straight forward, just Click Next a few times and then Click Finish.

YouSendIt Download Link

3. Time to open up Microsoft Outlook!  Provided you used your outlook email when signing up for youSENDit, in your Outlook inbox there will be an account activation email.  Click the activation link and complete activation.  YouSendIt Activation Link in Outlook

4. Once your account has been activated, Click the YouSendIt bar in Outlook.  Under the drop-menu Click Sign in. Enter your login information and Click OK.

Note: If you are having trouble finding the YouSendit bar, go to the top menu and select View > Toolbars.  Ensure the YouSendIt is an enabled bar, and look again.

YouSendIt Configuration Screen

Once the Outlook Plugin is installed you can send attachments either manually or automatically through the YouSendIt service.  Let’s take a look at the Automatic method first.


5. YouSendIt may be overkill for small attachments, so I suggest modifying the Configuration to only call the YouSendIt service for attachments over 5 or 10 megs.  This way the service will ignore smaller attachments.  That being said, you can set this to 1 MB if you want.

YouSendIt Configuration Menu

6. To manually attach a file or folder using YouSendIt, simply Click the YouSendIt Icon on the Outlook Ribbon.    Once the file is attached finish writing your email and Click Send just as you would normally.

YouSendIt Buttons on Outlook 2007 Ribbon

Back in the main Outlook window while the upload is being sent, you should see a status bar tracking the upload % complete.  If you hover your mouse over the bar it should give you the exact percentage completed as well.

YouSendIt Upload Status

A link to the file stored on the YouSendIt service will be inserted into the Email you sent.  The Recipient will have 14 days to grab the attachment before it’s deleted so keep that in mind.   The paid service allows you to adjust this along with about 15 other options however with the free service, 14 days is all you get.

Direct Links:

YouSendIt trial account signup:

Plug-in download page:

Do you have a favorite Large File Transfer service/tool?  Tell us about it in the comments!

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2 Responses to Send Large Files In Outlook For Free Using YouSendIt [How-To]

  1. FREE LARGE FILE TRANSFER November 7, 2011 at 1:17 pm #

    Thanks a bunch for sharing this with all of us you actually recognize what you are talking approximately! Bookmarked. Please also talk over with my website =). We can have a link trade contract between us

  2. Justin Hawley February 12, 2014 at 1:26 pm #

    Hey Austin! Any way you can review now that YouSendIt has been bought out by HighTail? Getalink offers up to 4GB uploads for free, and the upload speeds are faster than wetransfer. In fact the entire process is quicker than any competitor. Please take a look and tell us what you think! 🙂 Thanks!

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