When you need to send large files, email is often the most restrictive transport. By default on-premise Exchange 2010 limits emails to just 10 megabytes, and Office 365 offers 25megabytes per email message. While you can increase your on-premise email server size limit, you cannot increase the size limit in Office 365 beyond 25megabytes. Even if you could increase it beyond 25megabytes, if your recipients are outside your organization, their email server may limit the size of email to 10 megabytes. For end-users, this is a frustrating experience, and it results in helpdesk requests like “why am I getting this bounce-back message when I email so and so.”
Many IT departments provide users with either FTP sites or SharePoint extranet sites to share large files with external users. However, those solutions require IT overhead to maintain.

There are now many free or low cost solutions for sharing files including:
1. Adobe SendNow – at $20/year this seems to be very reasonable. The Outlook plug-in does not yet work with Office 2013.
2. Box.com – offers a free account. The business account ($15/month) includes a pretty amazing outlook plug-in.
3. YouSendit – Free accounts can send up to 100MB. Paid plans start at $10/month or $100/year and the size per email increases to 2GB.  The biggest plus is the outlook plug-in because it will automatically detect when attachments exceed a pre-determined size, ex: 10mb or 35mb. I verified that the Outlook plug-in works with Office 2013.

Once I signed up for a free account with YouSendIT, I downloaded the free Outlook Plug-In.

YouSendit’s Outlook plug-in offers a single-sign in option to integrate with Active Directory.

While there are other cloud storage providers, most are consumer oriented and do not natively integrate with Microsoft Outlook.

Xobni is a 3rd party tool that allows Outlook to to send files from DropBox or SkyDrive.
Likewise, Harmon.ie has an Outlook 2007/2010 plug-in that converts large attachments to links on Google Drive. The plug-in does not support Office 2013.

For quick ad/hoc file transfers, check out 7. DropSend and 8. WeTransfer.com. Within seconds of visiting their websites you can transfer large files (up to 2 Gigabytes! for free).

Here are the other 12 sites that offer file sharing services: Egnyte, SendThisFile (offers Outlook plug-in), Send6, MediaMax, MailBigFile, SendSpace, MegaUpload, zUpload, MyOtherDrive, DivShare, TransferBigFiles and MediaFire