A: Email is a great non-real-time communication system with the ability to deliver small attachments in an efficient manner. However, it remains ineffective for transporting larger files. The definition of larger varies with different enterprises, but I see 10MB to 20MB as a typical maximum file size for email attachments. For sharing larger files with remote clients, you need alternatives to email.

Some typical alternatives include a collaboration solution such as SharePoint or an FTP server, for which the recipient needs an FTP client (or command-line skills). By separating file transfers from your email infrastructure, you'll help keep your Microsoft Exchange Server more efficient, both in its performance and in the amount of storage it requires. Also, users won't fill their mail quota as fast if large attachments aren't occupying their Sent Items folders.

Several companies provide online file sharing services for large files. YouSendIt is one such cloud-based service I've used for sending large files, even full virtual machine (VM) images, rather than shipping them on other media or hosting my own SharePoint site. YouSendIt has an impressive list of clients, and they offer a set of plug-ins that work with products such as Adobe Photoshop and Microsoft Office.

YouSendIt's Outlook plug-in lets users send large files directly from Outlook. YouSendIt uses a web interface for users to send large files over HTTP. It also has a standalone application called YouSendIt Express, which looks like an email client itself and facilitates transfers. However, adding this functionality to Outlook with the plug-in lets companies deploy YouSendIt with less training and impact compared to the full YouSendIt application and lets users who spend most of their time within Outlook continue to use that familiar application.

The Outlook plug-in for YouSendIt is less than 5MB and you can download it from the YouSendIt website. It works with Outlook 2010/2007/2003 and requires Windows XP SP2 or any Windows version after that. The installation is simple; however, the plug-in isn't compatible with the 64-bit version of Outlook. It does work with the 32-bit version of Office and Outlook installed on a 64-bit version of Windows, though. Outlook must be shut down before the installation will begin. I used version 2.14.1 for this article.

After the installation is complete, the YouSendIt plug-in adds a menu bar (Outlook 2003) or extends the Office Ribbon (Outlook 2010/2007). The menu options for YouSendIt are the same for all of the Outlook versions—Sign In (or Sign Out), Configuration, Help, and About. Figure 1 shows the configuration window.
Figure 1: The YouSendIt configuration window
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The Configuration tab lets you control the size of attachments that should automatically trigger the YouSendIt plug-in and whether YouSendIt should ask for confirmation before using the service. When a user includes an Outlook email attachment that meets the size specified in the Configuration tab with no confirmation configured, the YouSendIt plug-in is used seamlessly. The Proxy Settings tab uses the same settings as your default browser for connecting to the internet. YouSendIt Outlook plug-in settings are registry-based and are located at HKEY_CURRENT_USER\Software\YouSendIt\Settings. Administrators can configure or lockdown those settings through Group Policy.

With the YouSendIt plug-in, users can send files or even entire folders up to 2GB through the Outlook interface. Attachments are sent to YouSendIt.com over HTTP instead of using SMTP to go to the recipient's email server. When the user creates a new email message, YouSendIt adds three buttons to the menu bar or Office Ribbon: Attach File, Attach Folder, and Send Options. The first two let the user select files to attach, which will be uploaded to YouSendIt.com. A text file with the extension .YouSendItFile is attached to the message indicating where the file to be uploaded is located. This text file is used by the YouSendIt plug-in and isn't sent with the message.

Whether you manually tell YouSendIt to attach a specific file to an email message or a file attachment meets the size requirements in the configuration to use the YouSendIt service, you have the option to control how long the uploaded file remains available to the recipient for downloading, as Figure 2 shows.
Figure 2: Setting the expiration option on the YouSendIt service
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The recipient gets an email message in his or her Inbox with a URL to download the attachment from the YouSendIt service. Figure 3 shows an example of such a message. The recipient doesn't require a special client or membership in the YouSendIt service to download content.
Figure 3: A example recipient message from the YouSendIt service
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YouSendIt offers three levels of service with different features and cost. Corporate level accounts have the ability to monitor downloads of their YouSendIt files, secure uploads with a password, and receive a return receipt confirming successful uploads of files through the YouSendIt service. The best part of using this service through the Outlook plug-in is that, after it's configured, the user doesn't have to even consider the size of an attachment when composing an email message. Based on the configuration you set, the YouSendIt service can be used to host large files without user intervention.

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