ZipSend is available on its own, and is also included in the file utility. As a standalone product, ZipSend is available in two versions: the free Lite version, which limits the file size to 50MB per message, and expires files in seven days; and the $50-per-year Pro version, which lets you attach files up to 2GB and does not expire files.

ZipSend has two components: a cloud-based service and a downloadable plug-in. Once you sign up for an account, you're prompted to download the plug-in, which is called . This plug-in works with your Outlook email client or your Web-based email account (Gmail, Hotmail, and Yahoo Mail are supported) to compress and upload files. (Note: You sign up with a single email address, and ZipSend is linked to that account, whether you check it on the Web or in Outlook.)

You can configure WinZip Courier to use the ZipSend service always, never, or when attachments are over a certain size, which you can set yourself. You also can choose the compression method (zipx or zip: legacy), the attachment name, and whether or not to encrypt the attachments. Then, you go about your daily business of emailing just as you always do.

When you browse for a file to attach to your email message, WinZip Courier's options display below the normal Windows Explorer interface. Here, you can click a box to encrypt or zip any files you're attaching to the message. And, if your attachment meets the criteria you've previously set for ZipSend, the entire process is handled automatically: When you select the file to attach, ZipSend zips it for you and uploads it to its servers.

A link to your files is placed in the body of the email message, with a note to the recipient that the files have been shared with them. If there is an expiration date on the files, ZipSend includes that info, too.