As we mentioned in our article earlier this summer, the lines are blurring between file sending and sync services and cloud drives. The latest entrant into this field is ZipSend, from the folks that make the popular WinZip file compression utility. It is somewhat disappointing on several reasons, but gives us an excuse to recap the major players in the marketplace.

As you mostly know by now, the major Webmail providers limit your attachments to 25 MB, and many corporate email servers have much lower limits because they don’t want their servers bogged down with attachments. To get around this problem, a number of file sending service providers have been created. Instead of using an attachment, they send a link in your email that connects you to their service, where you can download the file outside of your email stream.
Each of the service providers have different limits of their own when it comes to how big a file that they can handle. With Zipsend, you have to upgrade to their paid ($50 a year) Pro version to be able to send up to a 2 GB file. This is the same price point and size that YouSendIt.com offers for their plan, which is no coincidence since Zipsend is an OEM of YouSendIt.
Two GBs For Free
But there are two free services that can handle up to 2 GB files: Sendthisfile.com and Dropsend.com. If you don’t send big files often, it might be worth using one of these services.
So why bother with Zipsend? Well, if you want to use the cloud completely for your file transfers, there are limitations on the browser in terms of how big a file it can upload and download. Most Web browsers restrict file uploads at 2GB. And IE8 restricts file downloads to 4GB, while the restriction in Firefox is for files smaller than 4GB.
For the biggest files, you need special client software to do the transfers. SendThisFile has one, as does Zipsend, but both are only available for Windows clients. The Zipsend client is actually WinZip, which may be a reason to go with their service if that is a utility that you use frequently. YouSendIt and Dropbox.com both have Mac versions, and the latter can upload as big a file to their cloud drive as you have storage capacity to take it on, provided you use their desktop client. And if you are looking for another service for particularly large files, you might want to check out TrendMicro’s SafeSync. Like Dropbox, SafeSync can store a file as big as your storage bucket allows. Both will cost you though a monthly fee (and Trend is updating their service next week).