How to Send Large Files for Free With Hightail

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The Bottom Line

Hightail (previously YouSendIt) makes it really easy to deliver files larger than what your email service may allow. Various subscription levels cover just about every file delivery need. Desktop applications along with plug-ins also make Hightail particularly convenient. Free Hightail accounts offer enough bandwidth only for occasional file sending, however.


  • Hightail lets you send files up to 100 MB (Lite, free) or 2 GB (Pro).
  • Extremely easy to use via the web, Hightail also offers desktop applications or plug-ins.
  • Hightail can track downloads, protect them with passwords, and offers interface branding.


  • Hightail cannot deliver files exceeding 2 GB, and 100 MB is not much for free delivery.
  • You cannot copy yourself on mail sent with Hightail easily.
  • Hightail has a monthly download limit of 1 GB for free accounts.


  • Hightail lets you send files up to 100 MB (for free) or 2 GB (paid accounts) via email.
  • The uploaded documents are stored at Hightail for 7 (free) or 14 days (paid accounts), read for download.
  • Email recipients get a message containing a unique link to the file.
  • Hightail scans sent files for known viruses and, for paid accounts, can track delivery and downloads.
  • File transfer can happen over secure TLS/SSL connections with Hightail.
  • A personal address book lets you remember people who often receive large files.
  • Paid Hightail accounts allow downloads to be protected with a password (also available for individual deliveries).
  • Hightail offers desktop applications for Windows and Mac OS X and plugs into Outlook as well as several image editors.
  • The Hightail Outlook add-on and Windows desktop application can resume interrupted uploads.


Unfortunately, if the file you're sending is just a bit too large — and with many email services it does not take much, 2 MB maybe — you're unable to send your email. Do you have to resort to a USB stick and mail it? Or is it necessary to upload the file to a web server and mail the address by hand?

All you have to do is visit Hightail, compose your message, specify the big file to be delivered — up to 100 MB in size for free accounts and 2 GB for paid ones —  and click "Send It". Sending large files is as easy as that with Hightail, and the recipient will get an email containing a link to a page from which the file can be downloaded.

Desktop applications for Windows and Mac OS X make the uploading even easier and faster, and you can resume interrupted uploads, too. Hightail also plugs into Outlook and a number of image editors.

With paid Hightail accounts, you can track how often each file has been downloaded. Certified delivery and password protection are further options, and business accounts can set up their own branded file uploading service with Hightail technology.

It's a pity Hightail file sending and downloading limits are a tad low for free accounts. You can always pay as you go for larger files or password protection, though.