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drop.io is dead, YouSendIt got renamed, updated other details
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Aditya
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I've experienced this problem very many times. Thankfully, there are a few good solutions. They all involve using file-sharing services.

Some of the ones I'm about to list have already been mentioned, but I want to compare them in detail.

  • [drop.io][1] - very easy to set up (a Flash uploader); up to 100MB; easy to share; lots of privacy controlsHightail (passwords, permissionspreviously YouSendIt); you can control when your Drop expires; paid plans available
  • [YouSendIt][2] - upload via the website; up to 100MB;50MB; not a lot of control in the free plan; paid plans available
  • [Dropbox][3]Dropbox - somewhat hard to set up (you have to install it once; afterwards, you can just upload via their site); up to 2GB; very private (to view, you have to give someone a username and password)

Personally, I prefer drop.io for quick and easy sharing of files < 100mb. [1]: http://drop.io "drop.io" [2]: http://yousendit.com "YouSendIt" [3]: http://dropbox.com "Dropbox"

I've experienced this problem very many times. Thankfully, there are a few good solutions. They all involve using file-sharing services.

Some of the ones I'm about to list have already been mentioned, but I want to compare them in detail.

  • [drop.io][1] - very easy to set up (a Flash uploader); up to 100MB; easy to share; lots of privacy controls (passwords, permissions); you can control when your Drop expires; paid plans available
  • [YouSendIt][2] - upload via the website; up to 100MB; not a lot of control in the free plan; paid plans available
  • [Dropbox][3] - somewhat hard to set up (you have to install it once; afterwards, you can just upload via their site); up to 2GB; very private (to view, you have to give someone a username and password)

Personally, I prefer drop.io for quick and easy sharing of files < 100mb. [1]: http://drop.io "drop.io" [2]: http://yousendit.com "YouSendIt" [3]: http://dropbox.com "Dropbox"

I've experienced this problem very many times. Thankfully, there are a few good solutions. They all involve using file-sharing services.

Some of the ones I'm about to list have already been mentioned, but I want to compare them in detail.

  • Hightail (previously YouSendIt) - upload via the website; up to 50MB; not a lot of control in the free plan; paid plans available
  • Dropbox - somewhat hard to set up (you have to install it once; afterwards, you can just upload via their site); up to 2GB; very private (to view, you have to give someone a username and password)
Post Made Community Wiki by user11097
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Maxim Zaslavsky
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I've experienced this problem very many times. Thankfully, there are a few good solutions. They all involve using file-sharing services.

Some of the ones I'm about to list have already been mentioned, but I want to compare them in detail.

  • [drop.io][1] - very easy to set up (a Flash uploader); up to 100MB; easy to share; lots of privacy controls (passwords, permissions); you can control when your Drop expires; paid plans available
  • [YouSendIt][2] - upload via the website; up to 100MB; not a lot of control in the free plan; paid plans available
  • [Dropbox][3] - somewhat hard to set up (you have to install it once; afterwards, you can just upload via their site); up to 2GB; very private (to view, you have to give someone a username and password)

Personally, I prefer drop.io for quick and easy sharing of files < 100mb. [1]: http://drop.io "drop.io" [2]: http://yousendit.com "YouSendIt" [3]: http://dropbox.com "Dropbox"