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After some heavy investigation there are 2 secure servers Microsoft uses for SkyDrive. I couldn't find any proper documentation on the forums about this so here is some more info...
1. SkyDrive - web service. This is simply their web service that you can log into at https://skydrive.live.com - In order to allow this you need unblock: https://18.104.22.168 (by default Websense blocks this under Social Networking)
2. SkyDrive - app service. If you download their app to run locally you need to unblock: https://22.214.171.124 - This needs unblocked because the service will just keep trying to sign in unsuccessfully because it can't reach the server. There is no error from the app either, the icon will just keep showing "signing in"
Hope this helps, let me know if you have any suggestions or other questions.
SkyDrive is no different than DropBox, YouSendIt, and the 50 other free online file sharing sites where the access is to the individual, never a company, and therefore the company loses control over its own data when these services are used. For some companies/organizations this isn't a concern, but for many others it's a nightmare. Until Microsoft comes out with an enterprise offering of Skydrive (with Win8 I believe) I'd recommend sticking with a service that does, like Accellion. Gives your employees the benefits of a cloud based file sharing site without the company losing access/control/visibility to its own data. Some other services offer enterprise versions but if you allow their website to be accessible at work there's nothing stopping employees from choosing to use the personal version instead.
Agreed. We block them and if a vendor insists on transferring files that way we require that they accept PGP encryption. Nicely, the DLP piece can detect whether PGP is in use so I'm considering whether to just allow those sites if PGP is used. Only a few people have PGP so that exposure is limited and it would keep me from having to open the site for a transfer and then close it again. We even have customers parking scanned W2's and tax returns on Dropbox and asking us to go get them. <sigh>