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Windows 2008 Server Backup to cloud instead of external disk drive (USB)

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Last Modified: 2015-06-15
Our Windows 2008 Server is currently backed up every night to external disk drive attached via USB cable (manually rotated) using Wbadmin, and we are considering a cloud solution.  Currently Wbadmin with daily full backup, starting at a time in the evening, is in place.

Questions:

(1) The Wbadmin help states that the destination folder will be overwritten every time, and in case the backup fails, there may not be any backup available it all.  Consideration:  create 5 subfolders on cloud, one for every day of the week, create 5 entries in the task scheduler, with Wbadmin backing up to the respective subfolder.  Is this a viable option, or how is this done normally (assuming that multiple backups are maintained in case one of them fails)?  Since backups are to run at night, the process would need to be automated.

(2) How is the server-to-cloud connection established?  IPsec / VPN?  What must be done to assure access rights, and to assure the data can be restored to the server if necessary?
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