Annual Backup Strategy Review

It’s been a year since I looked at my backup strategy. Having just rebuilt my PC twice in the last few weeks it was a good time to go through the review. It’s a bit of a hodgepodge but it’s automatic and works. Here’s the tools I use and a high-level view of how I do the backups.

Backup Logo - Laptops connected to backupIt’s been over a year since I last reviewed my backup strategy. I’ve also rebuilt my PC twice in the last month so combined with some other changes it’s a good time to review my backup strategy and the tools I use.

My Backup Philosophy

I’ll start off my repeating my backup rules:

  1. A file doesn’t exist unless it exists in at least three places.  (Was two places last year)
  2. RAID (or RAID like technologies such as Drobo or Windows Home Server) does not mean the file exists in two places.
  3. To be truly protected, two of the three places must be geographically separated.
  4. The backup has to be automatic and unobtrusive. I’m lazy, if I have to manually initiate the backup it won’t happen.

Software Used

The following software provides backup services for me. I keep my files in a central location on my Windows Home Server, so PC backups are not so critical for me. In fact, with my two recent PC rebuilds, both planned, I rebuilt the OS from scratch because I wanted to make changes. While I did restore some application configuration files I don’t restore any data because there is none.

Windows Home Server

In addition to being where my files live, Windows Home Server provides the backup service for my Windows PCs. I’ve occasionally restored individual files or directories and it’s worked well.

I’m currently running both Windows Home Server Version 1 along with the Version 2 (Vail) beta. But because I’m now backing up to beta software I no longer consider these backups reliable, just nice to have.

I keep file duplication on for all shares. As I mentioned, this isn’t a backup, but it does provide redundancy to keep the files available should a drive fail so that I don’t need to go to the backup just to get the server running.

KeepVault for Windows Home Server

I’ve changed the way I’ve used KeepVault since my first review of KeepVault back in May, but I still use it and I suspect I will be buying even more storage. KeepVault backs up my files to the cloud, giving me offsite backup. It meets my requirement of allowing me to pick my own encryption key that they don’t have (assuming I believe them when they say they don’t have, it which I do). But some features of KeepVault keep it from being an all-around offsite solution for me.

  • There’s no archival history for files. If a file is changed it overwrites the previous backed up version.
  • Files are never deleted (unless done manually). Once a file is backed up it remains unless I go in and delete it. For directories where I add/delete/move a lot of files this would become a space problem.

So I’ve moved to using KeepVault for backing up files that don’t change a lot but take a lot of space. Such as Music, Software and some videos.

Jungle Disk

JungleDiskThis is my primary offsite backup software. I’ve been using Jungle Disk since it’s inception and because of that I have been grandfathered into a slightly lower monthly subscription fee than what’s currently available.

Jungle Disk backs up to either Amazon S3 (and the Amazon S3 charges apply) or Rackspace Cloudfiles (and Rackspace charges apply). I’ve moved over to Rackspace as I’ve found it to be reliable. I did stay with Amazon S3 long after Rackspace became available so they could work out the bugs.

I run Jungle Disk on my Windows PC but back up the shares on my Windows Home Server.


Chronosync is a Mac app that can be used to move files around, and as the name suggests, synchronize folders. I have a Drobo attached to my Mac Mini and I use Chronosync to make a copy of files on my Windows Home Server to the Drobo. This gives me my second local copy of these files.


I pay for a 50GB DropBox account along with the “Packrat” option that saves deleted files and previous file versions. I mainly use this as a way to share files between my PCs, phone, iPad and to make files available via the web. But the offsite storage allows me to use it for some backups.


I use WinSCP to backup my web server using a script run as a scheduled task.

OS X Time Machine

I have even less true data on my Mac than I do on my PC. Almost everything is saved on the Windows Home Server or on the attached Drobo. If it’s on the Drobo it gets copied up to the Windows Home Server at night.

Still, I use Time Machine to get setting changes and to allow a quick rebuild if necessary.

How The Backups Happen

Purchased Music & Purchased Video

I have a share on my Windows Home Server called Archive. I have a ChronoSync job that copies purchased music and video from my Music library to the Archive share. From there KeepVault backs up any new files. Since I rarely delete these files the lack of KeepVault deletions is actually a benefit as an unnoticed accidental deletion from my library can be restored when it’s finally noticed.

I only do this for music and videos I’ve purchased online and downloaded.

Ripped Music and Video

This is by far my most problematic set of files since there are around 3 TB worth of files. For these I use Robocopy and some batch files to synchronize them with a set of hard drives I have. I keep these hard drives in the office so they are out of the house. They aren’t critical data so a delay in getting them may be annoying, but not a real problem.

My third copy of these files is the original physical media packed away in boxes. It would be annoying and time consuming to re-rip them. I’ve accumulated enough older hard drives I may be able to set up a second set of hard drives with a copy to keep in the house.

I have had to restore these files due to a past server failure and the robocopy strategy does work.

Web Server

I run a scheduled task that fires off a WinSCP script to download my website files to a folder in my DropBox. This gives me a local copy across PCs along with one in the cloud. The DropBox Packrat feature also keeps old file versions available should I need them.

Windows Home Server & Dropbox Data

I keep copies of software I purchase or use in a share on the WHS. If I received the software on CD/DVD I make an ISO file of the disc and save it to the server. These files get backed up to KeepVault. While I may eventually want to delete these files (something I need to do manually with KeepVault) I want to keep most software long after I stop using it, just in case.

Everything else gets backup up with Jungle Disk. I have a user share with my critical (mostly financial and records) data and that gets backed up to both Rackspace and Amazon S3. Both of these services use an encryption key I specify and only I know.

Since space is money I’ve changed the time to keep replaced/deleted files from the default 60 days down to 10 days. My main concern is accidental deletions and hopefully I’d notice within 10 days.

As for the second local copy of these files – the DropBox files duplicate themselves. I use ChronoSync to copy the remaining WHS files to my Drobo as a local backup.

One thought on “Annual Backup Strategy Review”

  1. Great info on how to ensure a proper degree of backup!

    FYI we will be releasing a new v4.0 of for Windows Home Server Vail and SBS Aurora in Q1 of next year. It includes versioning and several other enhancements our customers have requested. Expect a beta in Jan/feb.


Comments are closed.