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How can a machine be securely migrated from "Ubuntu - single partition - home directory encrypted" to "Debian - separated partitions for OS and home, and maybe for swap too if that is an advantage - with either encrypted home directory or full-disk encryption"?

We have:

* no free space available to make copies of the home directory for triangulation
* triangulation through external hard drive possible but very undesirable
* passwords don't change

I'm not experienced with repartitioning or fiddling with encrypted homes, so I'm worried about the order of things and dealing with all those problems at the same time. I'm thinking

  • first a backup of most important files, although it wouldn't be possible to back up everything, then a repartition is made by booting with a Live CD, then new OS is installed and then home is already encrypted in the separate partition, nothing to change. But I'm not sure if this is correct, or if there areb't important details that could end up in data loss
  • full-disk encryption is an improvement but I recall reading there're still serious issues in the setup (like risk of irreversible damages), so if this is not true, then FDE is better, otherwise encrypted home directory is good enough, but in any of the two cases I'm unsure how to proceed in a simple way.
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How much data are we talking? Is your data of so little value that a complete backup (on a new aprox 60USD external HDD) would not be a most justifyable investment? What are the disk/partition sizes involved? – humanityANDpeace May 31 '13 at 6:24
Enough data to fill a new external HDD. As I said, this is an option if no other is available, but for many reasons undesirable. I was hoping to be able to partition as it is, with just the most critical data in a big flash drive in case things go wrong. – Strapakowsky May 31 '13 at 6:31
For this, while it's not impossible, there are way too many pitfalls for a casual reply. So please, do it the old fashioned way, get another HDD if necessary. – frostschutz May 31 '13 at 21:18
I could get a hard drive just to be sure and have a backup. But after I've done it, is it possible to partition as it is and then install the OS in the installation partition? – Strapakowsky Jun 14 '13 at 6:56
The encrypted home is a fuse thing. Eg. The files are wherever /home is. If /home is not a separate partition you can't do it without temporary storing home before repartitioning. – Sylwester Jun 19 '13 at 0:09

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