Web lists-archives.com

RE: Upgrading from very-old Debian

>Backup the data to an external usb drive or the whole source drive if you 
>are keen on that, for example. Then do a "clean" install of a new system
> on the original drive. Otherwise you might run into issues, where you 
>might miss out on an important package, if you snapshot upgrade one 
>by one.

Just saying this....

In my 40 years of messing with PC and servers that are many major lessons I have learned. I will only bore you with TWO lessons right now....

To frame this, my understanding it's a critical/important system that needs to be updated:

1) MULTIPLE backups - TWO different medias:
   a. USB Stick

2) NEVER INSTALL a brand new system on the OLD drive.
   a. Backups fail!
   b. The human WILL forget to backup something (when NOT cloning the drive)
   c. If the system is THAT old, you probably ought to consider a new drive anyhow. Nothing runs or last forever.
   d. Installing on a new drive gives you an automatic backup (by not using old drive)
   e. Give you a point to go to get the stuff you forgot to copy :)

1)  1a - The human CAN and will forget to copy some files or a backup is just flat is broken for some reason.
2) 2 - You install the new OS on the old drive, then realize oh S***, I forgot to backup X, Y or Z
3) 2 - You click on the WRONG option and format the old drive destroying the data

Take it for what it's worth. I've Been There, Done it on all the above mistakes.

I suggest the clone the drive twice thing not so much because a single clone will fail, but it gives the human two ADDITIONAL chances to fix "oops" before you become screwed and lose everything. 

Again, experience speaking here.

You folks have blessed day!