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I think I'll clearn and update my Server this weekend (since it's still on Debian 8).Wish me luck or dig my grave.

P.s.: Tips/suggestions/experiences are also very appreciated

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  • 2
    Debian 8->9 was mostly fine for me, only stunnel broke. 7->8 was far worse...

    I would suggest to do some backups, but you probably did already.
  • 2
    I'll wish you good luck while digging your grave.

    And like @sbiewald said, backup again.
  • 0
    Why not come at it with a blue/green kind of approach?
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