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I want to set up a personal Server where i am hosting all kind of services for myself (mainly gitlab, nextcloud, NAS, and some others). I currently go with the strategie of installing a small debian on the server and pushing all services into VM's. This way the server itself is incredible stable, and even when having aproblem with a virtual machine i can always connect to the debian below via ssh.

For the last server i set up, i was using Debian Jessie but for this server i don't want to install Jessie in march when setting up the machine. And upgrading to Stretch when it will be released (No release date yet, but this Summer might be a good guess). I read that upgrading Debian is not as easy as upgrading a Ubuntu, for example.

So my idea is: I will install the testing version of stretch. While setting up the server i can live with the "unability" in testing branch. I would directly get the new features and can test them. After a while when stretch stable is released i want to switch to it.

The questions are:

  1. Is this possible, and is this an easier operation as upgrading from jessie stable to stretch stable?
  2. Would you recommend such a step in general or is this to risky for you? Why would you think so ?
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  1. "I read that upgrading Debian is not as easy as upgrading a Ubuntu, for example." - avoid to read more from this source
  2. simply use stretch word in /etc/apt/sources.list instead of testing, then you'll always have stretch whether it is stable yet or not.
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You could just install stretch directly...and, thus, bypass the need to upgrade from an older version. https://www.debian.org/devel/debian-installer/

And yes....It's possible to run stretch right now (that's what I'm doing and it seems to run fairly well -- it does seem to have an issue every now and then but they are often rather minor issues)

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