update is a must?

[azairaz]

To what extent is it advisable to continue in debian jessie? I am aware that I no longer receive security support from the debian team, but I do not have the time to install and configure everything again when debian 9 is installed.

[sunrat]

Jessie support is now handled by the LTS team rather than Security team. You should be OK until June 30, 2020.

https://wiki.debian.org/LTS

[Head_on_a_Stick]

I do not have the time to install and configure everything again when debian 9 is installed.

Follow the upgrade guide then:

https://www.debian.org/releases/stable/ ... ng.en.html

I've been through the process *many* times for both wheezy and jessie and it seems to be pretty reliable.

[rivenathos]

Jessie was an excellent release, and I understand your wish to stick with it as long as possible. This is still a viable option as per the above comments.

Switching to Stretch is not that bad, so when the time comes, you will hopefully have an easy transition. Personally, I had no issues. Good luck!

[p.H]

Jessie support is now handled by the LTS team rather than Security team. You should be OK until June 30, 2020.

If you only use supported architectures. The LTS team does not support all the architectures which are supported by Jessie.

[GarryRicketson]

It is not advisable to any extent. If you upgrade, there is no need to install again.

---snip---but I do not have the time to install and configure everything again when debian 9 is installed.

The longer you wait to upgrade, the harder it will be, and if you keep putting it off, then yes, you will end up needing to do a fresh install. It is your choice.

I do not have the time to install and configure everything again when debian 9 is installed.

Follow the upgrade guide then:

https://www.debian.org/releases/stable/ ... ng.en.html

I've been through the process *many* times for both wheezy and jessie and it seems to be pretty reliable.

You all ready were advised to upgrade, What is the point in pursuing this further ? If you do not have the time, maybe you should hire someone to do these routine maintenance procedures.
If security is not important to you, you can keep using Debian Jessie as long as you want, but no one is going to advise you to do that.
Please mark the topic solved by editing the subject line in the first post.