Can I upgrade from Raspbian 8 (jessie) to Raspbian 9 (stretch)?

Nextcloud version: 14.0.3
Operating system and version: Raspbian 8 (jessie)
Apache or nginx version: Apache 2.4
PHP version: 7.0

Can I upgrade from Raspbian 8 (jessie) to Raspbian 9 (stretch) without considering anything else?

I thought about upgrading but I am a little bit afraid of breaking my server.
Are there any reasonable pros or cons of upgrading?
Or should I keep staying on Raspbian 8?

My 2 cents.

I fresh install stretch on ARM base SBC and things work fine. It is also where I have my NC instance accommodated.

I have a LAMP server on jessie vm (dist-upgrade from squeeze before). I tried dist-upgrade to stretch and failed. Main issue is on mysql -> mariadb, couple of strange problems with lot of google-solutions but none of them work.

Besides mysql, ntpd is replaced by systemd-timesyncd that you may need to know if you use 2FA. I always use headless light installation, so not sure if there are other new stuffs that need your attention.

Suggest you dd sdcard to a backup. Do the dist-upgrade. Judge if you can handle those issues emerge and then make you decision.

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