Upgrading your Debian VPS from Wheezy to Jessie
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Just follow the regular Debian apt-get upgrade, dist-upgrade, reboot process:
https://www.debian.org/releases/jessie/i386/release-notes/index
Big changes are:
new apache directives eg Require all granted. and locations conf-available, conf-enabled etc. conf.d is ignored. Cyrus executables have moved so use maintainer cyrus.conf. Important samba global "acl allow execute always = yes" to allow files to be executed as per all previous versions of samba