Since Debian has quite some time to evolve in-between stable releases, you should read the release notes before upgrading.

In this section, we will focus on upgrading a Wheezy system to Jessie. This is a major operation on a system; as such, it is never 100% risk-free, and should not be attempted before all important data has been backed up.

Another good habit which makes the upgrade easier (and shorter) is to tidy your installed packages and keep only the ones that are really needed. Helpful tools to do that include aptitude, deborphan and debfoster (see Section 6.2.7, “Tracking Automatically Installed Packages”). For example, you can use the following command, and then use aptitude's interactive mode to double check and fine-tune the scheduled removals:

# deborphan | xargs aptitude --schedule-only remove

Now for the upgrading itself. First, you need to change the /etc/apt/sources.list file to tell APT to get its packages from Jessie instead of Wheezy. If the file only contains references to Stable rather than explicit codenames, the change isn't even required, since Stable always refers to the latest released version of Debian. In both cases, the database of available packages must be refreshed (with the apt update command or the refresh button in synaptic).

Once these new package sources are registered, you should first do a minimal upgrade with apt upgrade. By doing the upgrade in two steps, we ease the job of the package management tools and often ensure that we have the latest versions of those, which might have accumulated bugfixes and improvements required to complete the full distribution upgrade.

Once this first upgrade is done, it is time to handle the upgrade itself, either with apt full-upgrade, aptitude, or synaptic. You should carefully check the suggested actions before applying them: you might want to add suggested packages or deselect packages which are only recommended and known not to be useful. In any case, the front-end should come up with a scenario ending in a coherent and up-to-date Jessie system. Then, all you need is to do is wait while the required packages are downloaded, answer the Debconf questions and possibly those about locally modified configuration files, and sit back while APT does its magic.

In spite of the Debian maintainers' best efforts, a major system upgrade isn't always as smooth as you could wish. New software versions may be incompatible with previous ones (for instance, their default behavior or their data format may have changed). Also, some bugs may slip through the cracks despite the testing phase which always precedes a Debian release.

To anticipate some of these problems, you can install the apt-listchanges package, which displays information about possible problems at the beginning of a package upgrade. This information is compiled by the package maintainers and put in /usr/share/doc/package/NEWS.Debian files for the benefit of users. Reading these files (possibly through apt-listchanges) should help you avoid bad surprises.

You might sometimes find that the new version of a software doesn't work at all. This generally happens if the application isn't particularly popular and hasn't been tested enough; a last-minute update can also introduce regressions which are only found after the stable release. In both cases, the first thing to do is to have a look at the bug tracking system at https://bugs.debian.org/package, and check whether the problem has already been reported. If it hasn't, you should report it yourself with reportbug. If it is already known, the bug report and the associated messages are usually an excellent source of information related to the bug:

Depending on the severity of the bug, a new version of the package may be prepared specifically for a new revision of the stable release. When this happens, the fixed package is made available in the proposed-updates section of the Debian mirrors (see Section 6.1.2.3, “Proposed Updates”). The corresponding entry can then be temporarily added to the sources.list file, and updated packages can be installed with apt or aptitude.

Sometimes the fixed package isn't available in this section yet because it is pending a validation by the Stable Release Managers. You can verify if that's the case on their web page. Packages listed there aren't available yet, but at least you know that the publication process is ongoing.