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Huh? I have the opposite experience. Major upgrades always went flawlessly for me. With the rolling testing-Release on my workstation/laptop, I sometimes run into dependency problems during upgrades. But these can always be solved by a few standard techniques. Not really beginner-friendly, but quite reliable. I have had many more problems when upgrading Ubuntu installations.

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If you are running testing, it doesn't get security updates except through regular package migrations from unstable, so I recommend pulling in security updates from there manually or automatically. At least Firefox and Linux have regular security fixes in unstable, so you might want to use apt pinning to use the unstable versions. You can also use debsecan to automatically and temporarily pin security uploads to unstable using the technique mentioned here:

https://wiki.debian.org/DebianTesting#Best_practices_for_Tes...

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