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I want to upgrade multiple components of a system including:

Linux distribution (debian lenny -> squeeze)

Mysql (5.0->5.1->5.5->5.6)

Apache tomcat 6 to 7

Java runtime version

What (and why) would be the right order to do those upgrades ? And I which of those phases am I most likely to encounter backwards compatibility issues ?

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The before and after Java runtime versions would probably help you to get a more complete answer. – Ladadadada Feb 21 '13 at 12:48
I tried to follow some upgrade instructions to upgrade debian (as the are at the linode help) I ended up without a DB :(. [Of course non of this was on my actual production machine but on a cloned one]. From more reading it seems that mysql 5.0 is not compatible with debian 6 so I will try to upgrade mysql first and only then move to debian 6. (somewhat opposite to what was suggested in the only answer I got so far). – epeleg Feb 24 '13 at 10:19

I would follow Debian guidelines for upgrading: this means upgrade your base system first, then the rest; if I were you I would let Debian choose which package upgrade first.

In case you would to update manually each of your "relevant" packages, I would follow this order: mysql, java, tomcat.

Remember you'll probably switch from sun-jdk6 to openjdk7, if I remember correctly.

To get a packaged version of oracle's jdk, take a look at java-package

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