If you mean that you skipped a release - predictable (if you read the release notes there is a rather large stumbling block preventing a direct upgrade from lenny to wheezy...)

If you mean that upgrading from lenny to squeeze to wheezy failed - post the output you're seeing from apt-get dist-upgrade and apt-get -f install

Should have been more clear in my previous post. I wanted to see what happens if i skip a release in the upgrade process. That an upgrade this way can fail was clear to me, I just wanted to experiment with it. I think I will try that with a Slackware installation next and see if that is possible there.

Did you try using aptitude since it was prefered in Lenny?

There was a major udev update in squeeze, which required a 2.6.26 kernel minimum, but lenny's 2.6.26 does not meet the requirements due to it's configuration (read release notes to find out why) so you have to install the squeeze 2.6.32 kernel, then upgrade udev, then reboot into the squeeze kernel and, only then dist-upgrade. You would have needed to install a newer kernel first before attempting the upgrade, then you would need to update udev... trying to get a kernel and udev from wheezy to install in lenny would be... interesting. That's just the start of all your troubles however.

Well, I for one am really happy to see the results of that experiment. Saves me from trying it for one thing.

Sometimes these things just need to be done. For FUN.

Amazing how satisfying it is, sometimes, to just break something.

Totally agreed.

In that case I would try to uninstall the offending packages and reinstall them again when the upgrade step is ready. I did that in situations when a dist-upgrade failed complaining of breakages, unmet dependencies and incompatible packages, and it worked without problems.