Hi everyone,

I am including as much information in here as I think will be useful. Since I can do snapshots on VMWare, I am happy to try any solution or diagnostics.
Steps I took to upgrade FreeBSD:
Using freebsd-update, I upgraded from 7.2-RELEASE to 7.2-RELEASE-p8
Then, to upgrade to 9.0-RELEASE, I ran the following commands, using http://www.freebsd.org/doc/handbook/updating-upgrading-freebsdupdate.html as my guide:
freebsd-update -r 9.0-RELEASE upgrade
freebsd-update install
reboot
freebsd-update install
portupgrade -f ruby
rm /var/db/pkg/pkgdb.db
portupgrade -f ruby18-bdb
rm /var/db/pkg/pkgdb.db /usr/ports/INDEX-*.db
portupgrade -af
freebsd-update install
reboot

I noticed that lots of things weren't working, and specifically that I was getting lots of complaints about /libexec/ld-elf.so.1. I also noticed that when I ran freebsd-update IDS, it seemed to report that every single file had the wrong signature.

So, this being a VMWare guest, I reluctantly reverted to a previous snapshot, putting me back at 7.2-RELEASE-p8.

I decided to try this time to go from 7.2-RELEASE-p8 to 7.4-RELEASE to 8.0-RELEASE to 8.3-RELEASE. I only got to 7.4-RELEASE before I had the same issues as above. As a specific example of errors I would get, I try to run sudo and I get:
[stuart@richelieu ~]$ sudo bash
/libexec/ld-elf.so.1: sudo: invalid PT_PHDR

This seems to be the most relevant thread to the problem I'm having: http://lists.freebsd.org/pipermail/freebsd-questions/2010-July/218443.html

However, I'd be more comfortable using an official upgrade path, like freebsd-update, exclusively. That thread involves replacing a file from a FreeBSD liveCD. Also, with freebsd-update IDS reporting so many files with incorrect signatures, I feel like my problem is bigger than fixing one file.

Right now I am back on 7.2-RELEASE-p8 eager to get my OS upgraded to something that is under current support by the security team. Optimally I'd like to be on 8.3 after looking at the EOL dates.

Also, I did see one other post _somewhere_ mentioning a similar problem, also on a VMWare guest. So I am suspicious that the problem might be related to VMWare.

Thanks, everyone.

- Stuart Matthews
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