While technically the update didn't break the Sendmail installation, it did fail to work with my configuration file.

For some reason the release upgrades of Ubuntu always seem to tweak my configuration and mail stops flowing. It seemed to be OK at first because sendmail was running, and there was traffic in the log--most of the traffic showing mail getting discarded, but that's really what most of the traffic is anyway.

It seems that changes to some of the libraries were causing sendmail to fail in parts. In particular, reading the maps for the virtual users and domains and such were failing, probably because the Berkeley database had changed.

I quickly tried to recompile sendmail from the source existing. It doesn't seem that the package-provided version of sendmail includes the SSL stuff I want, so I always need to rebuild from source. The old source failed to build. I downloaded the new source (v8.14.7) and copied my devtools/Site/site.config.m4 file from the old build and gave it a go.

The new source also failed.

I did some Internet searching and cleaned the file and came up with the following that finally did work.

APPENDDEF(`confENVDEF', `-DSASL=2 -DSTARTTLS')
APPENDDEF(`conf_sendmail_LIBS', `-lsasl2')
APPENDDEF(`confLIBS', `-lssl -lcrypto -lresolv -ldb')
APPENDDEF(`confMAPDEF', `-DNEWDB')

I also had to remove the source directory and start over as all of the Makefiles weren't getting refreshed as I changed the config file. With a clean source, and newly copied site.config.m4 file, I finally got a successful build and install. I reused my existing sendmail.mc file to rebuild a new sendmail.cf file, tripped through the alias files so they'd all get rebuilt with the new makemap, and the new server works just fine.

A flood of mail that wasn't getting handled confirmed this was a problem. A few test messages passed through the server as expected. I'm calling this bit done.