(Or "Today's yak shaving exercise")
I'm trying to get back into some Debian work today, which involved trying to send an email from my laptop, relayed through daedalus, which is in a colo facility.
Then I started shaving my yak.
daedalus rejected the email, because the relay attempt wasn't authenticated. It wasn't authenticated because Exim on my laptop wasn't happy about the Diffie-Hellman parameters Sendmail on daedalus was advertising, and had failed STARTTLS, and like a sensible person, I only allow encrypted authentication. Along the way, I figured I'd need to address the fact that the host certificate has expired long ago (truth is, I probably just needed to fix the Diffie-Hellman parameters file), but my whole CA certificate expired over a year ago.
I couldn't find the encrypted USB key with my CA on it, so I decided to cut my losses and start from scratch. It's good to see OpenSSL hasn't got any more user friendly with time. I futzed around and generated a new CA key and certificate, a new CSR for Sendmail, signed it, did the appropriate sacrifices, and confirmed that STARTTLS now worked using OpenSSL s_client.
Still couldn't send an email. Still had some bleating in the Exim logs:
2014-02-17 11:29:26 1WFD1M-00086p-KI TLS error on connection to daedalus.andrew.net.au [126.96.36.199] (gnutls_handshake): The Diffie-Hellman prime sent by the server is not acceptable (not long enough).
Back on daedalus, /etc/mail/tls/sendmail-common.prm has been an empty file since time immemorial. I managed to find something in Google's cache suggesting I should put something in it with
openssl dhparam -out /etc/mail/tls/sendmail-common.prm -2 1024
I initially went for 4096 bits, because it must be better, right? I'm still waiting for the key generation to come back, while I'm writing this. At least it warned me in advance it was going to take a long time. How thoughtful. What would be more thoughtful was verifying the write permission to the file before the long operation so it could fail fast, rather. Sigh. I ended up giving up on 4096 and sticking with 1024, because I was getting old waiting.
Yak shaved, I can send mail from my laptop now.