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Grant Sewell wrote: > > I have read that Google routinely forget to update their certificates, > and they're not updated at the same time so certificate errors can occur > if you happen to connect to a different server in their cloud, and that > ClawsMail is more prone to problems along those lines unless you enable > some "unsafe" options in the config file - which I have done! You can of course pull the certificate using openssl client, and verify and inspect it using "openssl verify" and "openssl x509". I did this, and the bit of the cloud I am connecting to is all perfect as far as I can tell (protocol bugs in TLS aside, and not applicable here), certificates verify, and are current, and trusted etc etc. > What's going on? Don't know. I eavesdropped on my TLS session to port 587 (why are you trying 465 that is for SMTP over SSL), and it does exactly what yours does (no AUTH advertised). Except I don't get the "couldn't start TLS" error with Thunderbird. After that it is all encrypted so tcpdump isn't much use, but the email went and came back, so I'm guessing the rest worked. If you use SMTP over SSL (I used openssl client) googlemail advertises AUTH PLAIN straight away, so I think they are correctly not advertising AUTH PLAIN until the connection itself is encrypted. TLS settings were: --- New, TLSv1/SSLv3, Cipher is RC4-MD5 Server public key is 1024 bit Compression: NONE Expansion: NONE SSL-Session: Protocol : TLSv1 Cipher : RC4-MD5 Session-ID: snip Session-ID-ctx: Master-Key: snip Key-Arg : None Start Time: 1257804105 Timeout : 300 (sec) Verify return code: 0 (ok) --- Presumably the client is failing to negotiate an acceptable set of cipher for the TLS connection. Can you connect using openssl client something like: openssl s_client -showcerts -CApath /etc/ssl/certs/ -starttls smtp -connect smtp.googlemail.com:587 Depending where your SSL certs are kept.... I get same protocol and cipher as above when doing this. Otherwise you'll have to persuade Claws to enable the verbose TLS negotiation so you can see how both ends fail to negotiate an encrypted connection. At that point I'd just use SMTP over SSL instead, as it is easier to troubleshoot and you don't even need SSL support in the client with stunnel. Simon -- The Mailing List for the Devon & Cornwall LUG http://mailman.dclug.org.uk/listinfo/list FAQ: http://www.dcglug.org.uk/linux_adm/list-faq.html