Send from Mac fails

[Peter Davis]

I'm trying to set up a new Mac for gnus, but I can't send messages. When
I try, I get these messages:

Sending via mail...
Opening TLS connection to `smtps-proxy.messagingengine.com'...
Opening TLS connection with `gnutls-cli --insecure -p 80
smtps-proxy.messagingengine.com'...failed
Opening TLS connection with `gnutls-cli --insecure -p 80
smtps-proxy.messagingengine.com --protocols ssl3'...failed
Opening TLS connection with `openssl s_client -connect
smtps-proxy.messagingengine.com:80 -no_ssl2 -ign_eof'...failed
Opening TLS connection to `smtps-proxy.messagingengine.com'...failed
Sending failed: Unable to contact server

I tried running gnutls-cli (installed via homebrew) from the command
line, and got this:

% gnutls-cli --insecure -p 80 smtps-proxy.messagingengine.com
Processed 0 CA certificate(s).
Resolving 'smtps-proxy.messagingengine.com'...
Connecting to '66.111.4.42:80'...
|<1>| Received record packet of unknown type 72
*** Fatal error: An unexpected TLS packet was received.
*** Handshake has failed
GnuTLS error: An unexpected TLS packet was received.

[Gijs Hillenius]

Post by Peter Davis
I'm trying to set up a new Mac for gnus, but I can't send
Sending via mail...
Opening TLS connection to `smtps-proxy.messagingengine.com'...
Opening TLS connection with `gnutls-cli --insecure -p 80

port 80? Why is that? try without the -p 80

gnutls-cli --insecure smtps-proxy.messagingengine.com
Processed 0 CA certificate(s).
Resolving 'smtps-proxy.messagingengine.com'...
Connecting to '66.111.4.42:443'...
- Certificate type: X.509
- Got a certificate list of 2 certificates.


[...]



- Simple Client Mode:
220 mail.messagingengine.com ESMTP ready

[Peter Davis]

Post by Gijs Hillenius

Post by Peter Davis
I'm trying to set up a new Mac for gnus, but I can't send
Sending via mail...
Opening TLS connection to `smtps-proxy.messagingengine.com'...
Opening TLS connection with `gnutls-cli --insecure -p 80

port 80? Why is that? try without the -p 80
gnutls-cli --insecure smtps-proxy.messagingengine.com
Processed 0 CA certificate(s).
Resolving 'smtps-proxy.messagingengine.com'...
Connecting to '66.111.4.42:443'...
- Certificate type: X.509
- Got a certificate list of 2 certificates.
[...]
220 mail.messagingengine.com ESMTP ready

These identical settings work on my other Macs. Fastmail has these
servers set up to get around firewalls that block outgoing connections
to certain ports.
<https://www.fastmail.com/help/technical/servernamesandports.html>

Thank you.
-pd

[Peter Davis]

Post by Gijs Hillenius

Post by Peter Davis
I'm trying to set up a new Mac for gnus, but I can't send
Sending via mail...
Opening TLS connection to `smtps-proxy.messagingengine.com'...
Opening TLS connection with `gnutls-cli --insecure -p 80

port 80? Why is that? try without the -p 80

So I tried it without port 80, as Gijs suggested, and it did
work. Thank you, Gijs!

However, on three other Macs, it worked perfectly *with* port 80
specified. I originally started using this to get around a firewall at
work that blocked outgoing SMTP, as suggested here:
https://www.fastmail.com/help/technical/servernamesandports.html

Now it appears my new office has some other firewall weirdness going
on. This call failed with -p 80, but worked without it. However, from
home, it worked on the same Mac *with* -p 80. I'm trying to get to the
bottom of this, as I'd like to use the same settings everywhere.

Thanks,
-pd