Send from Mac fails

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.


-- 
----
Peter Davis
The Tech Curmudgeon
www.techcurmudgeon.com

Re: Send from Mac fails

[Gijs Hillenius]

On  4 Jun 2015, Peter Davis wrote:

>
> 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

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

Re: Send from Mac fails

[Peter Davis]

Gijs Hillenius <gijs@hillenius.net> writes:

> On  4 Jun 2015, Peter Davis wrote:
>
>>
>> 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
>
> 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

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

Re: Send from Mac fails

[Peter Davis]

Gijs Hillenius <gijs@hillenius.net> writes:

> On  4 Jun 2015, Peter Davis wrote:
>
>>
>> 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
>
> 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