Re: embarrassing mail problem

2022-10-05 Thread Tom Smyth
howdy Steve...
on newer versions of openBSD open SMTPD
legacy tls versions / ciphers are disabled by default...
there is an option to allow legact tls versions ( i cant remember the
option off hand but man smtpd.conf and search for tls you should find it
handy enough...( this caught me out on an upgrade to 7.0

btw mxtoolbox.com has some useful tests that could help you diagnose mail
flow issues...

DMARC + DKIM   would be worth looking at...

also check the spamhaus PBL... if your isp suddenly added their subscriber
ip ranges to the PBL this could negatively impact you if your mail server
ip is in the ranges the ISP included in Spamhaus Policy Block List...

hope this helps



On Wed 5 Oct 2022, 23:07 Steve Fairhead,  wrote:

> I've searched and failed, and I realise I'm going to show my total
> ignorance by not having found an answer (and no, I've not been keeping
> up these last few years - mea culpa - demanding day-job). But - I'd be
> grateful for any (gentle or otherwise) cluebats.
>
> I have several OpenBSD email servers, some elderly (Sendmail) and some
> brand-spanking new (smtpd). Recently I've noticed that some (of both
> kinds) are failing to deliver mail to some major UK ISPs. (Mostly
> domestic; business ISPs not so much.)
>
> For Sendmail, the error is "TLS handshake failed"; for smtpd, it's
> "Network error on destination MXs".
>
> I do have SPF etc setup; thought that might be it, but no. I've read
> that some ISPs have closed port 25. I presume that's relevant, but I
> simply don't know.
>
> As I said, all cluebats gratefully (and probably painfully) accepted.
>
> Steve
>
> --
>
> --
>Steve Fairhead
>   email: st...@fivetrees.com
> --
>
>


Re: embarrassing mail problem

2022-10-05 Thread Jeremy Mates
On Wed, Oct 05, 2022 at 10:04:36PM +0100, Steve Fairhead wrote:
> For Sendmail, the error is "TLS handshake failed"; for smtpd, it's
> "Network error on destination MXs".

one "fix" would be to disable TLS for the domains in question, which
at least would let the mail go through until the encryption can be
set aright, perhaps with an access map entry along the lines of

Try_TLS:badhost.example.com NO



Re: embarrassing mail problem

2022-10-06 Thread Stuart Henderson
On 2022-10-05, Steve Fairhead  wrote:
> I have several OpenBSD email servers, some elderly (Sendmail) and some 
> brand-spanking new (smtpd). Recently I've noticed that some (of both 
> kinds) are failing to deliver mail to some major UK ISPs. (Mostly 
> domestic; business ISPs not so much.)
>
> For Sendmail, the error is "TLS handshake failed"; for smtpd, it's 
> "Network error on destination MXs".

Can you show some example servers that are having the problem?

Has anything changed network-wise on your side that might coincide
with this breaking?

> I do have SPF etc setup; thought that might be it, but no. I've read 
> that some ISPs have closed port 25. I presume that's relevant, but I 
> simply don't know.

Delivery to MXes is done on port 25 so nobody is closing that on the
server side.

Some access ISPs may filter port 25 (and if so, may or may not have a
way to unblock it) but that would usually block everything on port 25,
not leave some working.

Shot in the dark: you could try lowering MTU as a test.

-- 
Please keep replies on the mailing list.



Re: embarrassing mail problem

2022-10-06 Thread Steven Shockley

On 10/5/2022 5:04 PM, Steve Fairhead wrote:

I have several OpenBSD email servers, some elderly (Sendmail) and some
brand-spanking new (smtpd). Recently I've noticed that some (of both
kinds) are failing to deliver mail to some major UK ISPs. (Mostly
domestic; business ISPs not so much.)

For Sendmail, the error is "TLS handshake failed"; for smtpd, it's
"Network error on destination MXs".


"TLS handshake failed" usually means a TLS cipher mismatch, but maybe 
they're requiring a valid public certificate.  You can also use 
testssl.sh to see what ciphers they're actually using.


Check the logs and do a tcpdump of one of the failed connections.  One 
of those should tell you directly what's wrong.