Re: Fwd: Re: Postfix 3.5 and outbound TLS/SSL

2022-08-23 Thread raf
On Tue, Aug 23, 2022 at 09:21:33AM -0700, nate wrote: > On 2022-08-22 14:46, Viktor Dukhovni wrote: > > [..] > > > You don't need to sign your own domain in order to secure outbound > > traffic > > to domains that others have signed. You just need a local validating > > resolver such as "unbou

Re: Fwd: Re: Postfix 3.5 and outbound TLS/SSL

2022-08-23 Thread nate
On 2022-08-22 14:46, Viktor Dukhovni wrote: [..] You don't need to sign your own domain in order to secure outbound traffic to domains that others have signed. You just need a local validating resolver such as "unbound", with DNSSEC validation turned on. Ok, yeah I was thinking more of DANE

Re: Fwd: Re: Postfix 3.5 and outbound TLS/SSL

2022-08-22 Thread Viktor Dukhovni
On Tue, Aug 23, 2022 at 01:13:56AM -0400, Demi Marie Obenour wrote: > You should definitely deploy DNSSEC, but only after you are able to > deploy it properly. That means having procedures to avoid nasty DNSSEC- > related downtime. That's needlessly scary and non-specific. Rather, it means, tha

Re: Fwd: Re: Postfix 3.5 and outbound TLS/SSL

2022-08-22 Thread Demi Marie Obenour
On 8/22/22 17:38, nate wrote: > On 2022-08-22 14:30, Viktor Dukhovni wrote: > >> Correct, because there's no point. Mail would be sent whether the >> certificate is trusted or not, and whether or not the DNS-ID matches >> expectations. >> >> Setting up a TLS policy for each domain that's hosted b

Re: Fwd: Re: Postfix 3.5 and outbound TLS/SSL

2022-08-22 Thread Viktor Dukhovni
On Mon, Aug 22, 2022 at 02:38:20PM -0700, nate wrote: > On 2022-08-22 14:30, Viktor Dukhovni wrote: > > > Correct, because there's no point. Mail would be sent whether the > > certificate is trusted or not, and whether or not the DNS-ID matches > > expectations. > > > > Setting up a TLS policy

Re: Fwd: Re: Postfix 3.5 and outbound TLS/SSL

2022-08-22 Thread nate
On 2022-08-22 14:30, Viktor Dukhovni wrote: Correct, because there's no point. Mail would be sent whether the certificate is trusted or not, and whether or not the DNS-ID matches expectations. Setting up a TLS policy for each domain that's hosted by Microsoft is unrealistic, and they don't yet

Re: Fwd: Re: Postfix 3.5 and outbound TLS/SSL

2022-08-22 Thread Viktor Dukhovni
On Mon, Aug 22, 2022 at 02:09:26PM -0700, nate wrote: > postfix/smtp[7329]: Untrusted TLS connection established to > example-com.mail.protection.outlook.com[104.47.55.110]:25: TLSv1.2 with > cipher ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits) > > I assume it says Untrusted because Postfix do

Fwd: Re: Postfix 3.5 and outbound TLS/SSL

2022-08-22 Thread nate
On 2022-08-22 13:55, Viktor Dukhovni wrote: This should be the full certificate chain, not just the lead certificate. For that, you need at least: smtp_tls_security_level = may or perhaps (given a local validating resolver and only loopback nameserver IPs in /etc/resolv.conf or equival

Re: Postfix 3.5 and outbound TLS/SSL

2022-08-22 Thread Viktor Dukhovni
On Mon, Aug 22, 2022 at 01:41:35PM -0700, nate wrote: > More recently I formalized this configuration even more in an attempt to > make my system more up to date, being able to send and receive with > TLS. > > This is my TLS related configuration > [..] > smtpd_sasl_tls_security_options = noanony

Re: Postfix 3.5 and outbound TLS/SSL

2022-08-22 Thread Jaroslaw Rafa
Dnia 22.08.2022 o godz. 13:41:35 nate pisze: > > What I am confused by is Postfix does not appear to be attempting > to use TLS on any outbound emails. I have tested with Gmail and > with MS Office 365. Sample tcpdump Your config contains TLS settings for inbound (stmpd_tls_...) but I don't see a

Postfix 3.5 and outbound TLS/SSL

2022-08-22 Thread nate
Hello list Been using postfix for over 20 years now, though haven't really spent much time on the SSL end of things for it. A few years ago I setup SSL for inbound mainly for SASL auth sending that has worked fine. More recently I formalized this configuration even more in an attempt to mak