Date: Thu, 23 Mar 2017 12:00:08 -0400 From: William Dudley <wfdudley@gmail.com> To: Matthew Seaman <matthew@freebsd.org> Cc: freebsd-questions@freebsd.org Subject: Re: how do I get STARTTLS working with sendmail on FreeBSD 10.3 ? Message-ID: <CAFsnNZKCv0UcwGKeMW7xLLhyN5qVLEya7z6h1DBVqYsjqGdJ-w@mail.gmail.com> In-Reply-To: <cae94183-aae8-781c-680d-b4c3c44b2dbd@FreeBSD.org> References: <mailman.110.1490270402.90011.freebsd-questions@freebsd.org> <20170323233742.R95579@sola.nimnet.asn.au> <d47700f6-7adf-1d51-2e8b-4431e9102ee5@FreeBSD.org> <CAFsnNZLcLrmKYLFKLhcLEBzQv7x-1dqbFi9GyEG-_LxSYapbog@mail.gmail.com> <cae94183-aae8-781c-680d-b4c3c44b2dbd@FreeBSD.org>
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To answer your questions: Yes, I'm using the right .mc file, and yes, I know how to make && make install && make restart when I make changes to it. (I assume service sendmail restart has the same effect as "make restart"; it *looks* the same when I "tail -f /var/log/maillog"). sockstat | grep sendmail root sendmail 78456 3 dgram -> /var/run/logpriv root sendmail 78456 4 tcp4 *:25 *:* root sendmail 78456 5 tcp4 *:465 *:* root sendmail 78456 6 tcp4 *:587 *:* smmsp sendmail 78454 3 dgram -> /var/run/log So that seems reasonable. sockstat | grep -E ':25\>' returns line two from above, so that's the same. /etc/mail/access has a handful of address "OK" and address "ERROR" lines I added to explicitly block or accept various emailers, and this: 192.168.27.26 RELAY junkemailfilter.com OK GreetPause:192.168.27.26 0 GreetPause:localhost 0 GreetPause:localhost.localdomain 0 GreetPause:pascal.junkemailfilter.com 0 srv_features: S The relay is for my workstation, on the same LAN (obviously). The GreetPause lines turn off the greeting delay for certain hosts. AND -- Ah-hah Hmmm, I don't remember adding any lines that would turn off STARTTLS, but that's what srv_features: S does. I'm SURE I didn't add that. I certainly didn't add it recently. Perhaps it was added by one of the blind alleys I've been sent down ("stunnel" comes to mind). So. Fixed. Removed that line, "make && make restart" and now STARTTLS is a capability of sendmail, *again*. The phone is still unhappy, but that's another problem. I declare this thread ended. Thanks everyone, even the snide Mr. Ohlstein, for their time. Bill Dudley This email is free of malware because I run Linux. On Thu, Mar 23, 2017 at 11:27 AM, Matthew Seaman <matthew@freebsd.org> wrote: > On 2017/03/23 15:00, William Dudley wrote: > > Let's assume that I have no idea what I'm talking about. > > However, I can successfully report what I SEE. > > > > 1. Android's mail app wants to use STARTTLS when it connects to my mail > > server, for > > whatever reason (send or receive) isn't important now. It wants it, and > I > > want it to be > > happy, or else it doesn't work. > > Ah -- in this case, you've potentially got two different software > systems that could involve STARTTLS. sendmail would only be involved > when you send an e-mail. Otherwise your android device will be > connecting to an IMAP server -- and that could either be configured to > listen on port 143 (the port for unencrypted IMAP) and expect to use > STARTTLS to upgrade to an encrypted connection; or it could listen on > port 993 which expects TLS straight away. There is a move by IANA (I > think) to prefer STARTTLS type mechanisms and so recover all of the > duplicated-except-for-requiring-TLS port numbers out of /etc/services. > > But, as you say, the sendmail problems need sorting anyhow. Time to > worry about IMAP later. > > > 2. When I telnet to port 25 of my mail server, sendmail does NOT announce > > STARTTLS > > as one of it's capabilities. This, despite my having all the > incantations > > *apparently" correct > > in my hostname.mc, fresh self signed cert and key file in > /etc/mail/certs, > > and various other > > things that have been suggested/intimated by various sources. > > Hmmm... well, I don't understand why it isn't working for you. The > sendmail in FreeBSD-10.3 is supplied with STARTTLS capabilities compiled > in and should have certs and keys created for it at install time. > > > It would be nice to solve the problem stated in the Subject of this > > insanely long thread: > > > > Why is my sendmail refusing to announce STARTTLS ? > > It is almost certainly some trivial little oversight, but it's > impossible to say what that might be. I'm sure you've been through all > this already, but have you checked and rechecked the simple and obvious > stuff: > > * Have you built and installed a fresh sendmail config: > > # cd /etc/mail > # make > # make install > > * Are you editing the correct .mc file? The one you want is > ${hostname}.mc -- where ${hostname} (if it isn't obvious) is the > hostname of your machine. If this doesn't exist, typing 'make' > will create it for you. > > * Did you restart sendmail after the last config update? > > # service sendmail restart > > * Is sendmail listening on the IP numbers and ports you expect it to > be listening on? Or is it some other piece of software > entirely answering on port 25? > > # sockstat | grep sendmail > # sockstat | grep -E ':25\>' > > will provide clues. > > * Do you have anything in /etc/mail/access ? > > * What's in /etc/mail/mailwrapper ? > > Cheers, > > Matthew > > >
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