Sunday, November 4, 2018

Goodness, Enumerated by Robots. Or, Handling Those Who Do Not Play Well With Greylisting

SMTP email is not going away any time soon. If you run a mail service, when and to whom you present the code signifying a temporary local problem code is well worth your attention.

SMTP email is everywhere and is used by everyone.

If you are a returning reader, there is a higher probability that you run a mail service yourself than in the general population.

This in turn means that you will be aware that one of the rather annoying oversights of the original and still-current specifications of the SMTP based mail system is that while it's straightforward to announce which systems are supposed to receive mail for a domain, specifying which hosts would be valid email senders was not part or the original specification at all.

Any functioning domain MUST have at least one MX (mail exchanger) record published via the domain name system, and registrars will generally not even let you register a domain unless you have set up somewhere to receive mail for the domain.

But email worked most of the time anyway, and while you would occasionally hear about valid mail not getting delivered, it was a rarer occurrence than you might think.

Then a few years along, the Internet grew out of the pure research arena and became commercial, and spam started happening. Even in the early days of spam it seems that a significant subset of the messages, possibly even the majority, was sent with faked sender addresses in domains not connected to the actual senders.

Over time people have tried a number of approaches to the problems involved in getting rid of unwanted commercial and/or malware carrying email. If you are interested in a deeper dive into the subject, you could jump over to my earlier piece Effective Spam and Malware Countermeasures - Network Noise Reduction Using Free Tools.

Two very different methods of reducing spam traffic were originally formulated at roughly the same time, and each method's adherents are still duking it out over which approach is the better one.

One method consists simply of implementing a strict interpretation of a requirement that was already formulated in the SMTP RFC at the time.

The other is a complicated extension of the SMTP-relevant data that is published via DNS, and full implementation would require reconfiguration of every SMTP email system in the world.

As you might have guessed, the first is what is commonly referred to as greylisting, where we point to the RFC's requirement that on encountering a temporary error, the sender MUST (RFC language does not get stronger than this) retry delivery at a later time and keep trying for a reasonable amount of time.

Spammers generally did not retry as per the RFC specifications, and even early greylisting adopters saw huge drop in the volume of spam that actually made it to mailboxes.

On the other hand, end users would sometimes wonder why their messages were delayed, and some mail administrators did not take well to seeing the volume of data sitting in the mail spool directories grow measurably, if not usually uncontrollably, while successive retries after waiting were in progress.

In what could almost almost appear as a separate, unconnected universe, other network engineers set out to fix the now glaringly obvious omission in the existing RFCs.

A way to announce valid senders was needed, and the specification that was to be known as the Sender Policy Framework (SPF for short) was offered to the world. SPF offered a way to specify which IP addresses valid mail from a domain were supposed to come from, and even included ways to specify how strictly the limitations it presented should be enforced at the receiving end.

The downsides were that all mail handling would need to be upgraded with code that supported the specification, and as it turned out, traditional forwarding such as performed by common mailing list software would not easily be made compatible with SPF.

The flame wars over both methods. You either remember them or should be able to imagine how they played out.

And while the flames grew less frequent and generally less fierce over time, mail volumes grew to the level where operators would have a large number of servers for outgoing mail, and while the site would honor the requirement to retry delivery, the retries would not be guaranteed to come from the same IP address as the original attempt.

It was becoming clear to greylisting practitioners that interpreting published SPF data as known good senders was the most workable way forward. Several of us already had started maintaining nospamd tables (see eg this slide and this), and using the output of

$ host -ttxt domain.tld

(sometimes many times over because some domains use include statements), we generally made do. I even made a habit of publishing my nospamd file.

As hinted in this slide, smtpctl (part of the OpenSMTPd system and in your OpenBSD base system) now since OpenBSD 6.3 is able to retrieve the entire contents of the published SPF information for any domain you feed it.

Looking over my old nospamd file during the last week or so I found enough sedimentary artifacts there, including IP addresses for which there was no explanation and that lacked a reverse lookup, that I turned instead to deciphering which domains had been problematic and wrote a tiny script to generate a fresh nospamd on demand, based on fresh SPF lookups on those domains.

For those wary of clicking links to scripts, it reads like this:

#!/bin/sh
domains=`cat thedomains.txt`
outfile=nospamd
generatedate=`date`
operator="Peter Hansteen <peter@bsdly.net>"
locals=local-additions

echo "##############################################################################################">$outfile;
echo "# This is the `hostname` nospamd generated from domains at $generatedate. ">>$outfile;
echo "# Any questions should be directed to $operator. ">>$outfile;
echo "##############################################################################################">>$outfile;
echo >>$outfile;

for dom in $domains; do 
 echo "processing $dom";
 echo "# $dom starts #########">>$outfile;
 echo >>$outfile;
 echo $dom | doas smtpctl spf walk >>$outfile;
 echo "# $dom ends ###########">>$outfile;
 echo >>$outfile;
done

echo "##############################################################################################">>$outfile;
echo "# processing done at `date`.">>$outfile; 
echo "##############################################################################################">>$outfile;

echo "adding local additions from $locals";
echo "# local additions below here ----" >>$outfile;
cat $locals >> $outfile;

If you have been in the habit of fetching my nospamd, you have been fetching the output of this script for the last day or so.

What it does is simply read a prepared list of domains, run them through smtpctl spf walk and slap the results in a file which you would then load into the pf configuration on your spamd machine. You can even tack on a few local additions that for whatever reason do not come naturally from the domains list.

But I would actually recommend you do not fetch my generated data, and rather use this script or a close relative of it (it's a truly trivial script and you probably can create a better version) and your own list of domains to generate a nospamd tailored to your local environment.

The specific list of domains is derived from more than a decade of maintaining my setup and the specific requests for whitelisting I have received from my users or quick fixes to observed problems in that period. It is conceivable that some domains that were problematic in the past no longer are, and unless we actually live in the same area, some of the domains in my list are probably not relevant to your users. There is even the possibility that some of the larger operators publish different SPF information in specific parts of the world, so the answers I get may not even match yours in all cases.

So go ahead, script and generate! This is your chance to help the robots generate some goodness, for the benefit of your users.

In related news, a request from my new colleagues gave me an opportunity to update the sometimes-repeated OpenBSD and you presentation so it now has at least some information on OpenBSD 6.4. You could call the presentation a bunch of links in a thin wrapper of advocacy and you would not be very wrong.

If you have comments or questions on any of the issues raised in this article, please let me know, preferably via the (moderated) comments field, but I have also been known to respond to email and via various social media message services.

Update 2018-11-11: A few days after I had posted this article, an incident happened that showed the importance of keeping track of both goodness and badness for your services. This tweet is my reaction to a few quick glances at the bsdly.net mail server log:

A little later I'm clearly pondering what to do, including doing another detailed writeup.
Fortunately I had had some interaction with this operator earlier, so I knew roughly how to approach them. I wrote a couple of quick messages to their abuse contacts and made sure to include links to both my spamtrap resources and a fresh log excerpt that indicated clearly that someone or someones in their network was indeed progressing from top to bottom of the spamtraps list.
As the last tweet says, delivery attempts stopped after progressing to somewhere into the Cs. The moral might be that a list of spamtraps like the one I publish might be useful for other sites to filtering their outgoing mail. Any activity involving the known-bad addresses would be a strong indication that somebody made a very unwise purchasing decision involving address lists.

Monday, August 13, 2018

Badness, Enumerated by Robots

A condensed summary of the blacklist data generated from traffic hitting bsdly.net and cooperating sites.

After my BSDjobs.com entry was posted, there has been an uptick in interest about the security related data generated at the bsdly.net site. I have written quite extensively about these issues earlier so I'll keep this piece short. If you want to go deeper, the field note-like articles I reference and links therein will offer some further insights.

There are three separate sets of downloadable data, all automatically generated and with only very occasional manual intervention.


Known spam sources during the last 24 hours

This is the list directly referenced in the BSDjobs.com piece.

This is a greytrapping based list, where the conditions for inclusion are simple: Attempts at delivery to known-bad addresses in domains we handle mail for have happened within the last 24 hours.

In addition there will occasionally be some addresses added by cron jobs I run that pick the IP addresses of hosts that sent mail that made it through greylisting performed by our spamd(8) but did not pass the subsequent spamassassin or clamav treatment. The bsdly.net system is part of the bgp-spamd cooperation.

The traplist has a home page and at one point was furnished with a set of guidelines.

A partial history (the log starts 2017-05-20) of when spamtraps were added and from which sources can be found in this log (or at this alternate location). Read on for a bit of information on the alternate sources.

Misc other bots: SSH Password bruteforcing, malicious web activity, POP3 Password Bruteforcing.

The bruteforcers list is really a combination of several things, delivered as one file but with minimal scripting ability you should be able to dig out the distinct elements, described in this piece.

The (usually) largest chunk is a list of hosts that hit the rate limit for SSH connections described in the article or that was caught trying to log on as a non-existent user or other undesirable activity aimed at my sshd(8) service. Some as yet unpublished scriptery helps me feed the miscreants that the automatic processes do not catch into the table after a manual quality check.

The second part is a list of IP addresses that tried to access our web service in undesirable ways, including trying for specific URLs or files that will never be found at any world-facing part of our site.

After years of advocating short lifetimes (typically 24 hours) for blacklist entries only to see my logs fill up with attempts made at slightly slower speeds, I set the lifetime for entries in this data set to 28 days. The background including some war stories of monitoring SSH password groping can be found in this piece, while the more recent piece here covers some of the weeding out bad web activity.

The POP3 gropers list comes in two variations. Again lists of IP addresses caught trying to access a service, most of those accesses are to non-existent user names with an almost perfect overlap with the spamtraps list, local-part only (the part before the @ sign).

The big list is a complete corpus of IP addresses that have tried these kinds of accesses since I started recording and trapping them (see this piece for some early experience and this one for the start of the big collection).

There is also a smaller set, produced from the longterm table described in this piece. For much the same reason I did not stick to 24-hour expiry for the SSH list, this one has six-week expiry. With some minimal scriptery I run by hand one or two times per day, any invalid POP3 accesses to valid accounts get their IP adresses added to the longterm table and the exported list.

If you're wondering about the title, the term "enumerating badness" stems from Marcus Ranum's classic piece The Six Dumbest Ideas in Computer Security. Please do read that one.

Here are a few other references other than those referenced in the paragraphs above that you might find useful:

The Book of PF, 3rd edition
Hey, spammer! Here's a list for you! which contains the announcement of the bsdly.net traplist.
Effective Spam and Malware Countermeasures, a more complete treatment of those keywords

If you're interested in further information on any of this, the most useful contact information is in the comment blocks in the exported lists.

Sunday, April 1, 2018

ed(1) mastery is a must for a real Unix person

ed(1) is the standard editor. Now there's a book out to help you master this fundamental Unix tool.

In some circles on the Internet, your choice of text editor is a serious matter.

We've all seen the threads on mailing lits, USENET news groups and web forums about the relative merits of Emacs vs vi, including endless iterations of flame wars, and sometimes even involving lesser known or non-portable editing environments.

And then of course, from the Linux newbies we have seen an endless stream of tweeted graphical 'memes' about the editor vim (aka 'vi Improved') versus the various apparently friendlier-to-some options such as GNU nano. Apparently even the 'improved' version of the classical and ubiquitous vi(1) editor is a challenge even to exit for a significant subset of the younger generation.

Yes, your choice of text editor or editing environment is a serious matter. Mainly because text processing is so fundamental to our interactions with computers.

But for those of us who keep our systems on a real Unix (such as OpenBSD or FreeBSD), there is no real contest. The OpenBSD base system contains several text editors including vi(1) and the almost-emacs mg(1), but ed(1) remains the standard editor.

Now Michael Lucas has written a book to guide the as yet uninitiated to the fundamentals of the original Unix text editor. It is worth keeping in mind that much of Unix and its original standard text editor written back when the standard output and default user interface was more likely than not a printing terminal.

To some of us, reading and following the narrative of Ed Mastery is a trip down memory lane. To others, following along the text will illustrate the horror of the world of pre-graphic computer interfaces. For others again, the fact that ed(1) doesn't use your terminal settings much at all offers hope of fixing things when something or somebody screwed up your system so you don't have a working terminal for that visual editor.

ed(1) is a line editor. And while you may have heard mutters that 'vi is just a line editor in drag', vi(1) does offer a distinctly visual interface that only became possible with the advent of the video terminal, affectionately known as the glass teletype. ed(1) offers no such luxury, but as the book demonstrates, even ed(1) is able to display any part of a file's content for when you are unsure what your file looks like.

The book Ed Mastery starts by walking the reader through a series of editing sessions using the classical ed(1) line editing interface. To some readers the thought of editing text while not actually seeing at least a few lines at the time onscreen probably sounds scary.  This book shows how it is done and while the author never explicitly mentions it, the text aptly demonstrates how the ed(1) command set is in fact the precursor of of how things are done in many Unix text processing programs.

As one might expect, the walkthrough of ed(1) text editing functionality is followed up by a sequence on searching and replacing which ultimately leads to a very readable introduction to regular expressions, which of course are part of the ed(1) package too. If you know your ed(1) command set, you are quite far along in the direction of mastering the stream editor sed(1), as well as a number of other systems where regular expressions play a crucial role.

After the basic editing functionality and some minor text processing magic has been dealt with, the book then proceeds to demonstrate ed(1) as a valuable tool in your Unix scripting environment. And once again, if you can do something with ed, you can probably transfer that knowledge pretty much intact to use with other Unix tools.

The eighty-some text pages of Ed Mastery are a source of solid information on the ed(1) tool itself with a good helping of historical context that will make it clearer to newcomers why certain design choices were made back when the Unix world was new. A number of these choices influence how we interact with the modern descendants of the Unix systems we had back then.

Your choice of text editor is a serious matter. With this book, you get a better foundation for choosing the proper tool for your text editing and text processing needs. I'm not saying that you have to switch to the standard editor, but after reading Ed Mastery , your choice of text editing and processing tools will be a much better informed one.

Ed Mastery  is available now directly from Michael W. Lucas' books site at https://www.michaelwlucas.com/tools/ed, and will most likely appear in other booksellers' catalogs as soon as their systems are able to digest the new data.

Do read the book, try out the standard editor and have fun!

Saturday, February 17, 2018

A Life Lesson in Mishandling SMTP Sender Verification

An attempt to report spam to a mail service provider's abuse address reveals how incompetence is sometimes indistinguishable from malice.

It all started with one of those rare spam mails that got through.

This one was hawking address lists, much like the ones I occasionally receive to addresses that I can not turn into spamtraps. The message was addressed to, of all things, root@skapet.bsdly.net. (The message with full headers has been preserved here for reference).

Yes, that's right, they sent their spam to root@. And a quick peek at the headers revealed that like most of those attempts at hawking address lists for spamming that actually make it to a mailbox here, this one had been sent by an outlook.com customer.

The problem with spam delivered via outlook.com is that you can't usefully blacklist the sending server, since the largish chunk of the world that uses some sort of Microsoft hosted email solution (Office365 and its ilk) have their usually legitimate mail delivered via the very same infrastructure.

And since outlook.com is one of the mail providers that doesn't play well with greylisting (it spreads its retries across no less than 81 subnets (the output of 'echo outlook.com | doas smtpctl spf walk' is preserved here), it's fairly common practice to just whitelist all those networks and avoid the hassle of lost or delayed mail to and from Microsoft customers.

I was going to just ignore this message too, but we've seen an increasing number of spammy outfits taking advantage of outlook.com's seeming right of way to innocent third parties' mail boxes.

So I decided to try both to do my best at demoralizing this particular sender and alert outlook.com to their problem. I wrote a messsage (preserved here) with a Cc: to abuse@outlook.com where the meat is,

Ms Farell,

The address root@skapet.bsdly.net has never been subscribed to any mailing list, for obvious reasons. Whoever sold you an address list with that address on it are criminals and you should at least demand your money back.

Whoever handles abuse@outlook.com will appreciate the attachment, which is a copy of the message as it arrived here with all headers intact.

Yours sincerely,
Peter N. M. Hansteen

What happened next is quite amazing.

If my analysis is correct, it may not be possible for senders who are not themselves outlook.com customers to actually reach the outlook.com abuse team.

Almost immediately after I sent the message to Ms Farell with a Cc: to abuse@outlook.com, two apparently identical messages from staff@hotmail.com, addressed to postmaster@bsdly.net appeared (preserved here and here), with the main content of both stating

This is an email abuse report for an email message received from IP 216.32.180.51 on Sat, 17 Feb 2018 01:59:21 -0800.
The message below did not meet the sending domain's authentication policy.
For more information about this format please see http://www.ietf.org/rfc/rfc5965.txt.

In order to understand what happened here, it is necessary to look at the mail server log for a time interval of a few seconds (preserved here).

The first few lines describe the processing of my outgoing message:

2018-02-17 10:59:14 1emzGs-0009wb-94 <= peter@bsdly.net H=(greyhame.bsdly.net) [192.168.103.164] P=esmtps X=TLSv1.2:ECDHE-RSA-AES128-GCM-SHA256:128 CV=no S=34977 id=31b4ffcf-bf87-de33-b53a-0 ebff4349b94@bsdly.net

My server receives the message from my laptop, and we can see that the connection was properly TLS encrypted

2018-02-17 10:59:15 1emzGs-0009wb-94 => peter <root@skapet.bsdly.net> R=localuser T=local_delivery

I had for some reason kept the original recipient among the To: addresses. Actually useless but also harmless.

2018-02-17 10:59:16 1emzGs-0009wb-94 [104.47.40.33] SSL verify error: certificate name mismatch: DN="/C=US/ST=WA/L=Redmond/O=Microsoft Corporation/OU=Microsoft Corporation/CN=mail.protection.outlook.com" H="outlook-com.olc.protection.outlook.com"
2018-02-17 10:59:18 1emzGs-0009wb-94 SMTP error from remote mail server after end of data: 451 4.4.0 Message failed to be made redundant due to A shadow copy was required but failed to be made with an AckStatus of Fail [CO1NAM03HT002.eop-NAM03.prod.protection.outlook.com] [CO1NAM03FT002.eop-NAM03.prod.protection.outlook.com]
2018-02-17 10:59:19 1emzGs-0009wb-94 [104.47.42.33] SSL verify error: certificate name mismatch: DN="/C=US/ST=WA/L=Redmond/O=Microsoft Corporation/OU=Microsoft Corporation/CN=mail.protection.outlook.com" H="outlook-com.olc.protection.outlook.com"


What we see here is that even a huge corporation like Microsoft does not always handle certificates properly. The certificate they present for setting up the encrypted connection is not actually valid for the host name that the outlook.com server presents.

There is also what I interpret as a file system related message which I assume is meaningful to someone well versed in Microsoft products, but we see that

2018-02-17 10:59:20 1emzGs-0009wb-94 => janet@prospectingsales.net R=dnslookup T=remote_smtp H=prospectingsales-net.mail.protection.outlook.com [23.103.140.138] X=TLSv1.2:ECDHE-RSA-AES256-SHA384:256 CV=yes K C="250 2.6.0 <31b4ffcf-bf87-de33-b53a-0ebff4349b94@bsdly.net> [InternalId=40926743365667, Hostname=BMXPR01MB0934.INDPRD01.PROD.OUTLOOK.COM] 44350 bytes in 0.868, 49.851 KB/sec Queued mail for delivery"

even though the certificate fails the verification part, the connection sets up with TLSv1.2 anyway, and the message is accepted with a "Queued mail for delivery" message.

The message is also delivered to the Cc: recipient:

2018-02-17 10:59:21 1emzGs-0009wb-94 => abuse@outlook.com R=dnslookup T=remote_smtp H=outlook-com.olc.protection.outlook.com [104.47.42.33] X=TLSv1.2:ECDHE-RSA-AES256-SHA384:256 CV=no K C="250 2.6.0 <31b4ffcf-bf87-de33-b53a-0ebff4349b94@bsdly.net> [InternalId=3491808500196, Hostname=BY2NAM03HT071.eop-NAM03.prod.protection.outlook.com] 42526 bytes in 0.125, 332.215 KB/sec Queued mail for delivery"
2018-02-17 10:59:21 1emzGs-0009wb-94 Completed


And the transactions involving my message would normally have been completed.

But ten seconds later this happens:

2018-02-17 10:59:31 1emzHG-0004w8-0l <= staff@hotmail.com H=bay004-omc1s10.hotmail.com [65.54.190.21] P=esmtps X=TLSv1.2:ECDHE-RSA-AES256-SHA384:256 CV=no K S=43968 id=BAY0-XMR-100m4KrfmH000a51d4@bay0-xmr-100.phx.gbl
2018-02-17 10:59:31 1emzHG-0004w8-0l => peter <postmaster@bsdly.net> R=localuser T=local_delivery
2018-02-17 10:59:31 1emzHG-0004w8-0l => peter <postmaster@bsdly.net> R=localuser T=local_delivery


That's the first message to my domain's postmaster@ address, followed two seconds later by

2018-02-17 10:59:33 1emzHI-0004w8-Fy <= staff@hotmail.com H=bay004-omc1s10.hotmail.com [65.54.190.21] P=esmtps X=TLSv1.2:ECDHE-RSA-AES256-SHA384:256 CV=no K S=43963 id=BAY0-XMR-100Q2wN0I8000a51d3@bay0-xmr-100.phx.gbl
2018-02-17 10:59:33 1emzHI-0004w8-Fy => peter <postmaster@bsdly.net> R=localuser T=local_delivery
2018-02-17 10:59:33 1emzHI-0004w8-Fy Completed


a second, apparently identical message.

Both of those messages state that the message I sent to abuse@outlook.com had failed SPF verification, because the check happened on connections from NAM03-BY2-obe.outbound.protection.outlook.com (216.32.180.51) by whatever handles incoming mail to the staff@hotmail.com address, which apparently is where the system forwards abuse@outlook.com's mail.

Reading Microsoft Exchange's variant SMTP headers has never been my forte, and I won't try decoding the exact chain of events here since that would probably also require you to have fairly intimate knowledge of Microsoft's internal mail delivery infrastructure.

But even a quick glance at the messages reveals that the message passed SPF and other checks on incoming to the outlook.com infrastructure, but may have ended up not getting delivered after all since a second SPF test happened on a connection from a host that is not in the sender domain's SPF record.

In fact, that second test would only succeed for domains that have

include:spf.protection.outlook.com

in their SPF record, and those would presumably be Outlook.com customers.

Any student or practitioner of SMTP mail delivery should know that SPF records should only happen on ingress, that is at the point where the mail traffic enters your infrastructure and the sender IP address is the original one. Leave the check for later when the message may have been forwarded, and you do not have sufficient data to perform the check.

Whenever I encounter incredibly stupid and functionally destructive configuration errors like this I tend to believe they're down to simple incompetence and not malice.

But this one has me wondering. If you essentially require incoming mail to include the contents of spf.outlook.com (currently no less than 81 subnets) as valid senders for the domain, you are essentially saying that only outlook.com customers are allowed to communicate.

If that restriction is a result of a deliberate choice rather than a simple configuration error, the problem moves out of the technical sphere and could conceivably become a legal matter, depending on what outlook.com have specified in their contracts that they are selling to their customers.

But let us assume that this is indeed a matter of simple bad luck or incompetence and that the solution is indeed technical.

I would have liked to report this to whoever does technical things at that domain via email, but unfortunately there are indications that being their customer is a precondition for using that channel of communication to them.

I hope they fix that, and soon. And then move on to terminating their spamming customers' contracts.

The main lesson to be learned from this is that when you shop around for email service, please do yourself a favor and make an effort to ensure that your prospective providers actually understand how the modern-ish SMTP addons SPF, DKIM and DMARC actually work.

Otherwise you may end up receiving more of the mail you don't want than what you do want, and your own mail may end up not being delivered as intended.

Update 2018-02-19: Just as I was going to get ready for bed (it's late here in CET) another message from Ms Farell arrived, this time to an alias I set up in order to make it easier to filter PF tutorial related messages into a separate mailbox.

I wrote another response, and as the mail server log will show, despite the fact that a friend with an Office365 contract contacted them quoting this article, outlook.com have still not fixed the problem. Two more messages (preserved here and here) shot back here immediately.

Update 2018-02-20: A response from Microsoft, with pointers to potentially useful information.

A message from somebody identifying as working for Microsoft Online Safety arrived, apparently responding to my message dated 2018-02-19, where the main material was,

Hi,

Based on the information you provided, it appears to have originated from an Office 365 or Exchange Online tenant account.

To report junk mail from Office 365 tenants, send an email to junk@office365.microsoft.com   and include the junk mail as an attachment.

This link provides further junk mail education https://technet.microsoft.com/en-us/library/jj200769(v=exchg.150).aspx.

Kindly,
I have asked for clarification of some points, but no response has arrived by this getting close to bedtime in CET.

However I did take the advice to forward the offending messages as attachment to the junk@ message, and put the outlook.com abuse address in the Cc: on that message. My logs indicate that the certificate error had not gone away, but no SPF-generated bounces appeared either.

If Microsoft responds with further clarifications, I will publish a useful condensate here.



In other news, there will be PF tutorial at the 2018 AsiaBSDCon in Tokyo. Follow the links for the most up to date information.