Re: [mailop] Good registrar?

2024-10-02 Thread Michael Orlitzky via mailop
On Wed, 2024-10-02 at 13:37 +0300, Otto J. Makela via mailop wrote:
> It seems Gandi has been hiking their prices rather significantly.
> 
> Do you have recommendations for a good domain registrar which still
> keeps prices at a reasonable level, and also isn't a problematic
> spammer/scammer haven?

https://www.simpleurl.com/ works with noscript enabled, what more could
you ask for?


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Re: [mailop] [EXTERNAL] Re: (Mis)use of DKIM's length tag and it's impact on DMARC and BIMI

2024-08-10 Thread Michael Orlitzky via mailop
On 2024-08-09 15:11:45, Brotman, Alex via mailop wrote:
> Yes, it should be updated.
> 
> It might also be worth trying to get a bug filed against opendkim to update 
> docs or comments in the sample configuration file that is provided in the 
> package to illustrate suggested practices.
> 
> (FWIW, lists.debian.org still doesn't sign anything they send)

The OpenDKIM project is dead, but the sample configuration file does
already mention this. The "full" sample config file says,

> This has security implications; see opendkim.conf(5) for details.

and then that man page says,

> This feature of the protocol exists to improve the likelihood that a
> signature will survive transit through a mailing list server, as
> they commonly append footers to messages.  Note, however, that this
> creates a potential security issue since someone could add arbitrary
> text to the signed message and the signature would still validate.
> See the DKIM specification for details.

(the other, simpler sample config files don't mention the body length
option at all).
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Re: [mailop] Mailserver software

2024-07-15 Thread Michael Orlitzky via mailop
On Tue, 2024-07-16 at 07:40 +0800, Jeff Pang via mailop wrote:
> Any experience on opensmtpd on debian?

Just use postfix. You lose the OpenBSD security dust when running on
Debian, and the last time OpenSMTPD had a remote (root) code execution
vulnerability we all learned that it delivers mail with
execle("/bin/sh", ...).

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Re: [mailop] Mailserver software

2024-07-15 Thread Michael Orlitzky via mailop
On Mon, 2024-07-15 at 22:39 +0800, Jeff Pang via mailop wrote:
> Hello
> 
> When I deploy a new mailserver, I consider postfix, exim and qmail.
> 
>  From practical experience, what are the advantages, disadvantages, and 
> adaptation scenarios of postfix, exim, and qmail?
> 

Forget qmail (and sendmail).

Both postfix and exim are secure, have great documentation, and have
great support. Both are portable and available everywhere, and they
have equally-idiosyncratic build systems. The main difference is that
exim has more batteries included, whereas postfix stays closer to the
UNIX principle and delegates things like DKIM to an external daemon.
Try both (in a real configuration) and see which one you prefer.

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Re: [mailop] Ubuntu Noble/24.04 - TLS 1.0, 1.1 and DTLS 1.0 are forcefully disabled

2024-03-13 Thread Michael Orlitzky via mailop
On Wed, 2024-03-13 at 15:54 +0100, Marco Moock via mailop wrote:

> Although, older SSL/TLS versions have some weaknesses and when they are
> not offered, they can't be used, not even for downgrading attacks. Many
> clients support an option to enforce TLS/STARTTLS. That will fail in
> such a situation.

Are there any scenarios where you can downgrade the protocol but not
steal the entire message due to the server's identity being unverified?

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Re: [mailop] Ubuntu Noble/24.04 - TLS 1.0, 1.1 and DTLS 1.0 are forcefully disabled

2024-03-13 Thread Michael Orlitzky via mailop
On Wed, 2024-03-13 at 11:28 +, L. Mark Stone via mailop wrote:
> FWIW, our view is that poor encryption can be worse than no encryption, as it 
> can give the participants a false sense of security.  This seems like a good 
> move to us.
> 
> We have configured Postfix in our Zimbra MTA servers to do only TLS 1.2/1.3, 
> and fall back to unencrypted if a TLS connection can't be negotiated (per RFC 
> 2487).
> 

Whose sense of security is improved by sending those messages in
plaintext?


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Re: [mailop] Verizon text to email on vtext.com - connection refused error

2024-01-02 Thread Michael Orlitzky via mailop
On Tue, 2024-01-02 at 17:32 +, Justin Krejci via mailop wrote:
> When a Verizon mobile user sends a text to an email recipient, I understand 
> it goes through some mail gateway system that converts the message to a 
> standard email and I think uses the @vtext.com as the sending domain with 
> some composition of obfuscated user data before the domain. We are receiving 
> many reports of people getting "connection refused" errors when a Verizon 
> user is sending with this method; see below for error message.
> 
> Is there anyone on the Verizon mail admin team we discuss/troubleshoot with 
> please?
> 
> Our receiving SMTP server is definitely not refusing connections so either 
> tcp traffic is getting blocked before arriving to us or the wording of the 
> error message is not accurate. But without knowing what all the sending IP 
> addresses are for sure, it is difficult to even troubleshoot. We are 
> attempting to run a packet capture on the IP addresses listed in the SPF 
> record for vtext.com but that uses assumptions which may be incorrect.
> 

Wild guess: a few weeks ago we were getting reports of missing SMS-to-
email messages because the Verizon servers involved were blacklisted.
If you have something like fail2ban running, maybe you're dropping them
at the firewall for some kind of abuse?

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Re: [mailop] Gmail now deferring email which meets their published reqs

2023-12-30 Thread Michael Orlitzky via mailop
On Sat, 2023-12-30 at 12:48 -0800, Randolf Richardson, Postmaster via
mailop wrote:
>   If that's what the problem is, then that can easily be set with the 
> following Postfix setting without the need for customization scripts:
> 
>   default_destination_recipient_limit = 1
> 
>   It may also be helpful to adjust the delivery rate, which can also 
> be set in Postfix's "default_destination_rate_delay" setting 


This will work, but you probably don't want to make your entire MTA
inefficient just to appease Google. Those two parameters have per-
transport counterparts,

  * _destination_concurrency_limit
  * _destination_rate_delay

where  is the name of your transport. So, for example, you
could create a transport called "slow", and then set

  * slow_destination_concurrency_limit = 1
  * slow_destination_rate_delay = 2s

after which all you have to do is configure postfix to send to gmail
via the "slow" transport instead of the default one. Now gmail is slow,
but nobody else suffers.

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Re: [mailop] Gmail deferrals resolved by transit encryption

2023-11-17 Thread Michael Orlitzky via mailop
On Fri, 2023-11-17 at 23:33 +0100, Jaroslaw Rafa via mailop wrote:
> Dnia 17.11.2023 o godz. 14:34:19 Lukas Tribus via mailop pisze:
> > 
> > Google probably wants you to enable STARTTLS, so reducing sending
> > limits for non STARTTLS senders can make sense from Google's POV.
> 
> That thread makes me wonder, how come anybody is sending mail without
> STARTTLS now? When all major MTAs do it just by default?

If you're sending junk from a custom MTA, it avoids a lot of
programming and saves a little CPU.

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Re: [mailop] [STATE of the UNION] Tails from the trenches of the spam auditing team..

2023-08-25 Thread Michael Orlitzky via mailop
On Fri, 2023-08-25 at 17:07 +, Slavko via mailop wrote:
> Dňa 25. augusta 2023 16:01:42 UTC používateľ Michael Orlitzky via mailop 
>  napísal:
> 
> > In short: cheap implies bad but bad doesn't imply cheap.
> 
> Yes, Windows is cheap. But Linux is even free, thus it must
> be really, really bad...
> 

Taking my comment out of context is both cheap and bad :)

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Re: [mailop] [STATE of the UNION] Tails from the trenches of the spam auditing team..

2023-08-25 Thread Michael Orlitzky via mailop
On Fri, 2023-08-25 at 09:34 +0200, Alessandro Vesely via mailop wrote:
> > 
> > Well, yeah, sometimes you get what you pay for.
> 
> 
> Hm... finding an expensive ISP is not a good business criterion.

In short: cheap implies bad but bad doesn't imply cheap.


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Re: [mailop] [STATE of the UNION] Tails from the trenches of the spam auditing team..

2023-08-24 Thread Michael Orlitzky via mailop
On Thu, 2023-08-24 at 12:10 +0200, Jaroslaw Rafa via mailop wrote:
> 
> Individual IP reputation - yes.
> 
> Netblock reputation - no. Only if you know that the entire netblock belongs
> to a spammer, it is justified to block the entire netblock.
> 
> If it is just a random netblock of some ISP that just happens to contain
> some spamming IPs (even a lot of them) inside - no, never block the netblock
> as a whole.

I know you're on OVH but it's hard to feel bad about this.

Morally, the ISP (the owner of the netblock) is responsible for the
spam. They have a responsibility to stop it. If they outright refuse to
respond to abuse complaints, it's good and correct to punish them for
that choice.

Practically, whack-a-mole is infeasible. It takes me five to ten
minutes to add a blacklist entry: I have to do the WHOIS lookup, PTR
lookup, scan the neighborhood, see if that block is part of a larger
block, document the spam, add the blacklist entry, write a commit
message, push to the repo, and then push the configuration change live.
It takes OVH less time than that to send me spam from a new IP address.
There's an obvious solution to that problem and it isn't me doing their
job for free, twenty four hours a day, for the rest of my life.

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Re: [mailop] Any old-school sendmail types here good with the m4?

2023-08-23 Thread Michael Orlitzky via mailop
On Wed, 2023-08-23 at 15:04 +0200, Johann Klasek via mailop wrote:
> 
> Wild claim, but funny. For most things or standard configuration stuff
> (even the ednsbl feature) m4's syntax is not to overcomplicated. It's
> more or less in the range of other configuration syntaxes ... (just from
> my perspective).

It's also POSIX, and at least tangentially familiar to anyone who works
with autoconf (when sendmail was written, all unix admins were C
programmers). There are worse choices for sure.

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Re: [mailop] No MX but A: broken MTA(s)

2023-07-11 Thread Michael Orlitzky via mailop
On Tue, 2023-07-11 at 15:00 -0500, Jarland Donnell via mailop wrote:
> 
> Does anyone actually receive mail by their A record in 2023? I'd just 
> assume break the RFC and save the resources for retrying and eventually 
> bouncing every email that ends up attempting delivery to an A record.
> 

The MX record for a domain name is usually a necessary level of
indirection, because the domain name itself usually points to a web
server and not a mail server.

But if I set up a mailing-list server on lists.orlitzky.com, then the
hostname already points to the right address. Why also create an MX
record and copy/paste?

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Re: [mailop] No MX but A: broken MTA(s)

2023-07-11 Thread Michael Orlitzky via mailop
On Tue, 2023-07-11 at 13:36 -0500, Grant Taylor via mailop wrote:
> 
> However, I don't see any mention of a-record fallback in RFC 5321.  -- 
> I didn't chase any updates.  --  I do see four occurances of "fall" in 
> the document, three of which are fall( )back and all three have to do 
> with something other than MX records vs a-records.
> 
> As such, I'd question the veracity of current SMTP needing to support 
> a-record fallback.


5.1.  Locating the Target Host

Once an SMTP client lexically identifies a domain to which mail will
be delivered for processing (as described in Sections 2.3.5 and 3.6),
a DNS lookup MUST be performed to resolve the domain name... The lookup
first attempts to locate an MX record associated with the name... If an
empty list of MXs is returned, the address is treated as if it was
associated with an implicit MX RR, with a preference of 0, pointing to
that host.

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Re: [mailop] No MX but A: broken MTA(s)

2023-07-11 Thread Michael Orlitzky via mailop
On Tue, 2023-07-11 at 17:13 +, ml+mailop--- via mailop wrote:
> 
> Which MTA is that?
> 

Microsoft Exchange Server 2003?

Seriously though, it's not a "fallback" in any pejorative sense. SMTP
predates much of DNS, including MX records. It's a fundamental part of
the specification.

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[mailop] SendGrid is deleting your mail (again)

2023-07-11 Thread Michael Orlitzky via mailop
Early yesterday morning, our upstream circuit was down from about
2:30am until 5:00am EDT. During that time, our MX was not answering;
so, no 4xx or 5xx response involved.

It's been over 24h, and I'm (personally) still missing five GitHub
notifications from that time:

4:03am EDT,
https://github.com/php/php-src/pull/11654?notification_referrer_id=NT_kwDOABXaR7I3MDEwODM5NzU0OjE0MzIxMzU#pullrequestreview-1521502822

4:24am EDT,
https://github.com/php/php-src/pull/11631?notification_referrer_id=NT_kwDOABXaR7I2OTk5ODQxMjEyOjE0MzIxMzU#pullrequestreview-1521540314

4:25am EDT,
https://github.com/php/php-src/commit/092e090cf00477e51802eae39651493b718c1415

4:42am EDT,
https://github.com/php/php-src/pull/11654?notification_referrer_id=NT_kwDOABXaR7I3MDEwODM5NzU0OjE0MzIxMzU#pullrequestreview-1521565401

4:43am EDT,
https://github.com/php/php-src/commit/893ca537b0a3dfb05d918d53e61fbf8cf9ca4f90


The complete lack of regard for your legitimate customers is maddening.

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[mailop] Microsoft: mismatched HELO/DNS

2023-07-06 Thread Michael Orlitzky via mailop
Saw this today,

  Jul  6 09:04:14 mx1 policyd-spf[19732]: : prepend Received-SPF: Pass 
  (sender SPF authorized) identity=helo; client-ip=40.107.243.78; 
  helo=nam12-dm6-obe.outbound.protection.outlook.com; 
  envelope-from=mela...@example.com; receiver=example.net

But,

  $ dig +short nam12-dm6-obe.outbound.protection.outlook.com
  157.56.209.183

and,

  $ dig +short -x 40.107.243.78
  mail-dm6nam12on2078.outbound.protection.outlook.com.

When the sending domain does not have its own SPF record, that mismatch
triggers spamassassin's FORGED_SPF_HELO rule. It's only adding one
point, but since you send a bajillion messages, it'd be nice to avoid.

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Re: [mailop] SendGrid is deleting your mail

2023-06-25 Thread Michael Orlitzky via mailop
On Sun, 2023-06-25 at 14:28 +0100, Dmytro Homoniuk via mailop wrote:
> 
> 450 4.3.2 Please retry immediately. If your message was rejected by a
> blacklist, see  for more information.
> 
> Now this just adds needless ambiguity: was it rejected because of the
> blacklist or not? Am I on a blacklist? Which one? Should I actually retry?
> And if I retry and see the same thing - does THAT mean I'm blacklisted?
> 

Your message wasn't rejected at all, it was deferred. You're trying to
out-think the RFC.


> The ESP decided not to retry which was not in user's
> best interests, the receiving MTA decided not to accept on first try
> - which was also not in user's best interests. I don't see either a
> winner here, nor anyone being right really - except the user who is
> being royally screwed by everyone

Except the part where I decided not to accept the message. I'm actually
not sitting in front of the mail server with a button that 4xx defers
messages I don't like. Temporary issues happen from time to time. And
if you were paying attention at all, you would know that I've been
going out of my way for YEARS to make sure that messages like these are
received.

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Re: [mailop] SendGrid is deleting your mail

2023-06-24 Thread Michael Orlitzky via mailop
On Sat, 2023-06-24 at 10:18 +, Louis Laureys via mailop wrote:
> Michael, I was with you until it was revealed you mention a blacklist in your
> response. Sendgrid assumes that the words in the response actually have
> something to do with the reason it's being temporarily rejected, which is a 
> fair
> assumption to make even if it doesn't follow spec. Then using different retry
> logic based on that reason does make sense at that scale. I mean effort wise,
> not "we're big so we can do whatever we want" wise. I'm personally no fan of
> them, but I don't think this behaviour specifically is odd at all.

Why take the time just to victim blame? A decade ago, I added some text
to our 5xx rejections to try to be helpful. The RFC explicitly
guarantees that doing so will have no negative effects. Fuck me I
guess? The response does *not* say that they're blacklisted.

The only reason they won't do the right thing and simply retry is
because it saves them money when sending spam. The arguments about
scale are smoke and mirrors.

Your opinions are yours, but you're defending billionaire spammers who
knowingly breaking the rules because the rest of us pay for it.

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Re: [mailop] SendGrid is deleting your mail

2023-06-24 Thread Michael Orlitzky via mailop
On Sat, 2023-06-24 at 08:42 +, Andy Smith via mailop wrote:
> 
> In the specific case at hand it seems that the OP is greylisting
> SendGrid for being on some sort of blocklist, and the specific
> mention of "blacklist" in the 4xx response is hitting a SendGrid
> heuristic that says "don't bother to retry these", so messages are
> actually being lost. I think it has implications beyond greylisting.
> 

We're not greylisting them for being on a blacklist, they'd just get
rejected in that case. The blacklist text is there for the people who
get a 5xx reject.

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Re: [mailop] SendGrid is deleting your mail

2023-06-23 Thread Michael Orlitzky via mailop
On Fri, 2023-06-23 at 13:29 -0700, Luke via mailop wrote:
> Default behavior is always to retry 4xx if there isn't a rule in place that
> overrides it. In this case, it was, and still is (i'm working on it)
> hitting another rule that was put in place to *not* retry a very specific
> 4xx that would never result in a successful delivery.
> 
> The full response in question is this: 450 4.3.2 Please retry immediately.
> If your message was rejected by a blacklist, see
> http://michael.orlitzky.com/articles/so_youre_blacklisted.xhtml for more
> information.
> 
> The bit of text in the string causing the trouble is the word blacklist.

I guess it's reassuring? that your system is fucking us specifically :)

It sounds like you've got yourself a spaghetti regex nightmare whose
behavior no one can truly predict. Maybe those ivory tower academics
who wrote RFC5321 were on to something when they wrote "An SMTP client
MUST determine its actions only by the reply code, not by the text."


> Unfortunately, we see a number of 4xx responses that contain the word
> blacklist and retries never succeed. For example, "450 4.3.2 your message
> was rejected because you're on a blacklist" is *not *retried because it's
> useless and *not* retrying is the appropriate thing to do for our
> customers.

I don't necessarily disagree with this, but here's another perspective.
Blacklists are hard to test in production because they rely on a third
party. When testing a new config, it's common (at least in postfix
land) to switch your reject code from 5xx to 4xx while you see how
things play out. Basically, you're giving yourself time to look at the
logs and decide if you're losing mail that you don't want to lose. When
you're satisfied, you switch the reject code back to 5xx. There are
several config parameters designed for this.

If someone is testing a new blacklist configuration and has switched
their reply code to 4xx to ensure that they don't lose any mail, you're
really doing a disservice by deleting their mail.


> What really confuses me about this discussion is the almost religious
> fervor around the idea that under no circumstances should a 4xx not be
> retried and under no circumstances should a 5xx ever be retried.

We just want things to work. The RFCs codify what's necessary for
everyone to get along. I've certainly had enough of my own time wasted
by this, and who knows how many important messages our customers have
lost as a result. All of it could have been avoided if you followed the
RFCs. I get that it would cost your company a little bit more money,
but saving yourself some money at everyone else's expense is selfish
and, in Bill's words, parasitic.

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Re: [mailop] SendGrid is deleting your mail

2023-06-23 Thread Michael Orlitzky via mailop
On Thu, 2023-06-22 at 16:14 -0700, Luke wrote:
> It's specifically targeting the response code and string you provided: 450
> 4.3.2 Please retry immediately

Ok, I've spent the morning patching out a few more of our MTA's 4xx
responses with that exact text. Some of them contained important
diagnostic information, so I'm sabotaging my coworkers (and everyone
else who sends us mail) to make this work.

Supposing it does, it will have fixed the problem for one person, with
one MTA, with one set of custom patches. You're still deleting everyone
else's mail.

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Re: [mailop] SendGrid is deleting your mail

2023-06-22 Thread Michael Orlitzky via mailop
On Thu, 2023-06-22 at 10:52 -0700, Luke via mailop wrote:
> I got a rule in place that should cover this. I'll monitor and make sure
> the desired behavior is occurring.
> 

Thanks, but which "this"? Should all 4xx replies now get a retry, or
just the ones containing a certain phrase? (And which phrase, in that
case?)


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Re: [mailop] SendGrid is deleting your mail

2023-06-21 Thread Michael Orlitzky via mailop
On 2023-06-22 04:21:59, Sebastian Nielsen via mailop wrote:
> >> We update kernels, reload AV signatures, have databases go down, 
> >> accidentally crash postfix during OS upgrades, typo config files, etc. 
> 
> Couldn't you make so if the inner servers are in trouble or go down
> or similar, then the perimeter server will buffer the email for you
> without a temporary reject?

We don't want to accept mail and then later bounce (backscatter) it,
so at a minimum, the outer servers need to be able to do recipient
validation and spam scanning, and those services can have hiccups.

No matter how far you push the problem down the road, there's a
fundamental limit you hit eventually.


> When it comes to spam and virus filtering, you could skip spam
> filtering for "buffered" email, ergo email that was received during
> outage. And just apply virus filtering.  For virus filtering, you
> ARE allowed to silently delete email according to RFC, and what I
> know, also for those countries that prohibit silently deleting
> emails for "spam":

I was referring to a European law that doesn't apply to us, so I don't
want to focus on it too much. Instead I'll just say that us silently
deleting emails is not a very satisfying solution to the problem of
someone else silently deleting emails.
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Re: [mailop] SendGrid is deleting your mail

2023-06-21 Thread Michael Orlitzky via mailop
On 2023-06-21 18:39:59, Luke wrote:
> Ahh. Thats funny. Apologies. You'll have to refresh my memory.
> 
> Happy to help if I can. Give me the full response, code and string, and
> tell me how you'd like us to handle it and if it makes sense, I can make
> the necessary changes.
>

In this case, before patching, the original response was,

  450 4.3.2 Service currently unavailable

After patching, it's

  450 4.3.2 Please retry immediately

I'd rather not patch our MTA for the rest of eternity, so a rule for
the first response would be preferable. But if that's not possible I
can live with the second. After all, that was my hope/plan after the
last discussion.

In either case, one quick retry (a minute?) followed by a few slower
attempts (1h, 12h, 24h, etc.) for 4-5 days would be perfect. The
quicker retries help with the planned hiccups, while the longer ones
accomodate the unplanned ones.

However, a custom rule would address only that one source of 4xx
error. Others are popular. For example,

  450 4.3.0 Queue file write error

when we kill a filter process while the MTA is waiting on it. And
that's just for our MTA.

I think I've already disproven the null hypothesis, that SendGrid
retries normally in the absense of statistical evidence discouraging
it. If that's not the case, it should be: the default should be to do
the right thing and retry. Otherwise, everyone is going to have to hack
their MTAs to return some magic phrase.

Still, I'll take what I can get. Thanks for responding again.
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Re: [mailop] SendGrid is deleting your mail

2023-06-21 Thread Michael Orlitzky via mailop
On 2023-06-21 18:19:41, Luke via mailop wrote:
> 
> I work at sendgrid and manage response handling. If someone were to reach
> out with an obvious problem, I'd be willing and able to adjust our response
> handling appropriately.
>

You're the guy I mentioned the problem to last time.
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Re: [mailop] SendGrid is deleting your mail

2023-06-21 Thread Michael Orlitzky via mailop
On 2023-06-22 02:05:40, Sebastian Nielsen via mailop wrote:
> >> They were going to get a 4xx anyway. I changed the message to *help* 
> >> SendGrid.
> 
> Yes but if you can change the message for SendGrid only, you can
> accept the mail and let it through... Apparently you were able to
> send custom text to just SendGrid.  Then you have some rule to be
> able to differentiate SendGrid mail from other mail.  Thus you just
> accept it.

I was unclear then. I patched the mail server to change the 4xx text
that we send to everyone, but I changed it only to help SendGrid.

I have no way to know ahead of time who is using SendGrid. Some
senders, like GitHub, have dedicated servers and send us enough mail
that, over time, I have been able to whitelist all(?) of them. This
helps but is not enough:

  * I can't whitelist a server until we've lost a message from it. The
way I find out that there's a server to whitelist is that a
customer calls to let us know that he's missing an important piece
of mail from it (e.g. the Hershey Park tickets).

  * Continuing the example, GitHub is constantly adding/changing
servers. When they do, we're at risk of losing mail until we can
whitelist the new addresses.

  * The non-dedicated SendGrid servers cannot be whitelisted, because
almost all mail from non-dedicated SendGrid servers is spam.

  * I think you're assuming that most of our 4xx errors are from the
spam filter or from overzealous action on my part to make a point;
they're not. We update kernels, reload AV signatures, have
databases go down, accidentally crash postfix during OS upgrades,
typo config files, etc. All of those result in 4xx errors and
whitelisting does nothing to help.

The bottom line is that avoiding 4xx *entirely* is impossible, even if
I could reduce them somewhat at great expense. If nothing else, then
in those unavoidable scenarios, you have to agree that SendGrid has a
responsibility not to delete important mail. But they do.
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Re: [mailop] SendGrid is deleting your mail

2023-06-21 Thread Michael Orlitzky via mailop
On 2023-06-22 00:32:37, Sebastian Nielsen via mailop wrote:
> Why even send retry requests to SendGrid?
> Just accept the email, whats the problem?
> 
> If your antivirus or mail scanning solution requires some time,
> buffer the email at your server instead. I do understand it creates
> the problem of, when deciding to keep or trash the email, SendGrid
> client is long gone, And sending back an error would create
> backscatter.  But then, just silently trash the email if it is
> deemed virus or similar.

If your spam filter is perfect this can work. Otherwise, silently
deleting mail is not nice for our customers, is not nice for the
senders, and is illegal in some places.


> You could try using stream scanning and then when arriving at final
> decision, let client wait for some seconds before getting an scan
> result.

We already do this, and I don't see how it's relevant. The transaction
can still time out, and there are lots of other reasons why we might
send a 4xx.


> >>These are a pair of tickets for Hershey Park that a family has been waiting 
> >>on for two days:
> 
> Your fault. You rejected the email with "Please retry immediately" just to 
> mock with SendGrid.

They were going to get a 4xx anyway. I changed the message to *help*
SendGrid.


> If you have the possibility to set an IP to have custom reject text,
> you have the possibility to whitelist that IP (and/or domain) so
> mail pass unaffected.

Where do I find out what the IP/domain is? Is it in my mail logs,
*after* they've deleted the message? Durr
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[mailop] SendGrid is deleting your mail

2023-06-21 Thread Michael Orlitzky via mailop
The last time SendGrid's failure to retry 4xx came up here, their
response was that, when determining whether or not to retry, they
analyze not only the 4xx code but also the associated text. If (based
on those data) a retry is statistically unlikely, they won't do it.

The RFC forbids doing that, and I argued against it -- not just on
principle, but because when 99% of your mail is spam and 1% is not,
grouping them together introduces a base-rate fallacy into your
decision-making process.

Regardless, it looks like I was wasting my time: their explanation is
incomplete at best. Since then I've patched our mail server to reply
with unique 4xx text. Retries to us will almost always succeed, so our
unique (code,text) pairs, being unaffected by anyone else, should be
associated with a high probability of success. Still, they choose not
to retry.

These are a pair of tickets for Hershey Park that a family has been
waiting on for two days:

  # grep 'hersheypa\.com' /var/log/mail/mail.log*

  mail.log-20230620:Jun 20 09:25:53 mx1 postfix/postscreen[23626]:
  NOQUEUE: reject: RCPT from [159.183.156.68]:36108: 450 4.3.2 Please
  retry immediately;
  from=,
  to=, proto=ESMTP, helo=

SendGrid silently deleted them. We want your mail; please stop using
SendGrid. Thanks for listening.
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Re: [mailop] Tightening of delivery rules for Exchange Online

2023-03-28 Thread Michael Orlitzky via mailop
On Tue, 2023-03-28 at 17:04 +0200, Tobias Fiebig via mailop wrote:
> 
> Are there any other thoughts on this?
> 

Microsoft has been breaking email for profit for thirty years. If you
haven't figured out their business model by now, the bad things that
happen to you are your own fault.

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Re: [mailop] sender domain reputation

2023-03-22 Thread Michael Orlitzky via mailop
On 2023-03-22 20:12:31, Slavko via mailop wrote:
> 
> But seriously, what is difference between .com and .pw (or any
> other domain name) other than that .com is here +- from start
> of DNS?

When dot-pw went public, it was heavily abused by spammers:

https://www.domainregistration.com.au/news/2013/1305-pw-domain-spam.php

It may be time to forgive them, but you'll still have to convince
people that the signal to noise ratio makes it worth their time. For
example, in the decade since we blocked it, I'm aware of exactly one
false positive... and that was from someone who worked at the
registrar.
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Re: [mailop] Gmail blocking of good customer

2023-02-28 Thread Michael Orlitzky via mailop
On Tue, 2023-02-28 at 12:31 +0100, Jaroslaw Rafa via mailop wrote:
> 
> I do greylisting, and that's how I found out about the immediate
> retries. I run postgrey with default setting which is 5 minutes, and
> I often see in logs multiple retries within those 5 minutes, with
> first ones being really almost immediate (15-30 seconds). I have no
> other MXes, so I can't observe retries to other MXes, but I often see
> retries FROM different IP address than the original attempt, which
> count as new entries for greylisting, as greylisting works on triplet
> (client IP address, sender, recipient).
> 

ONE immediate retry can be helpful. Since you mention postfix, the
"accidental greylisting" caused by its deep protocol tests can be
mitigated by sharing the postscreen cache across MX, even if one of
them is simply an alias:

  https://www.postfix.org/POSTSCREEN_README.html#after_220

In those situations, the immediate retry will go through. (And FWIW I
would suggest lowering the timeout on postgrey; spambots don't come
back after a few seconds.)

That doesn't help when the retries all come from different IPs though.
That is indeed stupid. It's not surprising however given that most of
those providers will loan you a consistent IP for a small fee.

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Re: [mailop] Gmail blocking of good customer

2023-02-28 Thread Michael Orlitzky via mailop
On Mon, 2023-02-27 at 21:38 -0700, Luke wrote:
> 
> First, we send a lot of email; 9 billion messages on black friday
> alone. Each message generates an average of 8 events (deferrals,
> opens, clicks, spam reports, unsubscribes etc). Storage cost is a
> small part of the reason for minimizing MTA chatter. It's not a big
> enough factor for us to make irresponsible decisions in this area to
> save money, but it's a factor.

I don't know if they're separate systems, but nobody is complaining
about the missing marketing emails. It's the password resets, two-
factor auths, email verifications, etc. disappearing that get noticed.


> Second factor (and the main factor) is our customers. We send 32
> deferral events over the course of 72 hours to our customers' data
> warehouses for each message...So do we read the RFC to our customers
> and tell them to pound sand? Or do we take some time and see if we
> can help make their experience a little better *and* save us some
> money at the same time?

It sounds like what they're unhappy with is the mountain of unwanted
data, not the retries themselves. And these sound like marketing
complaints that are being used to make decisions for transactional
customers.

I know your transactional customers don't want this, because they call
me and ask why they're not getting the emails from their website. The
answer is that a lot of people aren't getting mail from your website,
and you're losing users because they can't complete the registration
process because SendGrid deletes the confirmation emails.
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Re: [mailop] Gmail blocking of good customer

2023-02-27 Thread Michael Orlitzky via mailop
On Mon, 2023-02-27 at 18:53 -0700, Luke via mailop wrote:
> For better or worse, *not *retrying *some *4xx is even easier to
> justify.
> Here are a few massive examples.
> 
> 421 4.7.1 Message permanently deferred:
> 
> 452 Sender Rejected:

Keeping in mind that the RFC says not to use the text in your decision,
these two sound the most reasonable. Skipping for brevity.


> 450 4.1.1 Recipient Address Rejected: this one is tough because with
> some MXs retries result in delivery, in others, it's a dead end.
> Dynamic rule handling per receiving MX would be awesome, but it would
> require machine learning to accomplish at scale.

This could  postfix's unverified_recipient_reject_code. When (for
example) postfix sits in front of an Exchange server and when a full
list of valid recipients is not available, postfix can launch a
background probe to see if the recipient is valid in Exchange before it
will accept a message destined for it (otherwise, you get backscatter).
If postfix is up but Exchange is down, it'll give you this rejection.


> 451 Relay Not Permitted: this one can mean a lot of things and comes
> in a few flavors, but when the data shows retrying never results in a
> delivery, we permfail it.

This happens when somebody's domain expires and the MX record gets
pointed somewhere it shouldn't. This is the right response because when
they finally find the guy who knows the guy who knows the guy who
receives the email that resets the password at the registrar three days
later, it's nice to have all their mail start flowing as if nothing
ever happened.


> Unlike the rare 5xx we decide to retry, these 4xx that shouldn't be
> retried are far more numerous and come from large-ish reputable
> receivers. Believe me, simply retrying 4xx and failing 5xx would make
> our jobs a lot easier. Unfortunately the real world isn't so simple

Not pounding on servers that have told you to go away with a 5xx has
obvious benefits for both sides though. What's the downside to leaving
the 4xx in the queue for a while? No one is going to fault you for
retrying a message they told you to retry, and even 1% of legitimate
mail is a lot to toss out without a good reason.

Finally, while it might be 1% of *your* mail it's not 1% of *our* mail.
Michael Scott said Wayne Gretzky said that you lose 100% of the
messages you don't retry to recipients who would have accepted them.

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Re: [mailop] Gmail blocking of good customer

2023-02-27 Thread Michael Orlitzky via mailop
On Mon, 2023-02-27 at 15:45 -0700, Luke via mailop wrote:
> 
> With that said, given the responses in this thread, we will be taking
> a close look at the few rules we have in place where we retry 5xx and
> see if A.) the rules are still being hit at all, and B.) are these
> retries still resulting in reliable and consistent delivery after a
> small number of attempts.
> 

That's a good idea anyway (thank you), but the original issue wasn't
about an extra retry or two for a 5xx, but the lack of any retry at all
for a 4xx.

That happens all day every day and is what makes mail go missing.

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Re: [mailop] Gmail blocking of good customer

2023-02-27 Thread Michael Orlitzky via mailop
On Mon, 2023-02-27 at 04:55 +, Denny Watson via mailop wrote:
> 
> All I have said (which you had conveniently redacted) is that RFC5321
> leaves the door open to process bounces differently should the
> sending MTA be able to determine the reason for non-delivery.[1]
> 
> ...
> 
> [1] See my original email on this subject about section 4.5.4.1 of 
> RFC5321 and why rejected mail can have a different queuing strategy 
> based on the sender's interpretation of the 4xx response the it had 
> received.

I didn't redact it to make my argument seem stronger, I redacted it
because it's irrelevant. That's not what SendGrid is doing. And you
quoted the RFC out of context anyway. Here's the full text of the first
two paragraphs of that section for anyone too lazy to look it up:

  4.5.4.1.  Sending Strategy

  The general model for an SMTP client is one or more processes that
  periodically attempt to transmit outgoing mail.  In a typical 
  system, the program that composes a message has some method for 
  requesting immediate attention for a new piece of outgoing mail,
  while mail that cannot be transmitted immediately MUST be queued and 
  periodically retried by the sender.  A mail queue entry will include 
  not only the message itself but also the envelope information.

  The sender MUST delay retrying a particular destination after one
  attempt has failed. In general, the retry interval SHOULD be at
  least 30 minutes; however, more sophisticated and variable strategies
  will be beneficial when the SMTP client can determine the reason for
  non-delivery.

It clearly states that messages must be retried. The "variable
strategies" you latched onto is in the context of how often the sender
should retry.

I don't care if SendGrid takes your money and pipes your mail to
/dev/null but we can stop pretending that they're playing 4d chess with
RFC5321 now.

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Re: [mailop] Gmail blocking of good customer

2023-02-26 Thread Michael Orlitzky via mailop
On Sun, 2023-02-26 at 19:43 +, Denny Watson via mailop wrote:
> This appears to be a specially built MTA, and with the (probable) 
> consent of its users, has policy in place to not resend after 4xx under 
> specific conditions.  I.e. the sending MTA is interpreting specific 4xx 
> responses (and more likely the text) to mean a permanent failure.
> 
> I do not see a problem with elevating a 4xx to mean 5xx where the users 
> of the system understand the policy as it does not appear to impact the 
> receiving system.

This is not whatever subtle and nuanced situation you are imagining
though. The users don't know, and the response code/text makes no
difference.

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Re: [mailop] Gmail blocking of good customer

2023-02-26 Thread Michael Orlitzky via mailop
On 2023-02-25 19:15:14, Luke via mailop wrote:
> I can assure you sendgrid retries 4xx. We also don't retry 4xx. We also
> retry 5xx. We also don't retry 5xx. How is it 2023 and people still think
> 4xx means retry and 5xx means don't retry?
> 

It's literally unexplainable if you've never read the part of the RFC
with the word "retry" in the title:

  mail that cannot be transmitted immediately MUST be queued and
  periodically retried by the sender
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Re: [mailop] Gmail blocking of good customer

2023-02-25 Thread Michael Orlitzky via mailop
On Fri, 2023-02-24 at 15:57 -0500, Christine Borgia via mailop wrote:
> It is transient, but they are blocks and are not retried. Weird, right?
> 

SendGrid doesn't retry on 4xx and haven't for many years.

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Re: [mailop] Outgoing filtering Re: Cyren

2023-02-03 Thread Michael Orlitzky via mailop
On Fri, 2023-02-03 at 09:28 -0800, Ken Simpson via mailop wrote:
> 
> 
> It’s a tough problem to solve at Google or Microsoft’s scale.

No, it's not, it scales linearly. They would just rather the rest of us
pay for it.

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Re: [mailop] Postfix.org borked?

2022-11-21 Thread Michael Orlitzky via mailop
On Mon, 2022-11-21 at 11:12 -0800, Dan Mahoney (Gushi) via mailop
wrote:
> 
> ;; OPT PSEUDOSECTION:
> ; EDNS: version: 0, flags:; udp: 512
> ;; QUESTION SECTION:
> ;postfix.org.   IN  A
> 
> 

You want www.postfix.org. The bare domain name has never(?) worked.

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Re: [mailop] two openssl (in OpenDKIM) questions for the masses

2022-09-15 Thread Michael Orlitzky via mailop
On Thu, 2022-09-15 at 14:44 -0700, Dan Mahoney (Gushi) via mailop
wrote:
> 
> * Does anyone know of an OS packager that's choosing to build with gnutls 
> instead of openssl.  (It would simplify autoconf a lot to remove the 
> gnutls support, as there are AC macros for openssl, but not for gtls).
> 

We used to let the user choose in Gentoo, but had to remove the GnuTLS
option when it stopped working:

  https://bugs.gentoo.org/682906

If you made it work again, I would add back the option... but if I were
you, I would take this opportunity to quickly and discreetly slit its
throat, saving us both the trouble.

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Re: [mailop] Hostkarma Black listing

2022-04-21 Thread Michael Orlitzky via mailop
On Thu, 2022-04-21 at 09:52 -0400, Chase Vance via mailop wrote:
> Hello all,  
>   
> Is there anyone with Hostkarma on this list that could assist me in
> removing an IP.  I have put in several delisting requests and tried
> sending some help tickets but I have gotten nothing back.  
>   
> Thank you all! 
> 

The owner and main(?) operator of junkemailfilter.com passed away a few
years ago. Someone else may have taken over the operation, but if you
don't get any other answer, that's why.


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Re: [mailop] spamhaus blocking Linode IPv6 (2a01: 7e01)

2021-11-26 Thread Michael Orlitzky via mailop
On 2021-11-26 11:25:06, Mary via mailop wrote:
> 
> Thinking out loud...
> 
> Would it be possible for the two sides (blocklists and a
> cloud/hosting providers) to come together and have some kind of
> automated notification?

The blocklists already provide a convenient API to the providers: if
you want to know if you're listed, do a DNS lookup. You can easily
script this for as many blacklists as you want and run it in a cron
job. Or if you want to get more complicated, you can use dedicated
plugins for e.g. nagios to check the lists and alert you if any of
your hosts are listed.
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Re: [mailop] Sendgrid spam of the day

2021-10-21 Thread Michael Orlitzky via mailop
On 2021-10-20 18:12:32, Luke via mailop wrote:
> For clarification, it has been 12 years. But point taken. Thanks.
>

The causal relationship may be me editorializing, but prior to the
Twilio acquisition, I held no strong opinions about SendGrid and
that's probably the best that can be said of any large ESP.
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Re: [mailop] Sendgrid spam of the day

2021-10-20 Thread Michael Orlitzky via mailop
On Wed, 2021-10-20 at 10:46 -0700, Luke wrote:
> Thanks, John. The account in question is being looked at as we speak.
> It should be terminated shortly.
> 
> Michael, do you have an example of a 4xx we aren't properly handling?
> Would love to take a look and adjust handling.
> 

Are you finally going to stop allowing the same criminals to sign up
and send the same textbook scams from the same obviously-forged domains
after two years? If not, then I prefer the status quo.



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Re: [mailop] Sendgrid spam of the day

2021-10-20 Thread Michael Orlitzky via mailop
On 2021-10-19 16:41:40, John R Levine via mailop wrote:
> Fake USPS spam, sent to my father who I am pretty sure has not ordered 
> anything 
> lately since he is dead.

Tragically, we lose most of these because they still haven't figured
out how to retry a 4xx.
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Re: [mailop] U.S. DoJ will elevate rasonware attacks to the same priority as terrorism

2021-06-04 Thread Michael Orlitzky via mailop
On Fri, 2021-06-04 at 16:26 -0400, Kevin A. McGrail via mailop wrote:
> I thought this news was very welcome today:
> 
> https://twitter.com/RichardEscobedo/status/1400529641065140225
> 
> “The U.S. Department of Justice is elevating investigations of 
> ransomware attacks to a similar priority as terrorism in the wake of the 
> Colonial Pipeline hack and mounting damage caused by cyber criminals, a 
> senior department official told Reuters.”
> 

If you're brown and innocent, try not to get blown up.


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Re: [mailop] [E] Re: Some Days I think that Gmail isn't even trying to stop outbound spam..

2021-02-05 Thread Michael Orlitzky via mailop
On Fri, 2021-02-05 at 08:32 -0800, Marcel Becker via mailop wrote:
> 
> > I don't see ignoring spam to decrease expenses
> > 
> 
> I see you actually didn’t read Brandon’s mail.
> 

On the contrary. Each starts from the position of having gotten rich
giving guns to children, and proceeds to discuss the technical
difficulties involved with keeping everyone from shooting each other in
the face.

If you're not willing to not be an asshole, it is indeed a difficult
problem.


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Re: [mailop] [E] Re: Some Days I think that Gmail isn't even trying to stop outbound spam..

2021-02-05 Thread Michael Orlitzky via mailop
On Fri, 2021-02-05 at 07:26 -0800, Marcel Becker via mailop wrote:
> 
> So you would gladly pay thousands of people to deal with abuse
> reports
> which are, well, not actually abuse reports. And a lot of them. I
> wouldn't.
> For the sake of the sanity of those people alone.
> 

Abuse reports for non-abuse also scale linearly.

I don't see ignoring spam to decrease expenses are morally superior to
sending spam to increase revenue, but feel free to think that the
negative signs make you a better person.


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Re: [mailop] Some Days I think that Gmail isn't even trying to stop outbound spam..

2021-02-05 Thread Michael Orlitzky via mailop
On Thu, 2021-02-04 at 19:23 -0800, Brandon Long via mailop wrote:
> If you received say... a million ab...@gmail.com emails a day, how
> would you handle that?
> 

Pay more and more people to do it, until the number of unhandled abuse
reports at the end of the day is zero. It scales linearly. If that
turns out to be overly expensive, I'd probably think we're letting
people send too much spam, or that our business model is fundamentally
parasitic.


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Re: [mailop] [External] Anyone from BlueHost on this list?

2020-12-22 Thread Michael Orlitzky via mailop

On 12/22/20 2:54 AM, Sidsel Jensen via mailop wrote:


Is this still a valid limit? I’d like to hear your thoughts about it.



The limit was chosen for performance reasons, and for that it's still 
valid. SPF validates envelope information, so those lookups happen even 
if the message will ultimately be rejected for its content. And 
forgeries create load on the VICTIM'S servers.


It's better for everyone if the domain administrator spends five minutes 
up-front to consolidate and denormalize things, rather than having every 
recipient of every message do it every time.

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Re: [mailop] What's the point of secondary MX servers?

2020-12-18 Thread Michael Orlitzky via mailop

On 12/17/20 8:22 PM, John R Levine via mailop wrote:

Unfortunately, many sending clients (newsletters, announcements, etc.)
do not retry if the initial delivery fails.


That's impressively broken.  Do you have specific examples?



SendGrid. They have a webpage that says "We continue to retry messages 
for up to 72 hours," but they (sometimes?) don't.


Good news is, they've been so spammy that I don't care any more.
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Re: [mailop] Trying to find the CIDR ranges for DigitalOcean

2020-10-09 Thread Michael Orlitzky via mailop
On 2020-10-09 03:19, Steve Atkins via mailop wrote:
>
> I like Hurricane Electric's tools.
> 
> https://bgp.he.net/AS14061
> 

After a copy/paste, grep, and consolidation of those ranges I wind up
with...

10.127.40.0/24
10.196.66.0/24
10.212.2.0/24
10.214.2.0/24
27.111.228.0/22
37.139.0.0/19
69.55.49.0/24
80.240.128.0/20
82.196.0.0/20
95.85.0.0/18
103.253.144.0/22
138.68.34.0/24
138.68.36.0/22
138.68.40.0/21
138.68.48.0/20
138.197.240.0/22
138.197.252.0/22
141.0.169.0/24
141.0.170.0/24
159.89.32.0/20
159.89.48.0/21
163.47.8.0/22
164.90.224.0/20
164.90.248.0/24
164.90.252.0/22
185.14.184.0/22
188.226.128.0/17
192.34.56.0/21
204.48.16.0/20
208.68.36.0/22
69.55.54.0/23
138.68.0.0/19
138.68.32.0/23
138.197.192.0/19
159.89.0.0/19
159.89.58.0/23
164.90.192.0/19
164.90.240.0/21
165.232.32.0/19
206.81.0.0/19
192.81.208.0/20
67.205.128.0/18
104.236.0.0/16
138.197.128.0/18
138.197.224.0/20
159.89.60.0/22
159.89.64.0/18
164.90.128.0/18
165.232.64.0/18
178.62.0.0/16
207.154.192.0/18
209.97.128.0/18
107.170.0.0/16
146.185.128.0/18
192.241.128.0/17
64.227.0.0/17
134.122.0.0/17
143.110.128.0/17
5.101.96.0/20
198.211.96.0/19
104.131.0.0/16
128.199.128.0/16
198.199.64.0/18
142.93.0.0/16
165.22.0.0/16
167.71.0.0/16
67.207.80.0/19
138.68.64.0/18
64.225.0.0/17
138.68.128.0/17
138.197.64.0/17
159.89.128.0/17
174.138.0.0/17
46.101.128.0/16
45.55.128.0/16
188.166.0.0/16
68.183.0.0/16
104.248.128.0/16
134.209.0.0/16
157.245.128.0/16
159.65.0.0/16
161.35.0.0/16
165.227.0.0/16
167.99.128.0/16
167.172.128.0/16
178.128.0.0/16
206.189.0.0/16
139.59.128.0/16
157.230.0.0/16
159.203.64.0/16
162.243.0.0/16
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Re: [mailop] STARTTLS - Constant Contact and yahoo.co.jp

2020-08-26 Thread Michael Orlitzky via mailop
On 2020-08-26 12:50, Scott Mutter via mailop wrote:
> I've been toying with the idea of forcing outbound SMTP connections to
> use TLS, but thought I'd take a quick look and see who might miss mail
> if this done. 

This sounds good at first but if you make a flow chart, all paths lead
to either "nothing changes" or "shoot yourself in the foot." There's no
scenario that I know of where forcing TLS (as opposed to "opportunistic"
TLS) improves anything.

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Re: [mailop] Delisting request from sendgrid customer about ip used in recent phishing campaign.

2020-08-11 Thread Michael Orlitzky via mailop
On 2020-08-11 16:53:46, Benoit Panizzon via mailop wrote:
> 
> Now a sendgrid customers complains to us, that his emails are being
> rejected because of this listing.
> 
> But that makes me wonder: Doesn't sendgrid deal with such issues like
> asking for delisting after blocking the sender itself and re-uses
> recently (last phish received on 14. July) 'abused' ip addresses for
> other customers?
> 

In the past few months there have been several threads on mailop and
similar lists (sdlu, spamassassin-users, nanog, ...) complaining about
how SendGrid doesn't seem to do anything at all to stop the ongoing
blatant phishing campaigns from their servers.

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Re: [mailop] Is DNS-over-HTTPS bad? Sure. (was: Happy Holidays Everyone!)

2020-07-07 Thread Michael Orlitzky via mailop
On 2020-07-06 06:37:54, Matt Harris via mailop wrote:
>
> If said fascist regime has decided to muddle their DNS
> infrastructure by serving bogus authoritative responses for some set
> of domains they don't like, why would anyone think they wouldn't
> just set up " use-application-dns.net" to force end-users to
> continue to use their DNS servers which implement that blocking,
> too?
>

On this episode of What Could Possibly Go Wrong: we use a centralized,
government-controlled database of who's good and bad to fight fascism.

Guess who's hanging out in your browser's root CA store?

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Re: [mailop] Microsoft Block list (S3150)

2020-06-25 Thread Michael Orlitzky via mailop
On 2020-06-25 01:33, Scott Mutter via mailop wrote:
> 
> Just once, I'd love to get a response from Microsoft that explains why
> they're the only ones blocking an IP address.

When your customers can't send email to Microsoft or Gmail, they cancel
their account with you and move their email to Microsoft or Gmail.

  * Why won't Exchange follow the SMTP standards?
  * Why can't Outlook implement STARTTLS correctly?
  * Can Outlook finally support CalDAV and CardDAV?
  * How come all my mail comes through as winmail.dat?

All of these questions from the past 20 years have the same answer. It's
simply a novel method to outlaw not paying them.

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[mailop] Microsoft: Forged SPF HELO

2020-05-15 Thread Michael Orlitzky via mailop
SpamAssassin now adds a point whenever the HELO name is forged but the
SPF check on that HELO name passes. Looking through our logs, the major
offender here seems to be outlook.com. For examples,

  helo : NAM11-CO1-obe.outbound.protection.outlook.com
  ip   : 40.107.220.95
  dig $helo A  : 23.103.198.207
  dig $helo TXT: v=spf1 include:spf.protection.outlook.com -all

  helo : nam11-dm6-obe.outbound.protection.outlook.com
  ip   : 40.107.223.121
  dig $helo A  : 23.103.135.207
  dig $helo TXT: v=spf1 include:spf.protection.outlook.com -all
  ...


All of them have the same generic SPF record, which is fine, and so they
all pass the HELO SPF check. But that means that every outbound
outlook.com server with a HELO that doesn't resolve to its IP is getting
hit with an extra spam point. I know these aren't real servers and these
aren't real names and there aren't real humans in charge over there et
cetera =) But if the names can be made to match when an SPF record is
present, it would eliminate a penalty that's getting added to a lot of
outlook.com mail.

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Re: [mailop] SendGrid Abuse unresponsive

2020-05-05 Thread Michael Orlitzky via mailop
On 5/4/20 10:49 PM, Will Boyd via mailop wrote:
> Hi Kyle,
> 
> I've located those tickets. It looks like a colleague did reply on
> Wednesday to 4218173 and the reply went to Angelo. I'm not on our abuse
> team but will ping them with both ticket numbers to follow up.
> 

If you'll allow me to hijack this thread while it has some eyeballs...

  Apr 30 15:27:58 mx1 postfix/postscreen[12495]: NOQUEUE: reject: RCPT
  from [198.37.144.39]:25470: 450 4.3.2 Service currently unavailable;
  from=,
  to=, proto=ESMTP,
  helo=

That message was never retried, even though this page says you'll retry
for 72 hours:

  https://sendgrid.com/docs/glossary/deferrals/

That sample is fresh in my mind, but it's not a unique problem. We do
pre-queue scanning and sometimes you're just gonna get a busy signal.
We'd all love it if you could re-send at least once per the RFC so that
people will stop calling us about lost messages =)

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Re: [mailop] [EXTERNAL] viva.com.do postmaster

2020-02-04 Thread Michael Orlitzky via mailop
On 2/4/20 3:48 PM, Michael Peddemors via mailop wrote:
> UCE-PROTECT-2 and UCE-PROTECT-3 to be more precise..
> It might be that you have bad 'neighbours'.

Am I confused? I mean, I know I'm confused now. Are you two confused? =)

I sent my message from 65.246.80.16. The recipient's server -- the one
that rejected the message -- is 190.8.37.13, and is listed on UCEPROTECT
L2/L3.

65.246.80.16 should be totally clean. I suspect the problem is with
190.8.37.13 (viva.com.do), which is why I was trying to contact them in
the first place.

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[mailop] viva.com.do postmaster

2020-02-04 Thread Michael Orlitzky via mailop
I am trying to report the fact that your blacklist check is broken:

> : host tiburon.viva.com.do[190.8.37.13] said: 550 
> 5.7.1
> Recipient not authorized, your IP has been found on a block list (in reply
> to RCPT TO command)

but I can't, because your blacklist check is broken. The sending server
is 65.246.80.16, and is not blacklisted as far as I can tell.

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Re: [mailop] How long to retry?

2020-02-03 Thread Michael Orlitzky via mailop
On 2/3/20 5:04 PM, Brandon Long wrote:
> 
> I always wanted to lower it, the messages that take longer than a day
> are in the noise, and a lot of time that's because a mailbox is so busy
> that it's on the edge of being able to actually handle the volume, and
> the problem is more one of flow control (twice in two threads, wow)

It's easy to lie (inadvertently) with statistics. If you draw the window
big enough, you can ignore any potential problem as statistical noise.
Basically 100% of the time, messages do go through instantaneously. But
when your office floods and you have to call someone in to replace,
reinstall, and restore the whole thing from backup, now 100% of your
messages are delayed.

You have problems with 100% of messages 0.0001% of the time -- it's not
a steady 99. success rate, even though that's what the numbers look
like if your window is five-years long.

Customers really love hearing that they're not going to lose any mail
when that happens. The rest of the time, yeah, it's a bit long. But
we're not trying to accomodate the one guy who's over quota on a random
Tuesday.

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Re: [mailop] How long to retry?

2020-02-02 Thread Michael Orlitzky via mailop
On 2/2/20 12:52 PM, Chris Adams via mailop wrote:
> Just an idle Sunday question... how long do you have your mail server(s)
> configured to queue and retry messages before bouncing them back to the
> sender?
> 
> I know back in the day, 5 days was the norm, to handle servers that were
> only sometimes connected, outages, etc.

The five-days number is recommended by the RFCs. I always assumed that
number was to account for "long weekends." If your server crashes on
somebody else's property on Friday, and if Monday is a holiday, you can
still get mail that is retried for 5 days.

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Re: [mailop] Best strategy to prune address list

2019-11-24 Thread Michael Orlitzky via mailop
On 11/24/19 12:17 PM, Jaroslaw Rafa via mailop wrote:
> 
> Just to be precise, you should check for either MX or A/ record.

This prevents you from eliminating a huge number of bad addresses,
though, to save a negligible amount of good ones.

For the same reason, I would recommend verifying the addresses against a
simple regular expression to catch typos, rather than against the full
rfc5322 grammar which allows basically anything.

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Re: [mailop] Gmail marking email from me as spam

2019-10-15 Thread Michael Orlitzky via mailop
On 10/14/19 9:29 PM, Brandon Long via mailop wrote:
> 
> 
> On Mon, Oct 14, 2019 at 3:54 PM Michael Orlitzky via mailop
> mailto:mailop@mailop.org>> wrote:.
> [snip]
> 
> They don't care if you or anyone else can send/receive mail, ...
> 
> 
> It seems like Gmail wouldn't last long as an email provider if no one
> could send/receive email to it.
> 

I don't believe that either (it's right out of the EEE playbook), but
it's not quite what I said. I said "Google doesn't care," and for that
the proof is in the pudding.

We've been delivering mail to gmail all day every day since it was born.
Bazillions of messages over however many years. Had thousands of
delivery/spam problems (on both ends) that the world is better off
having resolved. And yet, after all those years, messages, and problems
-- you're the closest thing to a real human "gmail support" person that
I've ever encountered. Even so, the best you can do is to tell this guy
that perhaps maybe if he potentially switches hosting providers then
probably in all likelihood it could fix his issue in theory with any luck.

So while you personally seem like a nice dude and I know you're trying
to help, the fact that you ultimately can't (and that begging on mailop
is tier 1 support in the first place) just cements my impression that
Google as an organization doesn't care.

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Re: [mailop] Gmail marking email from me as spam

2019-10-14 Thread Michael Orlitzky via mailop
On 10/14/19 6:03 AM, Jaroslaw Rafa via mailop wrote:
>> Small senders do just fine getting into Google. 
> 
> Well, as I already mentioned, I moved my mailserver to my current hosting
> right about 18 months ago. Had no problems - until now. So, the fact that
> you have no problems currently doesn't mean you can't run into problems
> later - with no fault on your part whatsoever. Email delivery to big
> receivers like Google just isn't as reliable as it should be.
> 

I'm replying at a random point in this thread. I see two separate
problems here that are getting conflated.

1. It's not fair to judge a sender by his neighbors.

Well, kind of. Our in-house blacklists are tended manually, and we keep
evidence for every listing so that if we later have to explain
ourselves, we can. If I get one spam from one IP in your netblock, I ban
that IP. If I get spam from two IPs in your netblock, I ban them both.
If I get spam from three, and I have to spend half an hour typing up
commit messages and pushing to repos and classifying evidence... then to
hell with you, I'm blocking the whole thing. It's now *your* problem.
That's the price you pay for having a real human over here.

However, if we block you, you can just read the rejection message and
get in touch with me or a coworker easily and we'll add an exception for
you, because we care that our users get your mail. This is where the
second issue comes into play. In general, overzealous blocking is not a
life or death issue; but with Google, there's no one to appeal to. And
that's the crux of your problem. This first issue about reputation is
being argued pointlessly. The real problem is that

2. Google doesn't give a shit about you.

They don't care if you or anyone else can send/receive mail, because
that's not how they make money. You're not going to convince them to
care, and so long as they don't, your problems are only going to get
worse. No one's going to tell you how to fix *this* issue because there
is no solution -- that's why you're getting the next best thing, namely
advice to switch providers and pray that Google doesn't feel like
blocking your new host, too.

"Old man yells at cloud," but that's the truth. Being a good guy isn't a
great business model in any unregulated industry.

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Re: [mailop] Howto be a good mailop (best practice / insights wanted)

2019-05-09 Thread Michael Orlitzky via mailop
On 5/8/19 1:48 PM, Ken O'Driscoll via mailop wrote:
> There is likely more, above is, as I said, off the top of my head. Good
> luck.
>

One to add:

  * Sign up for feedback loops with the major providers.

I see a remarkable number of phished-credential bots that are smart
enough to send one message every ~five minutes. Our automated defenses
miss those, until Comcast or AOL starts sending me complaints.

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Re: [mailop] No MX record on domain is a bounce by Gmail

2019-05-05 Thread Michael Orlitzky via mailop
On 5/4/19 2:06 PM, Reynold McGuire via mailop wrote:
> 
> Industry standards, best practices and 30+ years of SMTP say to follow MX.

You're lying about at least two of those things. Throw away your users'
mail if you want, but don't spread dangerous misinformation.

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