Re: [mailop] Did Google become stricter about RFC 5322?

[Robert L Mathews via mailop]

On 7/18/22 4:45 PM, Brandon Long via mailop wrote:
Are they using Windows Mail to send mail through your service via 
message submission?


Adding a message-id header is a SHOULD in that case: 
https://datatracker.ietf.org/doc/html/rfc6409#page-14 


If you're just forwarding, then yes, it's unfortunate.


I see both situations in my logs. I guess I'll fix what I can and tell 
the rest of the people that doesn't work anymore. 


--
Robert L Mathews
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Suresh Ramasubramanian via mailop]

The thing about dkim is that you’re supposed to sign mail AFTER adding 
corporate disclaimers, fixing missing headers and what not.

Go ahead and fix whatever missing header you can - it’s all good

--srs

From: mailop  on behalf of Robert L Mathews via 
mailop 
Sent: Tuesday, July 19, 2022 4:40:59 AM
To: mailop@mailop.org 
Subject: Re: [mailop] Did Google become stricter about RFC 5322?

On 7/13/22 12:31 AM, Philip Paeps via mailop wrote:
> In the past couple of days, I'm seeing an uptick in rejects from Gmail
> as follows:
>
> >Our system has detected that this message is not RFC 5322 compliant.

Similar to this, some our customers complained that messages sent to
Gmail have been bouncing since June 15 with:

550-5.7.1 [ip_redacted] Messages missing a valid messageId header are not
550 5.7.1 accepted.

The messages indeed do not have a "Message-ID" header; they're being
sent from the Windows 10 built-in "Mail" app.

I'm a little surprised that the Windows Mail app doesn't include a
Message-ID, but
<https://datatracker.ietf.org/doc/html/rfc5322#section-3.6.4> says it's
only a SHOULD, not a MUST.

Anyone else seeing the same thing? Now I'm in the position of having to
either start adding missing Message-ID headers, which people online
recommend against because it potentially breaks DKIM, or telling people
  Windows Mail no longer works to send to Gmail. Neither is ideal.

--
Robert L Mathews
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Brandon Long via mailop]

Are they using Windows Mail to send mail through your service via message
submission?

Adding a message-id header is a SHOULD in that case:
https://datatracker.ietf.org/doc/html/rfc6409#page-14

If you're just forwarding, then yes, it's unfortunate.

Brandon

On Mon, Jul 18, 2022 at 4:24 PM Robert L Mathews via mailop <
mailop@mailop.org> wrote:

> On 7/13/22 12:31 AM, Philip Paeps via mailop wrote:
> > In the past couple of days, I'm seeing an uptick in rejects from Gmail
> > as follows:
> >
> > >Our system has detected that this message is not RFC 5322 compliant.
>
> Similar to this, some our customers complained that messages sent to
> Gmail have been bouncing since June 15 with:
>
> 550-5.7.1 [ip_redacted] Messages missing a valid messageId header are not
> 550 5.7.1 accepted.
>
> The messages indeed do not have a "Message-ID" header; they're being
> sent from the Windows 10 built-in "Mail" app.
>
> I'm a little surprised that the Windows Mail app doesn't include a
> Message-ID, but
>  says it's
> only a SHOULD, not a MUST.
>
> Anyone else seeing the same thing? Now I'm in the position of having to
> either start adding missing Message-ID headers, which people online
> recommend against because it potentially breaks DKIM, or telling people
>   Windows Mail no longer works to send to Gmail. Neither is ideal.
>
> --
> Robert L Mathews
> ___
> mailop mailing list
> mailop@mailop.org
> https://list.mailop.org/listinfo/mailop
>
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Robert L Mathews via mailop]

On 7/13/22 12:31 AM, Philip Paeps via mailop wrote:
In the past couple of days, I'm seeing an uptick in rejects from Gmail 
as follows:


>Our system has detected that this message is not RFC 5322 compliant.


Similar to this, some our customers complained that messages sent to 
Gmail have been bouncing since June 15 with:


550-5.7.1 [ip_redacted] Messages missing a valid messageId header are not
550 5.7.1 accepted.

The messages indeed do not have a "Message-ID" header; they're being 
sent from the Windows 10 built-in "Mail" app.


I'm a little surprised that the Windows Mail app doesn't include a 
Message-ID, but 
 says it's 
only a SHOULD, not a MUST.


Anyone else seeing the same thing? Now I'm in the position of having to 
either start adding missing Message-ID headers, which people online 
recommend against because it potentially breaks DKIM, or telling people 
 Windows Mail no longer works to send to Gmail. Neither is ideal.


--
Robert L Mathews
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Larry M. Smith via mailop]

On 7/13/2022, Philip Paeps via mailop wrote:
In the past couple of days, I'm seeing an uptick in rejects from Gmail 
as follows:


<[elided]@gmail.com>: host
     gmail-smtp-in.l.google.com[2607:f8b0:4004:c17::1a] said: 550-5.7.1
     [2610:1c1:1:606c::19:2] Our system has detected that this message is
     550-5.7.1 not RFC 5322 compliant. To reduce the amount of spam sent to
     Gmail, 550-5.7.1 this message has been blocked. Please review 550 
5.7.1

     RFC 5322 specifications for more information.
     bp41-20020a05620a45a900b006a64dbdb75asi7765031qkb.308 - gsmtp (in 
reply to

     end of DATA command)



Heh, Isn't that neat.  Gmail re-queues and re-sends messages if your 5xx 
response isn't to their liking.  And being worried about their users 
_getting_ spam while they seemingly ignore notifications about the spam 
their users are _sending_.


SgtChains
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Brandon Long via mailop]

As far as the rfc ignorant rejections, the rules about some duplicate
headers have been ramping for a couple months, but only recently was the
error message updated to point out what the issue is, before it was a more
generic might be spam message.

This is in addition to the rules we've had for years about the from header
and proper email addresses in the envelope.

These are due to increasing replay attacks and differences between clients
of which ones of these headers they show when there are multiple ones.

Brandon

On Wed, Jul 13, 2022, 10:08 AM John Levine via mailop 
wrote:

> It appears that Al Iverson via mailop  said:
> >Yeah, I'm not seeing Google be "hostile" to mailing lists if the mail
> >fully authenticates properly. I've felt mailing lists and
> >authentication and Gmail were a solved problem, at least from my
> >perspective, for a number of years now.
>
> Same here. I set up a kludge to rewrite From: headers several years
> ago (not rewriting to the list address, which sucks) and it still
> works fine.
>
> R's,
> John
> ___
> mailop mailing list
> mailop@mailop.org
> https://list.mailop.org/listinfo/mailop
>
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[John Levine via mailop]

It appears that Chris Adams via mailop  said:
>Once upon a time, John Levine  said:
>> Same here. I set up a kludge to rewrite From: headers several years
>> ago (not rewriting to the list address, which sucks) and it still
>> works fine.
>
>Is there a standard for doing rewrites like that?

No, because all From: rewrites suck, some just suck more than others.

For mine, if it sees a message from a domain with a DMARC policy that
will cause trouble, such as st...@aol.com, it rewrites it liks this:

  st...@aol.com.dmarc.fail

It also tweaks the config so that address will forward back to the real
address for a few days.  That domain has no DMARC policy so it works OK
for mail.

The IETF's mailing list do a similar rewrite to steve=40aol@dmarc.ietf.org.

In the long run ARC is intended to help recipient mail systems recognize
list mail they want, even from addresses with overstrict DMARC policies,
but it's not there yet.

R's,
John
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Chris Adams via mailop]

Once upon a time, John Levine  said:
> Same here. I set up a kludge to rewrite From: headers several years
> ago (not rewriting to the list address, which sucks) and it still
> works fine.

Is there a standard for doing rewrites like that?  Because I like to see
actual senders in the From: line (while recognizing the need to do the
rewrites), I have a script that recognizes a couple of rewrite methods
I've seen and reverses them for messages going into my mailing list
folders.  It's very much just done based on what I've seen though, so
probably doesn't "fix" a lot.

-- 
Chris Adams 
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[John Levine via mailop]

It appears that Al Iverson via mailop  said:
>Yeah, I'm not seeing Google be "hostile" to mailing lists if the mail
>fully authenticates properly. I've felt mailing lists and
>authentication and Gmail were a solved problem, at least from my
>perspective, for a number of years now.

Same here. I set up a kludge to rewrite From: headers several years
ago (not rewriting to the list address, which sucks) and it still
works fine.

R's,
John
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Miles Fidelman via mailop]

Mark Fletcher via mailop wrote:
On Wed, Jul 13, 2022 at 8:29 AM Miles Fidelman via mailop 
mailto:mailop@mailop.org>> wrote:


It's been over a month now, since Google became hostile to email
lists.
I'm still dealing with the aftermath.

How so? We haven't seen any issues.

Mark

___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop
I've been hosting a bunch of small lists, for years - using a slightly 
dated version of Sympa.


When DMARC hit, we installed the patch that supported the list-as-sender 
patch, and set up all the SPF records and such - and we had no problems 
- until about a month ago, when all of the gmail addresses on our lists 
started bouncing.  Not a problem anywhere else, just gmail.


Miles Fidelman

--
In theory, there is no difference between theory and practice.
In practice, there is.   Yogi Berra

Theory is when you know everything but nothing works.
Practice is when everything works but no one knows why.
In our lab, theory and practice are combined:
nothing works and no one knows why.  ... unknown

___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Al Iverson via mailop]

Yeah, I'm not seeing Google be "hostile" to mailing lists if the mail
fully authenticates properly. I've felt mailing lists and
authentication and Gmail were a solved problem, at least from my
perspective, for a number of years now.
What bit me recently was a bug, not some pushback against my business model.

Cheers,
Al

On Wed, Jul 13, 2022 at 10:47 AM Mark Fletcher via mailop
 wrote:
>
> On Wed, Jul 13, 2022 at 8:29 AM Miles Fidelman via mailop  
> wrote:
>>
>> It's been over a month now, since Google became hostile to email lists.
>> I'm still dealing with the aftermath.
>>
> How so? We haven't seen any issues.
>
> Mark
> ___
> mailop mailing list
> mailop@mailop.org
> https://list.mailop.org/listinfo/mailop



-- 

Al Iverson / Deliverability blogging at www.spamresource.com
Subscribe to the weekly newsletter at wombatmail.com/sr.cgi
DNS Tools at xnnd.com / (312) 725-0130 / Chicago (Central Time)
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Mark Fletcher via mailop]

On Wed, Jul 13, 2022 at 8:29 AM Miles Fidelman via mailop 
wrote:

> It's been over a month now, since Google became hostile to email lists.
> I'm still dealing with the aftermath.
>
> How so? We haven't seen any issues.

Mark
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Miles Fidelman via mailop]

It's been over a month now, since Google became hostile to email lists.  
I'm still dealing with the aftermath.


Miles Fidelman

Philip Paeps via mailop wrote:
In the past couple of days, I'm seeing an uptick in rejects from Gmail 
as follows:


<[elided]@gmail.com>: host
    gmail-smtp-in.l.google.com[2607:f8b0:4004:c17::1a] said: 550-5.7.1
    [2610:1c1:1:606c::19:2] Our system has detected that this message is
    550-5.7.1 not RFC 5322 compliant. To reduce the amount of spam 
sent to
    Gmail, 550-5.7.1 this message has been blocked. Please review 550 
5.7.1

    RFC 5322 specifications for more information.
    bp41-20020a05620a45a900b006a64dbdb75asi7765031qkb.308 - gsmtp (in 
reply to

    end of DATA command)

As far as I can tell, the message is compliant.  It doesn't have any 
of the obvious problems, at least.  From, To, Message-ID and Date are 
supplied.  No duplicate headers.


These are text/plain messages: commit mail from an svn repository.

I like to think I have a reasonably robust understanding of RFC 5322.  
I'm sure I must be missing something very subtle.


Has anyone else seen (more of) these?

Thanks.

Philip




--
In theory, there is no difference between theory and practice.
In practice, there is.   Yogi Berra

Theory is when you know everything but nothing works.
Practice is when everything works but no one knows why.
In our lab, theory and practice are combined:
nothing works and no one knows why.  ... unknown

___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Al Iverson via mailop]

I've gotten bitten by this too, as I had my homebrew mailing list
manager intermittently generating messages with two message ID headers
-- but not in the past few days -- more like a couple of months ago.
So it could be new-ish, I guess.

Cheers,
Al

On Wed, Jul 13, 2022 at 5:34 AM Philip Paeps via mailop
 wrote:
>
> On 2022-07-13 17:52:33 (+0800), Laura Atkins wrote:
> > On 13 Jul 2022, at 09:07, Philip Paeps via mailop 
> > wrote:
> >> On 2022-07-13 15:31:17 (+0800), Philip Paeps via mailop wrote:
> >>> In the past couple of days, I'm seeing an uptick in rejects from
> >>> Gmail as follows: [...]
> >>>
> >>> As far as I can tell, the message is compliant.  It doesn't have any
> >>> of the obvious problems, at least.  From, To, Message-ID and Date
> >>> are supplied.  No duplicate headers.
> >>
> >> It turns out there was, in fact, a duplicate Date: header.  Sigh.  I
> >> am blind.  I was looking for duplicate To: headers, which are a lot
> >> easier to introduce.  I wonder how that happened.
> >>
> >> Apologies for the noise.
> >>
> >> (Still wondering if Google has gotten stricter though...  As far as I
> >> know, this commit mail script hasn't been touched in a very long
> >> time.  Though I won't exclude the possibility of something else in
> >> the mail pipeline having changed.)
> >
> > There are currently quite a number of anecdotal reports that Google is
> > moving towards rejecting more email that doesn’t comply with their
> > interpretation of the standards. This includes 5321/2 and the
> > authentication standards.
>
> For fans of anecdata... :-)
>
> The duplicate Date: header was introduced on 2021-06-05 at 11:00:56 UTC.
>
> As far as I can tell, we saw our first reject on 2022-07-08 at 23:15:18
> UTC.
>
> We only keep 7 days of outbound logs and this this particular script
> only sends a handful to a few dozen messages daily.  A slow enough
> trickle for patterns to take a while before becoming obvious.
>
> Philip
>
> --
> Philip Paeps
> Senior Reality Engineer
> Alternative Enterprises
> ___
> mailop mailing list
> mailop@mailop.org
> https://list.mailop.org/listinfo/mailop



-- 

Al Iverson / Deliverability blogging at www.spamresource.com
Subscribe to the weekly newsletter at wombatmail.com/sr.cgi
DNS Tools at xnnd.com / (312) 725-0130 / Chicago (Central Time)
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Bill Cole via mailop]

On 2022-07-13 at 05:52:33 UTC-0400 (Wed, 13 Jul 2022 10:52:33 +0100)
Laura Atkins via mailop 
is rumored to have said:

[...]

There are currently quite a number of anecdotal reports that Google is 
moving towards rejecting more email that doesn’t comply with their 
interpretation of the standards. This includes 5321/2 and the 
authentication standards.


So I guess that makes the cycle time on "RFC Ignorant" enforcement about 
15 years?



--
Bill Cole
b...@scconsult.com or billc...@apache.org
(AKA @grumpybozo and many *@billmail.scconsult.com addresses)
Not Currently Available For Hire
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Philip Paeps via mailop]

On 2022-07-13 17:52:33 (+0800), Laura Atkins wrote:
On 13 Jul 2022, at 09:07, Philip Paeps via mailop  
wrote:

On 2022-07-13 15:31:17 (+0800), Philip Paeps via mailop wrote:
In the past couple of days, I'm seeing an uptick in rejects from 
Gmail as follows: [...]


As far as I can tell, the message is compliant.  It doesn't have any 
of the obvious problems, at least.  From, To, Message-ID and Date 
are supplied.  No duplicate headers.


It turns out there was, in fact, a duplicate Date: header.  Sigh.  I 
am blind.  I was looking for duplicate To: headers, which are a lot 
easier to introduce.  I wonder how that happened.


Apologies for the noise.

(Still wondering if Google has gotten stricter though...  As far as I 
know, this commit mail script hasn't been touched in a very long 
time.  Though I won't exclude the possibility of something else in 
the mail pipeline having changed.)


There are currently quite a number of anecdotal reports that Google is 
moving towards rejecting more email that doesn’t comply with their 
interpretation of the standards. This includes 5321/2 and the 
authentication standards.


For fans of anecdata... :-)

The duplicate Date: header was introduced on 2021-06-05 at 11:00:56 UTC.

As far as I can tell, we saw our first reject on 2022-07-08 at 23:15:18 
UTC.


We only keep 7 days of outbound logs and this this particular script 
only sends a handful to a few dozen messages daily.  A slow enough 
trickle for patterns to take a while before becoming obvious.


Philip

--
Philip Paeps
Senior Reality Engineer
Alternative Enterprises
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Laura Atkins via mailop]

> On 13 Jul 2022, at 09:07, Philip Paeps via mailop  wrote:
> 
> On 2022-07-13 15:31:17 (+0800), Philip Paeps via mailop wrote:
>> In the past couple of days, I'm seeing an uptick in rejects from Gmail as 
>> follows: [...]
>> 
>> As far as I can tell, the message is compliant.  It doesn't have any of the 
>> obvious problems, at least.  From, To, Message-ID and Date are supplied.  No 
>> duplicate headers.
> 
> It turns out there was, in fact, a duplicate Date: header.  Sigh.  I am 
> blind.  I was looking for duplicate To: headers, which are a lot easier to 
> introduce.  I wonder how that happened.
> 
> Apologies for the noise.
> 
> (Still wondering if Google has gotten stricter though...  As far as I know, 
> this commit mail script hasn't been touched in a very long time.  Though I 
> won't exclude the possibility of something else in the mail pipeline having 
> changed.)

There are currently quite a number of anecdotal reports that Google is moving 
towards rejecting more email that doesn’t comply with their interpretation of 
the standards. This includes 5321/2 and the authentication standards. 

laura

-- 
The Delivery Experts

Laura Atkins
Word to the Wise
la...@wordtothewise.com 

Email Delivery Blog: http://wordtothewise.com/blog  






___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Łukasz Wąsikowski via mailop]

W dniu 2022-07-13 o 09:31, Philip Paeps via mailop pisze:

In the past couple of days, I'm seeing an uptick in rejects from Gmail 
as follows:


<[elided]@gmail.com>: host
     gmail-smtp-in.l.google.com[2607:f8b0:4004:c17::1a] said: 550-5.7.1
     [2610:1c1:1:606c::19:2] Our system has detected that this message is
     550-5.7.1 not RFC 5322 compliant. To reduce the amount of spam sent to
     Gmail, 550-5.7.1 this message has been blocked. Please review 550 
5.7.1

     RFC 5322 specifications for more information.
     bp41-20020a05620a45a900b006a64dbdb75asi7765031qkb.308 - gsmtp (in 
reply to

     end of DATA command)

As far as I can tell, the message is compliant.  It doesn't have any of 
the obvious problems, at least.  From, To, Message-ID and Date are 
supplied.  No duplicate headers.


These are text/plain messages: commit mail from an svn repository.

I like to think I have a reasonably robust understanding of RFC 5322. 
I'm sure I must be missing something very subtle.


Has anyone else seen (more of) these?


It hit me too a few days ago. In my case there was a duplicate CC: header.

--
Best regards,
Łukasz Wąsikowski
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[Philip Paeps via mailop]

On 2022-07-13 15:31:17 (+0800), Philip Paeps via mailop wrote:
In the past couple of days, I'm seeing an uptick in rejects from Gmail 
as follows: [...]


As far as I can tell, the message is compliant.  It doesn't have any 
of the obvious problems, at least.  From, To, Message-ID and Date are 
supplied.  No duplicate headers.


It turns out there was, in fact, a duplicate Date: header.  Sigh.  I am 
blind.  I was looking for duplicate To: headers, which are a lot easier 
to introduce.  I wonder how that happened.


Apologies for the noise.

(Still wondering if Google has gotten stricter though...  As far as I 
know, this commit mail script hasn't been touched in a very long time.  
Though I won't exclude the possibility of something else in the mail 
pipeline having changed.)


Philip

--
Philip Paeps
Senior Reality Engineer
Alternative Enterprises
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Re: [mailop] Did Google become stricter about RFC 5322?

[ml+mailop--- via mailop]

On Wed, Jul 13, 2022, Philip Paeps via mailop wrote:

> As far as I can tell, the message is compliant.  It doesn't have any of the

Can you post it so others can check?
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

[mailop] Did Google become stricter about RFC 5322?

[Philip Paeps via mailop]

In the past couple of days, I'm seeing an uptick in rejects from Gmail 
as follows:


<[elided]@gmail.com>: host
gmail-smtp-in.l.google.com[2607:f8b0:4004:c17::1a] said: 550-5.7.1
[2610:1c1:1:606c::19:2] Our system has detected that this message 
is
550-5.7.1 not RFC 5322 compliant. To reduce the amount of spam sent 
to
Gmail, 550-5.7.1 this message has been blocked. Please review 550 
5.7.1

RFC 5322 specifications for more information.
bp41-20020a05620a45a900b006a64dbdb75asi7765031qkb.308 - gsmtp (in 
reply to

end of DATA command)

As far as I can tell, the message is compliant.  It doesn't have any of 
the obvious problems, at least.  From, To, Message-ID and Date are 
supplied.  No duplicate headers.


These are text/plain messages: commit mail from an svn repository.

I like to think I have a reasonably robust understanding of RFC 5322.  
I'm sure I must be missing something very subtle.


Has anyone else seen (more of) these?

Thanks.

Philip

--
Philip Paeps
Senior Reality Engineer
Alternative Enterprises
___
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop