Re: [mailop] Gmail Dynamic Email / Impact on Email Ecosystem

2022-08-12 Thread Tobias Fiebig via mailop
Heho,

> Brandon Long via mailop
> https://developers.google.com/gmail/ampemail is the Google developer 
> information about dynamic email, that link was about controlling the 
> content with Google Workspace.
Thanks for sharing, this has some rather interesting examples. Do I need to be 
specially vetted to send AMP email, or could I--as long as it is compliant to 
the standard--send one myself, i.e., without being a registered newsletter 
sender? The AMP page is somewhat unclear there.

> Brandon Long via mailop
> The standardization is via AMP, docs at https://amp.dev/about/email/ 
> and a pretty short list of other providers who support it.
I acknowledge that mail's UX is currently 'fresh and outstanding' and something 
will have to change. Still, change is naturally driven by those who do, 
which--in this case--is the group of organizations around AMP. However, I'd 
argue that changes will be aligned with the needs of these organizations in 
terms of providing consistent services to their customer base under their 
business model [1], which naturally inflicts on how these systems are being 
designed. This also inflicts on the governance of venues for organizing and 
coordinating such changes, as for example AMP, implementing a model that allows 
decision making to follow operational needs [2].  And, to be clear, I am not 
claiming that this is a google-specific thing, or try to pick on google, but 
instead argue that any rational actor with that scale of operations will 
ultimately operate in this way to match its objectives.

> Brandon Long via mailop
> The death of email will come from outside the eco-system, not from 
> individual attempts to extend it.
I wouldn't necessarily call AMP an individual attempt, given the market share 
of some of the involved parties.

Also, I was referring to the death of XMPP. If I remember correctly, XMPP's 
rise and fall actually started with major players [3,4] committing to XMPP 
federation.
However, over time, and with needs, roadmaps, and available features in clients 
diverging more and more, federation was discontinued by Facebook and Google [5].
At this point, the role of others being less sharing and more consuming--Page 
explicitly calling out Microsoft here [6]--certainly should also be mentioned. 
What ultimately broke the neck of XMPP was then its ill suitedness to the 
evolving User Experience on smartphones.
With its complicated protocol, and federation needs--the classical finding 
others problem--it was simply no match for centralized services using simple 
but usable identifiers (phone numbers), even if they may have been using XMPP 
'under the hood'.
That then is what gave us the current zoo of messengers we all love and like 
(if someone wants to further discuss this point, please feel free to write me 
on What'sApp, Signal, Telegram, Threema, Facebook Messenger, Skype, 
Skype4Bussiness/Lync, Google Meet, reddit, or via netcat on tcp/2342).

So, in the end, the dynamics around new features adopted by a few players 
representing a major subset of the ecosystem can have a long-lasting impact 
that may ultimately interact with, e.g., the deliverability discussions we 
regularly have. (Most recently, tightened SPF requirements by Google, and I am 
not claiming that _that_ move was necessarily a bad one; But one with 
consequences to consider that are not strictly technical in nature, but cross 
influence technology, i.e., in this case, mail.)

With best regards,
Tobias

[1] 
https://doing-stupid-things.as59645.net/burning/world/resillience/2022/06/30/propositions-part-4.html
[2] Page 78, Sec. VII.E.6, Point 206 ff 
https://www.texasattorneygeneral.gov/sites/default/files/images/admin/2020/Press/20201216%20COMPLAINT_REDACTED.pdf
  
[3] https://googletalk.blogspot.com/2006/01/xmpp-federation.html
[4] https://www.facebook.com/notes/10160197317616729/ 
[5] 
https://blogs.fsfe.org/hugo/2013/05/google-talk-discontinued-will-google-keep-its-promise-and-give-xmpp-users-a-way-out/
 
[6] 
https://www.theverge.com/2013/5/15/4334242/larry-page-to-tech-world-being-negative-is-not-how-we-make-progress

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Re: [mailop] Gmail spam scoring via IPv6 different than IPv4?

2022-08-12 Thread Simon Arlott via mailop
On 12/08/2022 17:22, Jesse Hathaway via mailop wrote:
> Back in 2013[1] we changed our mail config to force MX lookups for gmail
> to only use IPv4 addresses.  We made these change after hearing reports
> of higher spam scoring when sending mail via IPv6. Would anyone from
> Google be able to comment as to whether forcing IPv4 is still needed?
> Yours kindly, Jesse Hathaway

My experience in the past is that because Google insist on a successful
matching reverse DNS lookup for IPv6, it will randomly permanently
reject email for a temporary error. It looks like Google are now doing
this for IPv4 too but I don't know if they've fixed it to handle
temporary DNS errors properly.

The other general problem is that your server's reputation will probably
be different for each address and suddenly swap between IPv6 and IPv4 on
a retry. Ideally random outgoing address selection across all IP address
families should be used to avoid this but Exim can't do that.

-- 
Simon Arlott
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Re: [mailop] Gmail spam scoring via IPv6 different than IPv4?

2022-08-12 Thread Slavko via mailop
Hi,

Dňa 12. augusta 2022 17:24:51 UTC používateľ Michael Peddemors via mailop 
 napísal:

>* Turn off ipv6 for MTA->MTA mail. (I know the IPv6 evangelists scream when I 
>say this, but email operators just want it to work) Slowly we work towards 
>first MTU->MTA over IPv6, I think we will see IPv4->IPv4 for server to server 
>communication for some time yet.

Interesting, all mails from (and to) google (as it is in question) are coming
via IPv6 to my MTA. The same eg. for mailop and other IPv6 aware sites...

regards

Slavko
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Re: [mailop] [E] Re: Gmail spam scoring via IPv6 different than IPv4?

2022-08-12 Thread Marcel Becker via mailop
On Fri, Aug 12, 2022 at 11:01 AM Michael Peddemors via mailop <
mailop@mailop.org> wrote:


>  Pop Quiz.. how many recursive DNS queries are supposed to be
> in SPF max?
>

42?

- Marcel
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Re: [mailop] Gmail spam scoring via IPv6 different than IPv4?

2022-08-12 Thread Michael Peddemors via mailop
Addendum: It's amazing how many billion dollar companies can't even get 
SPF right.. Pop Quiz.. how many recursive DNS queries are supposed to be 
in SPF max?


On 2022-08-12 10:24, Michael Peddemors via mailop wrote:

And frankly, for most people it is the easiest solution.

So many time we tell people, turn off IPv6 and all their problems go 
away, but asking them to set up all the extra layers such as SPF, DKIM 
etc, and to do it right.. well.. in practice, people have better things 
to do..


We of course still say:

* Sane PTR, only a single one unless you are forced to have two (small 
subnet DNS responsibility)

* Only a couple of A records, keep the list small (UDP vs retry to TCP0
* Implement a sane SPF record (Amazing how many people have trouble with 
this, or simply add everyone.. if you include all of google, amazon, and 
microsoft, why bother having an SPF record ;)
* Turn off ipv6 for MTA->MTA mail. (I know the IPv6 evangelists scream 
when I say this, but email operators just want it to work) Slowly we 
work towards first MTU->MTA over IPv6, I think we will see IPv4->IPv4 
for server to server communication for some time yet.


Let's not try to make it too difficult for the little guys, we should be 
encouraging more people operating email servers, not making it so 
difficult that they throw their hands in the air, and move to Gmail..

(of course, that might be the plan all along ;)

On 2022-08-12 09:47, Al Iverson via mailop wrote:

Hey Jesse,

This is sort of controversial and you'll get some people saying very
vehemently that you should never do this ever, for various reasons of
interoperability or strong opinions about how the internet works. But
instead, here's my take from an operational perspective...

I personally would keep forcing mail to Gmail over IPv4, and I do
indeed do this on my own hobbyist systems. Every time I spin up a new
VPS and forget this, I notice it rather quickly because of bouncing
mail. Not only are they quicker to block IPv6 mail overall (IMHO),
they also are more likely to block IPv6 mail from IPs without rDNS,
and mail that lacks either SPF or DKIM authentication. Their filters
are evolving and it feels as though their IPv4 blocking is catching up
a bit -- more likely to block unauthenticated IPv4 mail today versus a
year or two ago, but that doesn't really mean it suddenly became
easier to send over IPv6.

I blogged about this a couple year ago - nothing you don't already
know, really - 
https://www.spamresource.com/2020/11/honestly-dont-send-to-gmail-over-ipv6.html 


- but recently that article got linked to on Reddit and a bunch of
nerds made noise that I don't know what I'm talking about and that
they can get mail to Gmail over IPv6 just fine. So, YMMV. (My point is
that it's not impossible, but it is annoying and that it has exacting,
but unclear requirements.)

Cheers,
Al Iverson

On Fri, Aug 12, 2022 at 11:26 AM Jesse Hathaway via mailop
 wrote:


Back in 2013[1] we changed our mail config to force MX lookups for gmail
to only use IPv4 addresses.  We made these change after hearing reports
of higher spam scoring when sending mail via IPv6. Would anyone from
Google be able to comment as to whether forcing IPv4 is still needed?
Yours kindly, Jesse Hathaway


[1]: https://gerrit.wikimedia.org/r/c/operations/puppet/+/79753
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--
"Catch the Magic of Linux..."

Michael Peddemors, President/CEO LinuxMagic Inc.
Visit us at http://www.linuxmagic.com @linuxmagic
A Wizard IT Company - For More Info http://www.wizard.ca
"LinuxMagic" a Registered TradeMark of Wizard Tower TechnoServices Ltd.

604-682-0300 Beautiful British Columbia, Canada

This email and any electronic data contained are confidential and intended
solely for the use of the individual or entity to which they are addressed.
Please note that any views or opinions presented in this email are solely
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Re: [mailop] Gmail spam scoring via IPv6 different than IPv4?

2022-08-12 Thread Michael Peddemors via mailop

And frankly, for most people it is the easiest solution.

So many time we tell people, turn off IPv6 and all their problems go 
away, but asking them to set up all the extra layers such as SPF, DKIM 
etc, and to do it right.. well.. in practice, people have better things 
to do..


We of course still say:

* Sane PTR, only a single one unless you are forced to have two (small 
subnet DNS responsibility)

* Only a couple of A records, keep the list small (UDP vs retry to TCP0
* Implement a sane SPF record (Amazing how many people have trouble with 
this, or simply add everyone.. if you include all of google, amazon, and 
microsoft, why bother having an SPF record ;)
* Turn off ipv6 for MTA->MTA mail. (I know the IPv6 evangelists scream 
when I say this, but email operators just want it to work) Slowly we 
work towards first MTU->MTA over IPv6, I think we will see IPv4->IPv4 
for server to server communication for some time yet.


Let's not try to make it too difficult for the little guys, we should be 
encouraging more people operating email servers, not making it so 
difficult that they throw their hands in the air, and move to Gmail..

(of course, that might be the plan all along ;)

On 2022-08-12 09:47, Al Iverson via mailop wrote:

Hey Jesse,

This is sort of controversial and you'll get some people saying very
vehemently that you should never do this ever, for various reasons of
interoperability or strong opinions about how the internet works. But
instead, here's my take from an operational perspective...

I personally would keep forcing mail to Gmail over IPv4, and I do
indeed do this on my own hobbyist systems. Every time I spin up a new
VPS and forget this, I notice it rather quickly because of bouncing
mail. Not only are they quicker to block IPv6 mail overall (IMHO),
they also are more likely to block IPv6 mail from IPs without rDNS,
and mail that lacks either SPF or DKIM authentication. Their filters
are evolving and it feels as though their IPv4 blocking is catching up
a bit -- more likely to block unauthenticated IPv4 mail today versus a
year or two ago, but that doesn't really mean it suddenly became
easier to send over IPv6.

I blogged about this a couple year ago - nothing you don't already
know, really - 
https://www.spamresource.com/2020/11/honestly-dont-send-to-gmail-over-ipv6.html
- but recently that article got linked to on Reddit and a bunch of
nerds made noise that I don't know what I'm talking about and that
they can get mail to Gmail over IPv6 just fine. So, YMMV. (My point is
that it's not impossible, but it is annoying and that it has exacting,
but unclear requirements.)

Cheers,
Al Iverson

On Fri, Aug 12, 2022 at 11:26 AM Jesse Hathaway via mailop
 wrote:


Back in 2013[1] we changed our mail config to force MX lookups for gmail
to only use IPv4 addresses.  We made these change after hearing reports
of higher spam scoring when sending mail via IPv6. Would anyone from
Google be able to comment as to whether forcing IPv4 is still needed?
Yours kindly, Jesse Hathaway


[1]: https://gerrit.wikimedia.org/r/c/operations/puppet/+/79753
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--
"Catch the Magic of Linux..."

Michael Peddemors, President/CEO LinuxMagic Inc.
Visit us at http://www.linuxmagic.com @linuxmagic
A Wizard IT Company - For More Info http://www.wizard.ca
"LinuxMagic" a Registered TradeMark of Wizard Tower TechnoServices Ltd.

604-682-0300 Beautiful British Columbia, Canada

This email and any electronic data contained are confidential and intended
solely for the use of the individual or entity to which they are addressed.
Please note that any views or opinions presented in this email are solely
those of the author and are not intended to represent those of the company.
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Re: [mailop] Gmail spam scoring via IPv6 different than IPv4?

2022-08-12 Thread Al Iverson via mailop
Hey Jesse,

This is sort of controversial and you'll get some people saying very
vehemently that you should never do this ever, for various reasons of
interoperability or strong opinions about how the internet works. But
instead, here's my take from an operational perspective...

I personally would keep forcing mail to Gmail over IPv4, and I do
indeed do this on my own hobbyist systems. Every time I spin up a new
VPS and forget this, I notice it rather quickly because of bouncing
mail. Not only are they quicker to block IPv6 mail overall (IMHO),
they also are more likely to block IPv6 mail from IPs without rDNS,
and mail that lacks either SPF or DKIM authentication. Their filters
are evolving and it feels as though their IPv4 blocking is catching up
a bit -- more likely to block unauthenticated IPv4 mail today versus a
year or two ago, but that doesn't really mean it suddenly became
easier to send over IPv6.

I blogged about this a couple year ago - nothing you don't already
know, really - 
https://www.spamresource.com/2020/11/honestly-dont-send-to-gmail-over-ipv6.html
- but recently that article got linked to on Reddit and a bunch of
nerds made noise that I don't know what I'm talking about and that
they can get mail to Gmail over IPv6 just fine. So, YMMV. (My point is
that it's not impossible, but it is annoying and that it has exacting,
but unclear requirements.)

Cheers,
Al Iverson

On Fri, Aug 12, 2022 at 11:26 AM Jesse Hathaway via mailop
 wrote:
>
> Back in 2013[1] we changed our mail config to force MX lookups for gmail
> to only use IPv4 addresses.  We made these change after hearing reports
> of higher spam scoring when sending mail via IPv6. Would anyone from
> Google be able to comment as to whether forcing IPv4 is still needed?
> Yours kindly, Jesse Hathaway
>
>
> [1]: https://gerrit.wikimedia.org/r/c/operations/puppet/+/79753
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-- 

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)
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[mailop] Gmail spam scoring via IPv6 different than IPv4?

2022-08-12 Thread Jesse Hathaway via mailop
Back in 2013[1] we changed our mail config to force MX lookups for gmail
to only use IPv4 addresses.  We made these change after hearing reports
of higher spam scoring when sending mail via IPv6. Would anyone from
Google be able to comment as to whether forcing IPv4 is still needed?
Yours kindly, Jesse Hathaway


[1]: https://gerrit.wikimedia.org/r/c/operations/puppet/+/79753
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Re: [mailop] Gmail Dynamic Email / Impact on Email Ecosystem

2022-08-12 Thread Taavi Eomäe via mailop



They seem to be a text/x-amp-html, and require a text/html or
text/plain fallback, so other clients would simply use the fallback.


I think many of us have seen the "fallback" from text/html to 
text/plain. "Sorry your e-mail client can't display HTML", well it can 
but I kinda prefer text first and you just sent me useless garbage.



The following is not directly related to your letter, just the topic.

I do understand the need for something better than the inconsistent (and 
thus difficult) text/html we have now. Static-only AMP might even fit 
the bill, but static letters do not seem to be the goal at the moment.


Unfortunately I don't see anyone but the giants succeeding in pushing 
for a new widely-supported content type either. Just looking at the 
deployment of other email improvements. I've long yearned for something 
like text/restructured or text/markdown that is trivial to convert to 
both text and HTML, but looks nicer if natively rendered and is easy to 
manually type out.


Anyways, point being that if we don't want AMP there should be an 
equally attractive alternative widely deployed.


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Re: [mailop] [E] Re: Gmail Dynamic Email / Impact on Email Ecosystem

2022-08-12 Thread Taavi Eomäe via mailop
Yeah, just like any website can "change". I encourage you to dive a 
little deeper into the capabilities (and non-capabilities) for that 
matter ;-)


Sure, and those of us who have had to deal with taking down phishing 
that is very selective know the pain. That pain shouldn't exist in 
emails themselves. Taking Gmail's other feature as well, confidential 
emails. YIKES


Imagine this scenario:
"I got this letter, it looks very suspicious"
"Can you forward it to me?"
"I can't it won't let me, says something about being marked confidential"
"Okay just show it to me then"
"I opened it again and it has changed"


No.  Not the MTA anyway.


It depends where you're doing your filtering.

Yes, and horses are sufficiently fast and 64kb ought to be enough for 
everybody ;-)


Just send links if you need to display dynamic content, that's what 
links are for. Alternatively implement a diff scheme that would allow 
building the end result. Messages already delivered shouldn't change 
without either clear indication or user preference that they may.


Even though I loathe "you just got a reply to your comment"-emails, 
they're better than ones I might open years from now, potentially broken.


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