Re: [mailop] So how do you actually manage to send mails to outlook/hotmail?

2021-07-12 Thread Al Iverson via mailop
Marcus, I'd be willing to offer up my server for use as an SMTP relay,
after getting a bit of understanding of the current mail stream and
its reputation. I'm running a server doing very similar things to
yours, and I generally don't have any Microsoft issues (today,
anyway). Combining good mail streams together is a potential
mitigation against future issues, as well. Feel free to reach out, if
you are interested and would like to discuss.

Cheers,
Al Iverson

On Mon, Jul 12, 2021 at 12:12 PM Christof Meerwald via mailop
 wrote:
>
> On Sun, Jul 11, 2021 at 07:39:31PM +0200, Marcus Hoffmann via mailop wrote:
> > for context, I run a small mailserver, used by mainly me and a couple of
> > friends and famely. I also run a few webservices which sometimes send
> > transactional emails to people who sign up there. (Mainly a weblate instance
> > with around 150 or so users).
>
> I used to be in a similar situation in that I am using a VPS as a
> private email server which happened to be in a bad network
> neighbourhood, so any emails to Microsoft got blocked.
>
> I eventually managed to got the sending IP unblocked by providing
> proof that I am in full control of the sending IP address (and have
> nothing to do with any other IP addresses in the network
> neighbourhood) - basically I was asked to send them an invoice from my
> VPS provider sowing the IP address. Now emails to Microsoft seem to
> get to the Inbox.
>
> Maybe I was actually lucky that emails got completely blocked - I
> guess the case of emails being marked as spam are harder to argue than
> an outright block.
>
>
> Christof
>
> --
>
> http://cmeerw.org  sip:cmeerw at cmeerw.org
> mailto:cmeerw at cmeerw.org   xmpp:cmeerw at cmeerw.org
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-- 
Al Iverson // Wombatmail // Chicago
Deliverability: https://spamresource.com
DNS Tools: https://xnnd.com
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Re: [mailop] So how do you actually manage to send mails to outlook/hotmail?

2021-07-12 Thread Hans-Martin Mosner via mailop
Am 11.07.21 um 19:39 schrieb Marcus Hoffmann via mailop:
...
>
> Original sending IP: 176.9.145.28
> New sender: 5.45.96.14 

As others have already noted, Hetzner has a somewhat bad reputation. From my 
experience, this may somewhat be explained
by their intransparent and subjectively ineffective abuse policies and 
implementation. Due to them being a german hoster
and the mailservers under my management being located in Germany and having 
german users, I'm very reluctant to outright
block them, but if they were in another country I'd be very inclined to do so.

As it is generally not very effective to request more effective abuse 
management from the position of an abuse reporter,
it would probably be something you as a customer (maybe in coordination with 
other Hetzner customers) could do.

I know this is sadly a matter of being too big to be blocked, Microsoft (and to 
a lesser extent, Google) definitively
belong into the same category and should themselves be blocked for inadequate 
abuse handling but still they can enforce
their somewhat arbitrary rules on senders wanting to send their customers mail 
due to their sheer size. I would
certainly love to have something that would force these (as well as Hetzner, 
OVH, DigitalOcean, etc.) to bring their
abuse handling performance to a level matching the volume of e-mail sent by 
their users.

Cheers,
Hans-Martin

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Re: [mailop] So how do you actually manage to send mails to outlook/hotmail?

2021-07-12 Thread Christof Meerwald via mailop
On Sun, Jul 11, 2021 at 07:39:31PM +0200, Marcus Hoffmann via mailop wrote:
> for context, I run a small mailserver, used by mainly me and a couple of
> friends and famely. I also run a few webservices which sometimes send
> transactional emails to people who sign up there. (Mainly a weblate instance
> with around 150 or so users).

I used to be in a similar situation in that I am using a VPS as a
private email server which happened to be in a bad network
neighbourhood, so any emails to Microsoft got blocked.

I eventually managed to got the sending IP unblocked by providing
proof that I am in full control of the sending IP address (and have
nothing to do with any other IP addresses in the network
neighbourhood) - basically I was asked to send them an invoice from my
VPS provider sowing the IP address. Now emails to Microsoft seem to
get to the Inbox.

Maybe I was actually lucky that emails got completely blocked - I
guess the case of emails being marked as spam are harder to argue than
an outright block.


Christof

-- 

http://cmeerw.org  sip:cmeerw at cmeerw.org
mailto:cmeerw at cmeerw.org   xmpp:cmeerw at cmeerw.org
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Re: [mailop] So how do you actually manage to send mails to outlook/hotmail?

2021-07-12 Thread Alan Hodgson via mailop
On Mon, 2021-07-12 at 00:11 +0200, Marcus Hoffmann via mailop wrote:
> 
> Someone suggested routing emails to MS and google domains through Amazon 
> SES. Would that actually make things better?

I'd suggest a more end-user friendly relay, like Duocircle or Dynu's relay
service, who don't mess with your envelope sender address, but yes it would
help.
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Re: [mailop] So how do you actually manage to send mails to outlook/hotmail?

2021-07-12 Thread Benoit Panizzon via mailop
Hi Marcus

I had a similar issue some time ago.

Google uses some 'Domain Reputation' Woodoo.

I used to operate an automated spam feedback loop from my spamtrap,
under a specific hostname in my domain. One only used for those reports.

Unfortunately, it looks like some 'abuse contact addresses' as reported
by RIPE or abusix.org which use Gmail, flagged my reports as spam,
pulling down the reputation not only of that single host and IP
address, but of the whole 1st level domain it was attached to. And
because this was a privately used domain with a handfull of email
traffic per day, those few emails never made enough traffic for google
to improve the reputation.

Solution was:

* Stopped that Feedback Loop so that would not keep pulling down the
  reputation of some rogue abuse contact flagged them as spam.
* Send a couple of emails to some friends google email addresses and
  asked them specifically via other channel, to flag those emails as
  non spam. This fixed the Google reputation of my domain in a week or
  so.

I guess there is not much more you can do. I attempted to contact the
google abuse desk to discuss the issue and persuade them of the
advantage to exempt ARF X-ARF and other messages types usually used to
send spam evidence or logfiles from their spam-checking and also maybe
detect if one of their email addresses is published as abuse contact @
RIPE or abusix.org and handle incoming emails accordingly.

But as always ab...@google.com is /dev/null

Mit freundlichen Grüssen

-Benoît Panizzon-
-- 
I m p r o W a r e   A G-Leiter Commerce Kunden
__

Zurlindenstrasse 29 Tel  +41 61 826 93 00
CH-4133 PrattelnFax  +41 61 826 93 01
Schweiz Web  http://www.imp.ch
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Re: [mailop] So how do you actually manage to send mails to outlook/hotmail?

2021-07-11 Thread Philip Paeps via mailop

On 2021-07-12 06:11:35 (+0800), Marcus Hoffmann via mailop wrote:

On 11.07.21 23:27, John Levine wrote:

Netcup isn't fabulous, but it's better than Hetzner.


So, what would be even better then? (Netcup was just the next best 
available option here in DE. And well, the cheapest.)


I've had very good experience with a VPS from Mythic Beasts in the UK.  
They also offer services in Amsterdam if you prefer to be hosted in 
Europe rather than on the island off the west coast.  Their service 
works well and their support staff are amazing.


Someone suggested routing emails to MS and google domains through 
Amazon SES. Would that actually make things better?


It's worth a try.  You still have to do a lot of work monitoring it.  
For a setup with a handful to a dozen users ... you have to wonder if 
it's worth it.


Anecdata: after helping the last of my paying email customers (and my 
parents!) migrate to Fastmail, I moved my own email to them a couple of 
months ago too.  I do not miss having conversations with people about 
email from my server being filed as spam.


Google and Microsoft have become large enough that they can get away 
with simply not caring about small operations with a few dozen users.  
They could drop all the email from low-volume senders outright and it 
would make no difference at all.


This centralisation is bad for everybody.  There is no point in tiny 
operators tilting at the windmill though.  The windmill doesn't even 
notice.  To keep these large internet conglomerates at least slightly 
honest, we need more, somewhat larger, email businesses like Fastmail.  
If enough of them poach enough users from Google and Microsoft, maybe 
there can be space for smaller operators to thrive again too.  I'm not 
holding my breath though.


(Note: I have no stake in Fastmail or Mythic Beasts.  I am merely a 
happy paying customer.)


Philip

--
Philip Paeps
Senior Reality Engineer
Alternative Enterprises
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Re: [mailop] So how do you actually manage to send mails to outlook/hotmail?

2021-07-11 Thread John R Levine via mailop

On Mon, 12 Jul 2021, Marcus Hoffmann wrote:

(Others at Hetzner seem to do fine. I really do not get the whole rating 
IP neighborhoods thing, but let's not get into that again. I can't change it anyway.)


I can only speak for myself, but I have all of Hetzner's IPs routed into 
the spam trap, and I poke holes on the rare occasion that one of my users 
reports missing mail they care about.  I suppose that if you send enough 
mail that the recepients notice they are missing, you can get exceptions 
added.  Seems like a lot of work.



Netcup isn't fabulous, but it's better than Hetzner.


So, what would be even better then? (Netcup was just the next best available 
option here in DE. And well, the cheapest.)


Someone suggested routing emails to MS and google domains through Amazon SES. 
Would that actually make things better?


It might, Amazon does some fairly sophisticated filtering.  But if your 
mail from Netcup works, you might as well stick with that.


Regards,
John Levine, jo...@taugh.com, Taughannock Networks, Trumansburg NY
Please consider the environment before reading this e-mail. https://jl.ly
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Re: [mailop] So how do you actually manage to send mails to outlook/hotmail?

2021-07-11 Thread Marcus Hoffmann via mailop

On 11.07.21 23:27, John Levine wrote:

It appears that Marcus Hoffmann via mailop  said:

I spent the whole weekend (again) trying to get mails from my server not
to be marked as spam by Google and Microsoft.


You're at Hetzner, so it's a losing battle.  You're in a bad neighborhood.


So I've heard on this list before, yes. (Others at Hetzner seem to do 
fine. I really do not get the whole rating IP neighborhoods thing, but 
let's not get into that again. I can't change it anyway.)





After trying about everything under the sun I ended up switching the
sending IP from the one I have had sole control over in the last 5 or so
years to a newly rented VPS. This seemed to dramatically improve google
opinion of me. (The old IP never sent spam in the last 5 years, it is
not and never was (in that timeframe) listed on any blocklist).


Netcup isn't fabulous, but it's better than Hetzner.


So, what would be even better then? (Netcup was just the next best 
available option here in DE. And well, the cheapest.)


Someone suggested routing emails to MS and google domains through Amazon 
SES. Would that actually make things better?


Marcus



R's,
John


Original sending IP: 176.9.145.28
New sender: 5.45.96.14



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Re: [mailop] So how do you actually manage to send mails to outlook/hotmail?

2021-07-11 Thread Hans-Martin Mosner via mailop
Am 11.07.21 um 19:39 schrieb Marcus Hoffmann via mailop:
> Which leads me to the question: What on earth would I need to do to be able 
> to send emails to MS controlled
> mailservers which people will actually read?

One does not simply send mails to outlook/hotmail

Sorry, could not resist. Hoping I'll be forgiven eventually.

Cheers,
Hans-Martin

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Re: [mailop] So how do you actually manage to send mails to outlook/hotmail?

2021-07-11 Thread John Levine via mailop
It appears that Marcus Hoffmann via mailop  said:
>I spent the whole weekend (again) trying to get mails from my server not 
>to be marked as spam by Google and Microsoft.

You're at Hetzner, so it's a losing battle.  You're in a bad neighborhood.

>After trying about everything under the sun I ended up switching the 
>sending IP from the one I have had sole control over in the last 5 or so 
>years to a newly rented VPS. This seemed to dramatically improve google 
>opinion of me. (The old IP never sent spam in the last 5 years, it is 
>not and never was (in that timeframe) listed on any blocklist).

Netcup isn't fabulous, but it's better than Hetzner.

R's,
John

>Original sending IP: 176.9.145.28
>New sender: 5.45.96.14

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Re: [mailop] So how do you actually manage to send mails to outlook/hotmail?

2021-07-11 Thread Scott Mutter via mailop
> If your correspondent opens a ticket with MS and says "I want to get
email from Marcus and it goes into spam and I don't think it should", they
may put mitigation in for you. It has less effect if you are the one
opening the ticket though.

What ticket form would these people need to fill out?  I'm curious about
this aspect.


On Sun, Jul 11, 2021 at 1:10 PM Mike Reed via mailop 
wrote:

> Hi Marcus,
>
> Is this mail ending up in spam folders or never appearing to your
> correspondents at all?
>
> It helps a lot if you can get your correspondents to mark the emails from
> you as "not spam" in their apps. You might learn some additional
> information if you can get some to send back the headers.
>
> If your correspondent opens a ticket with MS and says "I want to get email
> from Marcus and it goes into spam and I don't think it should", they may
> put mitigation in for you. It has less effect if you are the one opening
> the ticket though.
>
> Best of luck,
> Mike
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Re: [mailop] So how do you actually manage to send mails to outlook/hotmail?

2021-07-11 Thread Mike Reed via mailop
Hi Marcus,

Is this mail ending up in spam folders or never appearing to your
correspondents at all?

It helps a lot if you can get your correspondents to mark the emails from
you as "not spam" in their apps. You might learn some additional
information if you can get some to send back the headers.

If your correspondent opens a ticket with MS and says "I want to get email
from Marcus and it goes into spam and I don't think it should", they may
put mitigation in for you. It has less effect if you are the one opening
the ticket though.

Best of luck,
Mike
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