[Mailman-Users] Re: Cloudmark blacklist

2024-04-17 Thread Michael Reeder LCPC
Jayson,

The top blog post on this site is currently on the topic of getting Gmail and 
others to accept self-hosted email:

https://infosec.engineering

Looks like Jerry uses Mailgun.

Michael Reeder
mich...@hygeiacounseling.com
Baltimore, MD

On April 14, 2024 11:48:20 AM EDT, Michael Reeder -- Hygeia MS 
 wrote:
>Jayson,
>
>I'm not sure I'm fully knowledgeable enough in this matter to help, but 
>maybe...
>
>For my Mastodon VPS I use sendpulse.com as the outgoing SMTP server.  They 
>have a surprisingly high threshold of free outbound SMTP messages they allow 
>per month before asking you for a paid plan.  So far, I have had no problem 
>with blocked messages, so you might try them?
>
>FYI -- This is a company based in Ukraine with their servers in Germany, so 
>not sure what happens if Russia makes further strides in the war.
>
>-- Michael
>
>*Michael Reeder, LCPC
>*
>*Hygeia Counseling Services : Baltimore / Mt. Washington Village location*
>*410-871-TALK / michael(at)hygeiacounseling.com*
>
>
>On 3/16/2024 11:10 AM, Jayson Smith wrote:
>> Hi,
>> 
>> What I mean is that I'd love to find a good, reliable smarthost I can direct 
>> my SMTP server on my VPS to use. I've heard knowledgeable friends say over 
>> and over and over again, "Anyone who runs their own Email server is just 
>> asking for trouble, it's not worth it any more." The real problem I'm seeing 
>> is that seemingly within the last few years, at least some VPS providers 
>> (Linode and Digital Ocean for sure) have started getting entire IP ranges 
>> put on blocklists. My first experience of being put on UCEPROTECT level 3 
>> was on January 20, 2021, and a few weeks ago my IP wound up on UCEPROTECT 
>> level 2. Yes, I know how the UCEPROTECT lists work, but the point is that I 
>> never used to find my IP on those lists, but now it happens every few 
>> months. I have to think something has happened to cause more spammers to use 
>> these providers.
>> 
>> As for incoming Email, I'd like for my own SMTP server to be able to 
>> continue handling it. The reason is that I don't want some other Email 
>> provider's spam blocking software deciding what I get to see. I have some 
>> incoming spam control measures in place for specific Email addresses that 
>> tend to receive a lot of spam, but for me and my family members, everything 
>> gets through. Yes this means we get incoming spam that comes our way, but it 
>> also means we don't have to worry about an important incoming message going 
>> missing because it was sent to the spam folder or silently discarded.
>> 
>> Thanks for any thoughts,
>> 
>> Jayson
>> 
>> On 3/16/2024 5:26 AM, Stephen J. Turnbull wrote:
>>> Jayson Smith writes:
>>> 
>>>   > I'm getting really tired of these unexplained blacklistings. Does
>>>   > anyone know of any reliable outgoing Email service providers?
>>> 
>>> What do you mean by that?  Gmail for example allows you (or did allow
>>> you 18 months ago) to validate an alternate address through the usual
>>> "can you read this mail and send back a cookie" dance, and use those
>>> validated addresses in From.
>>> 
>>> Unfortunately, in my experience at least Gmail won't allow you to use
>>> a non-gmail address in From unless you're using their app or browser
>>> client.  Authenticated SMTP to port 587 doesn't cut it for whatever
>>> reason.  The best I could figure out was sending through eg gmail
>>> using From: m...@gmail.com and setting Reply-To.
>>> 
>>>   > Ideally I want to continue to handle my own incoming Email because
>>>   > I don't want someone else's spam blocking software deciding what
>>>   > Emails I receive.
>>> 
>>> I don't know of freemail who allows that, unfortunately.  The closest
>>> I know of is Google, as above.
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[Mailman-Users] Re: Cloudmark blacklist

2024-04-14 Thread Michael Reeder -- Hygeia MS

Jayson,

I'm not sure I'm fully knowledgeable enough in this matter to help, but 
maybe...


For my Mastodon VPS I use sendpulse.com as the outgoing SMTP server.  
They have a surprisingly high threshold of free outbound SMTP messages 
they allow per month before asking you for a paid plan.  So far, I have 
had no problem with blocked messages, so you might try them?


FYI -- This is a company based in Ukraine with their servers in Germany, 
so not sure what happens if Russia makes further strides in the war.


-- Michael

*Michael Reeder, LCPC
*
*Hygeia Counseling Services : Baltimore / Mt. Washington Village location*
*410-871-TALK / michael(at)hygeiacounseling.com*


On 3/16/2024 11:10 AM, Jayson Smith wrote:

Hi,

What I mean is that I'd love to find a good, reliable smarthost I can 
direct my SMTP server on my VPS to use. I've heard knowledgeable 
friends say over and over and over again, "Anyone who runs their own 
Email server is just asking for trouble, it's not worth it any more." 
The real problem I'm seeing is that seemingly within the last few 
years, at least some VPS providers (Linode and Digital Ocean for sure) 
have started getting entire IP ranges put on blocklists. My first 
experience of being put on UCEPROTECT level 3 was on January 20, 2021, 
and a few weeks ago my IP wound up on UCEPROTECT level 2. Yes, I know 
how the UCEPROTECT lists work, but the point is that I never used to 
find my IP on those lists, but now it happens every few months. I have 
to think something has happened to cause more spammers to use these 
providers.


As for incoming Email, I'd like for my own SMTP server to be able to 
continue handling it. The reason is that I don't want some other Email 
provider's spam blocking software deciding what I get to see. I have 
some incoming spam control measures in place for specific Email 
addresses that tend to receive a lot of spam, but for me and my family 
members, everything gets through. Yes this means we get incoming spam 
that comes our way, but it also means we don't have to worry about an 
important incoming message going missing because it was sent to the 
spam folder or silently discarded.


Thanks for any thoughts,

Jayson

On 3/16/2024 5:26 AM, Stephen J. Turnbull wrote:

Jayson Smith writes:

  > I'm getting really tired of these unexplained blacklistings. Does
  > anyone know of any reliable outgoing Email service providers?

What do you mean by that?  Gmail for example allows you (or did allow
you 18 months ago) to validate an alternate address through the usual
"can you read this mail and send back a cookie" dance, and use those
validated addresses in From.

Unfortunately, in my experience at least Gmail won't allow you to use
a non-gmail address in From unless you're using their app or browser
client.  Authenticated SMTP to port 587 doesn't cut it for whatever
reason.  The best I could figure out was sending through eg gmail
using From: m...@gmail.com and setting Reply-To.

  > Ideally I want to continue to handle my own incoming Email because
  > I don't want someone else's spam blocking software deciding what
  > Emails I receive.

I don't know of freemail who allows that, unfortunately.  The closest
I know of is Google, as above.

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[Mailman-Users] Re: Cloudmark blacklist

2024-03-19 Thread Stephen J. Turnbull
Jayson Smith writes:

 > Comcast/Charter (found out about that one Saturday night when
 > trying to reply to a legit individual message) both reject the
 > message as soon as a blocked server connects,

Comcast is really bad for any number of reasons.  Unfortunately, if I
remember correctly they're effectively a monopoly ISP for broadband in
parts of the country.  Never heard of Charter.

 > Microsoft, when they decide you're evil and put you on their
 > internal blacklist, reject after Mail from:.

That's bizarre.  Even though I have no respect for the morals or
technology of Microsoft "security" in the broadest sense, the only
sensible reason for blocking at that point (rather than connect or
HELO) I can think of is that they do a lookup on the SPF record for
the domain in MAIL FROM and block based on "From alignment".  I assume
you've checked and rechecked that, but if not, check your SPF record.

 > I find these rejections quite annoying, because clearly this means
 > their spam analytics software is missing out on a lot of details
 > that could help them make a more informed decision about whether to
 > accept the message.

The quantity of spam that they're handling is mind-boggling.  In 2014,
the head of email security at Yahoo (who is very good; disclaimer, she
gave me a kitten many decades ago :-) reported to the DMARC working
group at IETF that after a different department leaked half a billion
contact lists to spammers (who used them for "recommended by a friend"
spam), they were facing sustained campaigns of more than 1 million
spams per minute.  In that context, finding ways to block on connect
makes sense.

What I don't understand is why they don't use rate-limiting techniques
where possible (ie, if they're not being DOS'ed).  For example, at
first contact, temporary failure for 15 minutes.  Upon retry (which
typically will take 4 hours in most MTAs' default configuration), it's
accepted and if not spam, it's delivered to the recipient(s) and the
source whitelisted.  If it *is* spam, you go back on the greylist with
longer and longer delays as a higher proportion of spam is detected.
If no legit mail is found, eventually you go on the blacklist.

 > But oh no, if your IP is on one of the blacklists we check,

I doubt the folks who provide email as an opt-in service (Gmail,
Microsoft) take RBLs very seriously.  They're in the business of
profiling traffic, and it makes sense and dollars to profile
everybody, customers and non-customers.  That's the only way I can
make sense of the way sometimes Microsoft will magically unblock you
after stonewalling for days or weeks.

The ISPs who provide email because that's what ISPs do aka Comcast I
wouldn't be surprised, though.

 > Go away and don't come back until you've solved your spam problem
 > that probably isn't even your problem. Goodbye!

Unfortunately email addresses aren't portable, although it wouldn't be
hard to make them so.  Sure, many customers would stick with their ISP
mailboxes despite losing mail, but for people willing to invest in
better service the big cost to switching email providers is getting
their correspondents to update contact lists.

Steve

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[Mailman-Users] Re: Cloudmark blacklist

2024-03-18 Thread Dmitri Maziuk

On 3/18/24 09:46, Jayson Smith wrote:

Hi,

Comcast/Charter (found out about that one Saturday night when trying to 
reply to a legit individual message) both reject the message as soon as 
a blocked server connects, you don't even get to say HELO. Microsoft, 
when they decide you're evil and put you on their internal blacklist, 
reject after Mail from:. I find these rejections quite annoying, because 
clearly this means their spam analytics software is missing out on a lot 
of details that could help them make a more informed decision about 
whether to accept the message.


That's the point of rejecting on HELO: you don't download megabytes of 
content and waste CPU cycles trying to make sense of it. It's a 
feature-not-a-bug.


Dima

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[Mailman-Users] Re: Cloudmark blacklist

2024-03-18 Thread Jayson Smith

Hi,

Comcast/Charter (found out about that one Saturday night when trying to 
reply to a legit individual message) both reject the message as soon as 
a blocked server connects, you don't even get to say HELO. Microsoft, 
when they decide you're evil and put you on their internal blacklist, 
reject after Mail from:. I find these rejections quite annoying, because 
clearly this means their spam analytics software is missing out on a lot 
of details that could help them make a more informed decision about 
whether to accept the message. Are my SPF and DKIM in order? (Yes I know 
spammers can and probably often do also have good SPF and DKIM but it's 
just one factor.) Is the message to a valid recipient? Does the content 
look spammy, as whatever their AI systems are would define spammy? Does 
my sending domain have a good reputation with this provider? Am I 
sending to someone I've sent messages deemed non-spammy to in the past? 
Am I perhaps replying to a message from this person which their software 
can, if they choose to, objectively prove was sent to me through their 
servers by that person?


But oh no, if your IP is on one of the blacklists we check, we won't 
just consider that a factor in delivery decisions, this means you must 
be totally evil and we're not even going to let you talk to us at all, 
even if it was your evil neighbors that got your entire IP range on that 
list. Go away and don't come back until you've solved your spam problem 
that probably isn't even your problem. Goodbye!


Jayson

On 3/18/2024 8:54 AM, Stephen J. Turnbull wrote:

Jayson Smith writes:

  > What I mean is that I'd love to find a good, reliable smarthost I
  > can direct my SMTP server on my VPS to use.

You could try some of the services listed here:
Hosting: https://wiki.list.org/COM/Mailman%20hosting%20services
Consulting: https://wiki.list.org/COM/Mailman%20consulting%20services
They might have a better idea or offer exactly the service you want.

Otherwise, I think you kinda have to move your VPS to the service you
want to use, and on top of the monthlies for running a server they'll
charge you for email volume.  AWS SES for example is 10,000 emails for
$1 billed monthly, and there's a throughput charge as well but that
too is probably negligible unless you're mailing videos.  They do
promise an IP with a clean reputation and they bonk your neighbors
(and you) automatically for sending more than a tiny amount of spam,
so I'd expect it to stay that way.  FWIW 

  > The real problem I'm seeing is that seemingly within the last few
  > years, at least some VPS providers (Linode and Digital Ocean for
  > sure) have started getting entire IP ranges put on blocklists.

This is nothing new.  Effort-minimizing admins have been blocking
whole netblocks for well over a decade.  I think one new aspect is
that non-admins have borrowed the technique of mass-reporting to try
to shut down all aspects of an individual's or organization's Internet
presence.  I wouldn't block at the SMTP CONNECT level based on IP or
domain alone for the reasons you give for running your own smtpd, and
I doubt Google or Microsoft do.  But I know a lot of admins who do.

I don't know what to do about it.  I think my own server at my
university got on Microsoft's bad side once, but it got better fairly
quickly.  I did contact Microsoft but I don't know if it had anything
to do with getting off their blocklist, the only reply I got was a
'bot saying thank you for contacting Microsoft, check this link.  I
don't think they have their best minds working on the problem.
Instead they get customers by being too big to block, is my guess.



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[Mailman-Users] Re: Cloudmark blacklist

2024-03-18 Thread Stephen J. Turnbull
Jayson Smith writes:

 > What I mean is that I'd love to find a good, reliable smarthost I
 > can direct my SMTP server on my VPS to use.

You could try some of the services listed here:
Hosting: https://wiki.list.org/COM/Mailman%20hosting%20services
Consulting: https://wiki.list.org/COM/Mailman%20consulting%20services
They might have a better idea or offer exactly the service you want.

Otherwise, I think you kinda have to move your VPS to the service you
want to use, and on top of the monthlies for running a server they'll
charge you for email volume.  AWS SES for example is 10,000 emails for
$1 billed monthly, and there's a throughput charge as well but that
too is probably negligible unless you're mailing videos.  They do
promise an IP with a clean reputation and they bonk your neighbors
(and you) automatically for sending more than a tiny amount of spam,
so I'd expect it to stay that way.  FWIW 

 > The real problem I'm seeing is that seemingly within the last few
 > years, at least some VPS providers (Linode and Digital Ocean for
 > sure) have started getting entire IP ranges put on blocklists.

This is nothing new.  Effort-minimizing admins have been blocking
whole netblocks for well over a decade.  I think one new aspect is
that non-admins have borrowed the technique of mass-reporting to try
to shut down all aspects of an individual's or organization's Internet
presence.  I wouldn't block at the SMTP CONNECT level based on IP or
domain alone for the reasons you give for running your own smtpd, and
I doubt Google or Microsoft do.  But I know a lot of admins who do.

I don't know what to do about it.  I think my own server at my
university got on Microsoft's bad side once, but it got better fairly
quickly.  I did contact Microsoft but I don't know if it had anything
to do with getting off their blocklist, the only reply I got was a
'bot saying thank you for contacting Microsoft, check this link.  I
don't think they have their best minds working on the problem.
Instead they get customers by being too big to block, is my guess.

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[Mailman-Users] Re: Cloudmark blacklist

2024-03-16 Thread Jayson Smith

Hi,

What I mean is that I'd love to find a good, reliable smarthost I can 
direct my SMTP server on my VPS to use. I've heard knowledgeable friends 
say over and over and over again, "Anyone who runs their own Email 
server is just asking for trouble, it's not worth it any more." The real 
problem I'm seeing is that seemingly within the last few years, at least 
some VPS providers (Linode and Digital Ocean for sure) have started 
getting entire IP ranges put on blocklists. My first experience of being 
put on UCEPROTECT level 3 was on January 20, 2021, and a few weeks ago 
my IP wound up on UCEPROTECT level 2. Yes, I know how the UCEPROTECT 
lists work, but the point is that I never used to find my IP on those 
lists, but now it happens every few months. I have to think something 
has happened to cause more spammers to use these providers.


As for incoming Email, I'd like for my own SMTP server to be able to 
continue handling it. The reason is that I don't want some other Email 
provider's spam blocking software deciding what I get to see. I have 
some incoming spam control measures in place for specific Email 
addresses that tend to receive a lot of spam, but for me and my family 
members, everything gets through. Yes this means we get incoming spam 
that comes our way, but it also means we don't have to worry about an 
important incoming message going missing because it was sent to the spam 
folder or silently discarded.


Thanks for any thoughts,

Jayson

On 3/16/2024 5:26 AM, Stephen J. Turnbull wrote:

Jayson Smith writes:

  > I'm getting really tired of these unexplained blacklistings. Does
  > anyone know of any reliable outgoing Email service providers?

What do you mean by that?  Gmail for example allows you (or did allow
you 18 months ago) to validate an alternate address through the usual
"can you read this mail and send back a cookie" dance, and use those
validated addresses in From.

Unfortunately, in my experience at least Gmail won't allow you to use
a non-gmail address in From unless you're using their app or browser
client.  Authenticated SMTP to port 587 doesn't cut it for whatever
reason.  The best I could figure out was sending through eg gmail
using From: m...@gmail.com and setting Reply-To.

  > Ideally I want to continue to handle my own incoming Email because
  > I don't want someone else's spam blocking software deciding what
  > Emails I receive.

I don't know of freemail who allows that, unfortunately.  The closest
I know of is Google, as above.



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[Mailman-Users] Re: Cloudmark blacklist

2024-03-15 Thread Jigme Datse
On Fri, 15 Mar 2024 22:17:55 -0400
Jayson Smith  wrote:

> I'm getting really tired of these unexplained blacklistings. Does
> anyone know of any reliable outgoing Email service providers? Ideally
> I want to continue to handle my own incoming Email because I don't
> want someone else's spam blocking software deciding what Emails I
> receive.

From what I can tell, you can reliably send to
Microsft/Google/AOL/Yahoo, or you can reliably send to people who run
their own mail servers.  There seems to be "no in between."  The
closest I can see is ProtonMail, but that would probably need to have a
lot of stuff setup to make work.  ProtonMail doesn't violate the
protocols like the big huge companies do, and it's big enough that the
big huge companies can't just dump the mail into spam.  I'd *love* to
have a better answer, but really so much of the mail that I get sent to
me gets filtered into spam, because they are using something like
mailgun.  Or...  Google.  


pgpt6jyCj8VdE.pgp
Description: OpenPGP digital signature
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