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Posted to server-dev@james.apache.org by Jerry Malcolm <te...@malcolms.com> on 2020/02/05 22:37:21 UTC

OT: Gmail Hates Me (Us?)

For months, every email I send through my JAMES server to a gmail 
account is flagged as spam.  I've been setting up a completely separate 
JAMES environment for a different client.  I figured this 
rebuild-from-scratch would be a good chance to verify that I'm following 
all best practices.  I thought the problem might have been related to 
the fact I was using virtual hosting in the other environment, and there 
might have been mismatches due to the sender domain vs. my hosting 
domain.  But this new environment has only one domain.  I am DKIM 
signing.  I have an SPF record.  I have a DMARC record. Yet every email 
I send to gmail accounts is still sent to the gmail spam folder.   I get 
a 10 out of 10 score in mail-tester.com.  And even when I open the email 
source view in gmail it says DKIM:PASS, SPF:PASS.  Yet there it sits... 
in the spam folder with the spam flag.  All of my environments are on 
Amazon Web Services.  I've tried requesting different IP addresses.  
Nothing works.  I even tried sending using my alternate out-of-the-box 
JAMES version on the new domain.  The out-of-the-box version doesn't 
have DKIM.  But it uses the same domain name, same ip address, and same 
database.  And mail sent with this version still goes to spam.

I would say it's just my stuff that gmail hates.  But with a brand new 
domain and latest build out-of-the-box JAMES, there's nothing specific 
about my stuff here.

Can someone test sending mail from JAMES to a gmail account (that hasn't 
already whitelisted the sender) and see if they can get an email to not 
be sent to gmail spam?

I'm stuck.  What else could be wrong?  This new client is heavily 
dependent upon account-verification via email.  If all of the 
verification emails end up in spam folders, it will be a disaster the 
company.

Please help!

Thx

Jerry


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Re: OT: (Update) Gmail Hates Me (Us?)

Posted by Jerry Malcolm <te...@malcolms.com>.
On 2/5/2020 8:55 PM, Simon Levesque wrote:
> Hi Jerry,
>
> I send through SES as well, but it was mostly because Hotmail was just
> dropping the emails unless the user had the sender's email address in his
> contacts. Not putting in "spam" ; just deleting them right away.
>
> For gmail, the first emails I sent were going into the spam and after
> unmarking some as "non spam", they never went back in the spam folder. It
> was a couple year ago, I wasn't using DKIM, so gmail was nice. I don't know
> if that is still the case.
Thanks for the info.  I'm not as concerned about my own gmail account as 
I am all of the other gmail accounts I send to.  We send an email 
confirmation to each new user that signs up for my client's service.  
Unless one user marking that email as not spam will affect other gmail's 
opinion of that same email when sent to a different gmail account, it's 
no help.  The first email from the client needs to appear in the inbox.
>
>> Still, I have no clue what SES cleans up and/or adds to the email to make
> gmail happy
> It is just a question of reputation. If you take Amazon, Google, Microsoft,
> ... they talk together and they whitelist themselves. That's it. Amazon is
> scanning the emails that are sent to try to remove spam and if someone
> marks an email as spam in gmail, then gmail will tell Amazon and Amazon
> will keep track of that bad user and drop him after a certain threshold.

With all of the gyrations I had to go through just to get my AWS IP 
address approved to send email, I just figured that any AWS IP sending 
email would be granted the same credibility by gmail, et al as AWS's SES 
server.   I know you are correct that if AWS gets wind of spam either 
being sent either from a direct AWS IP or laundered thru SES, they will 
definitely shut down the account. So it seems to me they would both get 
the same trust ratings. Apparently, though, SES gets higher trust than a 
direct SMTP IP address, even though both are AWS.  But at this point, a 
fix is a fix.  Best to now spend my time fighting a different battle on 
a different hill.... There never seems to be a shortage of hills or 
battles.... :-)

Thanks.

>
> Cheers
>
>
>
> On Wed, 5 Feb 2020 at 18:39, Jerry Malcolm <te...@malcolms.com> wrote:
>
>> Update.... I tried 'laundering' my JAMES outbound mail through SES,
>> which is an Amazon-provide SMTP server.  An intermediate smtp relay
>> server shouldn't be necessary.  But desperation will drive a person to
>> try anything once.... I had to configure the SES service and get a
>> server name and ID/PW to access it.  I configured it as a gateway in the
>> james transport processor.  I sent a test email through JAMES via SES to
>> my gmail account, and, viola, 'not spam'.  There's a charge for SES
>> usage, but it's not much.  Still, I have no clue what SES cleans up
>> and/or adds to the email to make gmail happy.  But if I can ensure that
>> gmail will be happy for all of my emails, it'll be worth it.  (Still
>> would like an understanding if anybody has any ideas)
>>
>> Thx
>>
>> Jerry
>>
>>
>> On 2/5/2020 4:37 PM, Jerry Malcolm wrote:
>>> For months, every email I send through my JAMES server to a gmail
>>> account is flagged as spam.  I've been setting up a completely
>>> separate JAMES environment for a different client.  I figured this
>>> rebuild-from-scratch would be a good chance to verify that I'm
>>> following all best practices.  I thought the problem might have been
>>> related to the fact I was using virtual hosting in the other
>>> environment, and there might have been mismatches due to the sender
>>> domain vs. my hosting domain.  But this new environment has only one
>>> domain.  I am DKIM signing.  I have an SPF record.  I have a DMARC
>>> record. Yet every email I send to gmail accounts is still sent to the
>>> gmail spam folder.   I get a 10 out of 10 score in mail-tester.com.
>>> And even when I open the email source view in gmail it says DKIM:PASS,
>>> SPF:PASS.  Yet there it sits... in the spam folder with the spam
>>> flag.  All of my environments are on Amazon Web Services.  I've tried
>>> requesting different IP addresses.  Nothing works.  I even tried
>>> sending using my alternate out-of-the-box JAMES version on the new
>>> domain.  The out-of-the-box version doesn't have DKIM.  But it uses
>>> the same domain name, same ip address, and same database.  And mail
>>> sent with this version still goes to spam.
>>>
>>> I would say it's just my stuff that gmail hates.  But with a brand new
>>> domain and latest build out-of-the-box JAMES, there's nothing specific
>>> about my stuff here.
>>>
>>> Can someone test sending mail from JAMES to a gmail account (that
>>> hasn't already whitelisted the sender) and see if they can get an
>>> email to not be sent to gmail spam?
>>>
>>> I'm stuck.  What else could be wrong?  This new client is heavily
>>> dependent upon account-verification via email.  If all of the
>>> verification emails end up in spam folders, it will be a disaster the
>>> company.
>>>
>>> Please help!
>>>
>>> Thx
>>>
>>> Jerry
>>>
>>>
>>> ---------------------------------------------------------------------
>>> To unsubscribe, e-mail: server-dev-unsubscribe@james.apache.org
>>> For additional commands, e-mail: server-dev-help@james.apache.org
>>>
>> ---------------------------------------------------------------------
>> To unsubscribe, e-mail: server-dev-unsubscribe@james.apache.org
>> For additional commands, e-mail: server-dev-help@james.apache.org
>>
>>

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Re: OT: (Update) Gmail Hates Me (Us?)

Posted by Simon Levesque <su...@gmail.com>.
Hi Jerry,

I send through SES as well, but it was mostly because Hotmail was just
dropping the emails unless the user had the sender's email address in his
contacts. Not putting in "spam" ; just deleting them right away.

For gmail, the first emails I sent were going into the spam and after
unmarking some as "non spam", they never went back in the spam folder. It
was a couple year ago, I wasn't using DKIM, so gmail was nice. I don't know
if that is still the case.

> Still, I have no clue what SES cleans up and/or adds to the email to make
gmail happy
It is just a question of reputation. If you take Amazon, Google, Microsoft,
... they talk together and they whitelist themselves. That's it. Amazon is
scanning the emails that are sent to try to remove spam and if someone
marks an email as spam in gmail, then gmail will tell Amazon and Amazon
will keep track of that bad user and drop him after a certain threshold.

Cheers



On Wed, 5 Feb 2020 at 18:39, Jerry Malcolm <te...@malcolms.com> wrote:

> Update.... I tried 'laundering' my JAMES outbound mail through SES,
> which is an Amazon-provide SMTP server.  An intermediate smtp relay
> server shouldn't be necessary.  But desperation will drive a person to
> try anything once.... I had to configure the SES service and get a
> server name and ID/PW to access it.  I configured it as a gateway in the
> james transport processor.  I sent a test email through JAMES via SES to
> my gmail account, and, viola, 'not spam'.  There's a charge for SES
> usage, but it's not much.  Still, I have no clue what SES cleans up
> and/or adds to the email to make gmail happy.  But if I can ensure that
> gmail will be happy for all of my emails, it'll be worth it.  (Still
> would like an understanding if anybody has any ideas)
>
> Thx
>
> Jerry
>
>
> On 2/5/2020 4:37 PM, Jerry Malcolm wrote:
> > For months, every email I send through my JAMES server to a gmail
> > account is flagged as spam.  I've been setting up a completely
> > separate JAMES environment for a different client.  I figured this
> > rebuild-from-scratch would be a good chance to verify that I'm
> > following all best practices.  I thought the problem might have been
> > related to the fact I was using virtual hosting in the other
> > environment, and there might have been mismatches due to the sender
> > domain vs. my hosting domain.  But this new environment has only one
> > domain.  I am DKIM signing.  I have an SPF record.  I have a DMARC
> > record. Yet every email I send to gmail accounts is still sent to the
> > gmail spam folder.   I get a 10 out of 10 score in mail-tester.com.
> > And even when I open the email source view in gmail it says DKIM:PASS,
> > SPF:PASS.  Yet there it sits... in the spam folder with the spam
> > flag.  All of my environments are on Amazon Web Services.  I've tried
> > requesting different IP addresses.  Nothing works.  I even tried
> > sending using my alternate out-of-the-box JAMES version on the new
> > domain.  The out-of-the-box version doesn't have DKIM.  But it uses
> > the same domain name, same ip address, and same database.  And mail
> > sent with this version still goes to spam.
> >
> > I would say it's just my stuff that gmail hates.  But with a brand new
> > domain and latest build out-of-the-box JAMES, there's nothing specific
> > about my stuff here.
> >
> > Can someone test sending mail from JAMES to a gmail account (that
> > hasn't already whitelisted the sender) and see if they can get an
> > email to not be sent to gmail spam?
> >
> > I'm stuck.  What else could be wrong?  This new client is heavily
> > dependent upon account-verification via email.  If all of the
> > verification emails end up in spam folders, it will be a disaster the
> > company.
> >
> > Please help!
> >
> > Thx
> >
> > Jerry
> >
> >
> > ---------------------------------------------------------------------
> > To unsubscribe, e-mail: server-dev-unsubscribe@james.apache.org
> > For additional commands, e-mail: server-dev-help@james.apache.org
> >
>
> ---------------------------------------------------------------------
> To unsubscribe, e-mail: server-dev-unsubscribe@james.apache.org
> For additional commands, e-mail: server-dev-help@james.apache.org
>
>

Re: OT: (Update) Gmail Hates Me (Us?)

Posted by Jerry Malcolm <te...@malcolms.com>.
Update.... I tried 'laundering' my JAMES outbound mail through SES, 
which is an Amazon-provide SMTP server.  An intermediate smtp relay 
server shouldn't be necessary.  But desperation will drive a person to 
try anything once.... I had to configure the SES service and get a 
server name and ID/PW to access it.  I configured it as a gateway in the 
james transport processor.  I sent a test email through JAMES via SES to 
my gmail account, and, viola, 'not spam'.  There's a charge for SES 
usage, but it's not much.  Still, I have no clue what SES cleans up 
and/or adds to the email to make gmail happy.  But if I can ensure that 
gmail will be happy for all of my emails, it'll be worth it.  (Still 
would like an understanding if anybody has any ideas)

Thx

Jerry


On 2/5/2020 4:37 PM, Jerry Malcolm wrote:
> For months, every email I send through my JAMES server to a gmail 
> account is flagged as spam.  I've been setting up a completely 
> separate JAMES environment for a different client.  I figured this 
> rebuild-from-scratch would be a good chance to verify that I'm 
> following all best practices.  I thought the problem might have been 
> related to the fact I was using virtual hosting in the other 
> environment, and there might have been mismatches due to the sender 
> domain vs. my hosting domain.  But this new environment has only one 
> domain.  I am DKIM signing.  I have an SPF record.  I have a DMARC 
> record. Yet every email I send to gmail accounts is still sent to the 
> gmail spam folder.   I get a 10 out of 10 score in mail-tester.com.  
> And even when I open the email source view in gmail it says DKIM:PASS, 
> SPF:PASS.  Yet there it sits... in the spam folder with the spam 
> flag.  All of my environments are on Amazon Web Services.  I've tried 
> requesting different IP addresses.  Nothing works.  I even tried 
> sending using my alternate out-of-the-box JAMES version on the new 
> domain.  The out-of-the-box version doesn't have DKIM.  But it uses 
> the same domain name, same ip address, and same database.  And mail 
> sent with this version still goes to spam.
>
> I would say it's just my stuff that gmail hates.  But with a brand new 
> domain and latest build out-of-the-box JAMES, there's nothing specific 
> about my stuff here.
>
> Can someone test sending mail from JAMES to a gmail account (that 
> hasn't already whitelisted the sender) and see if they can get an 
> email to not be sent to gmail spam?
>
> I'm stuck.  What else could be wrong?  This new client is heavily 
> dependent upon account-verification via email.  If all of the 
> verification emails end up in spam folders, it will be a disaster the 
> company.
>
> Please help!
>
> Thx
>
> Jerry
>
>
> ---------------------------------------------------------------------
> To unsubscribe, e-mail: server-dev-unsubscribe@james.apache.org
> For additional commands, e-mail: server-dev-help@james.apache.org
>

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