Postfix update resulted in mails going to spam?

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Postfix update resulted in mails going to spam?

John Gateley
Hello,

I recently upgraded my mail server OS (Debian 7 to Debian 9), and at the
same time got
the latest postfix package for Debian 9.

It is hosted in the cloud (Linode), and I completely rebuilt the
instance, rather than
doing an upgrade. The IP addresses (v4 and v6) are the same. The config
didn't
change (I use ansible to deploy both the software and config - no manual
steps required).

After the upgrade, I sent a test e-mail to my gmail account, and it went
to the
Junk folder. I moved it to my regular folder, and after that e-mail to
my gmail
account was delivered normally.

My wife sends e-mail to the Washington Post (perhaps hosted by Google as
well)
and they are not receiving her e-mails. They are delivered to the mail
server, so I
strongly suspect they are going to junk as well.

Is there any reason the software upgrade would cause this behavior?
I can't think of one, but the timing is very coincidental.

Thank you

John

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Re: Postfix update resulted in mails going to spam?

Wietse Venema
John Gateley:

> Hello,
>
> I recently upgraded my mail server OS (Debian 7 to Debian 9), and
> at the same time got the latest postfix package for Debian 9.
>
> It is hosted in the cloud (Linode), and I completely rebuilt the
> instance, rather than doing an upgrade. The IP addresses (v4 and
> v6) are the same. The config didn't change (I use ansible to deploy
> both the software and config - no manual steps required).
>
> After the upgrade, I sent a test e-mail to my gmail account, and
> it went to the Junk folder. I moved it to my regular folder, and
> after that e-mail to my gmail account was delivered normally.
>
> My wife sends e-mail to the Washington Post (perhaps hosted by
> Google as well) and they are not receiving her e-mails. They are
> delivered to the mail server, so I strongly suspect they are going
> to junk as well.
>
> Is there any reason the software upgrade would cause this behavior?
> I can't think of one, but the timing is very coincidental.

There is no known problem with mail from Postfix ending up in
SPAM folders after a Postfix update. The problem is therefore
specific to something that you did or did not do.

It would be helpful if you could specify the changes that you made
in the process of rebuilding your server. For example changing the
IP address, hostname, or DNS can already have a major effect. So
can changes to Postfix configurations.

        Wietse
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Re: Postfix update resulted in mails going to spam?

John Gateley


On 6/13/19 10:22 AM, Wietse Venema wrote:

> John Gateley:
>> Is there any reason the software upgrade would cause this behavior?
>> I can't think of one, but the timing is very coincidental.
> There is no known problem with mail from Postfix ending up in
> SPAM folders after a Postfix update. The problem is therefore
> specific to something that you did or did not do.
>
> It would be helpful if you could specify the changes that you made
> in the process of rebuilding your server. For example changing the
> IP address, hostname, or DNS can already have a major effect. So
> can changes to Postfix configurations.
>
> Wietse
Thank you Wietse.

I changed the SPF record at the same time: the SPF record has two IP
addresses
in it, the second for a backup host that is not in use at this time, and
I changed
that second IP address.

I did not change the hostname, or IP address or any other DNS record
relating to
the mailserver.

The mail server was down for just over an hour during the upgrade: I
shut down
Postfix, checked the queue, moved the Maildirs off, upgraded, moved the
maildirs
back, and then restarted Postfix.

During this period, there was about 30 minutes where Postfix was running
on the server, but refusing mail - it was a basic install of Postfix
without my
configuration. Could this have done it?

Thank you very much

John
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Re: Postfix update resulted in mails going to spam?

Scott Kitterman-4
In reply to this post by John Gateley


On June 13, 2019 2:43:53 PM UTC, John Gateley <[hidden email]> wrote:

>Hello,
>
>I recently upgraded my mail server OS (Debian 7 to Debian 9), and at
>the
>same time got
>the latest postfix package for Debian 9.
>
>It is hosted in the cloud (Linode), and I completely rebuilt the
>instance, rather than
>doing an upgrade. The IP addresses (v4 and v6) are the same. The config
>
>didn't
>change (I use ansible to deploy both the software and config - no
>manual
>steps required).
>
>After the upgrade, I sent a test e-mail to my gmail account, and it
>went
>to the
>Junk folder. I moved it to my regular folder, and after that e-mail to
>my gmail
>account was delivered normally.
>
>My wife sends e-mail to the Washington Post (perhaps hosted by Google
>as
>well)
>and they are not receiving her e-mails. They are delivered to the mail
>server, so I
>strongly suspect they are going to junk as well.
>
>Is there any reason the software upgrade would cause this behavior?
>I can't think of one, but the timing is very coincidental.

Did you check your mail logs for any warnings or errors?  If you reuse a postfix 2.7 configuration with postfix 3.1, I'm not certain it's completely compatible.

Scott K
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Re: Postfix update resulted in mails going to spam?

Viktor Dukhovni
> On Jun 14, 2019, at 2:14 AM, Scott Kitterman <[hidden email]> wrote:
>
> Did you check your mail logs for any warnings or errors?  If you reuse a postfix 2.7 configuration with postfix 3.1, I'm not certain it's completely compatible.

Nothing major enough to cause the reported symptoms.
The only things that are vaguely related are:

  * Rejection of inbound mail while the system was misconfigured,
    might cause the bounced addresses to be treated as bogus for
    later outbound mail.

  * The change in the default value of append_dot_mydomain, could
    hypothetically cause some mail to go out with just a "bare"
    hostname.

My money is on the former, or something else.  Without detailed
analysis of the logs, nothing useful can be said, and the whole
thing could be a coincidence.  Indeed the symptoms may not even
be entirely new, just more closely watched after the upgrade.

--
        Viktor.

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Re: Postfix update resulted in mails going to spam?

martijn.list
In reply to this post by John Gateley
On 13-06-19 16:43, John Gateley wrote:

> I recently upgraded my mail server OS (Debian 7 to Debian 9), and at the
> same time got
> the latest postfix package for Debian 9.
>
> It is hosted in the cloud (Linode), and I completely rebuilt the
> instance, rather than
> doing an upgrade. The IP addresses (v4 and v6) are the same. The config
> didn't
> change (I use ansible to deploy both the software and config - no manual
> steps required).
>
> After the upgrade, I sent a test e-mail to my gmail account, and it went
> to the
> Junk folder. I moved it to my regular folder, and after that e-mail to
> my gmail
> account was delivered normally.
>
> My wife sends e-mail to the Washington Post (perhaps hosted by Google as
> well)
> and they are not receiving her e-mails. They are delivered to the mail
> server, so I
> strongly suspect they are going to junk as well.
>
> Is there any reason the software upgrade would cause this behavior?
> I can't think of one, but the timing is very coincidental.

Just a guess. I'm not sure what version of postfix was installed with
Debian 7 but if it was <= 2.8 could it be that your postfix server now
favors ipv6 over ipv4?  According to the docs, inet_protocols for <= 2.8
was set to ipv4 but is now set to all. There are other reports of issues
with using ipv6 and Gmail (for example
http://postfix.1071664.n5.nabble.com/disable-ipv6-when-sending-to-gmail-td60672.html)

Kind regards,

Martijn Brinkers
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Re: Postfix update resulted in mails going to spam?

Scott Kitterman-4


On June 14, 2019 7:43:56 AM UTC, Martijn Brinkers <[hidden email]> wrote:

>On 13-06-19 16:43, John Gateley wrote:
>> I recently upgraded my mail server OS (Debian 7 to Debian 9), and at
>the
>> same time got
>> the latest postfix package for Debian 9.
>>
>> It is hosted in the cloud (Linode), and I completely rebuilt the
>> instance, rather than
>> doing an upgrade. The IP addresses (v4 and v6) are the same. The
>config
>> didn't
>> change (I use ansible to deploy both the software and config - no
>manual
>> steps required).
>>
>> After the upgrade, I sent a test e-mail to my gmail account, and it
>went
>> to the
>> Junk folder. I moved it to my regular folder, and after that e-mail
>to
>> my gmail
>> account was delivered normally.
>>
>> My wife sends e-mail to the Washington Post (perhaps hosted by Google
>as
>> well)
>> and they are not receiving her e-mails. They are delivered to the
>mail
>> server, so I
>> strongly suspect they are going to junk as well.
>>
>> Is there any reason the software upgrade would cause this behavior?
>> I can't think of one, but the timing is very coincidental.
>
>Just a guess. I'm not sure what version of postfix was installed with
>Debian 7 but if it was <= 2.8 could it be that your postfix server now
>favors ipv6 over ipv4?  According to the docs, inet_protocols for <=
>2.8
>was set to ipv4 but is now set to all. There are other reports of
>issues
>with using ipv6 and Gmail (for example
>http://postfix.1071664.n5.nabble.com/disable-ipv6-when-sending-to-gmail-td60672.html)

It was postfix 2.7.

Scott K
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Re: Postfix update resulted in mails going to spam?

Wietse Venema
In reply to this post by John Gateley
John Gateley:

>
>
> On 6/13/19 10:22 AM, Wietse Venema wrote:
> > John Gateley:
> >> Is there any reason the software upgrade would cause this behavior?
> >> I can't think of one, but the timing is very coincidental.
> > There is no known problem with mail from Postfix ending up in
> > SPAM folders after a Postfix update. The problem is therefore
> > specific to something that you did or did not do.
> >
> > It would be helpful if you could specify the changes that you made
> > in the process of rebuilding your server. For example changing the
> > IP address, hostname, or DNS can already have a major effect. So
> > can changes to Postfix configurations.
> >
> > Wietse
> Thank you Wietse.
>
> I changed the SPF record at the same time: the SPF record has two IP
> addresses
> in it, the second for a backup host that is not in use at this time, and
> I changed
> that second IP address.

What about IPv6? If you fail to have proper PTR records then that
would explain why mail is treated differently.

        Wietse