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
