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Ensure Toolforge and Cloud VPS comply with Google's new email sender guidelines
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Description

Google has announced new requirements for sending email to gmail accounts effective 2024-02-01, and we should ensure we meet those.

Requirements for all senders

  • Set up SPF or DKIM email authentication for your domain.
    • SPF should be OK. For DKIM I think we currently sign with ed25519 keys only and I think Google only supports RSA keys so we may need to double-sign here.
    • Fixed.
  • Ensure that sending domains or IPs have valid forward and reverse DNS records, also referred to as PTR records.
    • We should be ok.
  • Use a TLS connection for transmitting email.
    • We should be ok.
  • Keep spam rates reported in Postmaster Tools below 0.10% and avoid ever reaching a spam rate of 0.30% or higher.
    • No idea, need to check.
  • Format messages according to the Internet Message Format standard (RFC 5322).
    • I assume we are ok here.
  • Don’t impersonate Gmail From: headers. Gmail will begin using a DMARC quarantine enforcement policy, and impersonating Gmail From: headers might impact your email delivery.
    • We should be ok, although restricting folks from using non-WMCS domains via our relays might be a smart move. T341004
    • Done.
  • If you regularly forward email, including using mailing lists or inbound gateways, add ARC headers to outgoing email.
    • Toolforge does this, and Cloud VPS does not relay emails. We do SRS but not ARC. Will need to fix.

Requirements for high-volume senders

I don't have data on this atm but I would not be surprised if we're over the 5k emails per day threshold.

  • Set up DMARC email authentication for your sending domain. Your DMARC enforcement policy can be set to none.
    • We don't have a DMARC policy at all at the moment.
    • Fixed.
  • For direct mail, the domain in the sender's From: header must be aligned with either the SPF domain or the DKIM domain. This is required to pass DMARC alignment.
    • Need to check if cron email etc passes this, or if we need to add some more rewrites.
  • Marketing messages and subscribed messages must support one-click unsubscribe, and include a clearly visible unsubscribe link in the message body.
    • No clue how they define marketing and subscribed messages, but we certainly don't support one-click unsubscribe for anything.

Event Timeline

Change 988489 had a related patch set uploaded (by Majavah; author: Majavah):

[operations/puppet@production] P:toolforge::mailrelay: double-sign mail with RSA DKIM keys

https://gerrit.wikimedia.org/r/988489

Change 988494 had a related patch set uploaded (by Majavah; author: Majavah):

[labs/private@master] Add fake toolforge-rsa DKIM keys

https://gerrit.wikimedia.org/r/988494

Change 988494 merged by Majavah:

[labs/private@master] Add fake toolforge-rsa DKIM keys

https://gerrit.wikimedia.org/r/988494

Change 988489 merged by Majavah:

[operations/puppet@production] P:toolforge::mailrelay: double-sign mail with RSA DKIM keys

https://gerrit.wikimedia.org/r/988489

Mentioned in SAL (#wikimedia-cloud) [2024-01-08T15:52:38Z] <taavi> verify wmcloud.org, wmflabs.org and toolforge.org in gmail postmaster console to figure out how much google likes us (T354112)

Change 989736 had a related patch set uploaded (by Majavah; author: Majavah):

[operations/puppet@production] P:mail::smarthost: support DKIM dual-signing

https://gerrit.wikimedia.org/r/989736

Change 989738 had a related patch set uploaded (by Majavah; author: Majavah):

[labs/private@master] Add fake wmcs-rsa DKIM keys for Cloud VPS

https://gerrit.wikimedia.org/r/989738

Change 989738 merged by Majavah:

[labs/private@master] Add fake wmcs-rsa DKIM keys for Cloud VPS

https://gerrit.wikimedia.org/r/989738

Change 971892 had a related patch set uploaded (by Majavah; author: Majavah):

[operations/puppet@production] P:toolforge::mailrelay: reject mail not using Toolforge domains

https://gerrit.wikimedia.org/r/971892

Change 989736 merged by Majavah:

[operations/puppet@production] P:mail::smarthost: support DKIM dual-signing

https://gerrit.wikimedia.org/r/989736

Change 971892 merged by Majavah:

[operations/puppet@production] P:toolforge::mailrelay: reject mail not using Toolforge domains

https://gerrit.wikimedia.org/r/971892

dcaro changed the task status from Open to In Progress.Jan 18 2024, 5:06 PM

Change 993697 had a related patch set uploaded (by Majavah; author: Majavah):

[operations/puppet@production] P:toolforge::mailrelay: add Authentication-Results header

https://gerrit.wikimedia.org/r/993697

Change 993697 merged by Majavah:

[operations/puppet@production] P:toolforge::mailrelay: add Authentication-Results header

https://gerrit.wikimedia.org/r/993697

Change 994163 had a related patch set uploaded (by Majavah; author: Majavah):

[labs/private@master] Add fake ARC signing keys

https://gerrit.wikimedia.org/r/994163

Change 994163 merged by Majavah:

[labs/private@master] Add fake ARC signing keys

https://gerrit.wikimedia.org/r/994163

Mentioned in SAL (#wikimedia-cloud) [2024-01-30T13:08:31Z] <taavi> create no-op DMARC record T354112

taavi moved this task from In Progress to Done on the Toolforge (Toolforge iteration 04) board.