HACKER Q&A
📣 jaggs

How to get through to someone at Google about broken Gmail function?


How can I alert Google to the following broken 'Send Mail As' issue to get it fixed? I've tried their forum option, but that just reaches some nice volunteer enthusiasts.

1. Gmail has a feature called Send Mail As. This feature allows the user to send email from another domain through their Gmail account. From their help page:

================================================ "If you own another email address, you can send mail as that address. For example:

Yahoo, Outlook, or other non-Gmail address Your work, school, or business domain or alias, like @yourschool.edu or youralias@gmail.com Another Gmail address Tip: You can send emails from up to 99 different email addresses." ================================================

2. I have happily been using it for sending and replying to my Hotmail/Outlook account for over a decade.

3. Suddenly Gmail is rejecting sending to these Hotmail addresses via alias. The error message reads:

550 5.7.26 This mail is unauthenticated, which poses a security risk to the sender and Gmail users, and has been blocked. The sender must authenticate with at least one of SPF or DKIM. For this message, DKIM checks did not pass and SPF check for [hotmail.com] did not pass with ip: 209.85.220.41.

4. On checking it appears that:

a) That IP belongs to Google. So Google is blocking its own feature b) The reason may be that Spamcop (and only Spamcop) has blacklisted that IP.

5. The bottom line is, a service which Google offers for free to its users for convenience is now broken (due to Google inaction?).

6. I'm not going to go down the rabbit hole of wondering whether this has anything to do with a general Google/Microsoft issue.

7. Yes I know I'm the product and I really should just stop using Gmail. But hey...

  👤 runjake Accepted Answer ✓
Good luck.

Having a paid enterprise account with Google and working with their "support" now, it's akin to angrily screaming into the void, while a level 1 person with no real situational awareness assures you Google cares and is diligently working on a fix.

It's been a couple months now...

👤 kevincox
It is worth noting that this feature is somewhat a bad idea, but it is strange that it is broken in this case.

The DMARC policy for hotmail.com is p=none. AKA, allow spoofing.

    _dmarc.hotmail.com. 3566 IN TXT "v=DMARC1; p=none; rua=mailto:rua@dmarc.microsoft;ruf=mailto:ruf@dmarc.microsoft;fo=1:s:d"
So GMail shouldn't really be rejecting messages because of SPF and DKIM failure. But maybe GMail has some logic that overrides Hotmail's DMARC policy.

Also IIRC GMail has an option to send from another address via the upstream SMTP server. This will ensure that your message is properly authenticated as it won't be spoofed.

👤 elljess
Add an spf record to your domains.
👤 elljess
Who is your domain registrar?
👤 remram
I wonder if this is related to my issue, which also started happening around September 1:

Email forwarding from my Gmail account (workspace) to another Gmail account (gmail.com) fails with a DMARC-related bounce depending on the original sender's configuration.

    <<< 550-5.7.26 Unauthenticated email from aa.com is not accepted due to domain's
    <<< 550-5.7.26 DMARC policy. Please contact the administrator of aa.com domain if
    <<< 550-5.7.26 this was a legitimate mail. Please visit
    <<< 550-5.7.26  https://support.google.com/mail/answer/2451690  to learn about the
    <<< 550 5.7.26 DMARC initiative.
👤 americanriver
Hi jaggs, I work in Gmail. Yes a lot of lurk on HN. I don't understand your "Send as" flow. Are you sending email to some 3rd party owned account? Usually that sends as SMTP MSA (login/password), so that should work. Is it broken when someone replies?
👤 b20000
googlers can only pass leetcode, they can’t actually build anything that works, because that requires experience, and that is not what they hire for