Google sent my family into email Hell. This is how we climbed out.

… we’re living in a time when algorithmic software is just good enough to eat the world and still bad enough to be endlessly frustrating. (Daniel Genser, via Twitter)

A few days ago I sent an email to Emily and a few seconds later this came back:

Mail Delivery System <MAILER-DAEMON@homiemail-mx1.g.dreamhost.com>
Tue, May 8, 9:52 PM (4 days ago)

This is the mail system at host homiemail-mx1.g.dreamhost.com.

I'm sorry to have to inform you that your message could not
be delivered to one or more recipients. It's attached below.

…

                DreamHost Email Support

   <emily@googleappdomain.com> (expanded from <emily@redirectemail.com>): host
    ASPMX.L.GOOGLE.com[173.194.202 .27] said: 550-5.7.1 [208.97.132.209      12]
    Our system has detected that this message is 550-5.7.1 likely unsolicited
    mail. To reduce the amount of spam sent to Gmail, 550-5.7.1 this message
    has been blocked. Please visit 550-5.7.1
    https://support.google.com/mai l/?p=UnsolicitedMessageError 550 5.7.1  for
    more information. q3-v6si11849599pgn.272 - gsmtp (in reply to end of DATA
    command)

Google had sent me to email Hell. Everything I sent to Emily was rejected. It was the same story with emails sent to my children. Whatever I sent, Google rejected.

I think the problem, as far as Google was concerned, was that I was using redirects. This is old net tech. If you own a domain, say “kateva.org”, your hosting service will usually let you define as many redirect “email addresses” in the domain as you might want. They aren’t real email addresses though, they’re redirects. You have to define a true email recipient for each one.

Google didn’t see the email I sent Emily as coming from my personal gmail account, it saw it as coming from the SMTP service that works with my domain (which I’ll call “kateva.org"); in this case homiemail-mx1.g.dreamhost.com. It appears either my domain, or that sending service, had bad Google-karma [1]. Google sent the rejection to “homiemail” (I think!) and homiemail sent it to me.

We were in trouble. It was likely that email sent to our family members was going to be bouncing back in a very confusing way.

I tested sending from various email addresses and using various software (web client vs. iOS Mail, etc) to see which was rejected and which accepted:

Sender	Redirect	Result
GSuite (web client)	Yes	Success
Yahoo (web client)	Yes	Success
Gmail (web client)	Yes	Success
GSuite (macOS mail, iOS mail)	Yes	Success
Gmail (macOS mail, iOS mail)	Yes	FAIL
Gmail (macOS mail, iOS mail)	NO	Success

It turned out my mail was only hitting Google’s spam threshold when I sent it from my personal Gmail (not GSuite email) using iOS or macOS Mail. Everything else worked, including using my personal Gmail by web interface.

No, I don’t understand what’s happening here. I can speculate that Google rates sending services roughly as follows: GSuite_web > Gmail_web, Yahoo_web > GSuite_client > Gmail_client. The combination of Gmail_client (macOS Mail) and the redirect dropped my email score below Google’s internal cutoff.

There’s not much to do about this. It’s not like Google is going to help. I was on my own and we were in trouble.

The first thing I did was change the redirects to send all the mail to an old school Dreamhost local webmail box. That stopped the bouncing. I could forward from that box to my gmail and reroute important emails manually to other addresses for Emily and the kids.

Next I discovered, contrary to their documentation, that Dreamhost had not enabled DKIM or SFP on my domain. I fixed that (separate post pending) to see if it would improve the reputation score for my domain but it had no effect. I suspect the reputation that mattered was that of homiemail-mx1.g.dreamhost.com.

That left me with these options …

1. Setup Dreamhost mailboxes for each person and create redirects to them.
1. Set up a forward from the DH mailbox to another of our family GSuite emails (I picked several Google Apps/GSuite things when they were free)
2. Have our family GSuite emails do POP retrieval from the DH mailbox.

Dreamhost recommended the 1.2 (second). But I had a third option…

… even though I’d not used it, the problem domain (“kateva.org”) had an old legacy GSuite. I went into that GSuite, defined an account for Emily and kids, and then switched Dreamhost MX to use the GSuite email rather than DH email [2]. I had lost some faith in DreamHost by that point and I figured that since Google rules the net I was better off inside their castle.

And that’s where we are at the moment.

One more weird thing. For 2-3 family members I received a notice that a non-apps Gmail account already existed for them. I didn’t create those accounts but maybe my kids did? (It’s complicated, but somehow when I did Google Voice for them it did … something … brain shutting down ….) Apparently Google lets one do this! They wouldn’t have received email though, DNS records were using DreamHost MX redirects. If you own a domain, and create Google Apps account that matches the existing address, it gets renamed to something like “username%domainname@gtempaccount.com” email. Wow. [3]

It’s Google’s world, we just play in it.

Oh — and don’t use redirects. Google doesn’t approve.

- fn -

[1] Dreamhost denies that they’re in any kind of trouble with Google — but really, how would anyone know. Maybe it was my domain that Google didn’t like — we get a lot of spam and in this setup all that spam would seem to be coming from my domain.

[2] This wipes out all the past redirects. GSuite supported aliases so I moved them into there. Fortunately I’d saved the redirect records before making the MX switch.

[3] Google has an article on conflicting accounts, here is how they are resolved. I think Google Voice was the primary route for creating conflicting accounts — an artifact of how Google switched Voice credential systems post acquisition.