Monday, March 13, 2023

Google Apps (Workspace) email failing? How to check DKIM and update in your DNS settings if needed.

When I travel every bit of IT in our family starts to malfunction. On a recent trip this included Emily's emails, they were intermittently rejected by Gmail recipients. Once I was home I had to dig up old knowledge; I found the answers in prior blog posts (see references below). It looks like something wiped out our Dreamhost DNS DKIM records a few weeks ago [1]. 

It's hard these days to do email with anything that's not full hosted on the big three.

The refs have more detail but here's the outline of the process:
  1. In Google Workspace - Apps - Gmail - Authenticate email get the DKIM text value. You will probably have to generate a new record.
  2. In Dreamhost control panel manage websites click on DNS settings for domain and enter google._domainkey as host and the TXT record value. (DH UI makes this look like it appends a suffix to this but it really doesn't.)
  3. Once DH says the record has propagated return to the Admin console and click "start authentication"
It can take 48 hours for this to fully propagate but a few minutes after adding the key it did work when I validated as below.

To see if DKIM is working follow the process Google outlines (Usual automated testing services don't work with the way Google Apps do DKIM -- the selector won't work):
Send an email message to someone who is using Gmail or Google Workspace. (You can't verify DKIM is on by sending yourself a test message.) 
In the message header, look for Authentication-Results. Receiving services use different formats for incoming message headers, however the DKIM results should say something like DKIM=pass or DKIM=OK.

If the message header doesn't include a line about DKIM, messages sent from your domain aren't signed with DKIM.

When I looked at view original sent form Emily's account to my personal gmail account I didn't see DKIM=pass or DKIM=OK but I did see two entries starting with:

DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;

X-Google-DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; 

More importantly when I scrolled up a bit (this is in Gmail View Original) I saw a header that's interpreting the email headers (I think this might be a newer feature):

Message ID ....

Created at: Mon, Mar 13, 2023 at 2:59 PM (Delivered after 12 seconds)

From: Emily ....

To: John ...

Subject: test DKIM content

SPF: NEUTRAL with IP ...

DKIM: 'PASS' with domain ...

You can also paste the "original message" headers into toolbox.googleapps.com/apps/messageheader/. That gave similar results.

When I tested on a second family domain that did NOT have DNS TXT entry for DKIM it showed as DKIM 'PASS" in the email header interpretation with an odd domain string -- BUT in Google Apps it showed as NOT authenticating. I cannot explain this. 

Once I updated the DNS TXT DKIM entry for that domain and allowed a few minutes for propagation it did show in the Google Apps admin console as authenticating with DKIM and the headers showed the correct domain name.

DH's note on SPF records says they cannot be updated if we are using Google Workspace. This is new since 2018 and I think that's correct.

- fn -

[1] Eons ago every Dreamhosted domain had a free option to add Google Apps (now Google Workspace). That went away and earlier this year Google said they would discontinue the legacy free Google Apps. That was a thrash but on the edge of doom Google relented. I figured a DH script wiped the records but their first tier support said they hadn't done anything and instead referred to Google automated scripts that might change their DNS records (!).

- refs -
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