B*tchwork my AI Did for Me - Part 14: I Had My AI Fix My Google DKIM and Re-Send a Bounced Customer Reply
A customer reply bounced, Microsoft blocked it, and instead of digging through DNS myself, I had my AI trace the problem, tell me exactly what to click, and get the reply out again.
A support reply bounced.
Not the draft. Not the writing. The actual sending.
I had already replied to the customer. Gmail showed the email as sent. Then Microsoft kicked it back.
That is the kind of problem that wastes a whole afternoon.
It is never one clean button.
It is five ugly little questions in a row.
Was the email even sent?
Did the customer get it?
Is Gmail broken?
Is the domain broken?
Is the fix in Google Admin, GoDaddy, DNS, or some weird email setting I have not looked at in two years?
That is exactly the kind of bitchwork I do not want in my head.
So I handed the whole mess to my AI.
I told it to find the real problem, verify it live, tell me what needed my approval, and only resend the reply after the email setup was actually fixed.
It traced the bounce, checked the domain records, found the missing DKIM setup, walked me through the Google Admin and GoDaddy clicks, verified the DNS record went live, and then sent the reply again.
That is the full breakdown.
[Inline image goes here in Substack editor — drag in 2026-06-05-google-dkim-bounced-reply-assets/cover.png. Caption: Cover: AI fixing Google DKIM and re-sending a bounced support reply]
The hard part was not writing the email. The hard part was figuring out why a sent email still did not make it to the customer.
Who this is for
This is for you if:
You run your business from Gmail and assume "sent" means delivered.
You use your own domain and have no interest in learning DNS until something breaks.
You reply to customers yourself and hate the idea of a real support email silently failing.
You want AI to do the system-chasing work, not just the writing.
You like the idea of keeping approval on risky steps while still handing off the annoying parts.
If that is you, keep reading.
The problem got urgent fast
The trigger was simple.
One customer needed a support reply.
The reply went out from Gmail.
Then a bounce came back from Microsoft saying the message was blocked because the domain failed DKIM.
That means the problem was not the words in the email. The problem was the trust signal behind the email.
If you run a business on your own domain, that matters a lot. DKIM is one of the checks inbox providers use to decide whether mail from your domain is real. If it fails, your email can bounce, land in spam, or get filtered hard.
So this was not some nerdy cleanup task.
This was a real customer support problem.
What paid subs get below
The free version stops in a minute. Paid subs get all of this:
The exact prompt shape I used to hand this off.
The live workflow the AI followed to prove the issue was DKIM and not something else.
The simple version of what DKIM actually does, in plain English.
The exact Google Admin and DNS steps it had me take.
What I still had to approve myself, and what I would never let AI do blindly.
The resend workflow after the fix.
The playbook you can use the next time a support email bounces from your own domain.
If you use Gmail with a custom domain, this one can save you from a very annoying support fire drill.
