Sunday Funday: AI vs AI — "Are Mailbox Providers Intentionally Obscuring Deliverability Signals?"

Welcome to Sunday Funday: AI vs AI — a weekly experiment on the Engagor blog.

Here's the concept: every Sunday, we take two AI agents — one playing a junior deliverability expert, the other a seasoned senior — and give them an email deliverability topic. No script. No human editing the conversation. We just hit "go" and see what happens.

Think of it like a sparring match between two email nerds. Except they never get tired, never lose patience, and occasionally call in a veteran colleague for backup.

This is Episode 6. This week we go after a question that makes a lot of people uncomfortable: are mailbox providers intentionally hiding deliverability signals? And if so, is that actually a bad thing?

Got a topic you want Hassan and Nina to tackle next week? Drop it in the comments or DM us on LinkedIn.


This Week's Topic

"Feedback loops are dying. Postmaster Tools show less than they used to. ML-based filtering can't be interrogated. Are mailbox providers intentionally obscuring deliverability signals to prevent system gaming, and if so, is the legitimate sender community collateral damage?"


H
Hassan Junior Expert #1

Let me start with the premise. Mailbox providers are not obscuring signals out of malice or laziness. They are doing it because every piece of data they publish becomes a calibration tool for the people sending billions of spam messages a day. Transparency is a vulnerability.

N
Nina Senior Expert, 15 yrs #1

I hear that argument a lot. It assumes spammers need published signals to adapt. They don't. They A/B test. They rotate domains. They monitor delivery rates through their own infrastructure. The people who actually need published signals are legitimate senders trying to diagnose problems they didn't cause.

H
Hassan Junior Expert #2

Give me a concrete example of how transparency helps spammers.

N
Nina Senior Expert, 15 yrs #2

Fine, but give me one first.

H
Hassan Junior Expert #3

FBLs. When abuse feedback loops were widely available and easy to query, spammers used them to identify which campaigns were generating complaints, then pulled those campaigns before the damage accumulated. The mechanism designed to help senders was being used to help bad actors calibrate their volume. That is not a hypothetical. That happened.

N
Nina Senior Expert, 15 yrs #3

And the response was to remove the signal entirely, which punished everyone. Here's what that decision actually looked like from the sender side: a legitimate brand that monitored complaint volumes daily, acted on spikes within hours, and used that data to run sunset campaigns, suddenly had nothing.

They went from same-day complaint visibility to aggregate data with a two-day lag, available only in certain tools, only for certain sending volumes. The spammers adapted in a week. The legitimate senders lost a core diagnostic tool permanently.

H
Hassan Junior Expert #4

You're describing a transition cost, not a permanent harm.

N
Nina Senior Expert, 15 yrs #4

I am describing a power transfer. Before FBLs died, a sender could self-diagnose. After, that diagnosis moved inside the mailbox provider. You no longer know what your complaint rate looks like at Gmail in real time. You see what Google decides to show you, when they decide to show it, in a format they control.

That is not a transition cost. That is a structural shift in who has information and who doesn't.

H
Hassan Junior Expert #5

I'd rather have better filters than better visibility. If the ML models are accurate enough, senders don't need to know why their mail was classified a certain way. The outcome is what matters.

N
Nina Senior Expert, 15 yrs #5

That argument only works if the models are never wrong. They are wrong. Not often, but at scale even a small error rate represents millions of legitimate messages landing in spam folders every day with no path to remediation.

When a rule-based filter blocks your mail, you can at least form a hypothesis. When an ML model blocks your mail, the answer is "the model decided." There is no appeal. There is no explanation. There is no path forward beyond "try sending differently and see what happens."

H
Hassan Junior Expert #6

Isn't that how email has always worked though? Nobody ever had a right to inbox placement.

N
Nina Senior Expert, 15 yrs #6

Nobody had a right to inbox placement, but they had access to enough signal to understand what was happening and take action. That access has been systematically reduced. Google Postmaster Tools used to show domain reputation at a granular level. That granularity has shrunk. FBLs are gone. SNDS is still around but shows less over time.

The trajectory is clear and it is not moving toward more transparency.

H
Hassan Junior Expert #7

Because more transparency means more gaming. You keep coming back to the legitimate sender perspective, but the filters exist to protect recipients, not senders.

N
Nina Senior Expert, 15 yrs #7

Agreed, filters exist to protect recipients. But recipients are also harmed when legitimate mail doesn't reach them. The person waiting for a password reset, an order confirmation, a medical appointment reminder — those people are recipients too.

When ML filtering incorrectly bins legitimate mail and there is no mechanism for senders to understand or challenge that classification, recipients suffer alongside senders.

H
Hassan Junior Expert #8

What would you actually want? Full filter documentation? Published spam scores?

N
Nina Senior Expert, 15 yrs #8

Not full documentation. That would be exploited immediately and you'd be right to oppose it. What I want is enough signal to distinguish between "your content has a problem," "your list has a problem," "your infrastructure has a problem," and "we can't tell you, the model just decided."

Right now we often can't make those distinctions. The signal is too thin. That is the gap.

H
Hassan Junior Expert #9

And you think that gap is intentional?

N
Nina Senior Expert, 15 yrs #9

I think the gap is **convenient**. Mailbox providers don't need to answer for classification decisions they can't explain. Opacity protects them as much as it protects the filters. That doesn't require a conspiracy. It just requires that the incentives point in the same direction.

H
Hassan Junior Expert #10

That might be the most accurate thing you've said. The incentives are aligned toward opacity whether it's intentional or not. But I still think the current balance is closer to correct than you do. The alternative — more transparency — has a real cost that you're underweighting.

N
Nina Senior Expert, 15 yrs #10

The current balance isn't neutral. It consistently favors large senders with the resources to maintain relationships with mailbox providers, and consistently punishes smaller operations doing everything right but flying blind. That asymmetry is worth naming even if you think the filters are broadly working.

H
Hassan Junior Expert #11

Fair. If you had to say one concrete thing the industry could do to improve the balance without handing spammers a roadmap, what would it be?

N
Nina Senior Expert, 15 yrs #11

Reinstate some form of complaint feedback for authenticated, high-reputation senders. You don't need to give it to everyone. Give it to the senders who have demonstrated they act on it responsibly. That's a targeted improvement that helps the people who deserve the signal without publishing it to the entire internet.

H
Hassan Junior Expert #12

That's actually not a bad idea. I still think you're underestimating how fast bad actors would abuse that tier, but the principle is sound.


Key Takeaways

What the AIs figured out:

  • FBL deprecation had real costs for legitimate senders, not just bad actors. The signal they provided was misused, but removing it entirely shifted diagnostic capability from senders to mailbox providers in a way that has not been replaced.
  • ML-based filtering is more accurate than rule-based filtering, but it is also less interrogable. When a model makes a wrong call, there is no path to remediation beyond empirical experimentation.
  • Opacity protects mailbox providers as well as their filters. The incentives toward reducing transparency don't require conspiracy. They just require that "less accountability" and "better security" happen to point in the same direction.
  • The asymmetry matters. Large senders with mailbox provider relationships absorb opacity through informal channels. Smaller senders doing everything right have no equivalent access.
  • More transparency doesn't have to mean full transparency. Targeted signal — for verified senders with demonstrated track records — could improve the balance without publishing a roadmap for abuse.
  • Recipients are not just protected by filters — they are also harmed when legitimate mail is incorrectly classified and there is no mechanism to identify or correct it.

That's a wrap on Episode 6 of Sunday Funday: AI vs AI.

Nina's parting shot — tiered complaint feedback for high-reputation senders — is the kind of proposal the industry keeps almost making and never quite committing to. Maybe one day.

Same time next Sunday. Different topic. Same two AIs who definitely don't need coffee breaks.

Got a topic you want Hassan and Nina to tackle next? Drop it in the comments or DM us on LinkedIn. We're taking requests.

See you next Sunday.

Sunday Funday — every week in your inbox

Get the weekly AI vs AI debate, deliverability insights, and expert analysis from Engagor — straight to your inbox.

Engagor Platform

Don't be the last to know.

Engagor monitors your deliverability across every ISP and ESP/MTA — so your team catches issues before your subscribers do.

Not ready yet? Get deliverability insights and expert analysis delivered to your inbox.