I’m Alan Chapell. Over the past 20+ years, I’ve worked as outside privacy counsel to hundreds of digital media companies and have brought over 40 of them to successful exits. I write a monthly syndicated report called The Chapell Regulatory Insider, and I’m also a regulatory analyst here at the Monopoly Report.

The big story over the past few weeks around here was the Open Web’s Apple problem. Just about everyone had an opinion, and most of those opinions involved the following question: Is there a limit to Apple’s willingness or ability to control the user experience?

This past week, Ari Paparo, Trey Tritone, and Eric Seufert expressed skepticism about the prospects of agentic commerce. Their collective skepticism can be synthesized into the following question: Are ecommerce sites willing to cede control of the user experience to AI agents?

Seems to me that we’re all asking the same question, albeit from a different vantage point. Agentic AI may be the next big thing, but if it can’t access your favorite web services and functionality, its impact will be limited.

It’s like when your local gym denies access to your personal trainer. In reality, trainer Chad can’t help you reach “apex peak performance” from the parking lot.

This week, I ran a little experiment using a popular AI assistant. I asked the AI tool to help me assess the adtech industry’s collective response to data subject access, deletion, and opt-out requests (DSARs). Are companies responding to requests in a timely manner? Are their DSAR processes clear and easy?

In case you’re wondering whether it’s kosher for me to “waste everyone’s time” launching these requests, let me share an uncomfortable truth. When it’s this easy to make a DSAR request, I can promise you that I’m not the only one making them. I know for a fact that regulators in Europe and the U.S. have figured this out as well and are making automated DSAR requests. Same with class-action litigants as they try to win CIPA cases.

Author’s note: Yeah, this is a tangent, but a few things come to mind:

What percent of DSAR requests are being made by actual consumers today? What will that number be by mid-2027 as agentic AI grows?

I didn’t want to use my real name for the test so as not to get stuffed into a locker at the next industry event. Similarly, I wasn’t super comfortable with the idea of the AI agent reading through all my emails at chapellassociates.com for a whole host of reasons.

So I used an alias that I created a few months ago via one of the free email platforms and created a test email account.

I then asked my AI agent to do the following things:

It’s amazing how quickly and easily the tool was able to accomplish the first three requests. It was step 4 where things got complicated.

After sending a lousy 30 emails on my behalf over a 90-minute period, the email platform shut things down. It didn’t just sever the login with the agent. Rather, it shut down my entire email account.

What’s strange is that I setup the test email account six months ago and have taken a number of precautions, such as asking the agent to throttle the number of emails so as to avoid triggering the email platform’s trust and safety team response. And it’s worth noting that the email platform doesn’t even have a no-bot policy in place.

To no avail.

I guess the free email services aren’t super keen to let AI agents operate on their systems either. Maybe they view them as potential exploits. Maybe they prefer that actual humans view the ads they place. The email platform did not have a specific “no bot” policy. And the email company hasn’t responded to my requests to understand what happened.

So, poof. Email account gone.

But my larger question is this: If an AI agent can’t handle the simple deployment of a few hundred emails without some boomer email platform getting angry and metaphorically chasing the AI agent off its front lawn, then what exactly can I trust the agent to do for me?

I’m actually pretty bullish on AI agents overall. But at this point, an agent is only as good as its ability to get the existing Web 2.0 infrastructure to play ball. And right now, that means the path to success for AI agents is as follows:

Of course, not everyone will have the resources to execute on this plan, which will favor large vertically integrated companies. Ultimately, I don’t think that bodes well for the truly independent agent that serves only the interests of users.

More on that later…

P.S. - Since I had the list of adtech companies anyway, I asked my agent to evaluate the DSAR process for all 600 adtechs based on concepts like readability and ease of use. Wanna see how your company was graded? Ping me.

If there’s an area that you want to see covered on these pages, if you agree or disagree with something I’ve written, if you want to tell me you dig my music, or if you just want to yell at me, please reach out to me on LinkedIn or in the comments below.

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