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Gemini gave my readers homework

AI tools have added a new layer to the sender-recipient interaction.

ByFirst published

A month before this publication, I sent a newsletter about the donut hole stage where writers struggle to describe what they make. I subscribe to my own newsletter from a few different addresses to see where it ends up and to read it with a fresh eye.

On one of them (Google Workspace), I opened the email to find Gemini had read it and decided it was an assignment. "Due March 18: Describe newsletter to five people."

View full sizeScreenshot = Due Mar 18 - Describe newsletter to fiv... ^ • MV described the "newsletter donut hole" stage where writers struggle to describe their newsletter for organic sharing. • MV contrasted low-context subscribers from ads with high-context subscribers from direct referrals, noting the latter improve deliverability signals. • MV provided advice for escaping the donut hole, including giving people specific sharing language and asking for direct forwards. Suggested task • Describe newsletter to five people • Mar 18 Remind me By Gemini; there may be mistakes.

The "not so funny"

Here's the one that's not funny.

A couple of weeks ago, on an old iCloud alias I haven't used in years, I got a fake Microsoft 365 renewal notice. Someone had abused StreamYard's actual registration system, using the same playbook as the PayPal invoice scams to inject malicious content into a legitimate confirmation email.

The email passed every authentication check because it really did come from StreamYard. Real DKIM. Real SPF. Real infrastructure.

The scam was injected through a user-input field in StreamYard's own confirmation flow.

View full sizeSummary: Microsoft 365 Business Standard subscription is scheduled for renewal on 15 April 2026. Contact support at +1 803 876 3049 if you did not expect this renewal or would like to make changes. above an email from StreamYard thanking me for registering for "This is a notification regarding your Microsoft 365 Business Standard..."

Apple Intelligence summarized it confidently: subscription renewing April 15, the scammer's phone number surfaced as support.

The contextual weirdness — wait, why is StreamYard telling me about Microsoft — was the only tell and the summary stripped it.

New sheriff in town

I didn't turn Gemini or Apple Intelligence on, they just showed up on my inbox one day and I decided to pay attention. These tools are sometimes "good luck opting out" rather than opt-in and they are now visibly making decisions about our inboxes and we're all just starting to notice, both as senders and as recipients.

For a decade we've been asked "How do I land in Primary?" 

The question is now changing. 

How do you use AI in your email flow? What have you noticed in your own inboxes?