10 questions (and answers) about how AI Gmail will affect your email outreach

James Milsom -

Google is turning Gmail into an AI-assisted inbox: it can summarize threads, help recipients search their inbox in natural language, and increasingly prioritize “important” relationships over generic outreach. 

In our webinar, "Gemini Gmail and email outreach in 2026," we framed this as an “AI gatekeeper” moment: if your emails feel like noise, they’ll be filtered; if they consistently deliver value, they’re more likely to be surfaced. 

The engagement was incredible, and the webinar was flooded with questions that get to the heart of what every sender is worried about: How do I stay in the inbox?

In the spirit of transparency, we’re sharing the top questions asked during the session and the answers we gave.

Strategy & Content

  1. Should I keep prospecting emails in one thread or start new ones?

While "nudging" in a single thread is recommended as best practice, Gemini’s introduction will re-emphasize this.

As we covered in our Gemini Gmail blog, you want summaries to show you’re adding value, not annoyance:

“The spammer’s summary: "The sender asked for a meeting on Tuesday. Then they asked if you saw the last email. Then they asked if you were the right person. Then they asked for a meeting again."

Now compare that to a non-spam-like email thread:

Your ideal summary: "The sender shared a calculator for hiring costs. Later, they provided research on Q3 salary trends. Recently, they invited you to a webinar on remote leadership."”

We recommend testing: try a single thread only if you are adding genuine new value in each reply, on the same topic. If the topic shifts, start a new email to keep the AI summary clean.

  1. Do attachments hurt deliverability? Should I send them in the 2nd email?

Yes, attachments can trigger spam filters.

A better strategy is to use your first email to "knock on the door" and ask if they’d like to see the report or case study. If they reply "yes," you’ve earned a positive signal from Gemini, and you can safely send the attachment in the second email.

  1. Does AI mean I should compress emails or keep them short?

Even though Gemini can read long emails, humans still prefer brevity.

Our data suggests keeping emails under 100 words remains the sweet spot for replies. Write for the human; let the AI handle the summary.

  1. Hunter recommends minimizing links. Is that still true?

Yes. While Gemini can "read" context, traditional spam filters still look for heavy HTML and link density.

Don’t give filters a reason to block you before Gemini even sees your message.

Technical & Deliverability

  1. Will Microsoft Copilot catch up to Gemini?

Absolutely. If one major player implements AI inbox filtering, the others very likely will follow.

Apple announced the infusion of Gemini into its devices. The change is coming.

  1. Can I still send 100 emails a day without hitting spam?

The “spray and pray” of sending highly generic emails to leads has long been out of sync with what works. Our research in 2025 proved that offer and message relevance create replies

The larger the list, the harder it is to be relevant, and the more likely you’ll be regarded as spam.

The focus must shift to "highly targeted lists" and to technical basics like email account warming.

If you send 100 emails to a broad, unsegmented list, you risk being flagged as spam.

If you send 100 highly relevant emails to a verified, segmented audience, you are safer.

  1. What constitutes a "small list"?

We often define a small list as 20–50 contacts. However, it’s less about the number and more about similarity.

Can you write one specific message that resonates perfectly with everyone on that list? If yes, the list size is right.

  1. When sending to large lists, should I use AI to generate unique content?

Yes, but don't just use AI to "spin" text.

Segment your large list into smaller sub-groups (e.g., by job title) first.

AI writes better copy when the audience segment is narrow and precise.

The Gemini Experience

  1. How do summaries show up?

It is currently a staged rollout. Some users see a "Summarize this" button, while others on mobile see summaries automatically.

Even then, some users are seeing summaries at a message thread level.

We expect automatic summaries to become the default standard across all views.

  1. Will sending lead gen emails take significantly more time now?

It shouldn't. The shift is from "blasting" to "segmenting." Tools like Hunter have automation to help you verify data and segment lists efficiently.

The work you put into segmentation pays off in deliverability.

Watch the replay

There's plenty more to uncover about adapting to the AI inbox. If you want to see the full breakdown of how to win with cold email in 2026, check out the full recording below.