Meet Checky, the AI Coach for Your Follow-Ups (Closed Beta)

Mailcheck started as a way to check whether an email was read. Today it starts doing the next thing: checking whether it is the right time to follow up, and how. Meet Checky, the AI follow-up coach built into the mailcheck extension, now in closed beta for a small group of subscribers. This post explains what it does, what it reads, where the text goes, and what it will never do.

Table of contents

Why we built it

The people who use mailcheck are freelancers sending quotes, small sales teams, recruiters chasing candidates, people on Zoho Mail and Gmail who track a few important threads rather than thousands. And after every open notification, the same question came back, phrased a dozen ways: so do I follow up now, and what do I say?

We wrote about the first half of that question two days ago: tracking answers "did they open it", and the hard part starts after. Yesterday we published the exact rules we use to decide whether now is the moment. Checky is the whole thing put together, plus the piece rules cannot do: writing the message.

Checky is also the small robot on the extension icon, if you were wondering who that was.

Two layers: rules first, then the coach

Checky has two layers, and it matters which is which.

Layer 1 has no AI in it. It is the three rules from yesterday's post: not opened after 3 days, follow up with a new subject; opened but no reply after 2 days, send a short nudge; three or more opens in 48 hours, hot prospect, call. Applied to the opens you already have, they produce a daily list of actions, each with its reason, and a quick ready-to-use follow-up text. This layer works on every tracked email, whether or not you let Checky read it, because it only needs the pixel.

Layer 2 is the AI coach. When you have turned Checky on for an email, it writes the follow-up from three inputs: your original email, the recipient's behaviour (opens, timing, whether a reply was detected), and the reason the rule fired, for example "opened 3 times, no reply". The result is a draft in the context of what you actually sent, not a template with a name filled in.

What the coach panel shows

The coach lives in a panel inside the extension. For each thread it shows the drafted follow-up, the reason it is suggesting one, and four buttons:

• Insert into a new email, which opens a compose window with the draft in it. You read it, edit it, and you send it. Checky does not.
• Regenerate, for a different draft when the first one is not right.
• Already replied, when the answer came by phone or in a thread the pixel never saw.
• Ignore, for threads you never meant to chase.

The reason is always visible next to the draft on purpose. If it says "opened once, no reply for 2 days" and you know the person answered you yesterday by text, you have everything you need to dismiss it.

Consent is per email

To draft a follow-up in context, Checky has to read the body of the original email. We did not want that to be a blanket permission, so it is not.

Next to the "Tracking ON" toggle in the compose window, there is now a second toggle: "Checky ON". Checky reads the body of an email only if you turned that toggle on for that email. Off means it does not read that message, full stop. The email is still tracked, and Layer 1 still applies to it, but there is no draft in context because there is no text to draft from.

There is also an account-level setting to allow Checky by default on new emails, for people who want it on most of the time. Even with that on, the per-email toggle is still there and still wins. You can turn it off for the message to your lawyer and leave it on for the quote.

Privacy, stated plainly

Here is exactly what happens to an email body when Checky is on for it.

• The body is stored encrypted on our side, so that a draft can be generated later, when a rule fires.
• It is kept for 90 days, then deleted.
• It is deleted on request, and deleted when you disable Checky.
• For drafting, the text is sent to an AI provider hosted in the United States, Hugging Face. This is declared in the privacy policy and on the extension's privacy page. We are saying it here as well because a reader should not have to go looking for it.

If sending the text of an email to a US provider is not acceptable for a given message, a given client, or your business as a whole, leave Checky off for that email or do not enable it at all. Tracking, verification and the rule-based suggestions all keep working without it. We covered the broader question of tracking and consent in is email tracking legal under the GDPR, and the right reflex when someone objects in what to do when a client asks you to stop tracking.

There is also a fair-use limit: 50 AI drafts per day per account. When you reach it, Checky stops drafting until the next day. Everything else keeps running.

The daily digest and the weekly report

Suggestions are only useful if you see them without having to go looking, so Checky sends a daily digest by email. By default it goes out on working days at 8am in your time zone; you can switch it to every day, weekly, or never. It lists three things: emails to follow up, hot prospects, and invalid addresses detected among your recipients.

Separately, a weekly report arrives on Mondays with the numbers for the previous week: emails sent, opened, follow-ups sent via Checky, and replies. It is on or off, your choice.

Hot-prospect alerts

The one rule that cannot wait for the morning digest is the third one. When a recipient opens the same email three or more times within 48 hours, the extension icon shows a badge and you get a notification. This is the "it is being discussed" moment from the earlier posts, and its whole value is in acting the same day, ideally with a call. We explained why a burst of opens means what it means in why an email gets opened multiple times.

Verification as a guardrail

There is one situation where a follow-up coach becomes actively annoying: nagging you to chase an address that does not exist. An email to a mistyped or dead address never gets opened, so on day three the "not opened" rule would fire, and you would be politely asked to follow up with a better subject line, twice.

So the extension checks the address when tracking is turned on, and the Checky plan includes 500 address verifications a month. An address that fails verification is reported as invalid in the digest instead of showing up as a follow-up to send. It is the same check we have always offered for lists, the one that separates a bounce from a block, now used as a guardrail for the coach.

Availability and price

Checky is in closed beta. A small group of paying subscribers gets it first, then we widen it as the drafts and the rules prove themselves. It requires a paid plan. The Checky plan is 29 USD per month, or 290 USD per year, and includes tracking, the two layers of the coach, the digests, the alerts and the 500 monthly verifications.

To ask for early access, click "Request early access" in the extension popup, or send an email to our contact form with the word Checky in it.

What Checky does not do

We would rather you were disappointed now than surprised later.

• It does not send anything by itself. Every draft goes into a compose window that you read and you send. There is no auto-send, no sequence, no scheduled follow-up.
• It does not read emails you did not opt in. No "Checky ON" on that email, no reading of that email.
• It does not access your inbox. Everything Checky knows comes from the tracking pixel and from the extension in your compose window. Reply detection is based on your own "Re:" going out, as described yesterday, plus the "Already replied" button.
• It can be wrong. It will sometimes suggest a follow-up when the reply is already sitting unread in your inbox, or read a burst of opens as a committee when it was one enthusiastic person on three devices. That is why every suggestion is a suggestion, with its reason next to it, and a button to say no.

The small robot on the icon is a coach, not an autopilot. It tells you when it thinks the moment has come and hands you a draft. The judgement, and the send button, stay with you.

Frequently asked questions

Does Checky work with Zoho Mail as well as Gmail?

Yes. Checky lives in the same extension that tracks emails in Gmail and Zoho Mail, and the "Checky ON" toggle appears next to "Tracking ON" in the compose window of both.

Can I use the rule-based suggestions without the AI drafting?

Yes. Layer 1 only needs the tracking pixel and never reads the body of an email. Leave "Checky ON" off, or never enable it at the account level, and you still get the daily list of threads to act on with a quick follow-up text.

Where is the text of my email sent when Checky drafts a follow-up?

To an AI provider hosted in the United States, Hugging Face. The body is stored encrypted on our side for 90 days, and deleted on request or when you disable Checky. This is declared in the privacy policy and on the extension's privacy page.

What happens after 50 drafts in a day?

Checky stops generating drafts for the rest of the day and resumes the next day. Tracking, the rule-based list, the digest and the alerts are not affected.

Is Checky available on the free plan or the Tracking plan?

No. Checky requires a paid plan and is currently limited to a closed beta of subscribers. The Checky plan is 29 USD per month or 290 USD per year.

How do I get into the beta?

Use the "Request early access" button in the extension popup, or use our contact form and mention Checky. A small group of paying subscribers is admitted first.

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