Cancellation Win-Back · Operations
Rebook canceled calls instead of quietly losing them
When someone cancels a Calendly booking, it drafts a short, no-pressure rebooking email with a one-time link to the same meeting. You approve before it goes out.
Can't be bought yet: waiting for Calendly approval. It opens for purchase on its own once approved.
- Starts from an event in a connected app
- 1 AI step
- A person approves before it acts
- About 10 min to set up
Sound familiar?
The job, before and after this agent.
What it feels like today
- “When a prospect cancels, nobody follows up and the lead just goes quiet.”
- “Writing the same “let's find another time” email every day gets old.”
- “When we're the ones who canceled, the follow-up email feels awkward to write.”
What you get with the agent
- Starts within seconds of each Calendly cancellation and leaves reschedules alone.
- A single-use booking link for the same event type, so they rebook the same meeting in one click.
- A short, no-pressure email that fits who canceled and why, with an apology when your side canceled.
- Recommends leaving it when the person said they're not interested.
- Each email approved in Reviews before sending, or let routine cancellations go out on their own.
Before
A demo gets canceled at 9am. You mean to follow up, the day fills up, and by Friday the slot and the lead are both gone.
After
Minutes after the cancellation, a friendly rebooking email with a one-click link is waiting for your OK. You approve it between calls and they rebook for next week.
How it works
The whole workflow, step by step.
Starts within seconds of each Calendly cancellation (Calendly webhook, Standard plan or higher) and leaves reschedules alone. It creates a single-use Calendly booking link for the same event type, and AI writes a short "let's find another time" email (an apology instead when your side canceled), or recommends leaving it when the person said they're not interested. A teammate approves each email in Reviews before it's sent, with replies going to your inbox; you can let routine cancellations go out without review. It handles cancellations only: Calendly gives no no-show signal.
- TriggerCalendly booking canceled
- LogicRescheduled?
- Rescheduled:Left alone
- Canceled:Create a one-time booking link
- App callCreate a one-time booking link
- AI stepDraft the rebooking email
- LogicSend it?
- Leave it:Left alone
- Send now:Email the rebooking link
- Check first:Check the email
- Human approvalCheck the email
- Approved:Email the rebooking link
- OutputEmail the rebooking link
- OutputLeft alone
This is the workflow that opens in your workspace when you set the agent up. Every step can be edited.
- Step 1Calendly booking canceledStarts within seconds of someone canceling one of your Calendly bookings, with their name, email, the event and the reason they gave (Calendly webhook; needs a paid Calendly plan).
- Step 2Rescheduled?A reschedule shows up in Calendly as a cancellation plus a new booking, so those are left alone.
- Step 3Create a one-time booking linkCreates a single-use Calendly booking link for the same event type that was canceled (it stops working after one booking).
- Step 4Draft the rebooking emailAI reads the cancellation (who canceled and why) and writes a short, warm "let's find another time" email with the one-time booking link, or recommends leaving it when the reason says they don't want to meet.
- Step 5Send it?Skipped cancellations are kept in the history; routine ones go out at once if you switched review off; everything else waits for a person.
- Step 6Check the emailA teammate reads the email in Reviews, edits it if needed and approves sending.
- Step 7Email the rebooking linkSends the email to the person who canceled, with replies going to your inbox.
- Step 8Left aloneReschedules and cancellations that shouldn't get a follow-up are kept in the run history.
Example run
What goes in, and what comes out.
Example with fictional data
Comes in
Calendly cancellation: fictional prospect Lena Ford canceled tomorrow's “30 Minute Product Walkthrough”, reason: “Something came up at work.”
The agent produces
Draft email: a short note saying no problem, with a single-use link to rebook the same walkthrough at a better time. Waiting in Reviews.
What you need
Everything it takes to run it.
About 10 minutes from purchase to live. A checklist above the canvas takes you through each step.
Plan
Included in Enterprise; on other paid plans it's $69 once. Agents run live on paid plans, from Basic ($39/mo).
Your AI key
Connect any of 14 AI providers on your own key. Your provider bills usage directly, at cost; we add no markup.
Apps
- CalendlyAwaiting approval
Checklist
- A paid plan (agents run live on paid plans).
- An AI provider key (Settings → AI Providers).
- Calendly on a Standard plan or higher (the instant cancellation trigger uses a Calendly webhook), connected in Settings → Integrations.
Setup, about 10 minutes
- Connect your AI provider. The AI steps run on your own key (OpenAI, Anthropic, Google and more). Add one in Settings → AI Providers.
- Connect Calendly. Connect the Calendly account people book with (Settings → Integrations → Calendly). The instant trigger needs a Standard plan or higher.
- Pick your Calendly account. Open the trigger and “Create a one-time booking link” and pick your Calendly account in each.
- Add your details. Open “Draft the rebooking email” and replace the placeholder with your details, then add your reply-to address in “Email the rebooking link”.
- Test it with Dry Run. Press Dry Run: the agent runs on sample data with no messages sent and nothing written to your apps.
- Switch the trigger on. Open the trigger and click “Activate app trigger”: Calendly then sends every cancellation to the agent.
Is it a fit?
Who it's for, and what it won't do.
Built for
- Sales reps booking demos through Calendly
- Consultants and coaches with paid consultations
- Agencies running discovery calls
- Clinics and studios that schedule through Calendly
What it doesn't do
- It doesn't handle no-shows: Calendly gives no no-show signal, only cancellations.
- It doesn't send reminders or a second follow-up if they don't rebook.
- It doesn't update your CRM.
We list the limits up front so you can decide before you buy.
Price
$69 one-time
Per workspace. It never renews.
- Included at no extra cost on Enterprise.
- Buying and running it live need a paid plan, from Basic ($39/mo).
- Dry Run costs nothing: simulated AI and app calls, nothing sent.
- AI usage is billed by your own provider, at cost. No AI credits to buy from us.
One-time agent purchases aren't covered by the 30-day money-back guarantee. Refund policy
FAQ
Questions about Cancellation Win-Back.
Which apps does it need?
Calendly Standard or higher, since the instant cancellation trigger uses a Calendly webhook. The agent's page shows whether each app is ready to connect.
Will it pester people who don't want to rebook?
No. It sends one email, recommends leaving it when someone says they're not interested, and nothing goes out without your OK unless you choose to auto-send routine cancellations.
Does it handle no-shows?
No. Calendly only tells other apps about cancellations, not no-shows. It also doesn't send a second follow-up or update your CRM.
What does it cost to run?
A one-time purchase that never renews, and setup takes about 10 minutes. To run it live you need a paid plan and your own AI provider key (OpenAI, Anthropic, Google and others), added in Settings. Dry Run on sample data is free, so you can see real output before you commit.
Can it send without me checking?
Yes, for routine cancellations: in “Draft the rebooking email” change “SEND WITHOUT REVIEW: no” to “yes”. Unusual reasons still go to Reviews.
Which event type is the new link for?
The same event type as the canceled booking, so the person rebooks the same kind of meeting.
Is this a subscription?
No. Cancellation Win-Back is a one-time purchase of $69 per workspace and never renews. The Enterprise plan includes it at no extra cost. Running it live needs a paid plan (from Basic ($39/mo)), and your AI provider bills you directly for usage.
Can I test it before it touches real data?
Yes. Once it's set up in your workspace, Dry Run plays every step on sample data with simulated AI and app calls: nothing is sent and nothing in your apps changes. Switch the trigger on only when you're happy.
Cancellation Win-Back is almost ready.
Can't be bought yet: waiting for Calendly approval. It opens for purchase on its own once approved. Create a free account now and you'll find it on your Agents page.