AI Assistant

Hand the back-and-forth of scheduling to an assistant that emails on your behalf. Forward or CC it on any thread and it replies with times drawn from your real availability, follows the rules you write in plain English, and books the meeting onto the calendar you pick. This guide walks every setting on the AI Assistant page — setup, availability, video conferencing, the rules textbox, the Try it out tester, conversations, and the assistant list.

JM Chad Gilles Updated May 10, 2026 10 min read

Assistant basics

Open AI Assistant from the side rail. The page is one card with three tabs at the top: Configuration, Conversations, and How does it work? Above the card sits the same Connected Accounts panel you’ll see on Schedulers — you need at least one calendar account connected before the assistant has anything to schedule against.

What the assistant does

Your CalendarBridge assistant is reachable at an email address that looks like assistant@ai.calendarbridge.com. Forward a thread to it — or CC it on a reply — and it:

Reads free/busy from your primary calendar (and any extra calendars you’ve marked as availability-only).
Suggests times that respect your working hours, timezone, and the plain-English rules in your User Configuration.
Replies in the thread from your assistant address, so the other person can keep emailing as if they were talking to a human EA.
Once everyone agrees on a time, books the meeting — with a video link, if you set a default provider — and writes it to your calendar.

The three tabs at a glance

Tab	What it’s for
Configuration	Pick your primary email account, availability-only calendars, timezone, default video conferencing, and the plain-English rules the assistant follows. Also where you add a second configuration or delete an existing one.
Conversations	Every email thread the assistant has handled, with status (waiting on reply / booked / declined) and a transcript view.
How does it work?	A four-step walkthrough of the assistant — useful for new users and shareable with teammates who are about to be CC’d.

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No accounts yet? Both the Configuration and Conversations tabs swap to a lock card that prompts you to connect a calendar first. The How does it work? tab is always readable.

Set up your assistant

The first time you visit Configuration, you’ll see a centered empty state — the mascot, three bullets describing what the assistant can do, and a Configure my assistant button. Click it to open the configuration form.

Step 1 — Pick the email account the assistant responds from

Under Email Assistant Responds To, choose Google, Microsoft, or Apple. This is the account whose calendar the assistant will read free/busy from and write bookings to. If the provider you want isn’t listed yet, click Add an account to select a primary calendar to jump to My Accounts and connect it.

Your assistant address is generated from this choice — for example assistant@ai.calendarbridge.com. It’s visible in the Configuration list once you save, and it’s the address people will see in the CC line of any thread the assistant joins.
Step 2 — Add availability-only calendars (optional)

Use the Availability only calendars dropdown to add secondary calendars whose events should block time but where you don’t want bookings written. Personal calendars, shared team calendars, and out-of-office calendars are the usual picks here.

Use + Add more accounts to connect another account and surface its calendars in the same dropdown.
Step 3 — Confirm your timezone

Pick your timezone from the Timezone dropdown — it defaults to whatever your browser reports. The assistant uses it to translate times in its replies (“how about Wednesday at 10am ET?”) and to interpret incoming times that don’t have an explicit zone.
Step 4 — Set a default video conferencing provider

Pick one of None, Zoom, Google Meet, or Microsoft Teams as the default. We cover this in detail in Default video conferencing.
Step 5 — Write your scheduling rules and save

The User Configuration textbox is where the assistant gets most of its personality — see Scheduling rules. Click Save changes when you’re done. The form closes and you land on the Configuration list with the new assistant card.

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You can have more than one. Use Add New on the Configuration list to create a second assistant — handy if you keep work and personal email totally separate and want each to schedule against its own primary calendar.

Availability & timezone

The assistant uses the same availability model as your schedulers, with a couple of differences worth knowing.

Primary calendar (writable)

The calendar attached to the account you picked in Step 1 is the booking calendar. Bookings the assistant confirms are written here; busy events here block availability.

Availability-only calendars (read-only)

Calendars added under Availability only calendars are read for free/busy but never written to. Use them to:

Block personal commitments without exposing them — only busy/free is shared, not titles.
Honor a team or shared calendar without giving the assistant write access.
Layer in a vacation/out-of-office calendar so the assistant won’t propose times during a trip.

Timezone

The timezone you pick here is the assistant’s “home” zone — it’s how it phrases times in outgoing replies. If a counterparty writes in a different zone (“how about 3pm CET?”), the assistant translates to yours when proposing alternatives.

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Working hours come from your rules. Unlike Schedulers, there is no separate weekly grid here — the assistant reads working hours from the natural-language User Configuration block (see below). Be explicit about days, hours, and exceptions there.

Default video conferencing

The Default Meeting Provider dropdown sets the kind of link the assistant attaches to bookings unless the email thread asks for something specific.

None — no link is added. Use this if most of your bookings are in-person or use a location your assistant should leave alone.
Zoom — generates a Zoom link from the Zoom account connected to your CalendarBridge profile. If you haven’t connected one yet, the + Add Zoom Account link under the dropdown launches that flow.
Google Meet — generates a Meet link. Requires a Google primary account; if your primary is Microsoft or Apple, the option is still selectable but the assistant will fall back to a written prompt asking the counterparty for their preferred conferencing tool.
Microsoft Teams — same as Meet, but for Teams. Best paired with a Microsoft primary account.

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Override per-thread. The assistant will respect explicit asks in the email thread (“can we do a phone call instead?” or “let’s use Zoom”) over your default. Set the default to the option you use most and let the conversation override it.

Scheduling rules (User Configuration)

The User Configuration textbox is the assistant’s personality. It’s a free-form, plain-English block (up to 1,000 characters) that the assistant consults on every reply. The character counter on the bottom-right of the field updates as you type.

What to put in it

Anything you’d tell a human EA on day one. The defaults we seed for new users cover the common categories — replace them with your own:

Working hours — e.g. “My schedule is 9AM–5PM Monday–Friday, except Wednesdays which are 8AM–4PM.”
Preferred meeting windows — e.g. “The best times for meetings are mid-morning or mid-afternoon.”
Hard blackouts — e.g. “Never book anything on holidays or weekends.”
Default duration — e.g. “Default meetings to 30 minutes unless the thread says otherwise.”
Buffers — e.g. “Leave 15 minutes between back-to-back meetings.”
Tone — e.g. “Be brief and professional; sign off with ‘— Sam (via assistant).’ ”

Check the sample configuration

The Check sample configuration link above the textbox opens a known-good example you can copy and edit down. It’s the fastest way to see how granular you can get without overshooting the 1,000-character limit.

How rules are applied

Rules are applied on every reply — there is no separate “publish” step. Save your changes and the next thread the assistant handles uses the new wording. If you’re mid-thread when you change a rule, the next reply in that thread already follows it.

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Don’t put secrets here. The configuration is sent with every prompt the assistant runs. Treat it like ad copy: helpful context, not credentials, addresses you wouldn’t share with a counterparty, or anything you wouldn’t put in an out-of-office reply.

Try it out

Every configured assistant has a Try it out button on its card. Clicking it opens the sample-email tester — a real email composed to your assistant, but pre-filled with one of four canned scenarios so you can preview the kind of reply you’ll get.

Inside the modal

From — your primary email address (the address attached to the configuration).
To — type the address you’d like the assistant to reply to. This is the only field you fill in.
CC — pre-set to your assistant address. Removing it would send a regular email, so the field is shown but locked.
Title — the scenario subject line.
Body — the scenario message.

Pick a scenario

Use the ‹ / › chevrons (or the pagination dots) to flip between four built-in samples:

General meeting request — “Looking for 30 minutes next week.”
Find a specific time — “Does Tuesday at 2pm work?”
Reschedule an existing meeting — “Can we move our call?”
Out-of-office check — “Are you free the week of the 14th?”

Send it

Click Send. A spinner runs for about a second, then a green confirmation strip appears at the top of the modal — “Sample sent. Check your inbox.” A real reply lands in the recipient inbox within a minute or two, and the thread shows up under the Conversations tab.

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This is a real send. The tester uses the same pipeline as production, so the To recipient really does get an email. Use your own address (or a teammate who knows what’s coming) the first time.

Conversations

The Conversations tab is a feed of every email thread the assistant has touched, grouped by status.

Thread states

Waiting on reply — the assistant has proposed times and is waiting on the other side.
Booked — a time was agreed and the event is on your calendar. The card links to the event.
Declined or cancelled — the counterparty backed out, or the meeting was cancelled after booking.
Needs your input — the assistant flagged the thread for human review. Usually triggered by an ambiguous request or a rule conflict it couldn’t resolve. Open the thread to see the assistant’s note and reply manually if needed.

Reading a transcript

Click any thread to expand the full back-and-forth. Each message is timestamped and tagged with who sent it (you, the assistant, or the counterparty). The right rail of the transcript shows the proposed and chosen times.

Empty states

Before anyone has emailed your assistant, the tab shows a centered mascot with No conversations yet — forward or CC your assistant on any scheduling email and replies will show up here. Send a sample from Try it out to seed your first row.

Manage existing assistants

The Configuration tab’s default view is a list of assistant cards. Each card shows the primary email address (with a provider chip — Outlook, Google, or iCloud), the assistant email address generated for it, and three actions.

Action	Where it lives	What it does
Try it out	Outlined pill on the card body	Opens the sample-email tester — see Try it out.
Edit	Top-right of the card	Reopens the configuration form with every field pre-filled. Saving overwrites the existing assistant — the assistant email address stays the same.
Delete	Red Delete button next to Edit	Removes the assistant card. The assistant email address stops accepting new mail immediately; threads in progress are closed with a note from the assistant explaining it’s been retired.
Add New	Top-right of the Configuration tab	Launches the configuration form with empty fields so you can add a second (or third) assistant tied to a different primary account.
Feedback	Dark pill at the bottom of every card	Opens a quick form to send a note about the assistant’s replies to the CalendarBridge team. Helpful when the assistant misreads a request or you want it to handle a new scenario.

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Deleting is irreversible. The assistant address tied to a deleted configuration cannot be recovered — recreating the assistant generates a new address. If you want to pause an assistant temporarily, clear its rules to a single line (“Do not book any meetings — reply that I’m unavailable.”) instead of deleting.