Use the When agent

The When agent answers questions about your calendar in chat and makes the changes you ask for. It also writes a daily briefing to your Inbox.

Note

The When agent needs a plan that includes AI chat: the Founder Plan or the free trial. Without one, chat shows Subscribe in place of the message field. It also needs AI features on in Settings → AI. With AI features off, When hides chat everywhere. See AI privacy and safety for what it sends.

Open the chat

• On desktop, type in the field at the bottom of the sidebar, or press /. With the sidebar hidden, choose Ask about your calendar... at the bottom right of the calendar.
• On the Dashboard, type in the chat field, or choose a suggested prompt under it. Recap my week and When am I free? send right away; Add an event… and Look up a date… start the message for you to finish.
• On a phone, tap Ask When in the calendar's bottom bar. The chat opens in a sheet.
• In the Inbox, ask about a briefing, a suggestion, or a draft in the field under it. See Ask about an Inbox item.

Every chat shows the same conversation. Try “What's on Friday?” or “Add lunch with Sam tomorrow at noon.”

While the agent works, a status line says what it is doing, such as “Checking your calendar”. The agent writes its reply on When's servers, so closing the chat does not stop it.

One ongoing conversation

You have one conversation with the agent, with no separate chats to start or switch between. Earlier messages load as you scroll up, or choose Show earlier messages. A label marks where each day starts.

Earlier messages carry over, so a follow-up such as “make it 30 minutes” or “the other one” refers to what you just discussed.

Plan an event together

You can start with a rough idea, such as “Plan dinner with Sam next week.” The agent saves a draft with what you know, then asks for the next useful detail. Follow up with “Thursday, somewhere quiet” or “Make it 90 minutes” to enrich that same draft. You can also open its receipt and edit it in Drafts.

A saved receipt appears while the agent continues working. The draft stays in Drafts until you give a time or ask the agent to choose and schedule one. A complete request, such as “Add lunch tomorrow at 1 PM,” can create the scheduled event directly. If that time overlaps something already on your calendar, the agent still adds it and tells you what it overlaps. Undo appears after the reply finishes.

What it reads

Each message tells the agent where you are: the page, the calendar on screen, the days you can see, and the item you have selected or open. “This week” means the days on screen, and “this” means the selected or open item. For questions about the calendar, the agent starts with the items on those days, so “What's on Thursday?” or “Move yoga to Sunday” needs no search.

For other days, it searches. It searches the calendar on screen, including the calendars it includes, unless you name another calendar or ask about all of them. It can read every calendar you can see, including shared and subscribed ones. It reads days and times in the time zone your calendar is showing, unless you name another.

To find free time, it looks inside Your day, set in Settings → General. It focuses on timed events in the time grid on your own and shared calendars, along with booking blocks. All-day events, including hotel stays and events marked Busy, leave those hours open. Subscribed calendars and Free events never block a slot.

It can also search When's help pages and Discover, and link you to what it finds.

Search the web

For a public fact your calendar can't tell it, such as a conference's dates or a team's games, the agent can search the web. It searches at most 3 times per message and 20 times a day.

Before it saves anything it found on the web, it asks you, listing each item with its day and time and linking the page it came from. Once you agree, each saved item gets a Source link to that page. If a Discover calendar already covers a repeating schedule, the agent links that calendar instead of copying its events.

What it can change

With Create and edit on, the agent adds, moves, and changes events and periods, including their reminders, labels, and repeat schedules. With Archive items on, it archives events and periods. It cannot archive a locked event.

A change to a repeating event changes the whole series. The agent cannot change one occurrence. To change one date, detach the occurrence first.

The agent does not change settings, connected accounts, sharing, or billing. Ask about one and it links the exact setting so you can change it yourself.

After a change, the reply says which calendar the item is on and lists each item it changed under its text. Choose an item to open it beside its place on the calendar. An archived item shows struck through.

When it asks first

The agent makes one clearly named change without asking. It asks first when several items match what you said, when you ask it to archive more than one item, when you ask it to archive a repeating event (archiving takes the whole series), or when it can't tell what you want.

When also holds these changes until you agree, whatever the agent was asked:

• adding a guest whose full email address your message didn't give
• changing who can see an item, other than making it private
• moving an item to a calendar other people can see
• adding a web address that you didn't give and the agent didn't read
• more than one archive, or more than five changes, in one reply

The agent's question lists exactly what your yes changes. Under a question, it can offer two or three answers, such as Yes, archive the series and No, keep the series. Choose one to send it as your reply, or type your own.

Undo a change

Under the newest reply's changes, choose Undo, or Undo all when the reply changed several items. Each item goes back to how it was before the change, and an archived item comes back. An item you changed yourself since then stays as it is, and a message names it. An undone item shows Undone.

Undo goes away when you send your next message. After that, change the item yourself, or restore an archived item from Settings → Archive.

Attach images

Choose Attach image, paste an image, or drop one on the message field. A message can carry up to four images, with or without text, such as a screenshot of a hotel confirmation to add.

Open links in a reply

Items, calendars, days, and settings the agent names are links:

• An event opens beside its place on the calendar; a draft opens in Inbox.
• A calendar or a day opens the calendar there.
• A setting opens Settings at that row.
• A help page or a Discover calendar opens that page.
• A search link opens the command menu with the words typed in.

When you ask from the sidebar or the floating chat to go somewhere, such as “Take me to next Thursday”, the calendar moves there once the reply finishes. After the agent adds or moves an item outside the days on screen, the calendar moves to it the same way. Press Back to return. The calendar stays put if you closed the chat, opened an editor, or went to another page before the reply finished.

If a reply fails

A failed reply shows what went wrong and Retry. Only the newest reply has Retry, and a reply can be retried 3 times. After that, send your message again.

You can send up to 200 messages in 24 hours.

To rate a reply, choose the thumbs up or thumbs down under it. See Send feedback.

Turn it off or limit it

Open Settings → AI. Under Agent:

• When agent turns the agent on or off. It starts on. While it is off, chat shows “Your When agent is off, so it can't answer in chat.” with Turn on, and the daily briefing stops.
• Create and edit lets it add, move, and change events and periods when you ask. With it off, the agent still answers questions about your calendar.
• Archive items lets it archive events and periods when you ask.
• Daily briefing, under Automations, turns the briefing on or off.
• Suggestions, under Automations, turns suggestions on or off. Turning them off clears the ones waiting in your Inbox.

Turning the agent off and on again keeps your Create and edit and Archive items choices. Without a plan that includes AI chat, or with AI features off, the When agent switch can't be turned on, and the line under it says why.

Read your daily briefing

Each morning between 6 and 7 AM in your time zone, the agent writes a briefing to your Inbox, under From your agent. It opens with a sentence or two on the shape of your day, then lists any overlapping events, today's items by start time, free blocks of an hour or more inside Your day, and what matters tomorrow. Releases and holidays from a calendar you subscribe to share one line under that calendar. Click an event or calendar in the briefing to open it. The briefing only reads your calendar.

The next briefing replaces it. To clear it sooner, open it and choose Dismiss.

Review suggestions

Once a day, the agent looks for things it could fix on your own calendars and leaves each one in your Inbox under From your agent. Today it finds birthdays that happen only once, such as "Mom's Birthday" added as a single all-day event, and suggests making each one a birthday that repeats every year.

Nothing changes until you choose Accept. Accepting saves the change like an edit of your own, and Undo in the message that follows puts it back. Dismiss clears a suggestion, and the agent won't suggest it again unless you edit that event. If you change the event first, the suggestion says it's out of date.

Ask about an Inbox item

Select a briefing, a suggestion, or a draft in your Inbox and type in the field under it, or press ⌥R to put the cursor there. Ask why the agent suggested something, ask about a conflict in your briefing, or ask for a different change, such as "Make it yearly, but on Family." The answer appears under the item.

These messages are part of your one conversation, so they also appear in the chat, marked with the item they're about. The agent changes things only as you ask, and Undo in its reply puts them back. When it changes a suggestion's event, the suggestion reads Done in chat and leaves your Inbox once you move to another item, and the agent won't suggest it again unless you edit that event.