[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Alex: lunch tomorrow at 1pm?
Me: works, the usual place

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Alex proposed lunch tomorrow at 1pm and it was accepted.", "events": [{"title": "Lunch with Alex", "start": "2026-06-09T13:00:00", "end": "2026-06-09T14:00:00", "location": "the usual place", "attendees": ["Alex"], "reminder_minutes": 30, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Perfect, see you at 1 at the usual place!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Sam: dentist moved to next Thursday 3:30
Me: noted

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Sam rescheduled the dentist to next Thursday at 3:30pm.", "events": [{"title": "Dentist", "start": "2026-06-11T15:30:00", "end": "2026-06-11T16:30:00", "location": null, "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Got it, I'll be there Thursday at 3:30.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Jo: haha that meme killed me
Me: lol

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Casual chat, no plan to schedule.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "😂", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Pat: you free sometime this week to grab coffee?

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A meetup is proposed but no concrete day/time was given.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Yeah! What day works for you?", "needs_clarification": "Which day/time this week works for coffee?"}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Riley: [image: screenshot of a concert ticket — 'The Lumens, Fri Jun 12, doors 7:30pm, The Fillmore']
Me: can't wait!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "The screenshot is a concert ticket with a concrete date, time, and venue.", "events": [{"title": "The Lumens concert", "start": "2026-06-12T19:30:00", "end": "2026-06-12T22:30:00", "location": "The Fillmore", "attendees": ["Riley"], "reminder_minutes": 120, "notes": "From ticket screenshot"}], "conflicts": [], "proposed_times": [], "reply_draft": "Added it — doors at 7:30, see you Friday!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T08:00:00
Existing calendar: (none provided)

Conversation:
Room parent: picture day is this Thursday at 9am, green shirts!
Coach Dana: heads up, soccer moves to Tuesday 5pm this week
Me: thanks, adding both

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Two concrete events: picture day Thursday 9am and the rescheduled soccer Tuesday 5pm.", "events": [{"title": "Picture day (green shirt)", "start": "2026-06-11T09:00:00", "end": "2026-06-11T09:30:00", "location": null, "attendees": [], "reminder_minutes": 720, "notes": "Wear the green class shirt"}, {"title": "Soccer practice", "start": "2026-06-09T17:00:00", "end": "2026-06-09T18:00:00", "location": null, "attendees": ["Coach Dana"], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Got both down — picture day Thursday 9am and soccer Tuesday 5pm!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Teacher: our class field trip permission slips are due next Friday
Me: ok!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A due date stated as 'next Friday' relative to Monday Jun 8 resolves to Jun 19.", "events": [{"title": "Permission slips due", "start": "2026-06-19T09:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 1440, "notes": "Class field trip"}], "conflicts": [], "proposed_times": [], "reply_draft": "Thanks — I'll have them signed before Friday.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Room parent: field trip to the science museum is Wed 9am–3pm, bring a bagged lunch
Me: noted

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A single all-day-ish event with an explicit start and end on Wednesday.", "events": [{"title": "Science museum field trip", "start": "2026-06-10T09:00:00", "end": "2026-06-10T15:00:00", "location": "Science museum", "attendees": [], "reminder_minutes": 720, "notes": "Bring a bagged lunch"}], "conflicts": [], "proposed_times": [], "reply_draft": "Got it — bagged lunch, 9 to 3 Wednesday.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
PTA: the book fair runs Mon–Wed next week in the library, open during pickup
Me: 👍

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A multi-day event spanning Monday to Wednesday of next week.", "events": [{"title": "Book fair", "start": "2026-06-15T08:00:00", "end": "2026-06-17T16:00:00", "location": "School library", "attendees": [], "reminder_minutes": 1440, "notes": "Open during pickup"}], "conflicts": [], "proposed_times": [], "reply_draft": "Thanks — we'll stop by after pickup.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Jess: did you see the class photo album?? so cute
Me: omg yes 😍

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Friendly chatter, nothing to schedule.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "They grow up so fast 🥹", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Coach Dana: great hustle from the kids today, proud of them
Me: such a fun season

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Encouragement, no plan or date mentioned.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Thanks Coach — they love it!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Existing calendar:
- Dentist (Mia): 2026-06-10T14:00..2026-06-10T15:00

Room parent: makeup class photo is Wednesday at 2pm
Me: hmm Mia has the dentist then

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "The makeup photo at Wed 2pm overlaps Mia's existing dentist appointment.", "events": [{"title": "Makeup class photo", "start": "2026-06-10T14:00:00", "end": "2026-06-10T14:30:00", "location": null, "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [{"event_index": 0, "clashes_with": "Dentist (Mia) 2:00-3:00pm", "severity": "overlap"}], "proposed_times": ["2026-06-10T15:00:00", "2026-06-11T14:00:00"], "reply_draft": "Mia has the dentist at 2 — could she do the makeup photo at 3, or Thursday?", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Existing calendar:
- Work standup: 2026-06-09T09:00..2026-06-09T09:30

Teacher: parent volunteers needed in class Tue 9–10am
Me: I'll try

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Volunteering Tue 9-10am butts against the 9:00-9:30 standup (overlap).", "events": [{"title": "Classroom volunteering", "start": "2026-06-09T09:00:00", "end": "2026-06-09T10:00:00", "location": "Classroom", "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [{"event_index": 0, "clashes_with": "Work standup 9:00-9:30am", "severity": "overlap"}], "proposed_times": ["2026-06-09T10:00:00", "2026-06-11T09:00:00"], "reply_draft": "I have a 9am call — could I come in at 10 instead?", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Room parent: [image: flyer — 'Spring Family Picnic, Sat Jun 13, 11am, Lincoln Park Shelter B, bring a dish to share']
Me: we'll be there

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "The flyer gives a concrete date, time, and location for the family picnic.", "events": [{"title": "Spring Family Picnic", "start": "2026-06-13T11:00:00", "end": "2026-06-13T14:00:00", "location": "Lincoln Park, Shelter B", "attendees": [], "reminder_minutes": 120, "notes": "Bring a dish to share (from flyer)"}], "conflicts": [], "proposed_times": [], "reply_draft": "Added it — we'll bring a salad!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Mom: [image: photo of a permission slip — 'Zoo trip Thursday June 11, depart 8:30am, return ~2:30pm, $12 due Mon']
Me: signing tonight

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Permission slip photo encodes the trip date/time and a separate payment deadline.", "events": [{"title": "Zoo trip", "start": "2026-06-11T08:30:00", "end": "2026-06-11T14:30:00", "location": "Zoo", "attendees": [], "reminder_minutes": 720, "notes": "$12 due Monday; from permission slip"}], "conflicts": [], "proposed_times": [], "reply_draft": "Signed and the $12 is ready for Monday!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Teacher: can a couple of parents help with the class party sometime next week?
Me: maybe!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A request without a fixed day or time — ask before scheduling anything.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Happy to help — what day and time is the party?", "needs_clarification": "Which day/time next week is the class party?"}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Coach Dana: end-of-season pizza party is the 14th at 6pm at Tony's
Me: yum, count us in

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'The 14th' resolves to Jun 14; concrete time and venue given.", "events": [{"title": "End-of-season pizza party", "start": "2026-06-14T18:00:00", "end": "2026-06-14T20:00:00", "location": "Tony's", "attendees": ["Coach Dana"], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Count us in — see you at Tony's at 6!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Teacher: the spring recital is in two weeks, Friday at 6pm in the gym
Me: 📅

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Friday two weeks out is Jun 19? The teacher pins it to Friday 6pm — Jun 19.", "events": [{"title": "Spring recital", "start": "2026-06-19T18:00:00", "end": "2026-06-19T19:30:00", "location": "School gym", "attendees": [], "reminder_minutes": 1440, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Can't wait — we'll be there Friday at 6!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
School office: reminder, early dismissal this Wednesday at 12:30pm
Me: thanks for the heads up

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A one-off schedule change parents need to plan pickup around.", "events": [{"title": "Early dismissal", "start": "2026-06-10T12:30:00", "end": null, "location": "School", "attendees": [], "reminder_minutes": 60, "notes": "Pickup at 12:30 instead of usual"}], "conflicts": [], "proposed_times": [], "reply_draft": "Noted — I'll be there at 12:30 Wednesday.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Teacher: your parent–teacher conference slot is Thursday 4:15pm, ~15 min
Me: works for me

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A confirmed 15-minute conference slot on Thursday.", "events": [{"title": "Parent–teacher conference", "start": "2026-06-11T16:15:00", "end": "2026-06-11T16:30:00", "location": "Classroom", "attendees": ["Teacher"], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "4:15 Thursday works — see you then!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Other parent: Leo's bday party Sat 2–4pm at Jump Zone, can Mia come?
Me: she'd love to!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A party invite with a clear window and venue, accepted.", "events": [{"title": "Leo's birthday party", "start": "2026-06-13T14:00:00", "end": "2026-06-13T16:00:00", "location": "Jump Zone", "attendees": ["Leo"], "reminder_minutes": 180, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "She'd love to — see you Saturday at Jump Zone!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Neighbor: I've got carpool drop-off Friday at 7:45am this week
Me: perfect, thank you!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A specific carpool commitment on Friday morning.", "events": [{"title": "Carpool drop-off (neighbor driving)", "start": "2026-06-12T07:45:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 30, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Thank you! I've got next Friday.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Coach Dana: practice this Tue is now 6pm, not 5
Me: ok updating

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A reschedule: practice Tuesday moves to 6pm.", "events": [{"title": "Soccer practice", "start": "2026-06-09T18:00:00", "end": "2026-06-09T19:00:00", "location": null, "attendees": ["Coach Dana"], "reminder_minutes": 60, "notes": "Moved from 5pm to 6pm"}], "conflicts": [], "proposed_times": [], "reply_draft": "Updated — 6pm Tuesday it is.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
PTA: bake sale items drop off Thursday by 8am at the front office
Me: I'll bring cookies

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A drop-off deadline Thursday morning.", "events": [{"title": "Bake sale drop-off", "start": "2026-06-11T08:00:00", "end": null, "location": "Front office", "attendees": [], "reminder_minutes": 720, "notes": "Bringing cookies"}], "conflicts": [], "proposed_times": [], "reply_draft": "Cookies will be there by 8 Thursday!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Other parent: we should set up a playdate soon!
Me: yes definitely

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Mutual interest but no concrete day, time, or place.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Let's do it — what day works for you two?", "needs_clarification": "Which day/time and where for the playdate?"}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Morgan: can we do a 30-min project sync next Monday at 10am?
Me: that works for me

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'Next Monday' from Monday Jun 8 resolves to Jun 15.", "events": [{"title": "Project sync with Morgan", "start": "2026-06-15T10:00:00", "end": "2026-06-15T10:30:00", "location": null, "attendees": ["Morgan"], "reminder_minutes": 15, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Monday the 15th at 10 works — talk soon!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Chris: [image: screenshot of OpenTable confirmation — 'Reservation at Osteria Mia, Sat Jun 13 at 7:30pm, party of 4, confirmation #OT98271']
Me: perfect!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "The OpenTable screenshot confirms a restaurant reservation Saturday at 7:30pm.", "events": [{"title": "Dinner at Osteria Mia", "start": "2026-06-13T19:30:00", "end": "2026-06-13T21:30:00", "location": "Osteria Mia", "attendees": ["Chris"], "reminder_minutes": 120, "notes": "Party of 4; confirmation #OT98271"}], "conflicts": [], "proposed_times": [], "reply_draft": "Added it — see you Saturday at 7:30!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Sam: thanks so much for watching the dog last weekend!
Me: any time, she's the best

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A thank-you exchange, nothing to schedule.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Anytime — she was a joy!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Manager: sprint review is Tuesday at 3pm, also block 4-4:30 for retro right after
Me: done

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Two back-to-back work meetings on Tuesday: sprint review 3pm and retro 4pm.", "events": [{"title": "Sprint review", "start": "2026-06-09T15:00:00", "end": "2026-06-09T16:00:00", "location": null, "attendees": ["Manager"], "reminder_minutes": 15, "notes": null}, {"title": "Sprint retro", "start": "2026-06-09T16:00:00", "end": "2026-06-09T16:30:00", "location": null, "attendees": ["Manager"], "reminder_minutes": 15, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Blocked both — review at 3, retro at 4.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Existing calendar:
- Team lunch: 2026-06-10T12:00..2026-06-10T13:00

Doctor: your 1pm appointment is confirmed for Wednesday
Me: see you then

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "The 1pm doctor appointment starts immediately after team lunch ends — adjacent.", "events": [{"title": "Doctor appointment", "start": "2026-06-10T13:00:00", "end": "2026-06-10T14:00:00", "location": null, "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [{"event_index": 0, "clashes_with": "Team lunch 12:00-1:00pm", "severity": "adjacent"}], "proposed_times": ["2026-06-10T14:00:00"], "reply_draft": "Confirmed — just note it is right after team lunch so I may be a couple minutes late.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T18:00:00
Existing calendar: (none provided)

Conversation:
Zoe: game night at our place tonight, 8pm — you coming?
Me: wouldn't miss it

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'Tonight' is Jun 8; explicit time is 8pm.", "events": [{"title": "Game night at Zoe's", "start": "2026-06-08T20:00:00", "end": "2026-06-08T22:30:00", "location": "Zoe's place", "attendees": ["Zoe"], "reminder_minutes": 30, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "See you at 8!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Olivia: just made that lemon pasta recipe you sent — total hit!
Me: so glad! it's a staple

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Friendly recipe chat, no scheduling.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Right? It never gets old!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Room parent: [image: flyer — 'Swim Club Sign-Ups, Tuesdays & Thursdays 3:30-4:30pm starting Jun 10, Lake Park Pool, $40/month']
Me: signing Lily up!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Flyer shows a recurring swim club starting Tuesday Jun 10 on Tues/Thurs 3:30-4:30pm.", "events": [{"title": "Swim club — Lily", "start": "2026-06-10T15:30:00", "end": "2026-06-10T16:30:00", "location": "Lake Park Pool", "attendees": [], "reminder_minutes": 60, "notes": "Recurring Tues & Thurs; $40/month. From flyer."}], "conflicts": [], "proposed_times": [], "reply_draft": "Lily's signed up — first session Tuesday the 10th!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Stylist: confirming your haircut Fri Jun 12 at 11am
School: reminder, Fri Jun 12 early release at 1pm
Me: got both!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Two distinct items on Friday: haircut at 11am and early school release at 1pm.", "events": [{"title": "Haircut", "start": "2026-06-12T11:00:00", "end": "2026-06-12T12:00:00", "location": null, "attendees": [], "reminder_minutes": 30, "notes": null}, {"title": "Early school release", "start": "2026-06-12T13:00:00", "end": null, "location": "School", "attendees": [], "reminder_minutes": 60, "notes": "Pickup at 1pm instead of usual time"}], "conflicts": [], "proposed_times": [], "reply_draft": "Got it — haircut at 11, school pickup at 1.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Team lead: heads up — design review deck due in three days
Me: will have it ready

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'In three days' from Jun 8 is Jun 11 (Thursday).", "events": [{"title": "Design review deck due", "start": "2026-06-11T09:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 1440, "notes": "Deadline: three days from Jun 8"}], "conflicts": [], "proposed_times": [], "reply_draft": "It'll be ready by Thursday!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Existing calendar:
- All-hands meeting: 2026-06-09T10:00..2026-06-09T11:00

Doctor office: we have a 10:30am slot Tuesday for your annual physical
Me: I'll take it

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "The 10:30am appointment overlaps the 10:00-11:00 all-hands meeting.", "events": [{"title": "Annual physical", "start": "2026-06-09T10:30:00", "end": "2026-06-09T11:30:00", "location": "Doctor office", "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [{"event_index": 0, "clashes_with": "All-hands meeting 10:00-11:00am", "severity": "overlap"}], "proposed_times": ["2026-06-09T14:00:00", "2026-06-10T10:30:00"], "reply_draft": "That slot overlaps my all-hands — could you do 2pm Tuesday or Wednesday morning instead?", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Nina: just checking in — hope you're feeling better!
Me: much better, thanks for asking

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A wellness check-in, no event to schedule.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "All good now, thanks! Really appreciate you checking in.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Marcus: [image: screenshot of flight confirmation — 'AA 412 departs SFO Mon Jun 22 6:00am, arrives JFK 2:30pm; return AA 721 Thu Jun 25 5:45pm JFK -> SFO']
Me: booked!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Flight confirmation shows two legs: outbound Jun 22 and return Jun 25.", "events": [{"title": "Flight SFO to JFK (AA 412)", "start": "2026-06-22T06:00:00", "end": "2026-06-22T14:30:00", "location": "SFO -> JFK", "attendees": [], "reminder_minutes": 120, "notes": "AA 412; from flight confirmation screenshot"}, {"title": "Flight JFK to SFO (AA 721)", "start": "2026-06-25T17:45:00", "end": "2026-06-25T21:00:00", "location": "JFK -> SFO", "attendees": [], "reminder_minutes": 120, "notes": "AA 721; from flight confirmation screenshot"}], "conflicts": [], "proposed_times": [], "reply_draft": "Both legs added — safe travels!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Dan: hiking trip this Saturday, meet at the trailhead at 7am, bring layers
Me: I'm in!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'This Saturday' from Monday Jun 8 is Jun 13.", "events": [{"title": "Hiking trip with Dan", "start": "2026-06-13T07:00:00", "end": "2026-06-13T13:00:00", "location": "Trailhead", "attendees": ["Dan"], "reminder_minutes": 60, "notes": "Bring layers"}], "conflicts": [], "proposed_times": [], "reply_draft": "See you at the trailhead Saturday at 7!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Priya: we should catch up soon, it's been forever
Me: yes! let's make it happen

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Mutual intent to meet but no date, time, or location mentioned.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "So overdue! What does your week look like?", "needs_clarification": "When and where works for a catch-up?"}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Carpool group: I can drive the Tuesday 3:15 pickup if someone takes Thursday
Me: I'll grab Thursday 3:15

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "I volunteered for the Thursday 3:15pm school pickup (Jun 11).", "events": [{"title": "Carpool — Thursday school pickup", "start": "2026-06-11T15:15:00", "end": "2026-06-11T15:45:00", "location": "School", "attendees": [], "reminder_minutes": 30, "notes": "My week to drive Thursday"}], "conflicts": [], "proposed_times": [], "reply_draft": "Got Thursday's 3:15 pickup covered!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Coach Dana: carpool to Saturday's away game leaves the school lot at 8am sharp
Me: we'll be there

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Carpool to the away game departs Saturday Jun 13 at 8am from the school lot.", "events": [{"title": "Carpool to away game", "start": "2026-06-13T08:00:00", "end": null, "location": "School lot", "attendees": ["Coach Dana"], "reminder_minutes": 45, "notes": "Leaves 8am sharp"}], "conflicts": [], "proposed_times": [], "reply_draft": "We'll be at the lot by 8 — thanks for organizing!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Dr. Lee's office: reminder, Maya's dental cleaning is Wed Jun 17 at 4:00pm
Me: thanks, we'll be there

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Dental cleaning confirmed for Wednesday Jun 17 at 4pm.", "events": [{"title": "Maya — dental cleaning", "start": "2026-06-17T16:00:00", "end": "2026-06-17T17:00:00", "location": "Dr. Lee's office", "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "See you Wednesday at 4!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Vet: Bella's vaccination appt is booked for Fri Jun 19, 10:30am
Me: perfect

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Vet vaccination appointment is Friday Jun 19 at 10:30am.", "events": [{"title": "Bella — vet vaccination", "start": "2026-06-19T10:30:00", "end": "2026-06-19T11:00:00", "location": "Vet", "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Booked — thanks!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Clinic: Sam's check-up is next Thursday at 9:15am
Me: see you then

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'Next Thursday' from Monday Jun 8 is Jun 18.", "events": [{"title": "Sam — check-up", "start": "2026-06-18T09:15:00", "end": "2026-06-18T10:00:00", "location": "Clinic", "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Got it — Thursday the 18th at 9:15.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Me: [image: appointment card — 'Orthodontist, Dr. Patel, Tue Jun 16, 8:00am']

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Appointment card photo shows an orthodontist visit Tuesday Jun 16 at 8am.", "events": [{"title": "Orthodontist — Dr. Patel", "start": "2026-06-16T08:00:00", "end": "2026-06-16T08:45:00", "location": "Dr. Patel", "attendees": [], "reminder_minutes": 60, "notes": "From appointment card"}], "conflicts": [], "proposed_times": [], "reply_draft": "Added the orthodontist appointment for Tuesday at 8.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Jenna: Leo's 7th birthday is Sat Jun 20, 2pm at Pump It Up — please RSVP by Thursday!
Me: we're in!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Birthday party Saturday Jun 20 2pm; RSVP requested by Thursday Jun 18.", "events": [{"title": "Leo's 7th birthday party", "start": "2026-06-20T14:00:00", "end": "2026-06-20T16:00:00", "location": "Pump It Up", "attendees": ["Jenna"], "reminder_minutes": 120, "notes": "RSVP by Thursday Jun 18"}], "conflicts": [], "proposed_times": [], "reply_draft": "We'll be there — count us in, thanks for the invite!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Sara: [image: birthday invitation — "You're invited! Emma turns 5 — Sun Jun 14, 3-5pm, 12 Oak St"]
Me: aww, we'll come

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Invitation card shows Emma's birthday Sunday Jun 14, 3-5pm at 12 Oak St.", "events": [{"title": "Emma's 5th birthday party", "start": "2026-06-14T15:00:00", "end": "2026-06-14T17:00:00", "location": "12 Oak St", "attendees": ["Sara"], "reminder_minutes": 120, "notes": "From invitation card"}], "conflicts": [], "proposed_times": [], "reply_draft": "We'll be there Sunday — can't wait!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Existing calendar:
- Piano lesson: 2026-06-09T17:00..2026-06-09T17:45

Coach: practice moves to Tuesday 5:30-6:30 this week
Me: noted

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Practice now Tuesday 5:30-6:30pm overlaps the 5:00-5:45 piano lesson.", "events": [{"title": "Soccer practice", "start": "2026-06-09T17:30:00", "end": "2026-06-09T18:30:00", "location": null, "attendees": ["Coach"], "reminder_minutes": 30, "notes": "Rescheduled from usual time"}], "conflicts": [{"event_index": 0, "clashes_with": "Piano lesson 5:00-5:45pm", "severity": "overlap"}], "proposed_times": [], "reply_draft": "Noted — heads up it overlaps piano, so we may be a few minutes late.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Coach: Saturday's game is at 11am, arrive 30 minutes early at Field 4
Me: got it

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Game Saturday Jun 13 at 11am at Field 4; arrive by 10:30.", "events": [{"title": "Soccer game", "start": "2026-06-13T11:00:00", "end": "2026-06-13T12:30:00", "location": "Field 4", "attendees": ["Coach"], "reminder_minutes": 60, "notes": "Arrive 30 min early (10:30)"}], "conflicts": [], "proposed_times": [], "reply_draft": "We'll be at Field 4 by 10:30!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Room parent: Picture day is Thursday — photos at 9am, kids wear the green class shirt
Me: thanks!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "School picture day Thursday Jun 11 at 9am; wear green shirt.", "events": [{"title": "School picture day", "start": "2026-06-11T09:00:00", "end": null, "location": "School", "attendees": [], "reminder_minutes": 720, "notes": "Wear green class shirt"}], "conflicts": [], "proposed_times": [], "reply_draft": "Got it — green shirt Thursday!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Teacher: your parent-teacher conference is Wed Jun 17 at 3:45pm
Me: confirmed

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Parent-teacher conference Wednesday Jun 17 at 3:45pm.", "events": [{"title": "Parent-teacher conference", "start": "2026-06-17T15:45:00", "end": "2026-06-17T16:15:00", "location": "School", "attendees": ["Teacher"], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Confirmed for Wednesday at 3:45.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
School: permission slip for the aquarium field trip (Jun 24) is due this Friday
Me: will send it in

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Two items: the slip is due Friday Jun 12, and the field trip is Jun 24.", "events": [{"title": "Permission slip due — aquarium trip", "start": "2026-06-12T09:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 1440, "notes": "Due Friday"}, {"title": "Aquarium field trip", "start": "2026-06-24T09:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 720, "notes": "School field trip"}], "conflicts": [], "proposed_times": [], "reply_draft": "Slip going in Friday — trip's on the 24th, noted!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
PTA: [image: newsletter — 'Spring concert Thu Jun 18 at 6:30pm in the gym']
Me: noted

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Newsletter screenshot announces the spring concert Thursday Jun 18 at 6:30pm.", "events": [{"title": "Spring concert", "start": "2026-06-18T18:30:00", "end": "2026-06-18T20:00:00", "location": "School gym", "attendees": [], "reminder_minutes": 120, "notes": "From PTA newsletter"}], "conflicts": [], "proposed_times": [], "reply_draft": "Added the spring concert — Thursday at 6:30!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Maria: book club meets tomorrow at 7pm at my place
Me: see you there

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'Tomorrow' from Jun 8 is Jun 9; book club at 7pm.", "events": [{"title": "Book club at Maria's", "start": "2026-06-09T19:00:00", "end": "2026-06-09T20:30:00", "location": "Maria's place", "attendees": ["Maria"], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "See you tomorrow at 7!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Landlord: friendly reminder, rent is due by the end of the month
Me: noted, thanks

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'End of the month' is Jun 30; rent deadline.", "events": [{"title": "Rent due", "start": "2026-06-30T09:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 1440, "notes": "Due by end of month"}], "conflicts": [], "proposed_times": [], "reply_draft": "Thanks — I'll have it in by the 30th.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Alex: let's grab dinner a week from Friday, 7pm?
Me: works!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Friday is Jun 12; a week from Friday is Jun 19.", "events": [{"title": "Dinner with Alex", "start": "2026-06-19T19:00:00", "end": "2026-06-19T21:00:00", "location": null, "attendees": ["Alex"], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Friday the 19th at 7 — perfect!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
HR: reminder that open enrollment closes the 25th
Me: thanks for the heads up

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'The 25th' is Jun 25; benefits deadline.", "events": [{"title": "Open enrollment closes", "start": "2026-06-25T09:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 1440, "notes": "Benefits deadline"}], "conflicts": [], "proposed_times": [], "reply_draft": "Thanks — I'll finish enrollment before the 25th.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Existing calendar:
- Dentist: 2026-06-09T09:00..2026-06-09T09:45

Vendor: can we do coffee tomorrow at 9:55?
Me: sure

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Coffee at 9:55 leaves only 10 minutes after the 9:45 dentist finish — tight.", "events": [{"title": "Coffee with vendor", "start": "2026-06-09T09:55:00", "end": "2026-06-09T10:30:00", "location": null, "attendees": ["Vendor"], "reminder_minutes": 15, "notes": null}], "conflicts": [{"event_index": 0, "clashes_with": "Dentist 9:00-9:45am", "severity": "tight"}], "proposed_times": ["2026-06-09T11:00:00"], "reply_draft": "9:55 is tight right after the dentist — could we make it 11 to be safe?", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T17:00:00
Existing calendar: (none provided)

Conversation:
Existing calendar:
- Yoga: 2026-06-08T18:00..2026-06-08T19:00

Friend: dinner tonight at 6:30?
Me: let me check

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Dinner at 6:30 overlaps the 6-7pm yoga class.", "events": [{"title": "Dinner with friend", "start": "2026-06-08T18:30:00", "end": "2026-06-08T20:00:00", "location": null, "attendees": ["Friend"], "reminder_minutes": 30, "notes": null}], "conflicts": [{"event_index": 0, "clashes_with": "Yoga 6:00-7:00pm", "severity": "overlap"}], "proposed_times": ["2026-06-08T19:30:00"], "reply_draft": "6:30 clashes with my yoga — could we push to 7:30?", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Spouse: Lily has ballet Wed 4pm and Noah has karate Wed 5:30pm
Me: adding both

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Two kids' activities Wednesday Jun 10: ballet 4pm and karate 5:30pm.", "events": [{"title": "Lily — ballet", "start": "2026-06-10T16:00:00", "end": "2026-06-10T17:00:00", "location": null, "attendees": [], "reminder_minutes": 30, "notes": null}, {"title": "Noah — karate", "start": "2026-06-10T17:30:00", "end": "2026-06-10T18:30:00", "location": null, "attendees": [], "reminder_minutes": 30, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Both on the calendar — ballet at 4, karate at 5:30.", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Family chat: Saturday plan — farmers market 9am, Mia's recital 2pm, dinner at grandma's 6pm
Me: busy day!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Three Saturday Jun 13 events: market 9am, recital 2pm, dinner 6pm.", "events": [{"title": "Farmers market", "start": "2026-06-13T09:00:00", "end": "2026-06-13T10:30:00", "location": null, "attendees": [], "reminder_minutes": 30, "notes": null}, {"title": "Mia's recital", "start": "2026-06-13T14:00:00", "end": "2026-06-13T15:30:00", "location": null, "attendees": [], "reminder_minutes": 60, "notes": null}, {"title": "Dinner at grandma's", "start": "2026-06-13T18:00:00", "end": "2026-06-13T20:00:00", "location": "Grandma's", "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Added all three — market, recital, then dinner. Busy day indeed!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Ben: did you catch the game last night? what a finish
Me: unreal, still buzzing

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Sports chat, nothing to schedule.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Best finish all season — still can't believe it!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Aunt Carol: happy Monday! hope the week's off to a good start
Me: you too, thanks!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A friendly greeting, no event.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Appreciate it — hope yours is great too!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Neighbor: thanks again for the plumber recommendation, he was great
Me: so glad it worked out

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A thank-you exchange, nothing to schedule.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Happy to help — he's saved us a few times!", "needs_clarification": null}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Coach: extra practice this week, I'll confirm the day soon
Me: ok, keep me posted

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "An extra practice is implied but no day or time is given yet.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Sounds good — just let me know the day and time.", "needs_clarification": "Which day and time is the extra practice?"}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Coworker: lunch sometime next week?
Me: yes, definitely!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Lunch intent for 'next week' but no specific day or time.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "I'm in — what day next week works for you?", "needs_clarification": "What day and time next week works for lunch?"}


[System]
You are a scheduling assistant reading a chat conversation (text, and sometimes images such as screenshots, invites, or flyers). Decide what calendar action is warranted and return ONLY a JSON object matching the ActionPlan schema:
- reasoning: one or two sentences of why.
- events: concrete events with ISO 8601 datetimes; resolve relative dates from the current datetime. Empty if there is no real plan.
- conflicts: for any event that clashes with the provided existing calendar, the event_index, what it clashes with, and severity (overlap|adjacent|tight).
- proposed_times: ISO 8601 alternatives when there is a conflict.
- reply_draft: a short, natural reply the user could send back.
- needs_clarification: a question if the plan is ambiguous, else null.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-06-08T09:00:00
Existing calendar: (none provided)

Conversation:
Camp: drop-off is 8:30am daily, Jun 22-26, at Riverside Center
Me: thanks!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Summer camp drop-off 8:30am each weekday Jun 22-26; anchor the first day.", "events": [{"title": "Summer camp drop-off", "start": "2026-06-22T08:30:00", "end": null, "location": "Riverside Center", "attendees": [], "reminder_minutes": 30, "notes": "Daily Jun 22-26"}], "conflicts": [], "proposed_times": [], "reply_draft": "Got it — drop-off at 8:30 starting Monday the 22nd.", "needs_clarification": null}