[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, 2026-06-08T16:00:00
Existing calendar: (none provided)

Conversation:
Pharmacy: your prescription is ready for pickup; we close at 8pm today
Me: I'll swing by after work

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Prescription pickup today before the 8pm close; plan an after-work pickup.", "events": [{"title": "Pick up prescription", "start": "2026-06-08T18:00:00", "end": null, "location": "Pharmacy", "attendees": [], "reminder_minutes": 30, "notes": "Pharmacy closes at 8pm"}], "conflicts": [], "proposed_times": [], "reply_draft": "Thanks — I'll grab it on my way home.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Dr. Reyes: your annual physical is November 10 at 2:45pm
Me: thanks

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Physical on Nov 10, 2026 at 2:45pm.", "events": [{"title": "Annual physical", "start": "2026-11-10T14:45:00", "end": null, "location": "Dr. Reyes", "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "See you November 10 at 2:45.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Studio: pottery class starts October 13 at 6pm
Me: signed up!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Pottery class begins Oct 13, 2026 at 6pm.", "events": [{"title": "Pottery class", "start": "2026-10-13T18:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Can't wait — see you the 13th!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Coach: playoffs are November 14 at 10am at Field 3
Me: we'll be there

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Playoff game Nov 14, 2026 at 10am.", "events": [{"title": "Playoffs", "start": "2026-11-14T10:00:00", "end": null, "location": "Field 3", "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "See you at Field 3 on the 14th!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
HR: open enrollment briefing is November 3 at 1pm
Me: noted

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Briefing Nov 3, 2026 at 1pm.", "events": [{"title": "Open enrollment briefing", "start": "2026-11-03T13:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Got it — November 3 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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Vet: Cooper's dental cleaning is October 20 at 11:45am
Me: perfect

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Vet dental Oct 20, 2026 at 11:45am.", "events": [{"title": "Cooper — dental cleaning", "start": "2026-10-20T11:45:00", "end": null, "location": "Vet", "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Booked — the 20th at 11:45.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
PTA: fall festival is October 24, 5 to 8pm at the school
Me: we'll come

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Festival Oct 24, 2026, 5-8pm at school.", "events": [{"title": "Fall festival", "start": "2026-10-24T17:00:00", "end": "2026-10-24T20:00:00", "location": "School", "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "See you at the festival on the 24th!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Civic Center: the holiday recital is December 12 at 2pm
Me: adding it

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Recital Dec 12, 2026 at 2pm.", "events": [{"title": "Holiday recital", "start": "2026-12-12T14:00:00", "end": null, "location": "Civic Center", "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Added — December 12 at 2.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Manager: Q4 planning offsite is December 1 at 9am
Me: blocked

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Offsite Dec 1, 2026 at 9am.", "events": [{"title": "Q4 planning offsite", "start": "2026-12-01T09:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Blocked December 1 at 9.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
School: parent conferences are November 5 at 4:15pm
Me: confirmed

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Conference Nov 5, 2026 at 4:15pm.", "events": [{"title": "Parent conference", "start": "2026-11-05T16:15:00", "end": null, "location": "School", "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Confirmed for the 5th at 4:15.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Coach: the team banquet is November 21 at 6pm at Rosa's
Me: count us in

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Banquet Nov 21, 2026 at 6pm.", "events": [{"title": "Team banquet", "start": "2026-11-21T18:00:00", "end": null, "location": "Rosa's", "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "We'll be at Rosa's on the 21st!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Clinic: your lab follow-up is October 29 at 10:30am
Me: see you

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Follow-up Oct 29, 2026 at 10:30am.", "events": [{"title": "Lab follow-up", "start": "2026-10-29T10:30:00", "end": null, "location": "Clinic", "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "See you the 29th at 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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Dance: the winter showcase is December 5 at 3:30pm
Me: noted

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Showcase Dec 5, 2026 at 3:30pm.", "events": [{"title": "Winter showcase", "start": "2026-12-05T15:30:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Added the showcase — Dec 5 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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Library: there's an author talk November 18 at 7pm
Me: I'll go

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Author talk Nov 18, 2026 at 7pm.", "events": [{"title": "Author talk", "start": "2026-11-18T19:00:00", "end": null, "location": "Library", "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "See you at the library on the 18th!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Orthodontist: next adjustment is October 27 at 8:00am
Me: got it

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Adjustment Oct 27, 2026 at 8am.", "events": [{"title": "Orthodontist adjustment", "start": "2026-10-27T08:00:00", "end": null, "location": "Orthodontist", "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Got it — the 27th 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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Spouse: October 9 — Mia has the orthodontist at 9am and her piano recital at 5pm
Me: adding both

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Two events Oct 9, 2026: 9am and 5pm.", "events": [{"title": "Mia — orthodontist", "start": "2026-10-09T09:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 60, "notes": null}, {"title": "Mia — piano recital", "start": "2026-10-09T17:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Both added — orthodontist 9, recital 5.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Office: November 12 — sprint review at 11am and retro at 3pm
Me: blocked both

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Two meetings Nov 12, 2026: 11am and 3pm.", "events": [{"title": "Sprint review", "start": "2026-11-12T11:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 15, "notes": null}, {"title": "Sprint retro", "start": "2026-11-12T15:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 15, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Blocked both — review 11, retro 3.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Salon: your color appointment is November 7 at 1:45pm
Me: thanks

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Salon Nov 7, 2026 at 1:45pm.", "events": [{"title": "Salon — color appointment", "start": "2026-11-07T13:45:00", "end": null, "location": "Salon", "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "See you the 7th at 1:45.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
School: early dismissal is November 25 at 12:30pm
Me: got it

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Early dismissal Nov 25, 2026 at 12:30pm.", "events": [{"title": "Early dismissal", "start": "2026-11-25T12:30:00", "end": null, "location": "School", "attendees": [], "reminder_minutes": 120, "notes": "Pickup at 12:30 instead of usual time"}], "conflicts": [], "proposed_times": [], "reply_draft": "Got it — pickup at 12:30 on 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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Coach: practice is moved from Tuesday to Thursday, still 5pm
Me: ok

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Practice moved to Thu Sep 17, 2026 at 5pm.", "events": [{"title": "Soccer practice", "start": "2026-09-17T17:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 30, "notes": "Moved from Tuesday"}], "conflicts": [], "proposed_times": [], "reply_draft": "Got it — Thursday at 5.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Dr. office: we need to move your Friday appointment to Monday Sept 21 at 10am
Me: that works

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Appointment moved to Mon Sep 21, 2026 at 10am.", "events": [{"title": "Doctor appointment", "start": "2026-09-21T10:00:00", "end": null, "location": "Dr. office", "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Monday the 21st at 10 works.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
School: tomorrow's assembly is cancelled
Me: thanks for letting me know

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "An assembly was cancelled — nothing to schedule.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Thanks for the heads up!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Coach: this Saturday's game is called off due to weather
Me: ok, stay dry

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Game cancelled — nothing to add.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "No problem — see everyone next time!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Studio: yoga is every Monday at 6pm starting next week
Me: signing up

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Weekly yoga starts Mon Sep 21, 2026 at 6pm.", "events": [{"title": "Yoga", "start": "2026-09-21T18:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 30, "notes": "Recurring weekly on Mondays"}], "conflicts": [], "proposed_times": [], "reply_draft": "See you Monday 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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
School: chess club meets Wednesdays 3:30 to 4:30, starting September 16
Me: great

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Weekly chess club from Wed Sep 16, 2026, 3:30-4:30pm.", "events": [{"title": "Chess club", "start": "2026-09-16T15:30:00", "end": "2026-09-16T16:30:00", "location": null, "attendees": [], "reminder_minutes": 30, "notes": "Recurring Wednesdays"}], "conflicts": [], "proposed_times": [], "reply_draft": "Added — Wednesdays 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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
School: no school on Sept 25 (teacher in-service)
Me: noted

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "All-day no-school on Sep 25, 2026.", "events": [{"title": "No school (teacher in-service)", "start": "2026-09-25T00:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": null, "notes": "All day"}], "conflicts": [], "proposed_times": [], "reply_draft": "Noted — no school 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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Library: the book sale is the 20th, all day
Me: I'll stop by

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "All-day book sale on Sep 20, 2026.", "events": [{"title": "Library book sale", "start": "2026-09-20T00:00:00", "end": null, "location": "Library", "attendees": [], "reminder_minutes": null, "notes": "All day"}], "conflicts": [], "proposed_times": [], "reply_draft": "I'll swing by on the 20th!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Dentist: see you 10/15 at 2pm
Me: confirmed

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'10/15' = Oct 15, 2026 at 2pm.", "events": [{"title": "Dentist", "start": "2026-10-15T14:00:00", "end": null, "location": "Dentist", "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Confirmed — 10/15 at 2.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Jordan: party on the 3rd, 7pm at my place
Me: I'll be there

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Next '3rd' from Sep 14 is Oct 3, 2026 at 7pm.", "events": [{"title": "Party at Jordan's", "start": "2026-10-03T19:00:00", "end": null, "location": "Jordan's place", "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "See you on the 3rd 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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Mom: lunch this Saturday at noon
Me: yes!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "This Saturday = Sep 19, 2026, noon.", "events": [{"title": "Lunch with Mom", "start": "2026-09-19T12:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Saturday noon — see you!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Coach: quick call at half past 7 tonight
Me: ok

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'Half past 7 tonight' = Sep 14, 2026 at 7:30pm.", "events": [{"title": "Call with coach", "start": "2026-09-14T19:30:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 15, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Talk 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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Clinic: your appointment is at noon on Friday
Me: see you

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Noon Friday = Sep 18, 2026 at 12:00.", "events": [{"title": "Clinic appointment", "start": "2026-09-18T12:00:00", "end": null, "location": "Clinic", "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "See you Friday at noon.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Team: standup at 0900 tomorrow
Me: got it

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'0900 tomorrow' = Sep 15, 2026 at 9am.", "events": [{"title": "Standup", "start": "2026-09-15T09:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 15, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "See you at 9.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Trainer: session Thursday 6 to 7:30am
Me: booked

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Thu Sep 17, 2026, 6-7:30am.", "events": [{"title": "Training session", "start": "2026-09-17T06:00:00", "end": "2026-09-17T07:30:00", "location": null, "attendees": [], "reminder_minutes": 30, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Booked — Thursday 6am.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Office: 2-hour workshop Monday at 1pm
Me: blocked

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "2-hour workshop Mon Sep 21, 2026, 1-3pm.", "events": [{"title": "Workshop", "start": "2026-09-21T13:00:00", "end": "2026-09-21T15:00:00", "location": null, "attendees": [], "reminder_minutes": 30, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Blocked 1-3 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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Prof: essay due Friday at midnight
Me: on it

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Friday midnight deadline = Sep 18, 2026 23:59.", "events": [{"title": "Essay due", "start": "2026-09-18T23:59:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 1440, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "It'll be in by Friday night!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Accountant: I need the tax docs by the 30th
Me: will send

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Deadline the 30th = Sep 30, 2026.", "events": [{"title": "Tax docs due", "start": "2026-09-30T09:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 1440, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Sending the docs before 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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Coach: there's a game next week, time TBD
Me: keep me posted

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Game intended but no day/time.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Sounds good — let me know the details.", "needs_clarification": "What day and time is next week's game?"}


[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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Riley: movie this weekend?
Me: yes!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "No specific day/time given.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "I'm in — what works for you?", "needs_clarification": "Which day and time this weekend for the movie?"}


[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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Sitter: I can do Friday or Saturday — which do you need?
Me: let me check the calendar

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Two options, none chosen.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Let me confirm and get back to you.", "needs_clarification": "Do you need the sitter Friday or Saturday, and what time?"}


[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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Boss: we should sync soon on the roadmap
Me: agreed

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Intent to meet, no time.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Agreed — when works for you?", "needs_clarification": "What day and time works to sync on the roadmap?"}


[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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Dad: traffic was brutal on the commute today
Me: ugh, same

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Commute venting — nothing to schedule.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Right? Hope tomorrow's better.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Neighbor: your package was delivered to my door, grab it anytime
Me: thanks!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A package note, no calendar event.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Thank you — I'll pop over!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Mom: the recital last night was just wonderful
Me: wasn't it!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Past event being discussed; nothing to add.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "It really was — so proud!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Coach: great game yesterday, team!
Me: thanks coach

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Past game; nothing to schedule.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Thanks, Coach — proud of the team!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Wes: we should maybe plan a trip sometime
Me: for sure, one day

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Vague hypothetical, no commitment.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Love that idea — want to pick some dates?", "needs_clarification": "Do you want to choose dates for the trip?"}


[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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Mike: [image: concert ticket — 'The Lumineers, Sat Oct 17, 8pm, Red Rocks']
Me: so hyped

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Ticket shows Sat Oct 17, 2026 8pm at Red Rocks.", "events": [{"title": "The Lumineers concert", "start": "2026-10-17T20:00:00", "end": null, "location": "Red Rocks", "attendees": [], "reminder_minutes": 180, "notes": "From ticket"}], "conflicts": [], "proposed_times": [], "reply_draft": "Can't wait — Oct 17!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
HR: [image: invite screenshot — 'Town Hall, Thu Sept 24, 12-1pm']
Me: noted

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Invite: Thu Sep 24, 2026, 12-1pm.", "events": [{"title": "Town Hall", "start": "2026-09-24T12:00:00", "end": "2026-09-24T13:00:00", "location": null, "attendees": [], "reminder_minutes": 30, "notes": "From invite"}], "conflicts": [], "proposed_times": [], "reply_draft": "Added the Town Hall.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
School: [image: notice — 'Report card pickup Tuesday Sept 22, 3-6pm']
Me: will come

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Notice: Tue Sep 22, 2026, 3-6pm.", "events": [{"title": "Report card pickup", "start": "2026-09-22T15:00:00", "end": "2026-09-22T18:00:00", "location": "School", "attendees": [], "reminder_minutes": 120, "notes": "From notice"}], "conflicts": [], "proposed_times": [], "reply_draft": "I'll come by Tuesday.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Spouse: busy Thursday — Leo dentist 8am, my haircut 1pm, dinner with the Patels 7pm
Me: adding all

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Three events Thu Sep 17, 2026: 8am, 1pm, 7pm.", "events": [{"title": "Leo — dentist", "start": "2026-09-17T08:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 60, "notes": null}, {"title": "Haircut", "start": "2026-09-17T13:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 30, "notes": null}, {"title": "Dinner with the Patels", "start": "2026-09-17T19:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "All three added for 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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Office: Friday — interviews at 10am and 2pm, then happy hour at 5pm
Me: blocked it all

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Three events Fri Sep 18, 2026: 10am, 2pm, 5pm.", "events": [{"title": "Interview", "start": "2026-09-18T10:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 15, "notes": null}, {"title": "Interview", "start": "2026-09-18T14:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 15, "notes": null}, {"title": "Happy hour", "start": "2026-09-18T17:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 30, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Blocked all three 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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Dentist: confirming your appointment is all set for tomorrow at 3
Me: thanks

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Confirmed tomorrow Sep 15, 2026 at 3pm.", "events": [{"title": "Dentist appointment", "start": "2026-09-15T15:00:00", "end": null, "location": "Dentist", "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Thanks — see you at 3 tomorrow.", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Pharmacy: flu shots walk-in this Saturday 9am to 4pm
Me: I'll come early

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Walk-in Sat Sep 19, 2026, 9am-4pm.", "events": [{"title": "Flu shot (walk-in)", "start": "2026-09-19T09:00:00", "end": "2026-09-19T16:00:00", "location": "Pharmacy", "attendees": [], "reminder_minutes": 60, "notes": "Walk-in window"}], "conflicts": [], "proposed_times": [], "reply_draft": "I'll come Saturday morning!", "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, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Work: the deadline for expense reports is end of day Wednesday
Me: noted

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "EOD Wednesday = Sep 16, 2026, ~5pm.", "events": [{"title": "Expense reports due", "start": "2026-09-16T17:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "I'll submit by Wednesday EOD.", "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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Band director: we're adding an extra rehearsal, date still TBD
Me: ok, keep me posted

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A rehearsal is planned but its date is TBD — ask, don't schedule.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Sounds good — just tell me the date when it's set.", "needs_clarification": "What date and time is the extra rehearsal?"}


[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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Lia: dinner party at ours soon — date TBD, will text you details
Me: sounds fun!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Party intent but the date is TBD.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Can't wait — let me know when you pick a date!", "needs_clarification": "What date and time is the dinner 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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
PM: kickoff call happening sometime next week, time still TBD
Me: noted

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Kickoff is next week but unconfirmed — clarify.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Noted — send the invite once the time is set.", "needs_clarification": "What day and time next week is the kickoff call?"}


[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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Dentist: your cleaning moved to next Wednesday at 2pm
Me: ok

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'Next Wednesday' from Monday Sep 14 is Sep 23 (next week), not Sep 16.", "events": [{"title": "Dental cleaning", "start": "2026-09-23T14:00:00", "end": null, "location": "Dentist", "attendees": [], "reminder_minutes": 120, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Got it — Wednesday the 23rd at 2.", "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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Gym: your fitness assessment is next Friday at 7am
Me: see you then

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'Next Friday' from Monday Sep 14 is Sep 25 (next week), not Sep 18.", "events": [{"title": "Fitness assessment", "start": "2026-09-25T07:00:00", "end": null, "location": "Gym", "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "See you Friday the 25th 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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Trainer: program review next Monday at 8am
Me: works for me

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'Next Monday' from Monday Sep 14 is Sep 21.", "events": [{"title": "Program review", "start": "2026-09-21T08:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Monday the 21st at 8 — works.", "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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Mara: brunch next Saturday at 10:30?
Me: in!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'Next Saturday' from Monday Sep 14 is Sep 26 (next week), not Sep 19.", "events": [{"title": "Brunch with Mara", "start": "2026-09-26T10:30:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Saturday the 26th at 10:30 — see you!", "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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Coach Kim: we may add a scrimmage this week, I'll let you know the day
Me: keep me posted

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A scrimmage is planned but the day is unannounced — ask, don't schedule.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Will do — just send the day when you have it.", "needs_clarification": "Which day is the scrimmage?"}


[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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
School office: there's a schedule change coming next week, details to follow
Me: ok thanks

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A change is announced with no specifics — clarify.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Thanks — I'll watch for the details.", "needs_clarification": "What is changing in next week's schedule, and when?"}


[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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Dr. Shah's office: we need to reschedule your appointment, we'll call with options
Me: ok

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Reschedule pending with no new time — ask, don't schedule.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Sounds good — I'll wait for the options.", "needs_clarification": "What new date and time options work for the appointment?"}


[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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Manager: planning a team offsite later this month, date not locked yet
Me: sounds good

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "Offsite intent without a date — clarify.", "events": [], "conflicts": [], "proposed_times": [], "reply_draft": "Great — let me know once the date is locked.", "needs_clarification": "What date is the team offsite?"}


[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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Karate studio: the belt test moved to next Tuesday at 4pm
Me: he'll be ready

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'Next Tuesday' from Monday Sep 14 is Sep 22 (next week), not Sep 15.", "events": [{"title": "Belt test", "start": "2026-09-22T16:00:00", "end": null, "location": "Karate studio", "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Tuesday the 22nd at 4 — he'll be ready!", "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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Hana: coffee next Thursday at 9?
Me: yes!

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'Next Thursday' from Monday Sep 14 is Sep 24 (next week), not Sep 17.", "events": [{"title": "Coffee with Hana", "start": "2026-09-24T09:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 30, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Thursday the 24th at 9 — see you!", "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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Landlord: maintenance visit next Wednesday at 10am
Me: I'll be home

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "'Next Wednesday' from Monday Sep 14 is Sep 23 (next week), not Sep 16.", "events": [{"title": "Maintenance visit", "start": "2026-09-23T10:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 60, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "I'll be home Wednesday the 23rd at 10.", "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. List EVERY distinct event separately — one thread often holds several (e.g. a drop-off AND a pickup, or two appointments, are separate events).
- 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. If something should be scheduled but its day or time is not yet known ("TBD", "I'll confirm", "sometime soon"), leave events empty and ASK via needs_clarification instead of guessing.
Do not invent events that were not discussed.

[User]
Current datetime: Monday, 2026-09-14T09:00:00
Existing calendar: (none provided)

Conversation:
Box office: ticket sales open Friday Sept 25 at 10am
Me: ready to pounce

Return the ActionPlan JSON now.

[Assistant] {"reasoning": "A sales-open time is a schedulable event: Fri Sep 25, 2026 at 10am.", "events": [{"title": "Ticket sales open", "start": "2026-09-25T10:00:00", "end": null, "location": null, "attendees": [], "reminder_minutes": 30, "notes": null}], "conflicts": [], "proposed_times": [], "reply_draft": "Alarm set for the 25th at 10!", "needs_clarification": null}