Schedule a skill

Most skills in this Playbook are worth running on a cadence — monthly, weekly, sometimes hourly. All three runtimes ship a built-in scheduler. Each individual skill page tells you the recommended cadence for that skill; this page covers the mechanics.

Before you start

You'll need:

• The skill already saved as a Project (Claude), Skill (Codex), or agent (Copilot Agent Builder). See Using a skill for that setup.
• A clear cadence — pick from the recommendations on the skill's page (e.g., "Monthly, first Friday").
• The input files the skill expects, accessible to the runtime when the schedule fires. For Claude that means files in a connected drive (Google Drive, OneDrive, Dropbox, SharePoint). For Codex use a connected drive or a URL input. For Copilot the inputs live in OneDrive or SharePoint — Copilot grounds on whatever the prompt or agent references at fire time.

The laptop-awake caveat (Codex and Claude only): scheduled tasks on Codex and Cowork only run while your computer is awake and the runtime app is open. If your laptop is closed at 8 AM Monday, the scheduled run is skipped — and re-runs the next time the app opens. Copilot scheduled prompts run server-side and don’t have this problem. If you need true server-side scheduling on Codex/Claude, jump to Cloud Routines at the bottom.

Claude Cowork — Scheduled tasks

In Claude Desktop, scheduled runs live under the Scheduled tab in Claude Cowork.

1. Open Claude Desktop. In the left sidebar, click Scheduled.
2. Click + New task.
3. Fill in:
   • Task name — Monthly distributor scorecard — MH BU
   • Prompt / instructions — paste the skill's prompt body, or reference the saved Project the skill lives in.
   • Recurrence — hourly, daily, weekdays, weekly, or manually.
   • (Optional) Model — Sonnet by default; pick Opus on Pro+ if the skill needs deeper reasoning.
   • (Optional) Working folder — point Claude at a folder it can read from / write to.
4. Save.

You can also trigger a scheduled task from inside any chat by typing /schedule and following the prompts.

Where the output goes: scheduled-task output appears in the Scheduled tab itself as a thread per run. Notifications appear in the macOS / Windows notification area. There's no native email-out yet on Claude Cowork — if you need the output emailed somewhere, the simplest pattern is "Slack me when the task completes" via Claude's Slack integration.

Plan availability: Claude Cowork scheduled tasks are available on all paid plans (Pro, Max, Team, Enterprise). Free does not include Cowork.

OpenAI Codex — Automations

In Codex, scheduled runs are configured per Skill, under the Automations feature.

1. Open the Skill you want to schedule.
2. Click Automations (in the Skill's settings).
3. Click New Automation.
4. Fill in:
   • Recurrence — hourly, daily, weekly, monthly, or a custom cron expression.
   • Time — uses your local time zone.
   • Inputs — point Codex at the file source. Codex supports Google Drive, OneDrive, Dropbox, and direct URL inputs. The file name pattern can include date variables (e.g., epicor-sell-through-{YYYY-MM}.csv).
   • Delivery — email, Slack, Microsoft Teams, or write back to a connected drive folder.
5. Save.

Where the output goes: wherever you set Delivery. Codex's per-Automation logs are under the Skill's Automations tab.

Plan availability: Automations require ChatGPT Plus or higher.

Microsoft 365 Copilot — Scheduled prompts

Copilot scheduled prompts run server-side, generally available since January 2026 in Teams, Office.com chat, and Outlook. (Microsoft Learn · Microsoft Support)

1. Open the prompt or agent you want to schedule in Copilot Chat (microsoft365.com/chat, Teams, or Outlook).
2. Hover over the prompt → click Schedule this prompt.
3. Fill in:
   • Recurrence — hourly, daily, weekly, monthly, or a custom cadence.
   • Time — uses your local time zone.
   • Email me the result — tick this to get the output dropped in Outlook when the run finishes.
4. Save.

Where the output goes: scheduled-run results appear in the Conversations section of the Copilot Chat sidebar, bolded with a clock icon. If you ticked Email me, the result also lands in Outlook at the scheduled time. There’s no built-in Slack delivery — if you need Slack, use a Power Automate "Email arrived → Post to Slack" flow on the Outlook side.

Plan availability: Microsoft 365 Copilot license required. Each user is capped at 10 scheduled prompts. (Microsoft Support)

Legacy schedules. If your team scheduled prompts during the 2025 public preview, those still run in Power Automate — they won’t appear in the new scheduled-prompts UI. New schedules use the native scheduler.

What to schedule vs. run on demand

Schedule it if…	Run on demand if…
Cadence is predictable (monthly scorecards, weekly competitive briefs, quarterly QBR pulls)	Cadence is irregular ("when the VP asks for X")
Input data lives in a connected drive that updates on schedule	Input data changes shape per run (different files, different formats)
Output shape is the same every time	You need to add per-run context before the skill runs
You'd otherwise forget to run it	You're still tuning the prompt

A reasonable starting point: schedule the 3–5 skills with an obvious cadence (the monthly scorecards, the weekly competitive intel, the quarterly content reports). Leave the rest as on-demand for the first 60 days, then schedule a second wave once you know which skills you're actually running every month.

When a scheduled task fails

All three runtimes notify you when a run fails. Common causes:

• The connected drive lost auth. Re-authenticate in the runtime's integrations settings (Claude: Settings → Connectors. Codex: Settings → Integrations. Copilot: the file may have been moved out of SharePoint/OneDrive — re-link the file or folder in the prompt).
• The input file was renamed or moved. Update the schedule's input pointer / file pattern.
• The output destination changed. A Slack channel was archived, an email distribution group was deleted. Update the delivery destination.
• Your laptop was closed at the scheduled time (Codex / Cowork only — Copilot runs server-side). The run is skipped, then re-fires when the app reopens. Switch the cadence to a time the laptop is reliably on, move the skill to Cloud Routines, or — for Microsoft shops — re-target the schedule to Copilot, which doesn’t care if your laptop is asleep.
• Optional connected experiences disabled (Copilot only). If your IT admin turned this off, scheduled prompts stop firing. Re-enable in Outlook → File → Account Privacy. (Microsoft Learn)
• You hit a plan rate limit. Free tiers rate-limit aggressively; Plus has hourly windows. Copilot caps you at 10 active scheduled prompts. Upgrade, stagger, or merge low-value schedules.

If a scheduled task fails twice in a row, all three runtimes pause it and notify you. Re-enable it once you've fixed the underlying issue.

Cloud Routines — when laptop-on-and-app-open isn't enough

In April 2026 Anthropic launched Cloud Routines (research preview): a scheduled task that runs on Anthropic's servers instead of your laptop. Daily, weekly, or hourly. Triggered by a schedule, an HTTP webhook, or a GitHub event.

Routines are currently aimed at Claude Code (the developer CLI), not the marketing-analyst flow. Daily run limits apply (Pro 5/day, Max 15/day, Team/Enterprise 25/day).

If you grow into a workload where "laptop closed = skipped run" is hurting you, this is the upgrade path. For most readers of this Playbook, the desktop-based schedules above are enough — and they don't burn a precious daily Routine slot.

Where to go next

• Skills sidebar — each skill page lists its Cadence in the meta row at the top. That's the recommended schedule.
• Using a skill — the on-demand workflow (load → attach → run → review).
• Guarantee and support — what to do when something stops working and you can't fix it yourself.