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Structured design dialogue that validates ideas before implementation begins.
clippy
Microsoft 365 / Outlook CLI for calendar and email. Use when managing Outlook calendar (view, create, update, delete events, find meeting times, respond to invitations), sending/reading emails, or searching for people/rooms in the organization.
Full skill instructions
Source: https://github.com/foeken/clippy
Works through the M365 web UI via browser automation (Playwright), not the Graph API. No Azure AD app registration required - just login with your browser.
git clone https://github.com/foeken/clippy.git
cd clippy && bun install
bun run src/cli.ts --help
Or link globally: bun link
# Interactive login (opens browser, establishes session)
clippy login --interactive
# Check auth status
clippy whoami
Keep a browser session alive to prevent token expiry:
# Start keepalive (keeps browser open, refreshes every 10min)
clippy keepalive --interval 10
For persistent operation, set up as a launchd service (macOS) or systemd (Linux).
Health monitoring: Keepalive writes to ~/.config/clippy/keepalive-health.txt on each successful refresh. Check if this file is stale (>15min) to detect failures.
# Today's events
clippy calendar
# Specific day
clippy calendar --day tomorrow
clippy calendar --day monday
clippy calendar --day 2024-02-15
# Week view
clippy calendar --week
# With details (description, attendees)
clippy calendar --details
clippy create-event "Title" 09:00 10:00
# Full options
clippy create-event "Meeting" 14:00 15:00 \
--day tomorrow \
--description "Meeting notes" \
--attendees "[email protected],[email protected]" \
--teams \
--find-room
# Recurring
clippy create-event "Standup" 09:00 09:15 --repeat daily
clippy create-event "Sync" 14:00 15:00 --repeat weekly --days mon,wed,fri
clippy update-event 1 --title "New Title"
clippy update-event 1 --start 10:00 --end 11:00
clippy delete-event 1
clippy delete-event 1 --message "Need to reschedule"
clippy respond # List pending
clippy respond accept --id <eventId>
clippy respond decline --id <eventId> --message "Conflict"
clippy respond tentative --id <eventId>
clippy findtime
clippy findtime --attendees "[email protected],[email protected]"
clippy findtime --duration 60 --days 5
# Inbox
clippy mail
clippy mail --unread
clippy mail -n 20
clippy mail --search "invoice"
# Other folders
clippy mail sent
clippy mail drafts
clippy mail archive
# Read email
clippy mail -r <number>
# Download attachments
clippy mail -d <number> -o ~/Downloads
clippy send \
--to "[email protected]" \
--subject "Subject" \
--body "Message body"
# With CC, attachments, markdown
clippy send \
--to "[email protected]" \
--cc "[email protected]" \
--subject "Report" \
--body "**See attached**" \
--markdown \
--attach "report.pdf"
clippy mail --reply <number> --message "Thanks!"
clippy mail --reply-all <number> --message "Got it"
clippy mail --forward <number> --to-addr "[email protected]"
clippy mail --mark-read <number>
clippy mail --flag <number>
clippy mail --move <number> --to archive
clippy find "john" # People
clippy find "conference" --rooms # Rooms
clippy calendar --json
clippy mail --json
Profile directory can be overridden:
export CLIPPY_PROFILE_DIR=~/.config/clippy/my-profile
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