outlook365-cli 0.1.2

Outlook 365 CLI — read, send, and manage emails from the terminal

outlook-cli

Read, send, and manage Outlook 365 emails, calendar events, and contacts from the terminal.

Uses OWA bearer token authentication via Playwright — no admin consent or API keys required.

Disclaimer: This is an unofficial, community-driven project. It is not affiliated with, endorsed by, or supported by Microsoft Corporation. "Outlook" and "Microsoft 365" are trademarks of Microsoft Corporation.

This tool accesses Microsoft Outlook services using intercepted browser tokens and, in some cases, undocumented internal APIs (OWA service.svc). Use of this tool may violate Microsoft's Terms of Service or your organization's acceptable use policies. The authors accept no responsibility for account suspensions, data loss, or other consequences arising from the use of this tool.

Use at your own risk. This software is provided "as is", without warranty of any kind. See LICENSE for details.

Install

pip install outlook365-cli
playwright install chromium

Auth

outlook login          # opens browser, captures token automatically
outlook login --force  # force re-login, ignore saved session
outlook whoami         # verify current user

Token is cached at ~/.cache/outlook-cli/token.json. Auto re-login on 401. You can also set OUTLOOK_TOKEN env var directly.

Usage

Inbox

outlook inbox                          # list inbox (shows unread/total count)
outlook inbox --unread                 # unread only
outlook inbox -n 10                    # last 10 messages
outlook inbox --from "john"            # filter by sender
outlook inbox --subject "report"       # filter by subject
outlook inbox --after 2026-03-01       # after date
outlook inbox --before 2026-03-08     # before date
outlook inbox --has-attachments        # only with attachments
outlook inbox --category "Urgent"      # filter by category
outlook inbox --no-category            # only uncategorized messages
outlook inbox -n 50 --no-category      # find 50 uncategorized messages

Read / Search / Thread

outlook read 3                 # read message #3
outlook read 3 --raw           # raw HTML body
outlook thread 3               # full conversation thread for message #3
outlook search "keyword"       # search messages
outlook search "from:john" --max 10

Send / Reply / Forward

All send commands show a confirmation prompt before sending. Use -y to skip.

outlook send "[e-mail]" "Subject" "Body"
outlook send "[e-mail],[e-mail]" "Subject" "Body" --cc [e-mail] -y
outlook send "[e-mail]" "Subject" "Body" --signature MySignature
outlook send "[e-mail]" "Subject" "<h1>HTML</h1>" --html -s MySignature
outlook send "[e-mail]" "Report" "See attached" -a report.pdf
outlook send "[e-mail]" "Files" "Here" -a file1.pdf -a file2.xlsx
outlook reply 3 "Thanks!"
outlook reply 3 "Thanks!" --all
outlook reply 3 "Here it is" --attach requested-file.pdf
outlook reply-draft 3                          # create reply draft without sending
outlook reply-draft 3 "Will check" --all       # reply-all draft with body
outlook reply-draft 3 "<p>HTML</p>" --html     # HTML body (preserves quoted original)
outlook reply-draft 3 "Body" -s MySignature    # reply draft with signature
outlook forward 3 "[e-mail]" --comment "FYI"
outlook forward 3 "[e-mail]" -a extra-doc.pdf

Drafts

outlook draft "[e-mail]" "Subject" "Body"              # create draft
outlook draft "[e-mail]" "Subject" "Body" --cc [e-mail] # draft with CC
outlook draft "[e-mail]" "Subject" "Body" -a file.pdf  # draft with attachment
outlook draft "[e-mail]" "Subject" "Body" -s MySignature # draft with signature
outlook draft-send 3                                        # send a draft (with confirmation)
outlook draft-send 3 -y                                     # send without confirmation

Scheduled Send

outlook schedule "[e-mail]" "Subject" "Body" "+1h"        # send in 1 hour
outlook schedule "[e-mail]" "Subject" "Body" "+30m" -y    # 30 min, skip confirm
outlook schedule "[e-mail]" "Subject" "Body" "tomorrow 09:00"
outlook schedule "[e-mail]" "Subject" "Body" "2026-03-15T10:00"
outlook schedule "[e-mail]" "Subject" "Body" "+2h30m" --html -s MySignature
outlook schedule "[e-mail]" "Report" "See attached" "+1h" -a report.pdf

outlook schedule-draft 3 "+1h"            # schedule an existing draft
outlook schedule-draft 3 "tomorrow 09:00" # schedule reply draft for morning

outlook schedule-list                     # list scheduled emails
outlook schedule-list --json

outlook schedule-cancel 1                 # cancel by list number
outlook schedule-cancel 1 -y              # skip confirmation

Time formats: +30m, +1h, +2h30m, today 17:00, tomorrow 09:00, 2026-03-15T10:00.

Folders

outlook folders                        # list folders with counts
outlook folder Archive -n 20           # messages in a folder
outlook folder Archive --category "Urgent"  # filter by category
outlook move 3 Archive                 # move message to folder
outlook move 3 4 5 Archive             # move multiple messages

Categories

outlook categories                         # list categories with counts
outlook categorize 3 "FYI"                 # add category to message
outlook categorize 3 4 5 "FYI"             # add to multiple messages
outlook uncategorize 3 "FYI"               # remove category from message
outlook uncategorize 3 4 5 "FYI"           # remove from multiple messages
outlook category-create "New Category"     # create master category
outlook category-create "Urgent" --color 0 # create with color (0-24)
outlook category-rename "FYI" "Info"       # rename + update all messages
outlook category-rename "FYI" "Info" --no-propagate  # master list only
outlook category-clear "FYI"               # remove category from all messages
outlook category-clear "FYI" -n 20         # remove from max 20 messages
outlook category-clear "FYI" --folder Inbox # remove only in Inbox
outlook category-delete "Old" -y           # delete master + clear all messages
outlook category-delete "Old" --no-propagate -y  # delete master only

Signatures

outlook signature-pull -n MySignature  # extract signature from sent emails
outlook signature-list                 # list saved signatures
outlook signature-show MySignature     # preview a signature
outlook signature-delete MySignature   # delete a saved signature

Signatures are saved as HTML in ~/.config/outlook-cli/signatures/. Set a default in config:

default_signature: MySignature

Management

outlook mark-read 3              # mark as read
outlook mark-read 3 4 5          # mark multiple as read
outlook mark-read 3 --unread     # mark as unread
outlook delete 3                 # delete (with confirmation)
outlook delete 3 4 5 -y          # delete multiple without confirmation
outlook flag 3                   # flag for follow-up
outlook flag 3 --due tomorrow    # flag with due date
outlook flag 3 --due 2026-03-20  # flag with specific date
outlook flag 3 --due +3d         # flag due in 3 days
outlook flag 3 --complete        # mark flag as complete
outlook flag 3 --clear           # remove flag
outlook pin 3                    # pin to top of inbox
outlook pin 3 4 5                # pin multiple
outlook pin 3 --unpin            # unpin

Calendar

outlook calendar                          # next 7 days
outlook calendar --days 14                # next 14 days
outlook calendar --calendar "John Smith"  # view a shared calendar

Events

outlook event 42                          # view event details (attendees, recurrence, etc.)

# Create
outlook event-create "Meeting" "2026-03-16 10:00" "2026-03-16 11:00"
outlook event-create "Meeting" "tomorrow 14:00" "+1h" \
  -a [e-mail] -a [e-mail] \
  -l "Room A" -b "Agenda: Q1 review" -y
outlook event-create "Standup" "2026-03-16 09:00" "2026-03-16 09:30" \
  --teams -a [e-mail]               # Teams online meeting

# Recurring events
outlook event-create "Weekly Sync" "2026-03-16 10:00" "2026-03-16 11:00" \
  --repeat weekly --repeat-count 8 -a [e-mail]
outlook event-create "Daily Standup" "2026-03-16 09:00" "2026-03-16 09:15" \
  --repeat daily --repeat-until 2026-04-30
outlook event-create "Sprint Review" "2026-03-16 14:00" "2026-03-16 15:00" \
  --repeat weekly --repeat-days Monday,Wednesday --repeat-count 12
outlook event-create "Monthly Report" "2026-03-16 10:00" "2026-03-16 11:00" \
  --repeat monthly --repeat-count 6

# Update
outlook event-update 42 --subject "New Title"
outlook event-update 42 --start "2026-03-16 14:00" --end "2026-03-16 15:00"
outlook event-update 42 --location "Room B"
outlook event-update 42 --add-attendee [e-mail]
outlook event-update 42 --remove-attendee [e-mail]

# Delete
outlook event-delete 42                    # delete single event/occurrence
outlook event-delete 42 --series           # delete entire recurring series
outlook event-delete 42 43 44 -y           # delete multiple

# Respond to invitations
outlook event-respond 42 accept
outlook event-respond 42 decline --comment "Can't make it"
outlook event-respond 42 tentative --silent  # don't notify organizer

# Recurring event instances
outlook event-instances 42                 # list all occurrences (90 days)
outlook event-instances 42 --days 180      # look further ahead

Calendars / Free-Busy / People

outlook calendars                          # list all calendars (own + shared)

outlook free-busy "[e-mail]" tomorrow
outlook free-busy "[e-mail],[e-mail]" 2026-03-16 -d 30   # 30-min slots

outlook people-search "john"               # find people for attendee autocomplete
outlook people-search "john" --max 5

Attachments / Contacts

outlook attachments 3          # list attachments
outlook attachments 3 -d       # download all
outlook contacts

JSON Output

Auto-JSON on pipe: When stdout is piped, JSON output is automatic — no --json flag needed.

outlook inbox | jq '.data[0].subject'        # auto-JSON when piped
outlook inbox --json                          # explicit JSON in terminal
outlook inbox --json -o emails.json           # save to file

All JSON output uses a structured envelope:

{"ok": true, "schema_version": "1", "data": [...]}

How It Works

1. outlook login opens Chromium via Playwright
2. Intercepts the OWA bearer token from network requests
3. Uses the token against Outlook REST API v2 (outlook.office.com/api/v2.0/)
4. Category management and message pinning use OWA service.svc (reverse-engineered internal endpoints)
5. Messages get short display numbers (#1, #2...) mapped to real Outlook IDs
6. Auto re-login on token expiry via cached browser SSO state

Security Notice

This tool caches sensitive authentication data on your local machine:

• Bearer token (~/.cache/outlook-cli/token.json) — grants full access to your mailbox, calendar, and contacts until it expires. Protect this file as you would a password.
• Browser session state (~/.cache/outlook-cli/browser-state.json) — contains cookies and SSO state that can be used to obtain new tokens without re-authentication.

Both files are created with 600 permissions (owner-only read/write) on Unix systems. Never share these files or commit them to version control.

To revoke access, delete the cache directory:

rm -rf ~/.cache/outlook-cli/

Undocumented API Notice

Category management commands (categories, category-create, category-delete, category-rename) and the pin command use a reverse-engineered OWA internal endpoint (service.svc) that is not a public or documented Microsoft API. These endpoints may change or stop working at any time without notice. All other commands use the Outlook REST API v2.0, which is a documented (though deprecated in favor of Microsoft Graph) API.

Config

~/.config/outlook-cli/config.yaml:

max_messages: 25
default_folder: Inbox
default_signature: null       # set to signature name for auto-append
timezone: UTC                 # Microsoft timezone ID for calendar operations
browser:
  headless: false
  timeout: 120
output_format: table

Development

git clone https://github.com/yusufaltunbicak/outlook-cli.git
cd outlook-cli
pip install -e ".[dev]"
playwright install chromium
pytest