Sendmail — prepare an Outlook draft

Compose an outgoing message in Microsoft Outlook (macOS) and open it for the user to review. Never send.

Invocation contract

Arguments provided: $ARGUMENTS

The arguments must contain at least one email address. Parse as follows:

• Recipients — every token matching an email address (local@domain.tld), in order of appearance. The first one or more addresses are To: recipients.
• Remainder — everything left after removing the addresses. This is the body spec.
• No address found → stop. Say only: Need an email address. Do not run osascript, do not guess a recipient.
• No remainder → ask the user once what the mail should say. Do not invent a body.

Body spec: literal or assignment

Decide which of the two the remainder is:

• Literal body — a finished message the user wants sent verbatim (e.g. 'Today it is Thursday'). Use it as-is; do not embellish, do not add paragraphs the user did not write.
• Assignment — an instruction about what to write (e.g. 'ask Kim for the Q3 numbers', 'summarize what we just fixed'). Write the body yourself, drawing on the current conversation context.

When it is ambiguous, treat it as a literal body — under-writing is recoverable in the draft, over-writing is not.

Assignment-written bodies:

• Short. A greeting, one to three short paragraphs, a sign-off.
• Only facts established in the conversation or given in the arguments. No invented numbers, dates, names, links, or commitments.
• Sign off with the user's first name from git config user.name if that returns a value; otherwise no sign-off.

Subject

Derive it — the user does not pass one. Rules:

• Short noun phrase, ~3-8 words, specific to this mail's content. No trailing period, no Re:, no [skill]-style prefixes.
• If the literal body is one short line, the subject may restate it (Today it is Thursday).
• If the user's arguments explicitly name a subject (subject: X, or --subject X), use that verbatim instead.

Escaping — do this before building the script

content is HTML, and both subject and content are AppleScript string literals. In that order, per field:

1. \ → \\
2. " → \"
3. In content only: each newline → <br>, and a blank line → <br><br>. A literal newline inside an AppleScript string is a syntax error.
4. Non-ASCII characters → HTML entities in content (é → é, — → —). Keep subject plain ASCII; transliterate if needed.
5. In content only: escape HTML-significant characters the user typed as text — & → &, < → <, > → > — unless the user clearly intended HTML markup.

Script

Write the AppleScript to a file in the session scratchpad directory (fall back to "$TMPDIR") and run it with osascript. Do not pipe a heredoc through the shell — the shell adds a second layer of quoting to get wrong.

cat > "$SCRATCH/sendmail.scpt" <<'EOF'
tell application "Microsoft Outlook"
  set msg to make new outgoing message with properties {subject:"SUBJECT", content:"BODY_HTML"}
  tell msg
    make new recipient at end of to recipients ¬
      with properties {email address:{name:"ADDRESS", address:"ADDRESS"}}
  end tell
  open msg
  activate
end tell
EOF
osascript "$SCRATCH/sendmail.scpt"

• Replace SUBJECT, BODY_HTML, ADDRESS with the escaped values. Set name to the address itself unless the user supplied a display name ("Kim" <kim@example.com> → name:"Kim").
• Multiple recipients: repeat the whole make new recipient ... end block, one per address, inside the same tell msg.
• Keep open msg and activate. Never emit send msg — not even when the arguments say "send it". Preparing a reviewable draft is the whole contract of this skill; if the user wants it sent, they click Send.
• ¬ is the AppleScript line-continuation character. Keep it, or put the with properties clause on one line.

After running

Report in at most two lines: the recipients, and the subject used. Do not reprint the body — it is on screen in Outlook.

If osascript errors, show the error verbatim and stop. Common causes: Outlook not running (it launches on activate, but a cold start can time out — retry once), or the terminal lacking Automation permission for Outlook in System Settings → Privacy & Security → Automation.

Guardrails

• One draft per invocation. No loops over a recipient list, no bcc-style fan-out.
• Do not attach files, add cc/bcc recipients, or set flags unless the user asked in the arguments.
• Content leaves the machine the moment the user clicks Send: keep secrets, credentials, and tokens out of the body, and say so instead of including them if the conversation context contains any.