send-email

Critical Constraints

• Recipient is hardcoded. [your-email]. Cannot be changed. Cannot email anyone else.
• Rate limit: 3 emails per calendar day. Exit code 2 = rate limit hit. Do not retry.
• From address: Jules <playbook@[previous-domain]> (verified Resend sender, still active post-rebrand).

Sending Email

Two paths: HTML (rich formatting via markdown pipeline) and plain text (quick notifications).

HTML email (structured content, reports, summaries)

Pipe markdown through build-digest-email.sh into jules-send-email.sh:

echo "## Summary\n\n- Point one\n- Point two\n\n**Key takeaway:** Thing." \
  | bash .claude/scripts/build-digest-email.sh "Report Title" \
  | bash .claude/scripts/jules-send-email.sh --subject "Subject Line" --html -

build-digest-email.sh converts markdown to branded HTML with the caramel/cream template. Pass the report title as the first argument (appears in the header bar). Reads markdown from stdin, outputs HTML to stdout.

Plain text email (quick notes, reminders, notifications)

bash .claude/scripts/jules-send-email.sh --subject "Reminder" --body "Follow up with Michael from AITX this week."

HTML from a file

bash .claude/scripts/jules-send-email.sh --subject "Subject" --html /path/to/body.html

Dry run (preview without sending)

bash .claude/scripts/jules-send-email.sh --subject "Test" --body "anything" --dry-run

Shows recipient, from address, subject, and today's send count. Does not consume a send.

When to Use HTML vs Plain Text

Content	Path
Session notes, briefings, reports, summaries	HTML (markdown pipeline)
Simple reminders, quick notifications, one-liners	Plain text (--body)
Anything with headers, lists, tables, or code blocks	HTML (markdown pipeline)

Rate Limit Check

Before sending, check how many emails have been sent today:

grep -c "\"date\":\"$(date +%Y-%m-%d)\"" ~/.claude/email-send-log.jsonl 2>/dev/null || echo 0

Report to user: "X/3 emails sent today."

If at 3/3, inform the user the limit is hit and suggest Slack as an alternative.

Composing Guidance

• Subject lines: Specific and scannable. "Session Notes: Quiz Migration" not "Update". [Your Name] filters by subject.
• Markdown content: Write clean markdown. build-digest-email.sh handles conversion. Tables, code blocks, headers, lists all work.
• Length: No hard limit, but emails should be scannable. Use headers to break up long content.
• When writing raw HTML (not using the markdown pipeline): consult references/html-best-practices.md for email client CSS constraints.

Error Handling

Exit Code	Meaning	Action
0	Sent successfully	Report the email ID and today's count
1	Missing args, API key not found, or HTTP error	Check the error message. API key: container has RESEND_API_KEY in env; Mac uses 1Password (op://Dev Secrets/Quiz App - All Env/RESEND_API_KEY)
2	Daily rate limit (3/day) reached	Inform user. Suggest Slack. Do not retry.

API Key Resolution

The send script uses RESEND_API_KEY from the environment. The overnight batch injects it via op read at startup. For manual runs, the service account token in the shell environment handles it automatically.

No manual key handling needed.

Send Log

Every send (success or failure) is logged to ~/.claude/email-send-log.jsonl. Each entry includes date, time, subject, HTTP status, and today's count. This is the rate limiter's data source.