macOS Personal AI Email Assistant — Apple Mail Triage + Calendar/iMessage Automation (local-first)

Posted 5 days ago

Worldwide

Summary

I'm looking for a strong macOS automation engineer to build (and harden) a local-first personal assistant that runs on my Mac and keeps my email, calendar, and messages triaged automatically. A working prototype already exists — I need someone to turn it into something reliable, maintainable, and extensible. The core idea: the inbox is a to-do list, not a filing cabinet. Across all my accounts, incoming mail should be auto-classified into a single color-coded priority view that syncs to my iPhone — without me sorting anything by hand. What's already prototyped (works, but brittle): Apple Mail flag-based triage across ~6 accounts (personal Gmail, Google Workspace, and corporate Exchange/Outlook), driven by AppleScript Classification logic: sender type (real human vs automated), To vs CC (sent directly to me = higher priority than CC'd on a thread), and financial/transactional detection A color scheme that maps to actions: Red = act now, Orange = reply needed, Yellow = waiting on someone, Green = financial, Blue = automated/review Calendar mirroring (corporate Exchange calendars → an iCloud calendar so they appear on my iPhone), running on a schedule via launchd Early iMessage awareness (surface texts needing a reply; weekly spam sweep) What I need built: Reliable "new mail" triage engine. Classify only newly arrived mail in Apple Mail and apply the correct flag — event-driven or efficient polling, not a fragile full-inbox re-scan. Must not choke on large mailboxes (I have accounts with 800+ messages). Robust classification. Combine deterministic rules with an LLM (I use Claude) for the judgment calls, with a clean rules fallback when the model is unavailable. Easy for me to correct a miscategorized email and have the rule adjust. Cross-account unified priority view that syncs to iPhone (built on Apple Mail flags, since smart mailboxes don't sync). Calendar sync — productionize the Exchange→iCloud mirror (idempotent, no duplicates, handles updates/cancellations). iMessage assistant — on-demand "what needs a reply?" and a weekly spam-surfacing sweep (surface only; never auto-send or delete). Scheduling + logging + recovery — launchd/cron jobs that are observable, log clearly, and fail safe. Hard requirements (non-negotiable): Local-first / privacy-preserving. Corporate mail must stay native on the machine — no routing work email through third-party servers (no SaneBox-style cloud relays for the managed accounts). Never destructive. The system may flag, archive, and mark-read — it must never delete, send, reply, or forward without my explicit approval. Everything must sync correctly to iPhone (flags, archive, read state). Tech environment: macOS (Apple Mail, Calendar, Messages) · AppleScript/JXA · launchd · Node.js · MCP (Model Context Protocol) servers · Claude API. I'm technical (senior Salesforce admin/developer), so you can talk to me directly about architecture.

  • Less than 30 hrs/week
    Hourly
  • < 1 month
    Duration
  • Intermediate
    Experience Level
  • $40.00

    -

    $100.00

    Hourly
  • Remote Job
  • One-time project
    Project Type
  • Contract-to-hire
    This job has the potential to turn into a full time role
Skills and Expertise
Mandatory skills
Email Communication
Automation
Nice-to-have skills
PHP
Activity on this job
  • Proposals:20 to 50
  • Last viewed by client:2 days ago
  • Interviewing:
    0
  • Invites sent:
    0
  • Unanswered invites:
    0
About the client
Member since Jun 24, 2026
  • United States
    1:33 AM
  • Tech & IT
    Individual client

Explore similar jobs on Upwork

Tesla Powerwall 3 InstallationFixed-price‐ Posted 3 weeks ago
Linux System Administration
PHP
MySQL
Web Development
SEO Specialist neededHourly‐ Posted 3 weeks ago
SEO Content
SEO Competitor Analysis
SEO Keyword Research
SEO Performance

How it works

  • Post a job icon
    Create your free profile
    Highlight your skills and experience, show your portfolio, and set your ideal pay rate.
  • Talent comes to you icon
    Work the way you want
    Apply for jobs, create easy-to-by projects, or access exclusive opportunities that come to you.
  • Payment simplified icon
    Get paid securely
    From contract to payment, we help you work safely and get paid securely.
Want to get started? Create a profile

About Upwork

  • Rating is 4.9 out of 5.
    4.9/5
    (Average rating of clients by professionals)
  • G2 2021
    #1 freelance platform
  • 49,000+
    Signed contract every week
  • $2.3B
    Freelancers earned on Upwork in 2020

Find the best freelance jobs

Growing your career is as easy as creating a free profile and finding work like this that fits your skills.

Trusted by

  • Microsoft Logo
  • Airbnb Logo
  • Bissell Logo
  • GoDaddy Logo