Tuesday, December 23, 2025

Show HN: Skyler – AI Email Organizer Closes Due to OAuth Compliance Issues

Discover Skyler: An AI-Powered Email Organizer

I built Skyler, an innovative email organizer that prioritizes privacy and uses semantic search technology. Live for a few months, it faced challenges that led to its shutdown due to compliance requirements from Google.

Key Features:

  • Privacy-First Design: Utilized client-side caching and minimal server storage.
  • AI/ML Integration: Powered by advanced models for sentiment analysis and semantic search.
  • Robust Tech Stack:
    • Frontend: Next.js, NextAuth, Tailwind
    • Backend: Express (TypeScript), Prisma, Supabase
    • Infrastructure: Docker and Nginx

Challenges Faced:

  • Navigating Gmail OAuth token refresh issues and rate limits.
  • Overcoming CASA compliance hurdles for user certification.
  • Integrating payment solutions for the Indian market.

While the infrastructure was sound, the compliance burden proved too much for a solo MVP.

💬 Explore the open-source code and watch the demo video here. I’m open to discussing the journey!

👉 If you find this valuable, please share your thoughts and experiences!

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