Author profile
Caleb Geene
Director, Site Reliability Engineering
Caleb focuses on reliability, infrastructure, and production safety for Nylas systems. His guides cover secure agent access, operational guardrails, and failure modes that matter when email automation reaches production.
Areas of expertise
- Site Reliability
- Infrastructure
- DevOps
- Cloud Architecture
Profiles
Guides on this site
- Calendar Invite Prompt Injection Defense
Calendar invites land in an AI agent's context without any click. Defend with organizer allowlists, metadata-first triage, human-run RSVPs, and audit logs.
- Email API SLAs: Uptime vs Success Rate
What a 99.99% email API SLA guarantees: uptime vs success-rate measurement, downtime math per tier, error budgets, and CLI checks to verify reliability.
- Contacts API: Google vs Microsoft vs CardDAV
Compare Google People API, Microsoft Graph Contacts, and CardDAV (RFC 6352). Auth, CRUD, search, sync, rate limits, and a decision matrix for choosing.
- Manage a Shared Mailbox from Terminal
Read, send, and manage shared mailbox email from the command line. Switch between personal and team grants, list messages, and send replies as the team address.
- Automate Meeting Notes to Email
Record meetings, generate AI summaries from transcripts, and email notes to attendees automatically. Combines notetaker bots with scheduled email sends.
- Microsoft Graph Email API Quick Start
Send and read email with Microsoft Graph API. App registration, OAuth 2.0 scopes, delegated vs app-only auth, and error fixes for common 403 and 401 codes.
- Best CLI Calendar Tools Compared
Compare gcalcli, khal, calcurse, remind, vdirsyncer, and Nylas CLI for terminal calendar management. Features, providers, sync, and installation.
- AgentMail vs Nylas vs Cloudflare Email
Compare AgentMail, Cloudflare Email for Agents, and Nylas Agent Accounts. Feature matrix, pricing, MCP support, and a decision guide for AI agent email in 2026.
- Email Prompt Injection Defense
Defend AI email agents against prompt injection attacks. Input separation, capability sandboxing, human-in-the-loop approvals, and audit logging patterns.
- IMAP vs Gmail API vs Graph API
Compare IMAP, Gmail API, and Microsoft Graph for email integration. Auth, search, push, rate limits, and code examples — plus a protocol decision matrix.
- Stop Your AI Agent From Going Rogue
Terminate rogue AI agent sessions at the connector layer. Outbound blocks, auto-reply kill switches, and prompt-injection containment — all before SMTP.
- EWS to Microsoft Graph Migration
EWS is blocked October 1, 2026. Migrate Exchange Web Services to Microsoft Graph API or skip both with a unified CLI. Timeline, auth changes, and feature gaps.