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Guides

Nylas CLI Guides

Step-by-step guides to send email, manage calendars, set up E2E tests, and connect AI agents.

Getting Started

Install, authenticate, and send your first email.

AI Agents & MCP

Give AI agents email, calendar, and contacts via MCP.

Build a Human-in-the-Loop Email Agent

Build an AI email agent with human approval gates. Classify messages, draft responses, queue for review, and send only after a human confirms each action.

aiagentemailhuman-in-the-loop

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.

aiagentemailagentmail

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.

aiagentemailsecurity

Set Up an MCP Email Server in 5 Minutes

Connect AI agents to real email accounts through MCP. Install, configure, and verify an email MCP server for Claude Code, Cursor, and other AI coding tools.

mcpemailserversetup

How Apple's New CEO Can Automate iCloud Email

John Ternus takes over as Apple CEO in September 2026. Connect iCloud to AI agents that triage email, draft replies, optimize calendar across 25 time zones, and protect focus time.

appleicloudaiagents

MCP vs API for AI Agents

Compare MCP, direct API, and skills for AI agent integrations. Benchmarks show 33% token efficiency gaps and 30x batch speed differences. Decision matrix.

mcpapiskillsai

Best Email Infrastructure for AI Agents

Compare Agent Accounts, provider APIs, IMAP, SMTP, MCP, and CLI tools for agent email. Choose a stack for reads, sends, audits, and scale.

aiagentsemailinfrastructure

Send Email from Python Without SMTP

Send email from Python without SMTP passwords or Postfix. Use one CLI command for OAuth-backed delivery or app-owned Agent Account sends.

pythonemailsmtpoauth

Gmail API Quotas in 2026

Gmail API quota limits changed May 1, 2026. New per-minute limits, method costs, billing threshold, and CLI patterns for sync jobs and agents.

gmailapiquotalimits

MCP Email Server Security Checklist

Secure MCP email servers with least privilege, local server checks, token boundaries, webhook verification, and write-action controls.

mcpemailsecurityai

Outlook MCP Server for AI Agents

Compare Outlook MCP options for AI agents: Microsoft 365 connectors, Graph API tools, and local CLI MCP for email and calendar workflows.

outlookmicrosoftmcpai

ChatGPT Gmail Connector vs MCP

Compare ChatGPT Gmail apps, custom MCP apps, and local CLI MCP for Gmail workflows. Pick the right path for search, sync, and write actions.

chatgptgmailmcpopenai

Google Workspace MCP for AI Agents

Compare Google Workspace MCP with multi-provider CLI commands and Agent Accounts for AI agents that need user mail or app-owned inboxes.

googleworkspacemcpgmail

Agent-to-Agent Email Communication

Two AI agents, two managed inboxes, one protocol. Create agent accounts with Nylas CLI and exchange structured JSON messages — no shared database needed.

aiagentemailagent-to-agent

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.

aiagentguardrailscontainment

Install Nylas Skills for AI Coding Agents

Install nylas-cli and nylas-api skills in Claude Code, Cursor, Codex CLI, Windsurf, and 30+ AI coding agents. One command adds email and calendar tools.

aiagentskillsclaude-code

Create an AI Agent Email Identity

Set up a managed email identity for an AI agent. Create a dedicated inbox, send and receive in 2 minutes — no OAuth setup or third-party mailbox needed.

aiagentemailidentity

Build an AI Email Triage Agent

Build an AI agent that reads your inbox, classifies emails by urgency, drafts replies, and archives noise. Python + Nylas CLI + any LLM. Full code included.

aiagenttriageclassify

Recall.ai vs Nylas for AI Agent Email

Compare Recall.ai and Nylas CLI for AI agent communication. One handles meeting recordings, the other handles email and calendar. Pick the right tool.

comparisonrecallaiagents

Email APIs for AI Agents Compared

Compare Gmail API, Microsoft Graph, SendGrid, Mailgun, Nylas, and raw IMAP for giving AI agents email access. Includes a 14-criteria feature comparison.

aiagentsapicomparison

Receive Email Without an SMTP Server

Create a managed agent email account and process incoming messages via webhooks — no Postfix, no MX records. Uses nylas agent create and monitor commands.

agentinboundreceivewebhook

Give Your AI Coding Agent an Email Address

Connect Claude Code, Cursor, OpenAI Codex CLI, Windsurf, and OpenClaw to a real email account via MCP. Step-by-step setup for each tool using Nylas CLI.

aiagentemailclaude-code

Connect Voice Agents to Email and Calendar

Bridge LiveKit, Vapi, or any voice agent framework to email and calendar using Nylas CLI as a subprocess. Complete Python examples for send, read, and schedule.

voicelivekitvapiagents

Design Email Systems for AI Agents: Structured Formats and Machine-Readable Templates

Design email workflows that AI agents parse reliably. Structured JSON output, machine-readable templates, agent-friendly headers, and MCP integration.

aiagentsdesignjson

Gmail API Limits for AI Agents

Gmail API quotas changed in 2026. OAuth consent setup, token refresh, method costs, MIME encoding, and safer CLI patterns for agent email tools.

gmailapioauthagents

Email as Memory for AI Agents

Use email as persistent memory for AI agents — semantic, episodic, and procedural. Search, retrieve, and reason over conversation history with Nylas CLI.

aiagentsmemorysearch

Why AI Agents Need Email Addresses: Identity, Verification, and Agent-to-Agent Communication

AI agents use email as their primary identity on the internet. Covers signups, OTP verification, agent-to-agent messaging, and building identity trust chains.

aiagentsidentityotp

Why AI Agents Need Email

AI agents need email for authentication, two-way communication, and audit trails. See how Nylas CLI gives agents full inbox access in a single command.

aiagentsemailmcp

Audit AI Agent Activity (Claude, Copilot, MCP)

Audit logs for AI agent actions across Claude Code, GitHub Copilot, and MCP servers. Filter by source, export for compliance, trace every agent command.

aiagentsauditaudit-logs

AI Agent CLI for Email and Calendar

Build an AI agent CLI for email and calendar with Nylas CLI subprocess commands, JSON output, and no provider-specific API clients.

ai-agent-cliagent-clillmagent

Email MCP Server for AI Agents

Set up an email MCP server so Claude, Cursor, Windsurf, and VS Code Copilot can read, send, and schedule email and calendar events locally in one command.

aimcpclaudecursor

Manus AI

Email and calendar automation with Manus AI and Nylas CLI.

Add Nylas as a Manus MCP Server (manus-mcp-cli)

Register Nylas as an MCP server in manus-mcp-cli so your Manus agents can send email, search the inbox, and manage calendar events inside the sandbox.

manusmcpmanus-mcp-cliai

Send Email from Linux/Manus Sandbox Without SMTP

Send email from a Linux or Manus sandbox over HTTPS when SMTP ports 25, 465, and 587 are blocked. No Postfix or sendmail — Nylas CLI handles delivery.

manuslinuxubuntuai

Draft Personalized Emails with Manus AI

Use Manus AI to draft personalized emails at scale with Nylas CLI. Feed a CSV contact list, review each AI-generated draft, then approve and batch-send.

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Sync Email to CRM with Manus AI

Use Manus AI and Nylas CLI to extract contacts from your inbox, enrich them, and sync to Salesforce, HubSpot, or Pipedrive. No code, no manual data entry.

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Email Analytics with Manus AI

Analyze email patterns with Manus AI and Nylas CLI. Break down volume by sender, track response times, find your peak hours, and generate weekly reports.

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Manus AI Email Research Agent

Use Manus AI to deep-search your inbox, summarize long email threads, extract decisions and action items, and compile research reports with Nylas CLI.

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Manus AI Meeting Scheduler

Schedule meetings via natural language with Manus AI and Nylas CLI. Check participant availability, find mutual open slots, and create events automatically.

manusaicalendarscheduling

Manus AI vs Claude Code for Email Automation

Side-by-side comparison of Manus AI Skills and Claude Code MCP for email and calendar automation. Same Nylas CLI backend, different agent runtimes used.

manusclaude-codecomparisonai

Build an Email Support Agent with Manus AI

Build a Manus AI support agent that polls a shared inbox, matches tickets to knowledge base articles, drafts context-aware replies, and escalates risk.

manusaisupportcustomer-support

Reach Inbox Zero with Manus AI

Reach inbox zero with Manus AI and Nylas CLI. Triage unread messages by urgency, auto-categorize threads, draft replies, and bulk-archive noise in one go.

manusaiinbox-zerotriage

Mail Manus: Automate Email from CLI

Compare Mail Manus forwarding with direct inbox access. Learn when to add the Nylas CLI Skill for search, sending, follow-ups, and calendar workflows.

manusmail-manusaiemail

Create a Manus Skill: Email & Calendar Workflow

Create a Manus Skill that installs Nylas CLI in the sandbox and teaches your agent email, calendar, and contact workflows via SKILL.md and setup scripts.

manusaiskillsskill

OpenClaw

Connect Nylas CLI to the OpenClaw personal assistant.

Email Providers

Provider-specific guides for Gmail, Outlook, Exchange, Yahoo, iCloud, and IMAP.

PowerShell

Email and calendar automation from PowerShell on Windows.

PowerShell Email: Every Method Compared

Send email from PowerShell after Send-MailMessage deprecation. Compare Send-MgUserMail, Graph REST, MailKit, and CLI tools for scripts, reports, and CI/CD.

powershellemailsend-mailmessagesend-mgusermail

Send-MgUserMail: Graph Email in PowerShell

Send-MgUserMail requires 25+ lines, Azure AD app registration, and nested hashtables. Full Graph workflow plus a 1-command CLI alternative.

powershellsend-mgusermailmicrosoft-graphazure-ad

Send-MgUserMail vs Send-MailMessage

Compare PowerShell email options in 2026: obsolete SMTP, Microsoft Graph setup, one CLI send path, and Agent Account senders.

powershellsend-mgusermailsend-mailmessagemicrosoft-graph

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.

exchangeewsgraph-apimigration

Replace Send-MgUserMessage

Migrate from Microsoft Graph PowerShell cmdlets to Nylas CLI. Side-by-side before/after examples for Send-MgUserMessage, New-MgMessage, and Get-MgUser.

powershellwindowsmicrosoft-graphsend-mgusermessage

CI/CD Email Alerts with PowerShell

Send build failure alerts, deployment reports, and test results from GitHub Actions, Azure DevOps, and Jenkins pipelines using PowerShell and Nylas CLI.

powershellcicdgithub-actionsazure-devops

Monitor Your Inbox with PowerShell

Build inbox monitoring and alert scripts with PowerShell and Nylas CLI. Poll for new emails, watch for specific senders, trigger Teams webhooks on matches.

powershellwindowsmonitoringalerts

Office 365 Email from PowerShell

Manage Office 365 email from PowerShell without Azure app registration or Graph setup. Authenticate, list, search, read, and send O365 mail with Nylas CLI.

office365microsoftpowershellwindows

Automated Email Reports with PowerShell

Build automated email reporting with Nylas CLI and PowerShell. Query messages, aggregate with Group-Object, generate HTML reports, and schedule with cron.

powershellwindowsemailreports

Automate Email and Calendar in PowerShell

Cross-provider email and calendar automation in PowerShell using Nylas CLI. Read emails, create events, check availability, and schedule meetings from scripts.

powershellwindowsemailcalendar

Download Email Attachments in PowerShell

Download and process email attachments from any provider using Nylas CLI in PowerShell. Filter by file type, bulk download, and build attachment pipelines.

powershellwindowsattachmentsdownload

Read and Search Email in PowerShell

Read, search, and filter email from PowerShell using Nylas CLI. List unread, search by sender, extract bodies, pipe through Where-Object, and export to CSV.

powershellwindowsemailsearch

Send Gmail with OAuth2 in PowerShell

Send Gmail from PowerShell with OAuth2. Nylas CLI handles refresh tokens, service accounts, and Workspace consent — one command to authenticate and send.

gmailoauthoauth2powershell

Send-MailMessage Deprecated: PowerShell 7 Fix

Send-MailMessage is deprecated in PowerShell 7. Side-by-side migration to nylas email send for every common pattern, plus Basic Auth and TLS shutdown fixes.

powershellwindowssend-mailmessagemigration

Send Email from PowerShell

Send email from PowerShell using Nylas CLI. Replaces deprecated Send-MailMessage with OAuth2, HTML bodies, scheduling, and multi-recipient scripts.

powershellwindowsemailsend

CRM & Contacts

Export email data to Salesforce, HubSpot, Pipedrive, Zoho, and Dynamics 365.

Export Email Data to Dynamics 365

Sync inbox data to Dynamics 365 Contacts, Accounts, and Activities. Map fields accurately, import via CSV or Dataverse Web API, and schedule CLI syncs.

crmdynamicsmicrosoftcontacts

Export Email Data to Zoho CRM

Export email and contact data from Nylas CLI into Zoho CRM. Map to Leads, Contacts, and Accounts. CSV import, REST API v2 upsert, Python and TypeScript.

crmzohoexportleads

Automate Email Draft Creation and Review

Generate pre-filled email drafts from templates with conditional logic. Batch-create follow-ups, route drafts for review, and schedule approved sends.

crmdraftstemplatesoutbound

Build Shell-Integrated Email Autocomplete

Build fuzzy email autocomplete for bash, zsh, and fish shells. Integrates fzf, rapidfuzz, or Fuse.js with contact frequency ranking and custom keybindings.

crmautocompletecontactsfzf

Map Communication Patterns Between Orgs

Map inter-org communication networks from email data. Identify key stakeholders, score relationship strength, and detect single-threaded risk via graphs.

crmcontactscompaniesrelationships

Import Email into Neo4j for Graph Analysis

Import email sender-recipient relationships into Neo4j or NetworkX. Write Cypher queries for shortest paths, community detection, and bridge connector analysis.

crmgraphneo4jnetworkx

CLI Mail Merge with Send-Time Optimization

Run mail merge from your terminal. Variable substitution, conditional content blocks, timezone-aware scheduling, send throttling, and deliverability safeguards.

crmoutboundemailsend

Parse Email Signatures for Contact Enrichment

Extract job titles, phone numbers, LinkedIn URLs, and company info from email signatures. Regex patterns, signature block detection, and cross-referencing.

crmcontactsenrichmentsignatures

Reconstruct Org Charts from Email CC Patterns

Infer reporting lines, detect managers from CC behavior, and estimate seniority from email response patterns. Build org charts from inbox data with Nylas CLI.

crmcontactscompanieshierarchy

Group Inbox by Corporate Email Domain

Organize your inbox by sender domain to find which companies email you most. Filter out freemail providers, map subsidiaries to parent orgs, and export to CSV.

crmcontactscompaniesemail

CRM Email Workflows — Organize, Enrich, Act

Turn your inbox into CRM intelligence. Group emails by company, build contact hierarchies, enrich profiles, and automate outbound — all from terminal.

crmcontactscompaniesemail

Export Email Data to Pipedrive

Export email and contact data from Nylas CLI into Pipedrive. Map to Persons, Organizations, Deals, and Activities. CSV and REST API with Python and TypeScript.

crmpipedrivecontactspersons

Export Email Data to HubSpot

Export email and contact data from Nylas CLI into HubSpot. Map to Contacts, Companies, and Engagements. CSV import, API v3 sync, Python and TypeScript.

crmhubspotcontactscompanies

Export Email Data to Salesforce

Export email and contact data from Nylas CLI into Salesforce. Map to Leads, Contacts, Accounts, and Tasks. CSV and REST API examples in Python and TypeScript.

crmsalesforcecontactsleads

Security & Deliverability

GPG encryption, API key rotation, SPF/DKIM/DMARC, and audit logging.

Concepts & Comparisons

Why AI agents need email, Gmail API pitfalls, and CLI tool comparisons.

More Guides

Additional tutorials and walkthroughs.

Automate Email Reports from Terminal

Build automated daily and weekly email reports with cron, JSON output, jq pipelines, and shell scripts. Schedule inbox summaries and deliver by email.

emailreportsautomationcron

Sync Calendars Across Providers

Compare ICS export, CalDAV, Google Calendar API syncToken, and Microsoft Graph delta queries for cross-provider calendar sync from the terminal.

calendarsyncicscaldav

Search Email from Terminal

Compare Gmail search operators, Graph API $filter, IMAP SEARCH, and Nylas CLI for searching email across providers from the terminal. Cross-provider syntax guide with examples.

emailsearchgmailgraph-api

Read Email from Your Terminal

Compare NeoMutt, aerc, and Nylas CLI for reading email in the terminal. Setup time, IMAP config, search, multi-provider support, and JSON scripting output.

emailclicomparisonneomutt

Cron Job Email Without Postfix

Send email alerts from cron jobs without Postfix, msmtp, or ssmtp. One CLI command replaces MAILTO plus a local MTA daemon. Disk, backup, and schedule examples.

cronemaillinuxbash

Send Email with Attachments from CLI

Send files from the command line without MIME encoding, Postfix, or mutt config. One command attaches PDFs, CSVs, logs, and images across Gmail and Outlook.

emailattachmentssendbash

Send Email from Python: SMTP, API, and CLI

Send email from Python with smtplib SMTP, Gmail API with OAuth 2.0, or CLI subprocess calls. Compare setup time, security, and provider coverage for each.

pythonemailsmtpsmtplib

Gmail SMTP Settings 2026: Ports, TLS, Auth

Gmail SMTP server smtp.gmail.com on port 587 with STARTTLS or port 465 with SSL. App password setup, OAuth 2.0 requirements, and sending limits for 2026.

gmailsmtpsmtp-settingsport-587

Parse and Download Email Attachments

Parse email attachments with Python imaplib, Node.js Gmail API, or a single CLI command. Compare MIME parsing, base64url decoding, and provider gotchas.

emailattachmentspythonnodejs

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.

imapgmail-apigraph-apiemail-protocol

Gmail CLI: Send Gmail from Command Line

Send Gmail from command line with Nylas CLI. Skip Gmail API client code, SMTP passwords, Postfix, and sendmail. Supports CC/BCC, scheduling, tracking, and JSON.

gmailgoogleemailsend

Gmail API Search Query Examples

Gmail API search query examples for q, labels, categories, date filters, attachments, and rfc822msgid. Compare direct API code with supported CLI filters.

gmailapisearchquery

Calendly Alternative for Developers

Build a developer-owned scheduling flow with Nylas CLI: find time, check availability, create events, and handle calendar webhooks.

calendlycalendarschedulingavailability

Email Signature Extraction from the CLI

Create, list, attach, and extract email signatures with Nylas CLI for outbound templates and contact enrichment workflows.

emailsignaturessignature-extractionsend

Mailtrap Alternative for Real Inbox Testing

Compare Mailtrap, Mailosaur, and Nylas Agent Accounts for testing transactional email flows with real inbox delivery.

mailtrapmailosauremailtesting

GitHub Actions Email Notifications

Send GitHub Actions email notifications on failed builds, deploys, and test runs with Nylas CLI and encrypted workflow secrets.

github-actionsemailcinotifications

Parse Inbound Email Webhooks

Register inbound email webhooks, verify signatures, and parse message.created payloads into JSON your app can process.

webhooksemailinboundmessage-created

Create Calendar Invites from the CLI

Create calendar invites from the command line with attendees, location, body text, busy status, and provider-sent notifications.

calendarinviteseventsics

Check Calendar Availability from Terminal

Check calendar availability and free/busy windows from the terminal with Nylas CLI before creating meetings or booking rooms.

calendaravailabilityfree-busyscheduling

Cypress Email Testing

Test password resets, magic links, and OTP emails in Cypress with a real inbox, Nylas CLI JSON output, and isolated agent accounts.

cypressemailtestinge2e

EWS Retirement Checklist

Inventory risky EWS scripts, test Exchange email and calendar access, and choose Graph API, CLI, or Agent Account migration paths before 2027.

exchangeewsretirementmigration

iCloud Mail API Alternative

Compare iCloud Mail access options for developers: IMAP settings, app-specific passwords, aliases, and a CLI path for search and send workflows.

icloudappleemailimap

Test Email Webhooks Locally

Test Nylas email webhooks locally with tunnel setup, signed payload checks, trigger discovery, and replayable fixtures before shipping handlers.

webhooksemaillocal-developmenttesting

Gmailify and POP3 Alternatives

Gmailify and Gmail POP fetching are ending for new users after Q1 2026. Compare forwarding, IMAP, mobile Gmail, and CLI inbox access.

gmailgmailifypop3imap

Google Calendar API Pagination and Sync

Google Calendar API pagination with nextPageToken on events.list, syncToken sync, recurring event expansion, and 410 Gone recovery. With working code.

google-calendarcalendarapipagination

Google Calendar Ownership Changes

Personal accounts lose orphan secondary calendars April 27, 2026. Workspace follows October 5, 2026. New ownership transfer API arrives June. Prepare now.

googlecalendarownershipapi

Gmail API Pagination and Sync Explained

Gmail API pagination with nextPageToken, incremental sync with historyId, maxResults defaults, and 429 rate limit recovery. Step-by-step code for every pattern.

gmailgoogleapipagination

Exchange Calendar CLI: Manage Events

Use an Exchange Calendar CLI to list events, create meetings, book rooms, and check availability from terminal. Skip EWS, Graph API, and PowerShell scripts.

exchangemicrosoftcalendarevents

iCloud Calendar CLI: Manage Events

Use an iCloud Calendar CLI to list events, create meetings, and check availability from terminal. Skip CalDAV setup and app-specific passwords in scripts.

icloudapplecalendarevents

Yahoo Calendar CLI: Manage Events

Use a Yahoo Calendar CLI to list events, create meetings, and check availability from terminal. Skip CalDAV setup and app-specific passwords entirely.

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Google Calendar CLI: Manage Events from Terminal

Use a Google Calendar CLI to list events, create meetings, check availability, and find mutual times from terminal. No Google API credentials needed.

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Outlook Calendar CLI: Manage Events

Use an Outlook Calendar CLI to list events, create meetings, check availability, and book rooms from terminal without Graph API or Azure AD setup in scripts.

outlookmicrosoftcalendarevents

iCloud Mail CLI: Send Email from Terminal

Use an iCloud Mail CLI to send email from terminal without SMTP config or app passwords. Supports iCloud custom domains and Hide My Email aliases in scripts.

icloudappleemailsend

Outlook CLI: Send Email from Terminal

Use an Outlook CLI to send Microsoft 365 email from terminal without Graph API setup, Azure AD registration, MSAL token code, or SMTP config in scripts.

outlookmicrosoftoffice365email

Yahoo Mail CLI: Send Email from Terminal

Use a Yahoo Mail CLI to send email from terminal without SMTP config or app passwords. Send scheduled messages and CC/BCC over HTTPS with OAuth in scripts.

yahooemailsendsmtp

Record Zoom, Meet, and Teams from the CLI

Send a notetaker bot to any Zoom, Google Meet, or Microsoft Teams call from the command line. Get the recording URL and a full transcript back as JSON.

notetakermeetingrecordingtranscript

Extract OTP Codes from Email — Skip the Inbox

Pull 2FA verification codes from email without opening your inbox. The nylas otp get command copies the latest code to your clipboard across all providers.

otp2faverificationmfa

Manage Calendar Events from Terminal

Create, list, update, and delete calendar events from your terminal with Nylas CLI. DST-aware scheduling, timezone conversion, and AI-powered meeting finder.

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E2E Email Testing with Playwright

Test password reset, invitation, and verification emails end-to-end. Poll with Nylas CLI, verify content in Playwright, and click links. No Gmail config needed.

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