Connect guide

Connect iCloud Mail to Claude and ChatGPT

Updated 16 September 2026

Yes — Claude and ChatGPT can both read, search and reply to your iCloud Mail through Mailopoly, which is listed in the Claude Connectors Directory and is an approved app in the ChatGPT app directory. Connect iCloud Mail to Mailopoly with an Apple app-specific password, add Mailopoly in Claude or ChatGPT, and ask. The whole setup takes about a minute. Apple requires a 16-character app-specific password (format xxxx-xxxx-xxxx-xxxx); your regular Apple Account password won't work, and your Apple Account needs two-factor authentication turned on to create one.

This guide also covers me.com and mac.com — the steps are the same.

Before you start

A Mailopoly account — 7-day free trial, no credit card.
Apple requires a 16-character app-specific password (format xxxx-xxxx-xxxx-xxxx); your regular Apple Account password won't work, and your Apple Account needs two-factor authentication turned on to create one.
Claude on any plan, including Free, or ChatGPT with apps enabled.

Connect iCloud Mail to Claude or ChatGPT in three steps

1Connect iCloud Mail to Mailopoly

Start a Mailopoly account at mailopoly.com/sign-up — 7-day free trial, no credit card.
Sign in at account.apple.com, open Sign-In and Security, then App-Specific Passwords.
Choose + (Generate an app-specific password), name it Mailopoly, and copy the password Apple shows you (format xxxx-xxxx-xxxx-xxxx).
In Mailopoly choose Add email account, enter your full iCloud, me.com or mac.com address, and paste the app-specific password in the password field. Mailopoly fills in the server settings for you.

Provider help: Manage your Apple Account ↗

2Add Mailopoly to Claude or ChatGPT

This part is the same whatever you connected in step 1. Mailopoly is listed in both directories, so it's a search and a tap — no endpoint URL to paste.

Claude

Open Settings → Connectors on claude.ai or in the Claude app — or choose Add connectors from the + menu in any chat.
Search the directory for Mailopoly and choose Connect.
Sign in with your Mailopoly account when prompted, then choose what Claude is allowed to do. Reading, making changes and sending are separate permissions.
Back in the chat, make sure the Mailopoly connector is switched on, then ask.

One listing covers Claude.ai, Claude Desktop, Claude mobile, Claude Code and Cowork, and it works on every Claude plan, including Free. In Claude Code you can also run claude mcp add --transport http mailopoly https://fastapi.prod.aws.mailopoly.com/mcp-server/ and then /mcp to sign in.

Mailopoly in the Claude Connectors Directory ↗

ChatGPT

Open the Apps directory in ChatGPT — from the + menu in any chat, or Settings → Apps & Connectors.
Search for Mailopoly and choose Connect.
Sign in with your Mailopoly account when prompted, then choose what ChatGPT is allowed to do. Reading, making changes and sending are separate permissions.
In any chat, type @Mailopoly and ask.

Mailopoly is an approved app in the ChatGPT app directory, so there's no developer mode and no endpoint URL to paste. Once connected it's available in every ChatGPT conversation on the web and in the mobile apps.

Mailopoly in the ChatGPT app directory ↗

Using something else? Claude Code, Cowork, Codex and any client that supports remote MCP servers connect the same way — the Mailopoly MCP page has the endpoint and per-client steps.

3Ask about your iCloud Mail

Whatever you've connected to Mailopoly is what your assistant can reach. Some things people ask on day one:

What's in my iCloud Cleanbox from the school this week?
Find the Apple receipt in my iCloud mail from last month and tell me the amount.
Reply to the last email from the strata manager from my iCloud address.

iCloud Mail server settings

Mailopoly fills these in for you when you enter your address. They're here in case you need to check them or your provider uses something unusual.

IMAP server	imap.mail.me.com
Port	993
Security	SSL/TLS
Username	Your full email address
Password	Apple app-specific password (xxxx-xxxx-xxxx-xxxx)

What Claude and ChatGPT can do with iCloud Mail through Mailopoly

Search iCloud Mail — and every other account you own — in one question. By sender, date, topic, or the half-remembered phrase somewhere in the body.
Read your Cleanbox, not your whole inbox. Mailopoly sorts iCloud Mail as it arrives: personal and important mail in Cleanbox, promotions and newsletters in Other. Ask for either.
Summarise a thread, a day or a week. "What did the school send this week?" comes back as an answer, not a list of links.
Reply from your iCloud Mail address, in your voice. Save a draft to Mailopoly for review, or send — sending is a separate permission and a confirm-first action.
Schedule a send for later, and cancel it if you change your mind.
Pull out invoices, events and deliveries. Amounts and due dates, calendar invitations, parcel tracking — extracted on arrival and added to My Day.
Find an attachment. Every attachment from iCloud Mail lands in PolyBox, so "find the PDF the accountant sent" just works.
Unsubscribe, snooze, file and mark read from the chat, on whichever account the mail belongs to.

Reading, making changes and sending are separate permissions you grant when you connect, and you can revoke an assistant at any time from Settings → Security in the Mailopoly app. More on the security page.

What goes wrong with iCloud Mail, and the fix

Your Apple Account password won't work. iCloud Mail only accepts app-specific passwords from third-party apps. A login failure almost always means the real password was pasted instead.
Two-factor authentication is required. Apple only issues app-specific passwords to accounts with two-factor authentication on. If the App-Specific Passwords option is missing, turn on two-factor first.
Use your full address. Sign in as the complete iCloud address (for example name@icloud.com), not just the name.
Custom domains on iCloud+ connect the same way — use the address on your custom domain and the same app-specific password.

Start a free trial

7-day free trial, no credit card. Connect iCloud Mail in about a minute.

Frequently asked questions

Does Claude or ChatGPT see my Apple app-specific password?

Can I connect iCloud Mail to ChatGPT without Mailopoly?

Can I connect more than one account?

Does it work in Claude Desktop, Claude mobile and Claude Code?

Is there a free trial?

How does Mailopoly keep the connection safe?

Claude and ChatGPT connect to Mailopoly through OAuth 2.1 — a revocable, scoped sign-in, never a password. Reading, making changes and sending are separate permissions, every tool call is audit-logged against your account, and you can revoke any assistant from Settings → Security → Connected AI assistants in the app. Mailopoly is independently security-assessed to CASA Tier 2 by TAC Security.