Connect guide

Connect iCloud Mail to Perplexity

Updated 1 November 2026

Yes — Perplexity can read, search and reply to your iCloud Mail through Mailopoly. Connect iCloud Mail to Mailopoly with an Apple app-specific password, add Mailopoly to Perplexity as a custom connector, sign in and ask. One connection covers iCloud Mail and every other account you own. 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.

Start a free trial

7-day free trial, no credit card.

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.
Perplexity Pro, Max or Enterprise — custom connectors aren't on the free plan. On Enterprise, an admin allows custom connectors first.

Connect iCloud Mail to Perplexity in three steps

1 Connect 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 ↗

2 Add Mailopoly to Perplexity

This part is the same whatever you connected in step 1.

Add Mailopoly to Perplexity

These steps are taken from public documentation, and we haven't yet checked each one in Perplexity ourselves. If a label doesn't match what you see, Perplexity's own help page, linked below, has the current wording.

In Perplexity, open Account settings → Connectors.
Choose + Custom connector at the top right, then Remote.
Name it Mailopoly and enter https://fastapi.prod.aws.mailopoly.com/mcp-server/ as the MCP Server URL. For Authentication choose OAuth 2.0 — there's no client ID or secret to fill in, Mailopoly registers Perplexity itself — and for Transport choose Streamable HTTP.
Tick the box confirming you understand the risks of custom connectors, choose Add, then click the Mailopoly card to sign in.
Sign in with your Mailopoly account, then choose what Perplexity is allowed to do. Reading, making changes and sending are separate permissions.
Back in Perplexity, ask.

Perplexity takes Mailopoly as a custom remote connector, so the only thing to paste is one address. Custom connectors are available on Perplexity Pro, Max and Enterprise; on Enterprise, an admin has to allow them for the organisation first.

Adding custom remote connectors — Perplexity Help Center ↗

3 Ask 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 Perplexity 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 Perplexity 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.
No + Custom connector button in Perplexity: custom connectors need Perplexity Pro, Max or Enterprise. On Enterprise, ask your admin to allow custom connectors for the organisation.
The Mailopoly card says it isn't connected: adding the connector doesn't sign you in. Click the Mailopoly card in Account settings → Connectors and finish the Mailopoly sign-in.
Perplexity can't reach the server: check the address is exactly https://fastapi.prod.aws.mailopoly.com/mcp-server/, Authentication is OAuth 2.0 and Transport is Streamable HTTP, then remove the connector and add it again.