How to use an AI reply assistant with Yahoo, iCloud or any IMAP inbox

Most AI email tools are built around Gmail and Outlook. If your main address is a Yahoo, iCloud, AOL, Fastmail or Zoho account, or an address on your own domain hosted somewhere else, you often get left out, or you are asked to forward everything to another service or switch to a different email app.

There is a more universal way to connect a mailbox: IMAP. This guide explains in plain language what IMAP is, how an app password works, how to set one up for the common providers, and what to think about before you give any tool access to your email.

What IMAP actually is

IMAP is a standard way for an app to read mail that stays stored with your email provider. SMTP is its companion for sending. Nearly every email host supports both, which is why a tool that speaks IMAP and SMTP can work with a huge range of mailboxes without a special deal with each provider.

When a tool connects to your mailbox this way, it logs in much like your phone's mail app does. It can read the new messages, and, if you approve a reply, send that reply through your provider's own mail server.

Why an app password, not your regular password

Most providers now require two-step verification. A normal password plus a code is fine for you, but an app cannot type a code each time. So providers let you create an app password: a long, random password that works only for connecting apps over IMAP and SMTP.

The benefits are worth understanding:

• It is separate from your main password, so you never share the one that protects your account.
• You can revoke it at any time, from your provider's security settings, without changing your main password.
• If you stop using a tool, you remove the app password and its access ends.

Treat an app password as a real credential. Don't paste it into chat, email it, or reuse it.

Setting it up, provider by provider

The exact menus change from time to time, so use these as a guide and follow your provider's own help pages if the screens differ.

1. Turn on two-step verification for the account if it isn't already on. Most providers require this before they will offer app passwords.
2. Open the account's security settings and look for “app passwords” or “app-specific passwords.”
3. Create a new one and give it a label you will recognize, such as the name of the tool.
4. Copy it once. Most providers show it only a single time.
5. Paste it into the tool along with your email address.

• Yahoo Mail: create an app password in Yahoo Account Security.
• iCloud Mail: create an app-specific password at account.apple.com.
• AOL Mail: create an app password in AOL Account Security.
• Fastmail: create one under Settings, then Privacy and Security.
• Zoho Mail: enable IMAP in the mail settings, and use an app password if two-factor authentication is on.
• Gmail and Google Workspace: app passwords exist, though Workspace administrators sometimes switch them off. Many tools also use Google's own sign-in instead.
• Own domain: ask your email host for the IMAP and SMTP server names and ports. Many hosting dashboards list them.

Questions to ask before you connect anything

Giving an app access to your inbox is a real decision, whatever the provider. Before you connect any AI email tool, find out:

• What it reads. Does it read only new mail, or your whole history? Does it look at sent mail?
• What it stores, and for how long. Is the text of your emails kept? Can you delete it?
• How credentials are protected. Are the passwords or tokens encrypted at rest?
• Whether anything sends on its own, and what the safeguards are.
• How to disconnect, and whether disconnecting actually ends access.

If a company can't answer these in plain words, treat that as an answer.

How ReplyPilot handles IMAP mailboxes

ReplyPilot is an AI email reply drafter. It reads new emails in the mailbox you connect, sorts them, and writes a draft reply in your own voice using facts you have approved. The draft then waits in an approval queue for you to approve, edit or discard.

On the connection screen you choose your provider from a list (Yahoo, iCloud, AOL, Zoho, Fastmail, GoDaddy, Gmail with an app password, or custom settings), type your email address and app password, and the usual server settings are filled in for you. For a custom provider you enter the IMAP and SMTP servers yourself.

Here is what its security page says, summarized so you can judge it. Mailbox credentials, including app passwords, are encrypted before they are saved, and the encryption key is kept outside the database. The server does decrypt them when it checks your mailbox or sends a reply you approved. Stored email text is cleared after 30 days, while sender, subject, category and drafts are kept. Disconnecting a mailbox stops access. The product is a new beta and has not had an independent security audit, which its own security page says plainly. You can read the details at the security page.

On sending: by default, nothing goes out until you approve it. Optional auto-send exists for simple routine replies, and replies about money, offers, contracts and complaints are never auto-sent.

Limits to know about

• It does not support Outlook or Microsoft 365 mailboxes yet.
• It works through your provider's normal IMAP checks, so new mail is picked up on a schedule rather than the instant it arrives.
• Gmail connects through Google sign-in during beta. Because Google has not finished reviewing the app, Google shows a warning screen first. Using Gmail with an app password through IMAP is the alternative.
• Drafts are only as good as the facts you give it. If a fact is not in your approved library, the draft is supposed to say you'll check and get back to them.

A sensible way to start

1. Create an app password just for this tool, and write down where you created it so you can revoke it later.
2. Connect the mailbox and leave it in the default mode, where every reply waits for your approval.
3. Read the first ten or twenty drafts. Edit the ones that aren't right, and add the facts it keeps lacking, such as hours, prices and policies.
4. Only consider auto-send after you trust the drafts, and only for routine questions.

ReplyPilot has a 14-day free trial with no card, so you can try this with your real inbox and judge it on your own mail rather than on a demo.