Connecting your email

Last updated: 2 August 2026

Fairlead needs access to your mailbox before it can read, draft or send anything on your behalf. For most people that takes one click. This page is for everyone else — Yahoo, iCloud, AOL and any business address on your own domain.

Start here: which option do I pick?

There are three buttons on the Permissions page, and only one of them will be right for you.

Microsoft / Outlook — for Outlook.com, Hotmail, Live, MSN, and any work address running on Microsoft 365. You sign in on Microsoft’s own page and approve Fairlead there. You never type your password into Fairlead.
Google / Gmail — for gmail.com addresses and any business address running on Google Workspace. Same idea: you approve Fairlead on Google’s page.
Other email (IMAP) — for everything else: Yahoo, iCloud, AOL, Zoho, Fastmail, GMX, and business addresses hosted by your web host (Hostinger, GoDaddy, IONOS, Namecheap and so on). This one asks for your email address and a password, because those providers have no “approve this app” screen to send you to.

If you have a choice, use the Microsoft or Google button. It is quicker, it never involves handing over a password, and you can withdraw Fairlead’s access from your own account settings at any time. Only use “Other email” if your provider is not one of those two.

Why your normal password may not work

This is the single most common reason a connection fails, and the error message rarely makes it obvious.

If your email account has two-factor authentication switched on — the code from a text message or an app — then your ordinary password is deliberately not enough to sign in, and your provider will refuse it every time no matter how carefully you type it. What you need instead is an app password (sometimes called an app-specific password): a long one-off password that your email provider generates for a single application. You create it once, paste it into Fairlead, and never need to remember it.

Yahoo, iCloud, AOL, Zoho and Fastmail require one in nearly all cases. An app password is safe to use here: it only works for mail, it does not let anyone change your account, and you can revoke it on its own — without changing your real password — from the same page you created it on.

Step by step, by provider

Yahoo Mail

Go to Yahoo Account Security and sign in.
Find App passwords (sometimes shown as “Generate app password”).
Give it a name you will recognise later — “Fairlead” — and generate it.
Copy the password Yahoo shows you. It is shown once, and the spaces in it do not matter.
In Fairlead, choose Other email (IMAP), enter your full Yahoo address and paste that password. Leave the server details alone — Fairlead fills them in.

If App passwords is not on that page, two-factor authentication is probably switched off. Turn it on first; Yahoo only offers app passwords to accounts that have it.

iCloud Mail (@icloud.com, @me.com, @mac.com)

Sign in at account.apple.com.
Open the Sign-In and Security section and choose App-Specific Passwords.
Generate one, label it “Fairlead”, and copy it.
Enter your iCloud address and that password in Fairlead.

Apple only offers app-specific passwords on accounts with two-factor authentication enabled, and your iCloud email address must already be set up on an Apple device before it will accept a mail connection at all.

AOL Mail

AOL works exactly like Yahoo — same company, same screens. Go to AOL Account Security, generate an app password, and paste it into Fairlead with your AOL address.

Gmail and Google Workspace

Use the Google / Gmail button. It is the supported route, it needs no password, and Google shows you exactly what Fairlead is asking for before you agree.

If you would rather connect over IMAP — some Workspace administrators block the consent screen — you will need an app password, which Google only offers on accounts with 2-Step Verification switched on. Google’s own instructions are here. Then connect with Other email (IMAP).

Outlook.com, Hotmail, Live, and Microsoft 365

Use the Microsoft / Outlook button. Microsoft has been retiring password-based IMAP access to personal Outlook.com accounts, so the IMAP route may simply be refused however correct your details are. The Microsoft button uses the modern sign-in Microsoft expects and is not affected.

Zoho Mail

Sign in to your Zoho account and open Security → App Passwords.
Generate one for “Fairlead” and copy it.
Enter your Zoho address and that password. If your account is on Zoho’s European data centre, your address ends in a European domain and Fairlead will use imap.zoho.eu — if it does not, set the servers manually from the table below.

Fastmail

Fastmail requires an app password for every mail application. In Fastmail, go to Settings → Privacy & Security → Connected apps & devices, create a new app password with Mail (IMAP/SMTP) access, and paste it into Fairlead.

A business address on your own domain

If your email looks like you@yourbusiness.co.uk, then whoever hosts your website or domain almost certainly runs your mailbox too — Hostinger, GoDaddy, IONOS, Namecheap, Titan, or a hosting control panel your web designer set up.

In most cases Fairlead works this out for you. Just enter the address and the mailbox password you use to log in to your webmail, and leave the server details blank — Fairlead looks up who runs your mail from your domain’s DNS records and fills the rest in.

If it cannot, open Advanced: set server details manually and copy the settings from your host. Every host publishes them on a page called something like Connect apps & devices, Mail client settings, or IMAP & SMTP settings, usually inside the email section of your hosting control panel. Copy four things: the incoming (IMAP) server and port, and the outgoing (SMTP) server and port.

Choose IMAP, not POP3. If your host offers both, take IMAP. POP3 downloads mail and can remove it from the server, so your assistant and your phone would stop seeing the same inbox.

Anything else

Try the address and password first — Fairlead recognises most providers automatically, and checks the public autoconfiguration database that email apps like Thunderbird use. If that does not work, your provider’s help pages will have an “IMAP settings” page; enter those under Advanced.

Server settings

You should not normally need these — Fairlead fills them in — but here they are if you are setting things up by hand. All were checked against the live servers on 2 August 2026.

Provider	Incoming (IMAP)	Outgoing (SMTP)	App password?
Yahoo Mail	imap.mail.yahoo.com — 993, SSL/TLS	smtp.mail.yahoo.com — 465, SSL/TLS	Yes
iCloud Mail	imap.mail.me.com — 993, SSL/TLS	smtp.mail.me.com — 587, STARTTLS	Yes
AOL Mail	imap.aol.com — 993, SSL/TLS	smtp.aol.com — 465, SSL/TLS	Yes
Gmail	imap.gmail.com — 993, SSL/TLS	smtp.gmail.com — 465, SSL/TLS	If 2FA is on
Outlook.com / Hotmail	outlook.office365.com — 993, SSL/TLS	smtp-mail.outlook.com — 587, STARTTLS	If 2FA is on
Zoho Mail	imap.zoho.com — 993, SSL/TLS	smtp.zoho.com — 465, SSL/TLS	Yes
Fastmail	imap.fastmail.com — 993, SSL/TLS	smtp.fastmail.com — 465, SSL/TLS	Yes
GMX	imap.gmx.com — 993, SSL/TLS	mail.gmx.com — 587, STARTTLS	No
mail.com	imap.mail.com — 993, SSL/TLS	smtp.mail.com — 465, SSL/TLS	No
BT Internet	mail.btinternet.com — 993, SSL/TLS	mail.btinternet.com — 465, SSL/TLS	No
Hostinger	imap.hostinger.com — 993, SSL/TLS	smtp.hostinger.com — 465, SSL/TLS	No
Titan	imap.titan.email — 993, SSL/TLS	smtp.titan.email — 465, SSL/TLS	No
Namecheap Private Email	mail.privateemail.com — 993, SSL/TLS	mail.privateemail.com — 465, SSL/TLS	No
GoDaddy	imap.secureserver.net — 993, SSL/TLS	smtpout.secureserver.net — 465, SSL/TLS	No
IONOS (UK)	imap.ionos.co.uk — 993, SSL/TLS	smtp.ionos.co.uk — 587, STARTTLS	No

SSL/TLS or STARTTLS? The port decides it, and getting the pair wrong is the most common cause of a connection that hangs rather than fails. Ports 993 and 465 always use SSL/TLS — tick the box. Ports 143 and 587 use STARTTLS — leave it unticked. Fairlead now ticks and unticks that box for you as you type the port, and tries both ways before giving up, but older instructions from your provider may still tell you to set it by hand.

If it will not connect

Fairlead tells you which of the two servers failed and why. Match the message below.

“…rejected the username or password” — the server is fine and your details reached it, so this is a credentials problem. Nine times out of ten you need an app password rather than your normal one. Also check you entered the full email address, not just the part before the @.
“…did not respond” or “Greeting never received” — nothing was listening in the way we expected. Almost always the port is wrong, or the port and the SSL/TLS setting do not match each other. Check them against the table above.
“There is no mail server called…” — the address is mistyped, or that name does not exist. Note that it is rarely your own domain: it is usually your host’s name, such as imap.hostinger.com rather than imap.yourbusiness.co.uk.
“…security certificate could not be verified” — the server answered but is known by a different name. Use the exact hostname your provider publishes.
Proton Mail — cannot be connected. Proton only allows mail apps to connect through Proton Mail Bridge, which runs on your own computer and cannot be reached from Fairlead.

Still stuck? Email support@fairlead.uk with your provider’s name and the message Fairlead showed you, and we will work it out with you. Never send us your password — we will never ask for it.

What Fairlead does with your password

When you connect a mailbox this way, the password (or app password) is encrypted and stored so that Fairlead can reconnect to your mailbox on your behalf. It is never shown back to you, never sent to the AI model, and never given to your assistant’s container — every mail action runs on our server, so disconnecting the mailbox cuts access off immediately. You can disconnect at any time from the Permissions page, and we delete the stored credential when you do. The full detail is in our Privacy Policy.

If you would rather not store a password with us at all, and your email is with Microsoft or Google, use their button instead — that route never gives us a password.