How can we help?

Adding an account

Choose Add Account, type your email address, and Glassmail works out your provider and its servers. Gmail, iCloud, Yahoo and Fastmail don’t let mail apps use your normal password; they ask for an app password instead, a separate password made for one app. It’s safer: you can revoke it at any time without changing your real password. Glassmail opens the right page for you.

Gmail and Google Workspace

1. Turn on 2-Step Verification for your Google account if it’s off. App passwords only appear once it’s on.
2. Open myaccount.google.com/apppasswords and create one named “Glassmail”.
3. Paste the 16-character password into Glassmail.

If the app passwords page says the setting isn’t available, your Workspace administrator has turned app passwords off. They can turn them on in the Google Admin console.

iCloud

1. Open account.apple.com and choose Sign-In and Security.
2. Choose App-Specific Passwords and create one named “Glassmail”.
3. Paste it into Glassmail.

Yahoo and AOL

1. Open Yahoo account security (or AOL’s).
2. Choose “Generate app password” and name it “Glassmail”.
3. Paste it into Glassmail.

Fastmail

1. In Fastmail, open Settings, then Privacy & Security, then Integrations.
2. Create an app password with access to Mail (IMAP/SMTP).
3. Paste it into Glassmail.

Outlook.com, Hotmail and Microsoft 365

These sign in with Microsoft: Glassmail opens Microsoft’s sign-in page and you approve access there. No app password needed. For work or school accounts, your organisation must allow IMAP and “Authenticated SMTP”, and may need an administrator to approve Glassmail the first time.

A Microsoft account created with a non-Microsoft address (for example a Gmail address) has no Outlook mailbox. Add that Gmail address directly instead.

Custom domains and other providers

Type your address and Glassmail looks up your domain’s mail servers. If it can’t find them, open “Label and server settings” and enter the IMAP and SMTP details from your host (usually ports 993 for IMAP and 465 or 587 for SMTP). Some hosts, like Zoho on its free plan, need IMAP turned on in their settings first.

Your licence

• Trial: Glassmail is free for 14 days with every feature. The days left show at the bottom of the sidebar.
• Adding your key: the key is in your purchase email and starts with GLASSMAIL. Choose Glassmail › Enter License Key…, or open Settings › General › License, and paste it.
• Up to three Macs: one licence works on three of your Macs. To move it, choose Remove from This Mac… in Settings › General on the old Mac, or free a Mac in the customer portal.
• Lost your key? It’s always in the customer portal. Sign in with the email you bought with.
• Refunds: 14 days, no questions. See the refund policy.

AI features

On macOS 26 or later with Apple silicon and Apple Intelligence turned on (System Settings › Apple Intelligence & Siri), Glassmail uses it automatically. On any other Mac, including Intel Macs and macOS 14 and 15, download a model in Settings › AI. Smaller models are quicker; larger ones write better. Everything runs on your Mac.

When something isn’t working

“The server didn’t accept the password”

Gmail, iCloud, Yahoo and Fastmail need an app password, not your normal password; make a new one using the steps above. If you changed your account password recently, app passwords may have been revoked, so make a new one.

“Couldn’t reach the server”

Check your connection, and turn off any VPN or firewall that blocks mail ports for a moment to test. For custom domains, check the server names and ports in Settings › Accounts.

Reading works, sending doesn’t

Your provider may have SMTP turned off for the account (common with Microsoft 365 work accounts) or need a different port. Settings › Accounts shows the server details and a Check Connection button.

Mail looks out of date

Choose Message › Check for New Mail (⇧⌘N). The first sync of a large mailbox can take a few minutes; after that, new mail arrives within seconds.

Glassmail asks for access to the Keychain

That’s macOS protecting your passwords. Choose Always Allow so Glassmail can read the passwords it saved.

Removing Glassmail completely

1. Quit Glassmail and drag it from Applications to the Bin.
2. Delete its mail copy: in Finder, choose Go › Go to Folder… and open ~/Library/Application Support/Glassmail, then delete that folder. Your mail is still with your provider.
3. Delete its caches at ~/Library/Caches/Glassmail.
4. In Keychain Access, search for app.glassmail and delete the items you find (saved passwords and the licence).
5. If you bought a licence, free this Mac in the customer portal so you can use it elsewhere.