Help
Connecting your inbox
This is the one step of setup with any friction in it, so this page covers every provider. If you would rather not do it alone, book fifteen minutes and we will do it together.
Why there is a fiddly step at all. Google, Yahoo and Apple will not let a desktop mail app sign in with your normal password. They issue a separate one, used only by that app, which you can revoke at any time without changing anything else. OleaDesk stores it in the Windows credential store on your own computer. It never reaches our servers.
In the app, choose Add inbox and type your email address. It recognises the provider and shows you the steps for that one. What follows is the same information, so you can read it before you start or while you are stuck.
Your own domain, hosted with your web host
The easiest path, and worth saying so. If your address is you@yourcompany.com, type it in and OleaDesk finds your mail servers for you. Your normal mailbox password usually works. If it asks for server names, they are in your hosting control panel under email or mail settings.
Gmail and Google Workspace
Google will not accept your normal password here. It gives you a separate one, just for OleaDesk.
- Open Google’s app password page and sign in. The app has a button that opens it for you.
- Name it OleaDesk.
- Copy the sixteen letters it shows you and paste them into the password box, with your normal Gmail address.
If Google says app passwords are unavailable, turn on 2 Step Verification first. Google only offers app passwords once it is on. On a work or school account, an administrator can also switch them off entirely, in which case ask them to allow app passwords or to enable IMAP for your account.
Outlook.com, Hotmail, Live and MSN
No password at all. Choose Sign in with Microsoft and approve it in the browser window that opens. There is deliberately no password box on this one: Microsoft stopped accepting passwords from other mail apps in September 2024, so an app password would fail exactly the same way a normal one does.
On a Microsoft 365 work account, some companies require an administrator to approve a new application before anyone can sign in. If sign in is refused, that is usually why. Write to us and we will send your administrator what they need.
Yahoo
Yahoo also issues a separate password.
- Open Yahoo’s app password page.
- Choose Generate app password.
- Copy what it shows you and paste it into the password box.
iCloud
Apple calls these app specific passwords, and you need two factor authentication on your Apple ID first.
- Open your Apple account and sign in.
- Under Sign-In and Security, choose App-Specific Passwords and create one.
- Paste it into the password box.
After it connects
OleaDesk starts pulling your folders. A large mailbox takes a while on the first pass and you can start reading while it fills. Opening a very old message before that pass reaches it can be slow, which is a one time cost rather than a fault.
Once your sent mail is in, the assistant begins learning how you write, on your own machine.
If it still will not connect
The message the app shows says which side refused, which is the useful part. Send it to hello@oleadesk.com along with your provider and we will get you connected. Or book fifteen minutes and we will do it together on a call. Founding members get this as standard, and it genuinely takes a quarter of an hour.
Next: installing OleaDesk if you have not yet.