Why does Outlook keep asking for my password?

How do I fix it?

Work through these in order, checking after each one.

1. Update Outlook and Windows or macOS. Older versions can struggle with current sign-in methods.
2. Sign out and back in to your Microsoft account inside Outlook. Approve the sign-in on your phone if asked.
3. Clear stale saved passwords. On Windows, open Credential Manager and remove entries for Outlook or Office. On a Mac, look in Keychain Access for old Exchange or Outlook entries.
4. Test the account on its own webmail: outlook.office.com for Microsoft 365, mail.google.com for Google Workspace, or mail.e3webmail.com for E-3 email. If that also fails, the issue is the account, not the app.
5. Create a new Outlook profile if it’s still stuck, but check first. With IMAP or Microsoft 365, mail stays on the server. With POP, or with local folders, archives or contacts kept on your computer, back it up first. On Windows it’s in an Outlook data file (.pst): open it in the new profile afterwards. On a Mac, “On My Computer” folders exist only on that computer: export them to an archive (.olm) first, as Microsoft explains. Or ask us to help.

The short version

• Update Outlook and your operating system first.
• Sign out of your account in Outlook, sign back in and complete any two-step approval.
• Remove old saved passwords in Windows Credential Manager or Mac Keychain Access.
• Try Outlook on the web; if that fails too, the account needs attention.
• Only type your password into Outlook itself or a sign-in page you opened.

Why does this happen?

Old sign-in methods no longer work. Microsoft has turned off basic authentication in Exchange Online for Outlook, POP, IMAP and mobile mail. Microsoft says Outlook 2007 and 2010 can’t use the newer method, and Outlook 2013 needs a setting changed. An old version may keep asking for a password it can’t use.

A saved password is out of date. Change your password on one device and the others keep trying the old one.

Two-step sign-in needs a fresh approval. If the approval never reaches your phone, the box keeps coming back.

Something changed on the account. A new license, password policy or security setting from your administrator can force everyone to sign in again.

Why does it matter?

Beyond the annoyance, a repeating prompt trains people to type their password into any box that appears. That’s exactly what phishing relies on. Fixing the cause keeps the habit safe.

What are the common mistakes and edge cases?

• Typing your password into a box from an email link. Fake sign-in pages are a common phishing trick. See how to spot a phishing email.
• Reinstalling Outlook first. It rarely helps if the cause is a stale saved password.
• Using an app password as a workaround. Microsoft notes that the basic authentication change also stops app passwords working in apps that don’t support two-step verification.
• Mail on a different system. If your email isn’t Microsoft 365, these steps differ. For E-3 email, see the next section.

What if my email is on E-3’s mail server?

E-3’s own email (SmarterMail) signs in with your full email address and password. Two-factor sign-in isn’t currently available on E-3’s mail server, so app passwords and codes don’t apply. If this changes, we’ll let you know. A repeating prompt usually means one of three things:

1. The password is wrong or stale. Sign in at mail.e3webmail.com in your browser. If webmail rejects it, reset your email password from the sign-in page, or call 814-399-4655.
2. The outgoing server isn’t set to sign in. In Outlook’s account settings, the outgoing server must require authentication with the same username and password as incoming.
3. The server names or ports are off. Both servers should be mail.e3webmail.com (not mail.yourdomain.com): incoming port 993 with SSL/TLS, outgoing port 587 with STARTTLS (or 465 with SSL/TLS).

The full settings table is in set up your email in Outlook or Apple Mail.

What if it still won’t stop?

Ask your email administrator to check the account’s sign-in log and any security alerts, and to look at the Microsoft 365 service health page for an outage. Never send your password to anyone to “test it”; an admin can reset it through a proper process instead.

How much does it cost, and how long does it take?

The fixes above are free, and each one takes a few minutes. A very old copy of Outlook may need replacing, which costs nothing extra if your Microsoft 365 plan includes the desktop apps.

How does E-3 handle this?

For the business email we look after, call 814-399-4655 or email support@e3help.me, and a person will reply, usually within one business day. Please don’t send your current password by email or text.

Related questions

• Should I turn on two-factor authentication?
• Microsoft 365 or Google Workspace for business email?
• How do I set up my email in Outlook or Apple Mail?
• How do I spot a phishing email?