Passwords are so deeply incorporated to our digital life that using them has become as natural as drinking water. Fortunately, services such as password managers or Apple's built-in Keychain Access ease the login process by replaying the password whenever we need it. That's until macOS gets stubborn and ‘forgets’ them and that annoying prompt appears, requiring you to type in the password that you’ve forgotten.
Apple Mail Password Prompt
Since Mail is one of the core apps we all use on a daily basis, getting prompted for the password by either a pop-up window requesting the password with the “Enter Password for Account (Name)” or when using the Connection Doctor feature is pretty frustrating, so here is how to fix it.
After ensuring that the password entered is correct:
- Open the Mail app Preferences and click on the “Accounts” tab.
- Select the email account you are having problems with.
- Under the “Server Settings” (in macOS 10.13 High Sierra) or “Account information” (in earlier versions) find the “Password” field.
- Delete the existing password and type in the new or correct one.
If the password prompt appears only when sending emails, you need to set the outbound mail server password in the Mail app.
macOS High Sierra
Select Mail Preferences > Accounts > Server Settings > Outgoing Mail Server (SMTP) and type the password into the corresponding field.
Earlier macOS Versions
This option appears in the Mail Preferences > Account Information tab > Outgoing Mail Server (SMTP) > Edit SMTP Server List > Advanced.
iCloud, FaceTime, iMessage Random Password Pop-Up
Some users might see this random macOS password pop-up window from iCloud, FaceTime or Messages. This seems to happen regularly on OS X Mavericks, but there have been reports from users running OS X Yosemite too.
If you are convinced that this isn't coming from a piece of adware, follow the steps below:
- Launch the System Preferences app.
- Click on the iCloud icon.
- Sign in with your Apple ID in the macOS preference panel. If you see yourself already signed in, you can sign out and sign in again to stop the password prompt.
macOS Won't Remember Wi-Fi Password
In some cases macOS fails to remember the password of wireless networks. This isn't because of the sleepless nights your Mac is having, but a bug that appears without any identifiable pattern. Fortunately, there is a super-easy fix for it, but it's important to know the password.
- After launching the Keychain Access app, type “Airport network” into the search field located in the top-right corner.
- Identify and select the name of the wireless network.
- Right-click on the network name and select “Delete [NetworkName]“.
- Type your admin password when prompted.
- Reboot your Mac. You should be able to connect to the problematic Wi-Fi network if you know the password.
Mac Keeps Asking for Login Keychain Password
The password of your macOS user account usually matches that of the Keychain login but in some cases it won’t, hence the prompt for the Keychain password. That's usually the case when you aren't the admin of the Mac.
The fix is very easy: if you don't know the old password, just create a new Keychain login to store all your usernames and passwords. If you know the old password, just change the password for Keychain login, which will require the old password and a new one.
How Password Managers Help
Password managers can help you in these instances by generating a unique and secure password for the Keychain login. For example, with the help of a password manager such as 1Password, Sticky Password, or Dashlane, you won't ever need to remember (and therefore never forget) the old Keychain or Wi-Fi password. When it comes to the Apple ecosystem, the iCloud Keychain does a very good job of protecting the user's digital life, but it's rendered useless if the user has the ‘courage’ to use another platform outside of Apple's. Password managers fill that gap, since they are available on every major platform and even on web browsers, which makes accessing all your passwords fast and convenient.
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