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.
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 passwordwith 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:
If the password prompt appears only when sending emails, you need to set the outbound mail server password in the Mail app.
Select Mail Preferences > Accounts > Server Settings > Outgoing Mail Server (SMTP) and type the password into the corresponding field.
This option appears in the Mail Preferences > Account Information tab > Outgoing Mail Server (SMTP) > Edit SMTP Server List > Advanced.
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:
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.
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.
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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