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Lets say I created an SQL login with a password that does not adhere to the AD password policy without checking "Enforce password policy" option. After creation, I go back and check the box. Looks like SQL Server lets you do this even thought the password does not comply with the policy.

Is there any issues doing this and does it just force us to follow the policy the next time we change password?

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  • Enabling the Enforce password policy option for an existing login won't retroactively enforce the password policy for the login's current password. The policy will only take effect on subsequent password changes for that login. You should test this but iirc, if the existing password does not comply with the password policy, the user will need to change their password to a new password that does comply with the policy before they will be able to log in again. Like I said, test to verify this with SQL Server 2014 just in case. Jan 30, 2023 at 23:03
  • Where you able to enforce password policy without any trouble?
    – Ronaldo
    Feb 4, 2023 at 14:19

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The Password Policy doc has some info that answers your question:

When password complexity policy is enforced, new passwords must meet the following guidelines [...]

Therefore, if you do not set the Enforce password expiration option to ON, you shouldn't have any trouble with that login. I mention this option just because it is marked automatically if you use SSMS GUI to Enforce password policy and it could force the login to be changed on a holiday when nobody is around resulting in a broken application.

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