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On the documentation it mentions the following:

NOTE If the user hasn’t set a security question, or doesn’t answer the security question correctly, the password isn’t reset.

What is the best way to approach this? Can I, as the administrator override the security question/answer when resetting the password? As I dont know who created these with which security question/answer...

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Yes, as an Administrator (or any user with Manage User permission or Delegated Administration that includes resetting passwords), you can reset anyone's password by going to the user detail page (Setup > Manage Users > Users / ⚙ > Setup > Users > Users), and click the Reset Password button. Doing so will email the user a new temporary password. Upon successfully logging in, they will set a new password, security question, and security answer.

In the same "Note" in the documentation, it specifies that:

Administrators can reset a user’s password as often as needed.

The "answer your security question" bit only applies when the user manually initiates a password reset, and does not apply to administrators.

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