I'm looking to find out if crowd supports the ability to enforce restrictions on a user repeatedly using the same password when the password expires?
If you use an AD/LDAP connector, then this has to be configured on your AD/LDAP directory. If you use an internal directory, then you have to configure the Password History Count property. See https://confluence.atlassian.com/crowd/configuring-an-internal-directory-18579551.html for more details.
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