You should create a new log recorder to have a closer look at the debugging messages concerning the RememberMe cookie. You can do this at Manage Jenkins > Logs.
Add a new log recorder with any name you like and then add a logger "org.acegisecurity.ui.rememberme" in its configuration, setting the severity in the drop-down list to "FINE".

This log recorder should then present you lots of messages around the RememberMe token. Upon a new login with "remember me" set, you should get a log line like this one:
"Feb 20, 2013 4:24:31 PM hudson.security.TokenBasedRememberMeServices2 loginSuccess
FINE: Added remember-me cookie for user 'millner', expiry: 'Wed Mar 06 16:24:31 CET 2013'"

What expiration date is shown there at your Jenkins?

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