Validators have issues with the UpdatePanel, see http://blogs.visoftinc.com/archive/2007/09/23/asp.net-ajax--updatepanel-not-working--common-problems.aspx tip #4 for some links to more information.
The most import link there is http://www.asp.net/ajax/documentation/live/overview/UpdatePanelOverview.aspx; specifically:
"To make the validators compatible with an UpdatePanel control, set the EnableClientScript property of the validators to false. This disables the client script that would ordinarily be used to perform validation in the browser. As a result, during an asynchronous postback, the validators perform validation on the server. However, because only the content of the UpdatePanel is refreshed, the validators can provide the kind of immediate feedback that is ordinarily provided by client script."
-Damien
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