I made a post titled "ASP.NET Ajax: UpdatePanel and ValidationSummary / ValildationGroup" earlier this week, and have since done some more investigation.
I built a simple test site containing an ajax-ified textbox with a validation summary, and validationgroup set on it - and it worked perfectly, so it's back to the original scenario to try and figure out precisely what causes this issue.
Will post again if I discover anything interesting - however it seems to be far more complex than first thought. *sigh*
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