My vb.net is shaky, (C # guy), but try:
Dim qry = From DirectCast(i, ListItem) In ddlOutcome.Items ...
I may have DirectCast syntax, but you know where I come from. The problem is that at compile time, items are not checked as a ListItem collection, since the IEnumerable Current property returns Object. Elements are not a common collection.
-Oisin
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