LINQ orderby on date field in descending order

I don't believe that Distinct() is guaranteed to maintain the order of the set.

Try pulling out an anonymous type first and distinct/sort on that before you convert to string:

var ud = env.Select(d => new 
                         {
                             d.ReportDate.Year,
                             d.ReportDate.Month,
                             FormattedDate = d.ReportDate.ToString("yyyy-MMM")
                         })
            .Distinct()
            .OrderByDescending(d => d.Year)
            .ThenByDescending(d => d.Month)
            .Select(d => d.FormattedDate);

env.OrderByDescending(x => x.ReportDate)