I think what is happening is that, EFCore expects a Collection Or IEnumerable To be able to map to the Collection Property of My Parent Entity
Looks like this is a bug with EF-Core. Maybe I'm overlooking the spec and only Collections should map to collections? As a work around I resolved this with SelectMany and Take.
var messages = query.SelectMany(x => x.Messages.OrderBy(m => m.Created).Take(1)) .OrderBy(x => x.ConversationId) .ToArray();
You can force includes with this syntax
var query = this._context.Conversations.Include("Messages").OrderBy(x => x.Id);
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