I worked on this over the past 2 days and found a solution. It relies on the OrderByFragmentTranslator I added for JPA's @OrderBy handling. There is a little trickery that goes on with ordering by properties that contain formula mappings. All the test suite tests pass, including quite a few that leverage formulas. The fix works with both @javax.persistence.@OrderBy and @org.hibernate.annotations.OrderBy.

The solution involved a number of concepts. First was the exposure of new method named org.hibernate.persister.entity.Loadable#getTableAliasForColumn. Loadable is an "optional" interface for @EntityPersister implementors. See the javadocs for its details.

Also had to change a few things in the org.hibernate.sql.ordering.antlr package. org.hibernate.sql.ordering.antlr.ColumnMapper was changed to return a new interface org.hibernate.sql.ordering.antlr.SqlValueReference instead of just Strings; this was needed to handle columns and formulas individually. org.hibernate.sql.ordering.antlr.SqlValueReference has 2 sub-interfaces: {{org.hibernate.sql.ordering.antlr.ColumnReference and {{org.hibernate.sql.ordering.antlr.FormulaReference.

The org.hibernate.sql.ordering.antlr.OrderByFragmentTranslator interface itself was altered to return a new contract org.hibernate.sql.ordering.antlr.OrderByTranslation rather than just a String. OrderByTranslation represents the "tokenized" form of the ordering fragment. The old form used a pattern of {{$PlaceHolder.[column_name]}} as the tokens; I changed that to just use {[column_name}}. This made search/replace much easier. OrderByTranslation is used to finalize the translation process, via its #injectAliases method which accepts a org.hibernate.sql.ordering.antlr.OrderByAliasResolver parameter. In the main code base, org.hibernate.sql.ordering.antlr.OrderByAliasResolver is the bridge back to the CollectionPersister to determine the appropriate table alias to use to qualify columns.