The example is a code at https://github.com/phadej/relaxed-json/tree/c3667434eb211b0f745872793723dcffe6e304d4
When running grunt less output is:
Running "less:web" (less) task
File web.min.css.map created.
File web.min.css.map created.
File web.min.css created.
Original: 7798 bytes.
Minified: 5564 bytes.
Looks like less itself doesn't support multiple input files for the source maps, but I guess it good to have this feature bug at least documented.