Hi Jonathan - it is possible that this section of the path has not been marked on the OSM map database as suitable for walking. Please see this topic on how to make changes to OSM based maps.
The paths map doesn't seem to recognise paths between Hollinsclough, Staffordshire and the point B in auto foot mode on the attached screen shot. I've tried it on two computers using different accounts and still can't get past this point. Any ideas what's going on. Otherwise a really excellent plotting programme.
DESKTOP TABLET MOBILE
(no app download required)