In some occasions a file doesn't open in job context, when opened in PackEdge via File > Open and then browsing to it manually on a mapped drive, despite the application being connected to the Automation Engine Server.
File isn't linked to an existing job on the server.
Job-dependent SmartMarks don't get resolved.
Remap the drive using the actual server name and not the CNAME (alias).
Browse to the file via the Network Locations instead of the mapped drives.
Select the correct job first via the Job Search window.