• But in my experience, whenever I've run a RESTORE LOG command with anything other than the correct TRN file, I get a "too early" or "too recent" error. Yet here I can successfully run Restore Log manually!

    One clue is the History Messages show the Last Restored File as "None" and when I run sp_help_log_shipping_secondary_database on the Database last_restored_file is NULL. Similar restore jobs on this instance that do work do show the last file restored. If I tinker with the Log Shipping configuration to insert the last trn file I restored might that fix it?