So, of interest it does find the files in the directory (discover_files {"count"=>2}) yet it doesn't process them. Can't determine why just yet. Maybe the trace will shed some additional light.
[2019-01-14T19:26:26,675][TRACE][filewatch.discoverer ] discover_files {"count"=>2}
[2019-01-14T19:26:26,833][TRACE][filewatch.discoverer ] discover_files handling: {"new discovery"=>true, "watched_file details"=>"<FileWatch::WatchedFile: @filename='SystemOut.log', @state='watched', @recent_states='[:watched]', @bytes_read='0', @bytes_unread='0', current_size='14081405', last_stat_size='14081405', file_open?='false', @initial=true, @sincedb_key='unknown 0 0'>"}
[2019-01-14T19:26:26,839][TRACE][filewatch.sincedbcollection] associate: finding {"inode"=>"unknown", "path"=>"C:/Logs/20190108/icnserver12/SystemOut.log"}
[2019-01-14T19:26:26,848][TRACE][filewatch.sincedbcollection] associate: unmatched
[2019-01-14T19:26:26,873][TRACE][filewatch.discoverer ] discover_files handling: {"new discovery"=>true, "watched_file details"=>"<FileWatch::WatchedFile: @filename='SystemOut_19.01.07_11.33.45.log', @state='watched', @recent_states='[:watched]', @bytes_read='0', @bytes_unread='0', current_size='26385775', last_stat_size='26385775', file_open?='false', @initial=true, @sincedb_key='unknown 0 0'>"}
[2019-01-14T19:26:26,874][TRACE][filewatch.sincedbcollection] associate: finding {"inode"=>"unknown", "path"=>"C:/Logs/20190108/icnserver12/SystemOut_19.01.07_11.33.45.log"}
[2019-01-14T19:26:26,875][TRACE][filewatch.sincedbcollection] associate: unmatched
[2019-01-14T19:26:26,951][TRACE][filewatch.tailmode.processor] Delayed Delete processing
[2019-01-14T19:26:26,964][TRACE][filewatch.tailmode.processor] Watched + Active restat processing
[2019-01-14T19:26:27,006][TRACE][filewatch.tailmode.processor] Rotation In Progress processing
[2019-01-14T19:26:27,018][TRACE][filewatch.tailmode.processor] Watched processing
[2019-01-14T19:26:27,036][TRACE][filewatch.tailmode.handlers.createinitial] handling: SystemOut.log
[2019-01-14T19:26:27,055][TRACE][filewatch.tailmode.handlers.createinitial] opening SystemOut.log
[2019-01-14T19:26:27,079][TRACE][filewatch.tailmode.handlers.createinitial] handle_specifically opened file handle: 100750, path: SystemOut.log
[2019-01-14T19:26:27,084][INFO ][logstash.agent ] Successfully started Logstash API endpoint {:port=>9600}
[2019-01-14T19:26:27,118][TRACE][filewatch.tailmode.handlers.createinitial] add_new_value_sincedb_collection {"position"=>0, "watched_file details"=>"<FileWatch::WatchedFile: @filename='SystemOut.log', @state='active', @recent_states='[:watched, :watched]', @bytes_read='0', @bytes_unread='14081405', current_size='14081405', last_stat_size='14081405', file_open?='true', @initial=true, @sincedb_key='unknown 0 0'>"}
[2019-01-14T19:26:27,127][TRACE][filewatch.tailmode.handlers.createinitial] handling: SystemOut_19.01.07_11.33.45.log
[2019-01-14T19:26:27,130][TRACE][filewatch.tailmode.handlers.createinitial] opening SystemOut_19.01.07_11.33.45.log
[2019-01-14T19:26:27,138][TRACE][filewatch.tailmode.handlers.createinitial] handle_specifically opened file handle: 100751, path: SystemOut_19.01.07_11.33.45.log
[2019-01-14T19:26:27,141][TRACE][filewatch.tailmode.handlers.createinitial] add_or_update_sincedb_collection: found sincedb record {"sincedb key"=>#<struct FileWatch::InodeStruct inode="unknown", maj=0, min=0>, "sincedb value"=>#<FileWatch::SincedbValue:0xb5d09d @last_changed_at=1547515587.112, @watched_file="<FileWatch::WatchedFile: @filename='SystemOut.log', @state='active', @sincedb_key='unknown 0 0, size=14081405>", @position=0>}
[2019-01-14T19:26:27,150][TRACE][filewatch.tailmode.handlers.createinitial] add_or_update_sincedb_collection: the found sincedb_value has a watched_file - this is a rename, switching inode to this watched file
[2019-01-14T19:26:27,154][TRACE][filewatch.tailmode.handlers.createinitial] add_or_update_sincedb_collection: switching from... {"watched_file details"=>"<FileWatch::WatchedFile: @filename='SystemOut_19.01.07_11.33.45.log', @state='active', @recent_states='[:watched, :watched]', @bytes_read='0', @bytes_unread='26385775', current_size='26385775', last_stat_size='26385775', file_open?='true', @initial=true, @sincedb_key='unknown 0 0'>"}
[2019-01-14T19:26:28,226][TRACE][filewatch.tailmode.handlers.unignore] handling: SystemOut_19.01.07_11.33.45.log
[2019-01-14T19:26:28,235][TRACE][filewatch.tailmode.handlers.unignore] update_existing_sincedb_collection_value: SystemOut_19.01.07_11.33.45.log, last value 0, cur size 26385775
[2019-01-14T19:26:28,239][TRACE][filewatch.tailmode.handlers.unignore] -------------------- >>>>> update_existing_specifically: unignore {"watched file"=>"<FileWatch::WatchedFile: @filename='SystemOut_19.01.07_11.33.45.log', @state='watched', @recent_states='[:watched, :watched, :active, :ignored]', @bytes_read='0', @bytes_unread='26385775', current_size='26385775', last_stat_size='26385775', file_open?='false', @initial=false, @sincedb_key='unknown 0 0'>", "sincedb value"=>#<FileWatch::SincedbValue:0xb5d09d @last_changed_at=1547515587.151, @watched_file="<FileWatch::WatchedFile: @filename='SystemOut_19.01.07_11.33.45.log', @state='watched', @sincedb_key='unknown 0 0, size=26385775>", @position=0>}
[2019-01-14T19:26:28,251][TRACE][filewatch.tailmode.processor] Delayed Delete processing
[2019-01-14T19:26:28,253][TRACE][filewatch.tailmode.processor] Watched + Active restat processing
[2019-01-14T19:26:28,256][TRACE][filewatch.tailmode.processor] Rotation In Progress processing
[2019-01-14T19:26:28,257][TRACE][filewatch.tailmode.processor] Watched processing
[2019-01-14T19:26:28,259][TRACE][filewatch.tailmode.handlers.createinitial] handling: SystemOut.log
[2019-01-14T19:26:28,261][TRACE][filewatch.tailmode.handlers.createinitial] opening SystemOut.log
[2019-01-14T19:26:28,265][TRACE][filewatch.tailmode.handlers.createinitial] handle_specifically opened file handle: 100752, path: SystemOut.log
[2019-01-14T19:26:28,266][TRACE][filewatch.tailmode.handlers.createinitial] add_or_update_sincedb_collection: found sincedb record {"sincedb key"=>#<struct FileWatch::InodeStruct inode="unknown", maj=0, min=0>, "sincedb value"=>#<FileWatch::SincedbValue:0xb5d09d @last_changed_at=1547515588.248, @watched_file="<FileWatch::WatchedFile: @filename='SystemOut_19.01.07_11.33.45.log', @state='watched', @sincedb_key='unknown 0 0, size=26385775>", @position=0>}
[2019-01-14T19:26:28,267][TRACE][filewatch.tailmode.handlers.createinitial] add_or_update_sincedb_collection: the found sincedb_value has a watched_file - this is a rename, switching inode to this watched file