I saw this happen once last week and wrote it off as an anomaly, but it JUST happened again. Scheduler looked at the queue which was going to end at the TOTH and thought it was going to end at 20 minutes sooner. It then scheduled an additional 20 minutes of tracks which would have delayed the legal ID until 20 after the hour.
Here's an excerpt from the log that shows the end of scheduling the 8:00 hour and beginning of the 9:00 hour.
Line 29 fill Min:52:30 Max:52:30 rua 1950s & 60s
(08:47:23) Added /Users/newuser/Music/iTunes/iTunes Media/Music/Danny Williamsw/Unknown Album/White on Whiteo.mp3
(08:50:06) Added /Users/newuser/Music/iTunes/iTunes Media/Music/The Rolling Stones/Through the Past, Darkly (Big Hits, Vol. 2)/05 Mother's Little Helper.mp3
6 tracks with endtime within a 1 second window of target
Attempting track Jay and The Americans - Lets Lock The Door within a 1 second window of target.
(08:52:30) Added /Users/newuser/Music/iTunes/iTunes Media/Music/Jay And the Americans/Unknown Album/Lets Lock The Door.mp3
Line 30 pick Jingles
(08:52:38) Added /Users/newuser/Music/iTunes/iTunes Media/Music/x/Jingles/id2.mp3
Line 31 fill Min:60:00 Max:60:00 rua 1950s & 60s
(08:55:22) Added /Users/newuser/Music/iTunes/iTunes Media/Music/Billy Haley & the Comets/Unknown Album/See You Later Alligator.mp3
(08:58:16) Added /Users/newuser/Music/iTunes/iTunes Media/Music/Marvin Gaye/Unknown Album/How Sweet it Is (to Be Loved By You)T.mp3
1 track with endtime within a 10 second window of target
Attempting track Newbeatsb - Bread And Buttern within a 10 second window of target.
1 track with endtime within a 12 second window of target
Attempting track Herman's Hermitss - Silhouettes within a 12 second window of target.
(09:00:11) Added /Users/newuser/Music/iTunes/iTunes Media/Music/Herman's Hermitss/Unknown Album/Silhouettes.mp3
7:41:19 AM Sending to DJ
----------- Programming Segment 1950s & 60s finished at 7:41:19 AM (79 seconds) -----------
----------- Programming Segment "1950s & 60s" (Start time: 9:00 AM Length: 60 mins) started on Jan 5, 2012 at 8:40:00 AM (Auto) -----------
8:40:00 AM Found Overlap of 1.8 in the Preference Set Default
Queue End Time: 8:40:00 AM + Top of the Program Time: 9:00:00 AM = Total Time: -0:20:00
8:40:00 AM Current program ends at -0:20:00 relative to start time
8:40:00 AM Getting playlist data...
8:40:02 AM Importing iTunes Library Tracks...
8:40:17 AM 8,237 tracks in Library, 489 tracks in 9 playlists
Actual spots=10 Spot Distribution Ratio=2.5
Line 1 fill Min:TOTH rua 1950s & 60s
(08:42:58) Added /Users/newuser/Music/iTunes/iTunes Media/Music/Gary Pucket And the Union Gap/Unknown Album/This Girl Is a Woman Nows.mp3
(08:45:50) Added /Users/newuser/Music/iTunes/iTunes Media/Music/Cherh/Unknown Album/All I Really Want to Do.mp3
(08:48:40) Added /Users/newuser/Music/iTunes/iTunes Media/Music/Claud King/Unknown Album/Wolverton Mountain.mp3
(08:50:44) Added /Users/newuser/Music/iTunes/iTunes Media/Music/Gene Vincent/Unknown Album/Lotta Lovin'.mp3
(08:53:27) Added /Users/newuser/Music/iTunes/iTunes Media/Music/Manfred Manne/Unknown Album/The Mighty Quinn (Quinn the Eskimo).mp3
(08:56:23) Added /Users/newuser/Music/iTunes/iTunes Media/Music/Four Tops/Unknown Album/Bernedatte.mp3
1 track with endtime within a 8 second window of target
Attempting track Beach Boysh - Good Vibrations within a 8 second window of target.
TOTH is best after this next track
(08:59:56) Added /Users/newuser/Music/iTunes/iTunes Media/Music/Beach Boysh/Unknown Album/Good Vibrations.mp3
Line 2 time
Added Time Announcement
Line 3 pick i Legal ID