WOW, I was just about to post about this. Here's my log when I try to enroll a device. Notice the URLs--the correct URL for the device is ##.##.##.38. When things start to go wrong, the log starts mentioned ##.##.##.165. I checked my DHCP and there's nothing of consequence on .165. Is ProfileManager getting confused about the correct URL of my device?
1:: [650] [2016/03/23 14:04:45.863] <192.168.1.38> Time since script start: 23406us [https://ourserver.org/devicemanagement/api/device/mdm_checkin]
1:: [650] [2016/03/23 14:04:45.863] <192.168.1.38> >>> Processing PUT mdm_checkin
0:: [650] [2016/03/23 14:04:45.865] <192.168.1.38> checkin: "CheckOut"
1:: [650] [2016/03/23 14:04:45.870] <192.168.1.38> Found target Mac: <'Name of Mac'[3518]>
1:: [650] [2016/03/23 14:04:45.924] <192.168.1.38> <<< Sent Final Output (0 bytes) - PUT mdm_checkin
0:: [650] [2016/03/23 14:04:45.924] <192.168.1.38> Completed in 84ms | 200 OK [https://ourserver.org/devicemanagement/api/device/mdm_checkin]
1:: [648] [2016/03/23 14:05:02.158] <192.168.1.38> Time since script start: 4927us [https://ourserver.org/devicemanagement/api/device/auto_join_ota_service]
1:: [648] [2016/03/23 14:05:02.158] <192.168.1.38> >>> Processing POST auto_join_ota_service
1:: [648] [2016/03/23 14:05:02.161] signerIndex = 0, signStatus = 1
1:: [648] [2016/03/23 14:05:02.682] <192.168.1.38> <<< Sent Final Output (6385 bytes) - POST auto_join_ota_service
0:: [648] [2016/03/23 14:05:02.682] <192.168.1.38> Completed in 528ms | 200 OK [https://ourserver.org/devicemanagement/api/device/auto_join_ota_service]
1:: [261] [2016/03/23 14:05:05.227] <192.168.1.38> Time since script start: 18993us [https://ourserver.org/devicemanagement/api/device/auto_join_ota_service]
1:: [261] [2016/03/23 14:05:05.228] <192.168.1.38> >>> Processing POST auto_join_ota_service
1:: [261] [2016/03/23 14:05:05.230] signerIndex = 0, signStatus = 1
1:: [261] [2016/03/23 14:05:05.512] <192.168.1.38> <<< Sent Final Output (12354 bytes) - POST auto_join_ota_service
0:: [261] [2016/03/23 14:05:05.512] <192.168.1.38> Completed in 303ms | 200 OK [https://ourserver.org/devicemanagement/api/device/auto_join_ota_service]
1:: [42246] [2016/03/23 14:05:11.793] <192.168.1.38> Time since script start: 4888us [https://ourserver.org/devicemanagement/api/device/mdm_checkin]
1:: [42246] [2016/03/23 14:05:11.793] <192.168.1.38> >>> Processing PUT mdm_checkin
0:: [42246] [2016/03/23 14:05:11.795] <192.168.1.38> checkin: "Authenticate"
1:: [42246] [2016/03/23 14:05:11.824] <192.168.1.38> <<< Sent Final Output (0 bytes) - PUT mdm_checkin
0:: [42246] [2016/03/23 14:05:11.824] <192.168.1.38> Completed in 35ms | 200 OK [https://ourserver.org/devicemanagement/api/device/mdm_checkin]
1:: [41016] [2016/03/23 14:05:20.945] <192.168.1.165> Time since script start: 5162us [https://ourserver.org/devicemanagement/api/device/mdm_checkin]
1:: [41016] [2016/03/23 14:05:20.945] <192.168.1.165> >>> Processing PUT mdm_checkin
0:: [41016] [2016/03/23 14:05:20.947] [FILTERED]
0:: [41016] [2016/03/23 14:05:20.951] <192.168.1.165> EXCEPTION: 403 Forbidden - No pending device for checkin_token 'b7ba5898-ca6c-4f1e-b598-d002931e62ec' at
#0 /Applications/Server.app/Contents/ServerRoot/usr/share/devicemgr/backend/php/ta rget.php(349): DieForbidden('No pending devi...')
#1 /Applications/Server.app/Contents/ServerRoot/usr/share/devicemgr/backend/php/md m_checkin.php(59): Target_for_checkin_request(Array, true)
#2 /Applications/Server.app/Contents/ServerRoot/usr/share/devicemgr/backend/php/db .php(396): _checkin_transaction(Array)
#3 /Applications/Server.app/Contents/ServerRoot/usr/share/devicemgr/backend/php/md m_checkin.php(173): PerformInTransaction('_checkin_transa...', Array)
#4 {main}
1:: [41016] [2016/03/23 14:05:20.952] <192.168.1.165> <<< Sent Final Output (14 bytes) - PUT mdm_checkin
0:: [41016] [2016/03/23 14:05:20.952] <192.168.1.165> Completed in 12ms | 403 Forbidden [https://ourserver.org/devicemanagement/api/device/mdm_checkin]
1:: [262] [2016/03/23 14:05:20.967] <192.168.1.165> Time since script start: 4868us [https://ourserver.org/devicemanagement/api/device/mdm_connect]
1:: [262] [2016/03/23 14:05:20.967] <192.168.1.165> >>> Processing PUT mdm_connect
0:: [262] [2016/03/23 14:05:20.972] <192.168.1.165> EXCEPTION: 403 Forbidden - Device not found for CN 'b7ba5898-ca6c-4f1e-b598-d002931e62ec' at
#0 /Applications/Server.app/Contents/ServerRoot/usr/share/devicemgr/backend/php/ta rget.php(395): DieForbidden('Device not foun...')
#1 /Applications/Server.app/Contents/ServerRoot/usr/share/devicemgr/backend/php/md m_connect.php(20): Target_for_incoming_request(Array)
#2 /Applications/Server.app/Contents/ServerRoot/usr/share/devicemgr/backend/php/db .php(396): _connect_transaction_1(Array)
#3 /Applications/Server.app/Contents/ServerRoot/usr/share/devicemgr/backend/php/md m_connect.php(128): PerformInTransaction('_connect_transa...', Array)
#4 {main}
1:: [262] [2016/03/23 14:05:20.973] <192.168.1.165> <<< Sent Final Output (14 bytes) - PUT mdm_connect
0:: [262] [2016/03/23 14:05:20.973] <192.168.1.165> Completed in 10ms | 403 Forbidden [https://ourserver.org/devicemanagement/api/device/mdm_connect]
1:: [650] [2016/03/23 14:05:21.069] <192.168.1.165> Time since script start: 5400us [https://ourserver.org/devicemanagement/api/device/mdm_checkin]
1:: [650] [2016/03/23 14:05:21.069] <192.168.1.165> >>> Processing PUT mdm_checkin
0:: [650] [2016/03/23 14:05:21.071] [FILTERED]
0:: [650] [2016/03/23 14:05:21.075] <192.168.1.165> EXCEPTION: 403 Forbidden - No pending device for checkin_token 'b7ba5898-ca6c-4f1e-b598-d002931e62ec' at
#0 /Applications/Server.app/Contents/ServerRoot/usr/share/devicemgr/backend/php/ta rget.php(349): DieForbidden('No pending devi...')
#1 /Applications/Server.app/Contents/ServerRoot/usr/share/devicemgr/backend/php/md m_checkin.php(59): Target_for_checkin_request(Array, true)
#2 /Applications/Server.app/Contents/ServerRoot/usr/share/devicemgr/backend/php/db .php(396): _checkin_transaction(Array)
#3 /Applications/Server.app/Contents/ServerRoot/usr/share/devicemgr/backend/php/md m_checkin.php(173): PerformInTransaction('_checkin_transa...', Array)
#4 {main}
1:: [650] [2016/03/23 14:05:21.075] <192.168.1.165> <<< Sent Final Output (14 bytes) - PUT mdm_checkin
0:: [650] [2016/03/23 14:05:21.075] <192.168.1.165> Completed in 11ms | 403 Forbidden [https://ourserver.org/devicemanagement/api/device/mdm_checkin]