$ cat file
081125_08:38 14315 2.39 SOM.exe

OPERATIONAL CONTEXT 1
AO Total = 8867
AO Outstanding = 42
AO Acknowledged = 0
AO Terminated = 8825
AO Not Handled = 42
AO Handled = 0
AO Closed = 8825
AO Archived = 0

OPERATIONAL CONTEXT 2
AO Total = 2570
AO Outstanding = 2365
AO Acknowledged = 32
AO Terminated = 173
AO Not Handled = 2397
AO Handled = 0
AO Closed = 173
AO Archived = 0

OPERATIONAL CONTEXT 3
AO Total = 403
AO Outstanding = 312
AO Acknowledged = 2
AO Terminated = 89
AO Not Handled = 314
AO Handled = 0
AO Closed = 89
AO Archived = 0

OPERATIONAL CONTEXT 4
AO Total = 44258
AO Outstanding = 650
AO Acknowledged = 0
AO Terminated = 43608
AO Not Handled = 650
AO Handled = 0
AO Closed = 43608
AO Archived = 0


081125_09:40 14315 2.32 SOM.exe

OPERATIONAL CONTEXT 1
AO Total = 9002
AO Outstanding = 46
AO Acknowledged = 0
AO Terminated = 8956
AO Not Handled = 46
AO Handled = 0
AO Closed = 8956
AO Archived = 0

OPERATIONAL CONTEXT 2
AO Total = 2543
AO Outstanding = 2357
AO Acknowledged = 32
AO Terminated = 154
AO Not Handled = 2389
AO Handled = 0
AO Closed = 154
AO Archived = 0

OPERATIONAL CONTEXT 3
AO Total = 434
AO Outstanding = 312
AO Acknowledged = 2
AO Terminated = 120
AO Not Handled = 314
AO Handled = 0
AO Closed = 120
AO Archived = 0

OPERATIONAL CONTEXT 4
AO Total = 45241
AO Outstanding = 664
AO Acknowledged = 0
AO Terminated = 44577
AO Not Handled = 664
AO Handled = 0
AO Closed = 44577
AO Archived = 0

$ awk 'END {
  if (t) 
    print e, "Total:", t
}
/exe$/ { 
  if (t) 
    print e, "Total:", t
  t = 0
  e = $0
  }
/Total/ { t += $NF }
' file
081125_08:38 14315 2.39 SOM.exe Total: 56098
081125_09:40 14315 2.32 SOM.exe Total: 57220
$

END {
  if (t) 
    print e, "Total:", t
  }
/exe$/ { 
  if (t) 
    print e, "Total:", t
  t = 0
  e = $0
  }
/Total/ { t += $NF }

awk -f <scriptname> <your_datafile>