Advanced topics 
Determining Outbound/Inbound/Internal mail 
This section applies only to the Exchange VS API mode 
GFI  MailSecurity  uses  a  set  of  rules  to  determine  whether  a  mail  is 
inbound,  internal  or  outbound.  In  some cases  it  may  be  important  to 
understand  the  logic  used.  This  logic  is  based  on  determining  if  the 
user is present in Active Directory or not. 
When is a mail outbound? 
GFI  MailSecurity  will  assume  a  mail  is  outbound  if  the  sender  is  an 
internal  user  and  the  recipient  is  an  external  user.  To  determine 
whether a sender or recipient is external or internal, GFI MailSecurity 
makes an Active Directory query. If the user is present, he is assumed 
to be an internal user. 
When is a mail inbound? 
GFI  MailSecurity  will  assume  a  mail  is  inbound  if  the  sender  is  an 
external  user  and  the  recipient  is  an  internal  user.  It  will  use  AD  to 
determine whether the sender/recipient is external or internal. 
When is a mail internal? 
If both the sender and the recipient appear in Active Directory then the 
mail  is  internal.  Because  of  various  reasons,  we  can  not  determine 
100%  if  an  email  is  internal  or  inbound.  This  is  the  reason  why,  for 
security  reasons,  you  can  not  create separate  rules for  internal mail. 
Assuming  you  would  set  up  more  relaxed  rules  for  internal  mail,  a 
security hole might appear. 
What if the mail has multiple recipients, both internal and 
In this case, all rules will be applied. So if a mail contains an internal 
recipient that has  a  specific  rule specified,  the  rule  will  be  applied.  If 
the mail also contains an outbound rule linked to the sender, then this 
rule will be applied also. 
User synchronization with Exchange 5.5 
If  you  are  using  GFI  MailSecurity  in  gateway  mode  with  Microsoft 
Exchange  server  5.5,  GFI  MailSecurity  installs  a  synchronization 
service  that  updates  the  GFI  MailSecurity  user  database 
automatically.  This  eliminates  the  hassle  of  synchronizing  users 
manually between Exchange Server 5.5 and GFI MailSecurity.  
Advanced topics 

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