Exchange Mailbox Monitoring

I currently have one Exchange 2007 server.  The owner of the company wants to be able to do the following for security purposes:

1.  Be able to view employee mailboxes at will.  Basically, select an employee and see their entire inbox, and go through them easily.

2.  Run reports and receive alerts to monitor emails with specific criteria to make sure emails are not being sent out to external addresses with sensitive information.

I am looking for software that is either free or paid for....  Just need it to work for a CEO type user that wants to do the above.
BSModlinAsked:
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AmitConnect With a Mentor IT ArchitectCommented:
just give full permission to your CEO on all user mailboxes and then use OWA to open it. For setting up alerts you can use transport rule or if you have software like mailmarshal or brightmail, you can create rules there as well.
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Miguel Angel Perez MuñozCommented:
First of all, first point may be illegal. Ask your law department because some countries consider professional email as personal.

As second, you can store all information on a Sharepoint (per example) and set blocking criteria: http://www.hisoftware.com/solutions/by-need/restrict-encrypt-content.aspx
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Asif BacchusCommented:
I second Miguel's point.  I had several owner's ask me to do the same thing and in many localities this is considered illegal unless waivers are signed by the employee and even then it's may not completely legal.  Check with in-house or retained council before doing this.

Also, depending on the size of the company, your CEO may not realize how much effort it is to go though all of his/her employee's email all the time.  Instead of full access (Amit is correct in his suggestion), would your CEO prefer to just receive an alert about outgoing email with certain words in the body/subject?  Is that moreso what you are looking for?  Does the CEO wish to moderate and/or approve such emails before they are sent out?
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AmitIT ArchitectCommented:
As said by other EE's above, make sure to check the legal part. Lot of countries prohibit such act. Normally such request go via legal advisor and as per legal advise mailboxes are set to litigation hold first and then legal team does the e-discovery according to the requirement. I worked for several customer and never heard any CEO need access to all user mailbox.
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Asif BacchusCommented:
Great point by Amit.  Litigation hold or similar may be exactly what your CEO is after.  If not, perhaps check if simple moderation of messages (i.e. approval before sending) would suffice?
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