How can I keep it that the "reply to" address is always the generic info@myoffice.com on email leaving the office but keep the personal address for in office messaging?
Hope that is clear. lol
What you're referring to is the Send As feature of Exchange, I believe. Here is how to set it up: http://technet.microsoft.com/en-us/library/aa998291%28EXCHG.80%29.aspx
Are you using Outlook or Outlook Web Access? Also, you could set up a rule so that all outgoing email is from that address but then to override that, you would need to disable the rule. So the Send As feature is probably your best bet, unless your pretty sure that all outgoing email needs to be sent from the generic email.
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