I am trying to connect an internal application we have that can email our clients but it keeps failing at our firewall (ISA2004). I have three possible cloud Exchange addresses all that end with outlook.com. Two include our cloud exchange server name one of which includes "mailbox" before the outlook.com. The third is a "pod" number then outlook.com. Which of the three do I use to allow my application to connect to our live@edu exchange server and what port(s) do I need to open?

Your post is way too unclear and confusing.

Okay, My application asks for smtp server address and port. We use live@edu so we connect to our exchange using either outlook.com with OWA or Outlook. I tried using the Outlook settings to connect the application to our our email server so it can mass email 50-100 families but it doesn't work. I have opened ports 443 and 587 in ISA 2004. I'm not sure which of these two I should use in the setting for "port" in the application but I have tried both and neither works. When I log in as administrator to the live@edu exchange portal that is a different server address that starts with pod12345.outlook.com (numbers of are not real as I would like to protect our information. If you aren't familiar with what settings to type in for exchange server name and port within the live@edu system then you won't be able to help but thanks for trying. I was purposefully vague to protect our exchange server name and address. Maybe you can point me in the right direction of who would know the answer.

It's not getting any better,...and the fake Domain Names only make it worse. However if you understand what ISA/TMG actually does,...and does not do,...that may help you sort it out. ISA/TMG Publishing is just a simple straight-forward use of Reverse-NAT,...which doesn't care one bit about Domain Names,...it only uses IP#. So if the Domain Name you use is resolved by the Host or Device you are running your Application from,.. then this would be all that really mattered and ISA/TMG would pass the traffic to the Service in question. Whatever happens after that (or fails to happen) really would have nothing to do with the ISA/TMG itself and your solution would be elsewhere. OWA, OMA, and ActiveSync Publishing leverages "web proxying" and is an entirely different thing. This side of things probably has nothing to do with what you are doing, so is likely not relevant to the situation.

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