I'm in a bit of a dilemma with outbound mail with the Ironport and Office 365. Some domains do not receive emails from my organization when we send it through the ironport. If I turn off the outbound connected and let outgoing emails bypass the Ironport it works fine. I spoke with Microsoft support and they said it had to do with ESMTP and that I should disable or bypass that on the Ironport since Office 365 already does it. I cannot for the life of me figure out how to go about doing this in the Ironport and I couldn't really find anything about it in the manuals. Has anyone run into this situation or can anyone point me in the right direction so that I can resolve this? I really need to keep outbound mail flowing through the Ironport because we are required to send secured email attachments. Thanks.
Table of ContentsIntroductionVersion HistoryPossible Future
UpdatesDocuments PurposeNAT Operation in ASA 8.3+ SectionsRule Types
Network Object NATTwice NAT / Manual NATRule Types used per SectionNAT
Types used with Twice NAT / Manual NAT and Network Obje...
Table of Contents Introduction:This document describes details on how
NAT-T works. Background: ESP encrypts all critical information,
encapsulating the entire inner TCP/UDP datagram within an ESP header.
ESP is an IP protocol in the same sense that TCP an...