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Outlook Anywhere works with netgear not with ASA

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  • Outlook Anywhere works with netgear not with ASA

    I was hoping someone might be able to help me with a strange issue i am experiencing.

    We currently have 2 Cisco ASA 5510s deployed on 2 separate ISPs with IP SLA enabled on the internal cisco 3850 switch (which is acting as in internal router).

    We also have a COLO couple of miles down from our main building which is housing all of our Exchange servers.

    Site to site VPN tunnel between primary ASA here and ASA at the colo.

    Users internally here are able to use outlook without any issues. So far so good.

    We also have wireless on a completely separate network using netgear router.

    Now the issue is:
    When i use wireless on our desktops and laptops (not connected to our network), i am able to use Outlook Anywhere feature and able to get to my Exchange and everything works like it should.

    When IP SLA kicks in and our primary route is switched to our secondary route (thanks to ip sla), internally internet works fine, end users donít see any problems, except outlook stops working. It says trying to connect.

    If i have the end user disable their NIC and enable wireless (which goes out through netgear), outlook anywhere connects instantly and they're able to get emails.

    Why am i not able to go out from the secondary ASA (internet works!) to connect to my exchange servers?


  • #2
    Re: Outlook Anywhere works with netgear not with ASA

    Sounds like the return traffic isn't routed to the backup line. How does this switchover work? BGP?

    A tracert from both ends should tell you what's really going on. A comparison of traces from the OWA server in both scenarios (regular vs. backup connection) would be of particular interest.