Currently in the early stages of a pilot phase for Office 365, the main focus is the Exchange Online for shared calendars and obviously email.
The school this is being piloted in, has an admin network and a curriculum network and has a Cisco 5505 box configured to allow the admin clients access across the curriculum file share and managed print solution. As it stands the admin clients have their gateways pointing to the ASA box, their primary DNS points to an admin file server which has an instance of DNS configured (pointing to the LEA's DNS).
On the whole, the pilot is going swimmingly for curriculum, however this is far from the case for the 5 admin clients.
As it stands when we configure the Outlook client on an admin computer, the setup procedure sometimes authenticates, other times it chooses not to, re-prompting for password. On the occasions when it does authenticate and the Outlook client opens, the client will eventually time out with a yellow exclamation mark, signalling not connection to the exchange.
I know that the LEA is using smoothwall, also that this could be one of their ISA server firewalls detecting and prevent access... But I just need your thoughts before I take this up with the LEA.
@Mr_Jiminy did you ever find a fix for this? I've got the exact same issue, so far i've found out that if I disable the connect to exchange with an ecrypted connection everything works fine, but I don't think that is ideal.
If you sorted it could you let me know what you did to sort it out, I really want this to work as it's all that is keeping me from rolling it out to staff.
It was filtering or a FW at the LEA side... To cut a long story short, we decided against implementing client side on the admin network (only 5 computers)... Opting instead to get them to route through webmail... The 40 users on curriculum have the option to set-up client side, as they don't route through the LEA filtering or FW's.