We have an ISA 2004 server setup to publish OWA from our Exchange 2003 FE. It is using SSL to SSL bridging. There is a matching SSL certificate on the ISA server and the OWA server. I did not originally set this up and the person that managed it has recently left. My question is our SSL certificate needs to be updated soon; when I install the updated SSL cert on the ISA server and OWA will it disconnect currently connected users? Does the order of installing the certificate matter? ISA then OWA or OWA then ISA. In the process of setting up ISA 2004 in our lab but it would be very helpful if I could get an answer for one of the experts out there that have already done this. Thank you in advance.

When you update the certificate on the ISA server or the OWA server, it will reset the TCP connection and thus the user will have to re-establish the session. Plus, the SSL session will have to be re-negotiated. I recommend you schedule a few minutes of downtime to do this. I would do the OWA server first so that I could test the internal SSL first, then do ISA server.