Hello, I hope I am going to be clear enough in my explanation: Basically, our OWA is https://mail.company1.com/owa We recently bought a new company2 and have set the company2 as accepted domain. We would like to be able through the OWA to be able to reach: https://mail.company1.com/owa AND https://mail.company2.com/owa I assume that we need to buy a special license but I am not sure it it is actually possible to have 2 OWA https addresses (we also use Outlook anywhere) Taht is what we think about: Server Licenses : 2 ( 2 cas servers) SAN url : 3 (mail.company1.com,mail.company2.com,autodiscover.company3.com) what do you think ? is it possible to handle 2 urls for owa ?

Does it matter what the URL is AFTER the user types it?for example you could tell your people to type:http://mail.company1.comORhttp://mail.company2.combecause the users didn't specify the S at the end of http they could get a custom 403.4 error which essentially redirects them to https://mail.company1.com/owa.If this would meet your business requirements you wouldn't have to get a new certificate.

Otherwise:Do you already have a SAN certificate? if so, just ask the provider to re-key it with the additional name. There is no extra Exchange license or anything required here.

We need to use https and no we don't have a SAN certificate.

I understand you need to use https. It is common practice however for users to be redirected to https from http. Instead of getting the normal "pagerequires secure channel" message it could redirect the users as necessary. because both URLs wouldn't have httpS they would both be redirected to the same place which is where you already have things going.All of this is pretty common practice and I believe there is a KB with instructions if you are interested. Otherwise you need to get a new certificate as mentioned above.