SSL-Problems when setting up a test environment with Exchange

Hello everyone,
I am trying to set up a test environment with Exchange 2013 to learn how the stuff works. However, I am facing some problems due to the fact that Exchange is designed for use with SSL certificates. The main thing that makes problems is the connection with
RPC over HTTP. I've used the MS remote connectivity analyzer to find out why it is not working and as I thought it is because of a missing SSL certificate (it seems the self signed doesn't work here). Now in order to get this working I just bought a certificate
for "mydomain.com". Now here is the first problem: This certificate is NOT a wildcard certificate. So if I understood correctly it works for mydomain.com but it won't work for subdomain.mydomain.com. Is this correct? (First question)
If this is correct I will probably another problem: As I said this is a learning-environment so the server is at home behind a router. This means: Only one WAN-IP. I think could get this working by forwarding everything to the Exchange Server (like mydomain.com
goes to the WAN-IP where the router is forwarding everything like port 25 or 443 directly to the exchange Server). This way I wouldn't have any problems I think: mydomain.com has a valid SSL cert, it resolves to my WAN-IP which forwards everything to the internal
Exchange Server. Now here is the problem: I plan to setup a SharePoint Server as well. I thought about using ARR (IIS) to make both available behind the same WAN-IP without using ports inside the url. Ideally the Exchange Server should then be available via
"mail.mydomain.com". This will work fine with ARR but then I probably have SSL problems again? (second question)
Do you have any ideas what I can do to solve such problems? Should I buy another certificate for mail.mydomain.com? But then I would need to buy several certificates (e.g. for autodiscover.mydomain.com to get this working as well). This can become very expensive...
Thanks!
Regards
Christian

Hi,
For your first question, if there is a single certificate just for “mydomain.com”, it cannot work for subdomain.mydomain.com.
Generally, antodiscover.domain.com is used to access the autodiscover service for external users. If you just need test users to access Exchange server from internal environment, it is not necessary to get a certificate for autodiscover.domain.com.
Therefore, for your second question what I can ensure is that if all URLs that used to connect Exchange from internal and external are configured to mail.mydomain.com with all services(IIS,SMTP,POP,IMAP), there will be no certificate problems in Exchange
side.
Best Regards,
Winnie Liang
TechNet Community Support

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Koen wrote:
> Hello,
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> Best regards
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