Hello all, 

Okay so a bit of a background to what's running - 
There are two servers (both running Windows Server 2012 R2 Standard) - one runs the Windows Essentials Experience role (because I find it useful) whilst the other is running Exchange Server 2013 SP1. The setup is small since there are only around six or seven people that intend to use email and since I have the hardware and a licence for all the products, thought I would save some money and host exchange myself. 

Since the whole setup essentially resides at a residential location, theres only ONE public IP address - so https://technet.microsoft.com/en-gb/library/jj200172.aspx?f=255&MSPPError=-2147217396 was used to set up ARR from the server running the essentials experience (1) to the server with exchange 2013 installed (2). 

FOR THE LIFE OF ME I cannot get HTTPS redirect working properly. URL Rewrite has been tried, the standard HTTP redirect has been tried and even the error pages method (403.4 or something) was redirected from http://mail.externaldomain.co.uk to ttps://mail.externaldomain.co.uk/owa but to no avail. 

Looking at the method of using ARR, are there any fundamental differences that should be noted when setting up the HTTPS redirect compared to a standard exchange install (which isnt set up via ARR and has multiple public IP's)? If so, what is the best method to proceed? 

Would be grateful for any input on this!

Hi,

Please confirm whether your have clear Require SSL in the Default Web Site:

1. Start IIS Manager.

2. Expand the local computer, expand Sites, and then click Default Web Site.

3. In the Default Web Site Home pane, double-click SSL Settings.

4. In SSL Settings, clear Require SSL.

If you dont clear Require SSL, users wont be redirected when they enter an unsecured URL. Instead, theyll get an access denied error. Then open a Command Prompt window, and type iisreset /noforce to restart IIS. Please refer to the article below to double confirm your Http redirection is configured correctly:

https://technet.microsoft.com/en-us/library/aa998359(v=exchg.150).aspx

Re

Hi there Winnie,
I can confirm that the Require SSL checkbox is unticked in IIS. With this unticked, when the end user enters http://mail.domain.co.uk, it does not redirect to HTTPS but DOES redirect to OWA -  sending the user to http://mail.domain.co.uk/owa 

Further to this, I've also tried using Exchange 2013 CU7, CU8 and the Exchange 2016 Preview. None of them decided to correctly redirect to HTTPS when using ARR. Again, has anyone used ARR in an environment where there is only one public IP - and actually got it working properly?