Microsoft Exchange 2016 - Additional OWA Virtual Directory

I haven't tried this one before but just to verify, are you using this command to provision it or trying to manually do it yourself?

https://learn.microsoft.com/en-us/powershell/module/exchange/new-owavirtualdirectory?view=exchange-ps

i hope you have created a different website where the owa virtual dir is created. did you run the  New-OwaVirtualDirectory ?
my client had tried it , but they shelved it off due to the Exchange CU breaking it.there is a blog by the MS Exchange team however no pointers to the redirection errors you are facing. you could probably check this out and retry
https://techcommunity.microsoft.com/t5/exchange-team-blog/configuring-multiple-owa-ecp-virtual-directories-on-the-exchange/ba-p/611217#:~:text=Microsoft%20supports%20creating%20additional%20OWA,internal%20or%20external%20URL%20values.

Yes, I did copy the working owa and ecp directories and then ran the New-OwaVirtualDirectory/New-EcpVirtualDirectory pointing to the newly copied directories. Also created a new website and setup the bindings 80/443.

https://learn.microsoft.com/en-us/exchange/clients/outlook-on-the-web/http-to-https-redirection?view=exchserver-2019   This article also describes the default redirect for Exchange virtual dirs, the defaults are none. if you see a redirection , check whether the default OWA has any redirection set, do you have a Loadbalancer or other devices infront of the Exchange server that could cause this ?

I reviewed the article and the redirects work for the default site. The new site still has a redirect loop. There is no load balancer. The original redirect is to a logon.aspx, subsequent redirects are to a 404 error page that is not found.

there is definitely something else. when you copied the content did you review the owa web config file. cant think of anything else if you have verified all the settings

also the web site IP bindings is it listening on all IP's

Reviewed the web config file, there is nothing that seems off. Also the default website is bound to ip 1 and the new website is bound to ip 2. Originally the default website was bound to all unassigned, I have changed that to the ip for 80 & 443, still get same result.

Logs and event tracing for windows if not enabled do so, if already there could these be reviewed ?

Interestingly, this line is in the log file for the new site

2023-04-11 14:45:37 192.168.1.129 RPC_IN_DATA /rpc/rpcproxy.dll ca98d0cf-1719-42ea-8334-486f6cd04679@nnn.local:6001 80 - 192.168.1.129 MSRPC - 404 0 2 2205

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certificate binding for the new OWA in IIS. is that setups correctly

The cert for the new site is self signed.

self signed should be ok, unless you are trying a cert with another domain all together which honestly i havent tried and donot know how it would behave. btw is the default owa using a cert from a CA and the new OWA site Selsigned ?

Yes, the default site is using a CA cert and the new site is a self signed (until I can get a CA one)

purely from IIS perspective The following default <httpRedirect> element is configured in the root ApplicationHost.config file in IIS 7 when the HTTP Redirection role service is installed. This configuration section inherits the default configuration settings unless you use the <clear> element.  appcmd to check/ disable redirection on the new owa could be an option. but difficult to say unless we find whats redirecting

When I turn on redirect on the default web site, it also turns on for the new site. I can turn them both off, yet I still get  the redirection loop

What is the alternative? Setting up an additional exchange server ?

Setting up an additional exchange  served for owa is an option, however i still believe there is something at the IIS level causing this. Did you by chance use appcmd to set re direction to false or try looking into application host config. Sorry am not being too helpful with the info but i know for sure it has worked in other env within Ex2013

Used appcmd and set redirect to false (this changed it for both websites) still get redirection loop. Also, the ApplicationHost.config does not have any entry for redirect in the new site sections.

great