Had to fix a broken Exchange 2007 and move it to a newer version thought I share my experience, it may help you to setup your exchange properly with certificates and outlook anywhere access with no cert warnings etc …

Please do NOT use any Exchange older then 2010 … old software often belongs in the trash not running on productive servers.

Setup your exchange according to your needs.

Now you want to activate outlook anywhere and setup access from outside your office over ssl. Here is a good documentation .. (and there are soo many crappy ones out there).

Do not follow their advice on ssl certificates, do not use wildcard and other stuff .. just read the link below. Good SSL certs are free these days.

https://community.spiceworks.com/topic/1144571-wildcard-ssl-cert-on-exchange

Now you need to setup the IIS with a proper certificate .. please STOP buying SSL certs, it is wasted money. Support Let's Encrypt. (https://letsencrypt.org/)

Here is a client for windows which runs great.

https://github.com/Lone-Coder/letsencrypt-win-simple/wiki/How-to-Run it will generate your certificate for your exchange.company.com for three month and renew it when needed.

https://weblog.west-wind.com/posts/2016/feb/22/using-lets-encrypt-with-iis-on-windows for those who need a better manual ..

Now just configure outlook to use a ssl http proxy all the time and your are set. Easy and clean.