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Exchange 2013 root domain autodiscover issue after enabling company website https

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Hi All,

Recently our company enabled "https://company.com" on its web server they decided that anything that hits it http://company.com https://company.com be redirected to https://www.company.com/

After we have configured that and it is working great, we started experiencing our external Outlook clients having issues maintaining/connecting to Exchange 2013. The clients will get something like "Connecting to account@company.com" without any password prompt. The only way I can fix this right now is if I implement a registry fix to disable root domain lookup which is not great because we have to run that on all remote employees.

I have already added our SRV entry _autodiscover._tcp.company.com to 0 0 443 webmail.company.com

  1. Set the autodiscovery to CNAME webmail.company.com

  2. Checked all OutlookAnywhere and they all resolve to https://webmail.company.com

  3. I tried to stop redirection from the https://company.com/autodiscover and autodiscover/autodiscover.xml still have issues with popup.

If we

  1. change company.com A record to point to webmail.company.com it works

  2. completely block port 443 for company.com from the firewall for it to fail externally -- it works

  3. Connect to VPN prior to starting Outlook - it works

Does anyone have any suggestions on how to solve this issue without going to individual remote computers and running the registry fix?

Thanks


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