Outlook 2016 installed in windows 10 is unable to configure the mailbox in Exchange 2010

Question

Hi All,

I request for your inputs on this issue, i am aware that Exchange 2010 is out of support from Microsoft, Please excuse us, We are in the process of upgrading our Exchange 2010 servers to Exchange 2016

We have installed Outlook 2016 in windows 10 , then attempted to configure the mailbox present in Exchange 2010, but it is not working. I have collected the network traces, When i am configuring the outlook profile, I was able to see outlook 2016 installed in windows 10 is sending request to Microsoft IP address rather than connecting to the Exchange server present in the LAN network, i have disabled the proxy settings in the user machine, but still outlook 2016 is sending connection to Microsoft IP address and finally it is failed to configure the profile

The same outlook 2016 version installed in windows 7 can connect that same mailbox present in Exchange 2010 without any issues.

This issue is only with the combination of outlook 2016 + Windows 10 + Exchange 2010

Answer 1

@Joy Zhang-MSFT

Many thanks for your response.

We were not able to configure the Email account in outlook 2016 installed in windows 10, So unable to run the test Email configuration. I can able to access the Autodiscover URL and see the output from the windows 10 machine. Exchange servers are not published over internet, So i don't think i cannot use EXRCA

Outlook 2016 installed in windows 7 is not sending https traffic to public ip address over port number 443

I have taken the netmon trace for outlook 2016 installed in windows 10, it is sending https traffic to public ip address over port number 443, Specific snips are given below for your reference

****Most importantly, when i use the fiddler to capture the traffic, outlook 2016 installed in windows 10 is working fine, when i close fiddler and re opened outlook it is not working ** The change i noticed when running fiddler, it is adding proxy settings to the user machine. This issue seems to be strange, Please share your insights.**

Answer 2

Hi All,

when i use the fiddler to capture the traffic, outlook 2016 installed in windows 10 started working , when i close fiddler and re opened outlook, it is not working . The change i noticed when running fiddler, it is adding proxy settings to the user machine. This issue seems to be strange, Please share if anyone has faced similar type of incident