Learn How to Resolve Exchange Autodiscover Proxy Certificate Issue

Anuraag Singh | Modified: July 14, 2016 | General Exchange Issue | 3 Minutes Reading

This article is written about how to resolve Exchange Autodiscover Proxy Certificate Issue.

Problem Statement

In Outlook Exchange Server, user generally face issues related to certificate of Proxy sever. Several error may occur during server’s functioning and hence, user faces a trouble in resolving certificate issues. Generally, user gets panic when errors related to Proxy certificate occurs in Exchange. Proxy server certificate issue

proxy certificate issue exchange server

Reasons Behind Exchange Autodiscover Proxy Certificate Issue

The main cause for such error is that MS Outlook is working with Outlook Anywhere. However, such Outlook is working with Exchange, but it is using a role that is not mentioned in the certificate of Exchange. Another common cause may be that there is improper configuration of Autodiscover feature in Exchange Server.

Troubleshoot Exchange Autodiscover Proxy Certificate Issue

There are two measures by which one can get rid of this trouble. First approach is to create a new certificate and add all the new roles, which you require for your functioning. Another approach is to configure Exchange in such a way that no longer the error occurs when user is using Outlook with Outlook Anywhere.
In this content, we are going to discuss about configuration of Exchange for resolving Exchange Autodiscover proxy certificate issue.

Step 1: Examine Existing Outlook Anywhere

By executing the following command, one need to examine all the hostname related to Outlook Anywhere: get outlookanywhere

Step 2: Creating a DNS Record

Select any one name, which is mentioned on the certificate and used by the CAS servers or reserve proxies. Since we are going to use split DNS therefore, we will choose identical name for internal & external DNS. Using one name for both DNS will make troubleshooting procedure simpler.
The internal DNS are required to solve the private IP of CAS server and the external DNS are required to resolve the public IP of CAS sever.

Step 3: Configure New Outlook Anywhere

By executing the following command, configure Autodiscover Outlook Anywhere with hostnames of external and internal DNS:
get outlookanywhere

Step 4: Again Examine Outlook Anywhere

Once again execute the same command that you have used in step 1, for analysis the updates made to Outlook Anywhere.
get outlookanywhere

Step 5: Restart the Machine

Immediately, restart MSExchangeAutodiscoverAppPool because changes made are commonly reflected when machine has been restarted.


One can wind up with the fact of how to resolve exchange autodiscover proxy certificate issue, one need to make changes in the certificate of Exchange. Users can also generate a new certificate in Exchange, if they don’t have any problem doing so. Otherwise, if one is well-known about Exchange certificates, then he/she can easily troubleshoot this problem by configuring Exchange.