Sep 25 2013

Out of Office not working – Using Exchange Autodiscover Redirect

Had an interesting one today with a bit of a lesson at the end of the article.


Users are able to connect to Exchange with Outlook, send and receive mails etc. Users are however unable to set up their Out of Office using Outlook but they are able to set it using Outlook WebApp. We have a hybrid Exchange environment with 2010 and 2007 CAS servers. In the back-end we are running an Exchange 2007 CCR Cluster.

Past troubleshooting with regards to Out of Office not working has taught me to check and test autodiscover. I bet that the OAB is also not downloading?
I ran the normal checks such as checking the certificates and running nslookup to see if redirects to asn it did.

My next step was to check IIS as I’ve had a previous issue there. Low and behold I noticed that an ex-admin used his credentials for authentication. This caused issues as the admin’s account has been deleted a few days ago as he left our company. I then created a service account and added the credentials in IIS to ensure that this does not happen again. Users reported that Out of Office is working again.

Below are some screenshots for where I changed the credentials. Note that when I tried opening any settings under the Autodiscoverredirect Webpage in IIS that the error explicitly told me that the account for admin-abc had problems authenticating. The challenge was that I was not too sure where this is supposed to be changed. But here you go:

1. Open IIS on your CAS server and browse to Sites => AutodiscoverRedirect (Or whatever you named it)


2. On the right click on “Advanced Settings”


3. Click on “Physical Path Credentials” and then set. Add your service account credentials and save.


This solved my issue with redirection.

Lesson: No matter how many years of experience admins have, the still seem to take the quick route of using their personal credentials where a service account should be used causing issues for your users and customers. Don’t be a lazy engineer and use the service accounts and remember to document EVERYTHING!

Jan 5 2011

OoO not working because AutoDiscover does not work

1     First: Always check Certificates and DNS



1.1 Check if your certificates are configured correctly and if they have expired.


Open the Exchange Management Console and run: Get-ExchangeCertificate | fl
Review your certificates and ensure that they have not expired

1.2 Check DNS


A good way to test DNS is using NSLOOKUP. Open cmd and type nslookup and hit enter.
(In our case we need to run nslookup to our client’s autodiscover address to test redirection as we user autodiscover redirect.)


Type (or .net etc.) this should return with the redirect address as per below screenshot.








  1.3 Additional Tests


You should also run the below tests in Outlook and in a Web Browser to test Autodiscover:




Hold Ctrl and Right click on the Outlook Icon in the task bar. Then choose “Test E-mail AutoConfiguration”.

Within the dialog box type your e-mail Address, password and untick Use Guessmart and Secure Guessmart Authentication. Then click on “Test”

















The test should be successful with doing a redirect.

You could also test autodiscover using http://testexchangeconnectivity .com but make sure there is no mail in the mailbox and OoO is not on as it will spit out an error.


2     IIS Settings


We found that the problem we had had nothing to do with DNS or Certs but the tests still failed. While testing the rules on ISA we saw an entry that pointed us to the following location.


IIS=>Computer Name=>Websites=>AutoDiscoverRedirect=>AutoDiscover=>AutoDiscover.xml


Right Click on AutoDiscover.xml ans untick the following tick box.




This resolved the issue and all AutoDiscover tests where successful. OoO and OAB was working once again.


Note: When we restarted IIS we noticed that the tick was back and we had to untick the checkbox again. We are still looking into this.