Oct 13 2015

Old Out of Office message is sent even after a new message has been created

We had a few instances this year where users create a new Out of Office message but then report that the previous Out of Office message is sent instead of the new Out of Office message or both are sent to people that sent mail to them.

I found that most of the time running outlook.exe /cleanrules works if that does not work please see method 2 below.

Method 1

  1. Close Outlook
  2. Click on start and in run type Outlook.exe /cleanrules then hit enter
  3. Wait for replication and send a test mail to the mailbox to see if the old Out of Office message is not sent out anymore
  4. If the old Out of Office message is still sent check method 2 below

Method 2 (Only had to do this on one occasion)

  1. Open Outlook
  2. Open the Out of Office assistant
  3. At the bottom of the Out of Office assistant window, click on Rules
  4. Delete all rules
  5. Close Outlook, re-open Outlook and test sending a mail to the mailbox. You should not receive the old Out of Office assistant anymore


An Out of Office message is only sent once to a sender. It’s a good idea to send the test mails from different e-mail addresses that have not as yet received the Out of Office message from the mailbox that you are troubleshooting

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 autodiscover.domain.com redirects to autodiscoverredirect.domain.com 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!