Exchange 2010 Autodiscover not working at all. I am sure that I set all of the configs correctly. I just noticed in AD Sites & Services that the subnets associated with these domain controllers have the wrong entries. The subnets that are entered are not correct. Would that cause this behavior? Also, in internal DNS, I have an IP address for autodiscover pointing to the VIP of the F5 load balancer and all of the web services are pointing to that location (mail.company.com). Do I also need an internal SRV record?

Domain-joined machines use the Autodiscover entries in the service connection point records in AD as defined by the AutodiscoverServiceInternalURI property set by the Set-ClientAccessServer cmdlet. This information is very definitely affected by improperly configured AD sites and subnets, so it's important that you fix that first. The only thing I can think of that would have messed that up would be administrator error or inattention. Non-domain-joined machines look to the autodiscover.company.com record in DNS. You do not need and probably don't want an SRV record. Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

OK. That does make sense. I ran the test-outlookwebservices cmdlet and got a few interesting responses from that test. I am also struggling with a certificate mismatch error in which i removed an Exchange certificate that had the subject name of webmail.company.com. I reissued one that had the subject of mail.company.com and then changed all of the web services to mail.company.com. When I browse to OWA for example, I still get a certificate reading webmail. I don't understand where it is getting that from? There is a hardware load balancer in front of the CAS array, an F5. Do they have the cert installed as well? I am really frustrated as this is chewing up my time.

Also, when running the cmdlet Get-ClientAccessServer -Identity CAS01 | fl AutodiscoverServiceInternalUri, I get https://autodiscover.company.com/autodiscover/autodiscover.xml. I get this for both Client Access Servers, so I think I have it setup correctly.

Have you tried entering that URL in a web browser? You should get an error, but it's a verification that Autodiscover is answering. Also, do you have a UCC certificate with both webmail and autodiscover as SANs? Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

Based on your post, I understand that Autodiscover cannot work normally. Also, the certificate mismatch error was received when trying to access OWA. If I have misunderstood, please feel free to let me know. Since we usually discuss one problem per thread, let’s discuss the Autodiscover first. When the first problem is addressed, you can create another thread and continue to discuss. To do this, we can avoid some confusion. Thank you for your understanding. First, I suggest you refer to the following article to assure CAS server is configured correctly in HLB environment. http://www.msexchange.org/articles_tutorials/exchange-server-2010/high-availability-recovery/load-balancing-exchange-2010-client-access-servers-using-hardware-load-balancer-solution-part1.html After that, please create a new mailbox and check whether it can be configured automatically when logging. If not, please post the error message here. Otherwise, please run Test E-mail AutoConfiguration and post the result. 1. While Outlook is running, hold down the CTRL key, right-click the Outlook icon in the notification area, and then select Test E-mail AutoConfiguration. 2. Verify that the correct e-mail address is in the box next to E-mail Address. 3. Clear the check boxes next to Use Guessmart and Secure Guessmart Authentication. 4. On the Test E-mail AutoConfiguration page, verify that the check box next to Use AutoDiscover is selected, and then click the Test button. 5. Then, please check whether there is any error code. If so, please post it here for research. Thanks. Novak Wu TechNet Subscriber Support in forum If you have any feedback on our support, please contact tngfb@microsoft.com Please remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.

Yes, I will stick to one topic. Sorry. Let's get Autodiscover working first. In Sites & Subnets, the specific IP range of the domain controllers and Exchange servers does not exist for this site. These servers are in a 10.16.6.0/24 and 10.16.4.0/24. The only subnet associated with this site is 10.16.0.0/16. Am I correct in saying that we need to enter the specific IP subnets for those servers? Or does that /16 cover it?

When I go to https://autodiscover.company.com/autodiscover/autodiscover.xml I get prompted for my username/password over and over again. Doesn't let me get past that. Same thing when I try to configure Outlook. I put in name and email address and it prompts for credentials. Doesn't let me get past that. I changed password and nothing.

This is the current setup: F5 Load Balancer (VIP IP Addresses) outlook.company.com ....10.16.12.218 mail.company.com .......10.16.12.217 autodiscover............10.16.12.217 Outlook.company.com is the RpcClientAccessArray name set on all databases. The FQDN of the F5 is The Certificate on both Hub/Cas servers has CN=mail.company.com, SAN names of mail.company.com, autodiscover.company.com, webmail.company.com The same certificate has been added to the F5 load balancer. Both Hub/Cas servers have the AutodiscoverServiceInternalUri set to https://autodiscover.company.com/autodiscover/autodiscover.xml. I understand that this needs to match the FQDN of the F5 load balancer. All of the other web services have both the Internal and External Urls set to https://mail.company.com/etc... When I open Outlook, should it not auto-populate the email address and e-mail settings and autoconfigure the account for Exchange? Instead, I get prompted for credentials but it never takes the username/password.

When I test Autodiscover in Outlook, it reads: Autoconfiguration was unable to determine your settings! Now, if Sites & Subnets are not set correctly, this could cause the behavior, correct? They have a ssite called XXX and the subnet associated with it is 10.16.0.0/16. However, the domain controllers and Exchange servers are on 10.16.4.0/24 and 10.16.6.0/24 and the F5 device is on 10.16.12.0/24. Do we need to add those subnets to Sites and Services and associate them with Site XXX?

The cas array name is Outlook.company.com. Does that also need to be added to the certificate?

Hi, If you only want to load balance MAPI connection, you need not add the array name in certificate name. For more information, please refer to the following article: http://itproafrica.com/technology/exchange/cas-array-names-certificates-and-load-balancers/ To troubleshoot the issue, please capture the screenshot of Result tab and Log tab, and then post it here or send it to me for research. 1. While Outlook is running, hold down the CTRL key, right-click the Outlook icon in the notification area, and then select Test E-mail AutoConfiguration. 2. Verify that the correct e-mail address is in the box next to E-mail Address. 3. Clear the check boxes next to Use Guessmart and Secure Guessmart Authentication. 4. On the Test E-mail AutoConfiguration page, verify that the check box next to Use AutoDiscover is selected, and then click the Test button. 5. Then, please capture the screenshot. Thanks. Novak Wu TechNet Subscriber Support in forum If you have any feedback on our support, please contact tngfb@microsoft.com Please remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.

How is thing going on? If there is any question, please feel free to post it here. Thanks. Novak Wu TechNet Subscriber Support in forum If you have any feedback on our support, please contact tngfb@microsoft.com Please remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.

It ended up being a misconfigured load balancer. It was very difficult to detect, but thanks anyway.