i have found a ton of post about autodiscovery. none of them have really helped. what i need is help understanding the process and how to troubleshoot it. I have a sbs 2008 server named server1. New install with a new domain. Once we started loading up line of business apps we got around to setting up the outlook clients. Outlook 2010. we noticed that we had some issue with autodiscovery right from the start. when outlook would auto populate the server name it was using the nameserver1 not mail.domainname.com. if we manually set up the account it works just fine. the autodiscovery prompts for a username and password from remote.domainname.com. What i have found is there was no autodiscovery A record, which i found after looking at another sbs2008 box that is working. Also mail.domainname.com was not set up as a zone even though i put that in the sbs2008 set up wizard. I changed all the ssl settings to mail.domainname.com and OAB, OWA, internal and external url. I also believe that ssl settings are wrong on most off the virtual directories based on looking at the other server. If i had of noticed this first thing i would have just reloaded the os. that is not an option any more. I really don't understand how autodiscovery is supposed to work and what it needs to work. Any ideas would be great. Email is working fine. OWA works with the correct url. Any thing that uses autodiscovery does not work like out of office setting in Outlook.

Your understanding of the server names etc is all wrong. The behaviour of Outlook that you have seen is correct. The server name in Outlook will be server.example.local. The "remote.example.com" is used for Outlook Anywhere which is configured elsewhere in Outlook. Therefore the behaviour you are seeing would appear to be correct. With regards to DNS, there is no need for an internal autodiscover DNS entry, unless you have clients who are off the domain. Domain attached clients get their autodiscover information from the domain. For external use, you do need to have some kind of DNS record. The annoying thing is that SBS presumes that you are using a single name SSL certificate of remote.example.com and are setting up SRV records (as their preferred DNS partners support those). However many DNS providers do not. That means you have to set things up in the normal Exchange 2007 way. I wrote a blog posting about it here: http://blog.sembee.co.uk/post/SBS-2008-Certificate-Installation.aspx Finally, SBS really wants you use remote.example.com - using anything else is going to be a losing battle. I would therefore suggest that you switch everything back to remote.example.com by running the wizards in SBS and then the Fix My Network wizard. Trying to configure some things outside of SBS is just asking for a whole heap of pain. Simon.Simon Butler, Exchange MVP Blog | Exchange Resources | In the UK? Hire Me.

Thanks for the reply. I will try your suggestion.

Hi, I would like to share how Autodiscovery works. At first , I suggest you reading this document. http://technet.microsoft.com/en-au/library/bb124251.aspx There are two important things about how Autodiscovery services works. 1. When the services work, it has description detailed in the document. When a new user account is configured or updated When an Outlook client periodically checks for changes to the Exchange Web Services URLs When underlying network connection changes occur in your Exchange messaging environment 2.How the services works in domain Autodiscover information is stored in a so called SCP or Service Connection Point. You can view this SCP using Active Directory Sites and Services after you have enabled the “View Services Node” option. You can find SCPs under this path: ServicesàMicrosoft ExchangeàOrganization nameàAdministrative GroupsàExchange Administrative Group (FYDIBOHF23SPDLT)àServersà Your CASàProtocolsàAutodiscover When installing the Client Access Server (Autodiscover is part of this Server Role) the SCP is automatically created in Active Directory and configured with the default values. If you have multiple CAS Servers there will be multiple SCP’s as well. See the Security property of SCP, Authenticated Users have read permission See the ServiceBindingInformation property of SCP under Attribute Editor, it is the URL of the Atuodiscover virtual directory. When Outlook 2007 or Outlook 2010 is installed on a domain joined workstation then the Outlook client will query Active Directory for the Autodiscover information. Active Directory will return a list of SCP’s and the Outlook client will automatically select the first SCP in this list. Using the ServiceBindingInformation attribute found in the SCP ,the Outlook client will contact the Client Access Server for its configuration information and the Outlook client will be configured automatically. 3.How the services works outside Non-domain clients are a bit trickier to configure since they will not query the Active Directory. Because of this non-domain clients try to retrieve information using the Autodiscover website. The FQDN that the Outlook client will use is based on the SMTP address that is used when starting the Outlook 2010 client the first time. So, when an e-mail address aaa@microsoft.com is entered, the Outlook client will start trying to connect to the Client Access Server using https://autodiscover.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.

thanks a lot for that. That is the info i was looking for on how it works. I will have to check those settings in AD.