AutoDiscover
This article will describe how to configure your organization's domain to ensure proper operation of Outlook features which rely on autodiscover and to eliminate any potential sync errors or security alerts about the SSL certificate for autodiscover.yourdomain.com.
Note that if Webville hosts the DNS (name servers) for your domain name we will create the appropriate AutoDiscover host record and SRV record in the DNS zone for your domain. The following instructions are for clients whose DNS is hosted elsewhere.
1. If applicable, remove any existing CNAME (Alias) or Host records for autodiscover in your domain's DNS zone.
2. Create a new host record for autodiscover in your domain's DNS zone pointing to IP address 65.115.231.152
3. Use the following parameters to create a new SRV record in your domain's DNS zone.
Service: _autodiscover
Protocol: _tcp
Priority: 0
Weight: 0
Port Number: 443
Host: mail.webville.net
If you are using Windows DNS, the steps to create an SRV record are as follows:
- Open the DNS Management MMC snap-in.
- Expand Forward Lookup Zones.
- Locate and right-click the external DNS zone corresponding with your primary email address, and then click Other New Records.
- Click Service Location (SRV).
- Enter the parameters by using the required values shown above and in the screen shot below.
- Click OK.
Note new server name for 2010,
now using mail.webville.net for autodiscover
If your domain's DNS is hosted by GoDaddy, create an SRV record with the following parameters:
Service: _autodiscover
Protocol: _tcp
Name: @
Priority: 0
Weight: 0
Port: 443
Target: mail.webville.net
The interface may look like the following GoDaddy DNS control panel screen shot. Click the graphic below to view full size.

When the records are configured correctly and have had time to propagate, start Outlook. It will prompt you as shown in the following screen shot to Allow this website to configure [you@yourdomain.com] server settings:

Check the box marked "Don't ask me about this website again" and click Allow.
Testing AutoDiscover
1. Testing your DNS configuration
If you created the autodiscover host record properly, you should be able to ping it. Ping autodiscover.yourdomain.com and you should receive replies from 65.115.231.152.
Use PING to test autodiscover host record
-
Click Start then click Run
-
In the Open box type CMD
-
At the command prompt type ping autodiscover.yourdomain.com (where yourdomain.com is the domain of your primary email address) then press Enter.
PING should return results from the IP address shown below, similar to the following:
Reply from 65.115.231.152: bytes=32 time<1ms TTL=128
Reply from 65.115.231.152: bytes=32 time<1ms TTL=128
Reply from 65.115.231.152: bytes=32 time<1ms TTL=128
Reply from 65.115.231.152: bytes=32 time<1ms TTL=128
Use NSLOOKUP to Verify SRV DNS Record
-
Click Start then click Run
-
In the Open box type CMD
-
At the command prompt type nslookup then press Enter
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At the nslookup prompt type set type=all then press Enter
-
Type _autodiscover._tcp.yourdomain.com where yourdomain.com is the domain of your primary email address, then press Enter.
NSLOOKUP should return results similar to the following:
_autodiscover._tcp.webville.net SRV service location:
priority = 0
weight = 0
port = 443
svr hostname = mail.webville.net
mail.webville.net internet address = 65.115.231.142
2. Testing from Outlook
After you confirm your DNS configuration, you may want to test autodiscover from within Outlook. Hold down Ctrl and right-click the Outlook icon in the system tray while Outlook is running. Choose Test E-mail AutoConfiguration. See screen shot below.

The Test E-mail AutoConfiguration dialog will appear (see screen shot below). Uncheck the Guessmart and Secure Guessmart options to focus on AutoDiscover. Confirm that your primary email address is in the E-mail Address field. Password is not necessary here and can be left blank. You should quickly get an error free return showing a lot of details about the URLs Outlook connects to.

3. Online Testing Tool
Run the tests available here to verify connectivity and AutoDiscover configuration:
Troubleshooting AutoDiscover
Synchronization Log Errors
If you simply ignore the whole issue and have no AutoDiscover record in your domain's DNS, you will get errors in the Outlook 2007 synchronization log and significant loss of functionality. If you implement a CNAME for AutoDiscover plus the well known registry tweak to suppess the security alert it leads to, you will get similar errros in the sync log and loss of functionality. See step 1 above about removing the registry tweak. Screen shot of security alert is shown below.
Create SRV Record in Internal and External DNS
Microsoft's published instructions on this topic refer to creating an SRV Record in your external DNS server, but the host and SRV Records need to exist in whatever DNS server responds to your users' requests, whether the user is inside or outside of your office location.
AutoDiscover is required for Outlook 2007 and later
Note: Outlook will generate errors if the AutoDiscover record is not found.
Outlook 2007 with cache mode enabled will generate the following error message:
"Microsoft Exchange offline address book
Not downloading Offline address book files. A server (URL) could not be located." 0X8004010F
Outlook 2007 without cache mode enabled will generate the following error message:
"Task reported error (0x8004010F): The operation failed. An object cannot be found."