amlydiate
asked on
Autodiscover very broken Server 2008 SBS
Hi Guys,
Quite literally on the point of a breakdown here.
I've installed a new 2008 SBS Server to replace an old 2003 SBS box. I've created and successfully installed a UCC certificate from GoDaddy with autodiscover.domain, remote.domain e.t.c. and that all seems fine. I've checked the bindings in IIS and everything is pointing to the right certificate. There is a valid record in the external domain DNS pointing autodiscover.domain.com to the IP address of the server
When I removed the first few clients and added them to the new domain Outlook connected automatically to the exchange server and all seemed well (autodiscover seemed to be working)
Since then however I had a bit of a fight with DNS as I had to change the router and the IP address of the router. The whole network went wrong for a while until I manually changed all IP addresses in DNS from the old Routers IP address to the new one. Then all things network started working again, and I can ping and see network shares and add machines the domain with no errors.
Problem is it seems Autodiscover is now broken. I've run testexchangeconnectivity and every single autodiscover test fails!
I've opened port 443 on the firewall and pointed it to the IP of the server but can anyone please give me some step by step instructions on how I can narrow down where the problem might lie?
Really urgent so would be so grateful if someone can please help! Thanks
Adam
Quite literally on the point of a breakdown here.
I've installed a new 2008 SBS Server to replace an old 2003 SBS box. I've created and successfully installed a UCC certificate from GoDaddy with autodiscover.domain, remote.domain e.t.c. and that all seems fine. I've checked the bindings in IIS and everything is pointing to the right certificate. There is a valid record in the external domain DNS pointing autodiscover.domain.com to the IP address of the server
When I removed the first few clients and added them to the new domain Outlook connected automatically to the exchange server and all seemed well (autodiscover seemed to be working)
Since then however I had a bit of a fight with DNS as I had to change the router and the IP address of the router. The whole network went wrong for a while until I manually changed all IP addresses in DNS from the old Routers IP address to the new one. Then all things network started working again, and I can ping and see network shares and add machines the domain with no errors.
Problem is it seems Autodiscover is now broken. I've run testexchangeconnectivity and every single autodiscover test fails!
I've opened port 443 on the firewall and pointed it to the IP of the server but can anyone please give me some step by step instructions on how I can narrow down where the problem might lie?
Really urgent so would be so grateful if someone can please help! Thanks
Adam
Dave Messman
can you post the info on how autodiscover fails? Please paste the text from testexchangeconnectivity and we can see why.
ASKER
OK here goes (have changed domain names and hidden Ip address e.t.c.)
ExRCA is attempting to test Autodiscover for user@domain.co.uk.
Testing Autodiscover failed.
Test Steps
Attempting each method of contacting the Autodiscover service.
The Autodiscover service couldn't be contacted successfully by any method.
Test Steps
Attempting to test potential Autodiscover URL https://domain.co.uk/AutoDiscover/AutoDiscover.xml
Testing of this potential Autodiscover URL failed.
Test Steps
Attempting to resolve the host name domain.co.uk in DNS.
The host name couldn't be resolved.
Tell me more about this issue and how to resolve it
Additional Details
Host domain.co.uk couldn't be resolved in DNS Exception details:
Message: The requested name is valid, but no data of the requested type was found
Type: System.Net.Sockets.SocketE
Stack trace:
at System.Net.Dns.GetAddrInfo
at System.Net.Dns.InternalGet
at System.Net.Dns.GetHostAddr
at Microsoft.Exchange.Tools.E
.
Attempting to test potential Autodiscover URL https://autodiscover.domain.co.uk/AutoDiscover/AutoDiscover.xml
Testing of this potential Autodiscover URL failed.
Test Steps
Attempting to resolve the host name autodiscover.domain.co.uk in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: This returned the correct external IP Address
Testing TCP port 443 on host autodiscover.domain.co.uk to ensure it's listening and open.
The port was opened successfully.
Testing the SSL certificate to make sure it's valid.
The certificate passed all validation requirements.
Test Steps
Validating the certificate name.
The certificate name was validated successfully.
Additional Details
Host name autodiscover.domain.co.uk was found in the Certificate Subject Alternative Name entry.
Certificate trust is being validated.
The test passed with some warnings encountered. Please expand the additional details.
Additional Details
ExRCA can only validate the certificate chain using the Root Certificate Update functionality from Windows Update. Your certificate may not be trusted on Windows if the "Update Root Certificates" feature isn't enabled.
Testing the certificate date to confirm the certificate is valid.
Date validation passed. The certificate hasn't expired.
Additional Details
The certificate is valid. NotBefore = 4/20/2011 3:29:12 PM, NotAfter = 4/20/2012 3:29:12 PM
Checking the IIS configuration for client certificate authentication.
Client certificate authentication wasn't detected.
Additional Details
Accept/Require Client Certificates isn't configured.
Attempting to send an Autodiscover POST request to potential Autodiscover URLs.
Autodiscover settings weren't obtained when the Autodiscover POST request was sent.
Test Steps
ExRCA is attempting to retrieve an XML Autodiscover response from URL https://autodiscover.domain.co.uk/AutoDiscover/AutoDiscover.xml for user user@domain.co.uk.
ExRCA failed to obtain an Autodiscover XML response.
Additional Details
A Web exception occurred because an HTTP 401 - Unauthorized response was received from Unknown.
Attempting to contact the Autodiscover service using the HTTP redirect method.
The attempt to contact Autodiscover using the HTTP Redirect method failed.
Test Steps
Attempting to resolve the host name autodiscover.domain.co.uk in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: This returned the correct IP address
Testing TCP port 80 on host autodiscover.domain.co.uk to ensure it's listening and open.
The specified port is either blocked, not listening, or not producing the expected response.
Tell me more about this issue and how to resolve it
Additional Details
A network error occurred while communicating with the remote host.
Exception details:
Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond external IP address:80
Type: System.Net.Sockets.SocketE
Stack trace:
at System.Net.Sockets.TcpClie
at Microsoft.Exchange.Tools.E
Attempting to contact the Autodiscover service using the DNS SRV redirect method.
ExRCA failed to contact the Autodiscover service using the DNS SRV redirect method.
Test Steps
Attempting to locate SRV record _autodiscover._tcp.domain in DNS.
The Autodiscover SRV record wasn't found in DNS.
Tell me more about this issue and how to resolve it
ExRCA is attempting to test Autodiscover for user@domain.co.uk.
Testing Autodiscover failed.
Test Steps
Attempting each method of contacting the Autodiscover service.
The Autodiscover service couldn't be contacted successfully by any method.
Test Steps
Attempting to test potential Autodiscover URL https://domain.co.uk/AutoDiscover/AutoDiscover.xml
Testing of this potential Autodiscover URL failed.
Test Steps
Attempting to resolve the host name domain.co.uk in DNS.
The host name couldn't be resolved.
Tell me more about this issue and how to resolve it
Additional Details
Host domain.co.uk couldn't be resolved in DNS Exception details:
Message: The requested name is valid, but no data of the requested type was found
Type: System.Net.Sockets.SocketE
Stack trace:
at System.Net.Dns.GetAddrInfo
at System.Net.Dns.InternalGet
at System.Net.Dns.GetHostAddr
at Microsoft.Exchange.Tools.E
.
Attempting to test potential Autodiscover URL https://autodiscover.domain.co.uk/AutoDiscover/AutoDiscover.xml
Testing of this potential Autodiscover URL failed.
Test Steps
Attempting to resolve the host name autodiscover.domain.co.uk in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: This returned the correct external IP Address
Testing TCP port 443 on host autodiscover.domain.co.uk to ensure it's listening and open.
The port was opened successfully.
Testing the SSL certificate to make sure it's valid.
The certificate passed all validation requirements.
Test Steps
Validating the certificate name.
The certificate name was validated successfully.
Additional Details
Host name autodiscover.domain.co.uk was found in the Certificate Subject Alternative Name entry.
Certificate trust is being validated.
The test passed with some warnings encountered. Please expand the additional details.
Additional Details
ExRCA can only validate the certificate chain using the Root Certificate Update functionality from Windows Update. Your certificate may not be trusted on Windows if the "Update Root Certificates" feature isn't enabled.
Testing the certificate date to confirm the certificate is valid.
Date validation passed. The certificate hasn't expired.
Additional Details
The certificate is valid. NotBefore = 4/20/2011 3:29:12 PM, NotAfter = 4/20/2012 3:29:12 PM
Checking the IIS configuration for client certificate authentication.
Client certificate authentication wasn't detected.
Additional Details
Accept/Require Client Certificates isn't configured.
Attempting to send an Autodiscover POST request to potential Autodiscover URLs.
Autodiscover settings weren't obtained when the Autodiscover POST request was sent.
Test Steps
ExRCA is attempting to retrieve an XML Autodiscover response from URL https://autodiscover.domain.co.uk/AutoDiscover/AutoDiscover.xml for user user@domain.co.uk.
ExRCA failed to obtain an Autodiscover XML response.
Additional Details
A Web exception occurred because an HTTP 401 - Unauthorized response was received from Unknown.
Attempting to contact the Autodiscover service using the HTTP redirect method.
The attempt to contact Autodiscover using the HTTP Redirect method failed.
Test Steps
Attempting to resolve the host name autodiscover.domain.co.uk in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: This returned the correct IP address
Testing TCP port 80 on host autodiscover.domain.co.uk to ensure it's listening and open.
The specified port is either blocked, not listening, or not producing the expected response.
Tell me more about this issue and how to resolve it
Additional Details
A network error occurred while communicating with the remote host.
Exception details:
Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond external IP address:80
Type: System.Net.Sockets.SocketE
Stack trace:
at System.Net.Sockets.TcpClie
at Microsoft.Exchange.Tools.E
Attempting to contact the Autodiscover service using the DNS SRV redirect method.
ExRCA failed to contact the Autodiscover service using the DNS SRV redirect method.
Test Steps
Attempting to locate SRV record _autodiscover._tcp.domain in DNS.
The Autodiscover SRV record wasn't found in DNS.
Tell me more about this issue and how to resolve it
ASKER
Just as a bit of additional information, when I open Outlook 2007 on a client machine and try to configure it on exchange I get a dialog box open titled "Connect to remote.domain.co.uk" Welcome back to remote.domain.co.uk and asking for username and password details. Whatever details I put in the dialog box just comes back.
Now is the fact that it is remote.domain.co.uk asking these details rather than autodiscover relevant?
Also I just tried pinging autodiscover.domain.co.uk from am external source and although it resolves to the right address there is no response.
We've got a bog standard netgear firewall router, the same as on many other servers I look after, incoming ports 443 and 25 are open for SMTP and SSL and pointing to the server, have I missed something there perhaps?
Many thanks
Adam
Now is the fact that it is remote.domain.co.uk asking these details rather than autodiscover relevant?
Also I just tried pinging autodiscover.domain.co.uk from am external source and although it resolves to the right address there is no response.
We've got a bog standard netgear firewall router, the same as on many other servers I look after, incoming ports 443 and 25 are open for SMTP and SSL and pointing to the server, have I missed something there perhaps?
Many thanks
Adam
This is the part of testexchangeconnectivity that should work given your configuration bit doesn't.
ExRCA is attempting to retrieve an XML Autodiscover response from URL https://autodiscover.domain.co.uk/AutoDiscover/AutoDiscover.xml for user user@domain.co.uk.
ExRCA failed to obtain an Autodiscover XML response.
Additional Details
A Web exception occurred because an HTTP 401 - Unauthorized response was received from Unknown.
I'll need to do a little more research on that. Your description of what happens when you open outlook is correct.
ExRCA is attempting to retrieve an XML Autodiscover response from URL https://autodiscover.domain.co.uk/AutoDiscover/AutoDiscover.xml for user user@domain.co.uk.
ExRCA failed to obtain an Autodiscover XML response.
Additional Details
A Web exception occurred because an HTTP 401 - Unauthorized response was received from Unknown.
I'll need to do a little more research on that. Your description of what happens when you open outlook is correct.
ASKER CERTIFIED SOLUTION
membership
This solution is only available to members.
To access this solution, you must be a member of Experts Exchange.
ASKER
Service Pack 3 fixed this