No it is not a hybrid deployment. Below are the results of the Outlook Anywhere test. Per the O365 instructions we added a CNAME record in our public DNS zone for autodiscover.roundtablepizza.com that points to autodiscover.outlook.com. (In short it looks like it's failing for port 443.)
esting RPC/HTTP connectivity.
The RPC/HTTP test failed.
Test Steps
ExRCA is attempting to test Autodiscover for janl@roundtablepizza.com.
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 roundtablepizza.com/.../AutoDiscover.xml
Testing of this potential Autodiscover URL failed.
Test Steps
Attempting to resolve the host name roundtablepizza.com in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: 207.213.203.15
Testing TCP port 443 on host roundtablepizza.com 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.
Attempting to test potential Autodiscover URL autodiscover.roundtablepizza.com/.../AutoDiscover.xml
Testing of this potential Autodiscover URL failed.
Test Steps
Attempting to resolve the host name autodiscover.roundtablepizza.com in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: 157.56.244.217, 157.56.234.137, 157.56.236.89, 157.56.240.137
Testing TCP port 443 on host autodiscover.roundtablepizza.com 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.
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.roundtablepizza.com in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: 157.56.244.217, 157.56.234.137, 157.56.236.89, 157.56.240.137
Testing TCP port 80 on host autodiscover.roundtablepizza.com to ensure it's listening and open.
The port was opened successfully.
ExRCA is checking the host autodiscover.roundtablepizza.com for an HTTP redirect to the Autodiscover service.
The redirect (HTTP 301/302) response was received successfully.
Additional Details
Redirect URL: autodiscover-s.outlook.com/.../Autodiscover.xml
Attempting to test potential Autodiscover URL autodiscover-s.outlook.com/.../Autodiscover.xml
Testing of this potential Autodiscover URL failed.
Test Steps
Attempting to resolve the host name autodiscover-s.outlook.com in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: 132.245.1.134, 157.56.232.182, 157.56.237.6, 157.56.236.134, 157.56.245.150, 132.245.2.70, 157.56.241.118, 157.56.240.246, 157.56.240.22, 132.245.1.166
Testing TCP port 443 on host autodiscover-s.outlook.com 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
ExRCA is attempting to obtain the SSL certificate from remote server autodiscover-s.outlook.com on port 443.
ExRCA successfully obtained the remote SSL certificate.
Additional Details
Remote Certificate Subject: CN=outlook.com, OU=Exchange, O=Microsoft Corporation, L=Redmond, S=Washington, C=US, Issuer: CN=Microsoft Secure Server Authority, DC=redmond, DC=corp, DC=microsoft, DC=com.
Validating the certificate name.
The certificate name was validated successfully.
Additional Details
Host name autodiscover-s.outlook.com was found in the Certificate Subject Alternative Name entry.
Certificate trust is being validated.
The certificate is trusted and all certificates are present in the chain.
Test Steps
ExRCA is attempting to build certificate chains for certificate CN=outlook.com, OU=Exchange, O=Microsoft Corporation, L=Redmond, S=Washington, C=US.
One or more certificate chains were constructed successfully.
Additional Details
A total of 1 chains were built. The highest quality chain ends in root certificate CN=GTE CyberTrust Global Root, OU="GTE CyberTrust Solutions, Inc.", O=GTE Corporation, C=US.
Analyzing the certificate chains for compatibility problems with versions of Windows.
No Windows compatibility problems were identified.
Additional Details
The certificate chain has been validated up to a trusted root. Root = CN=GTE CyberTrust Global Root, OU="GTE CyberTrust Solutions, Inc.", O=GTE Corporation, C=US.
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 = 4/17/2012 9:26:21 PM, NotAfter = 4/17/2014 9:26:21 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 autodiscover-s.outlook.com/.../Autodiscover.xml for user janl@roundtablepizza.com.
ExRCA failed to obtain an Autodiscover XML response.
Additional Details
An HTTP 401 Unauthorized response was received from the remote Unknown server. This is usually the result of an incorrect username or password. If you are attempting to log onto an Office 365 service, ensure you are using your full User Principal Name (UPN).