Outlook Anywhere connection with standard users

Attempting to test Autodiscover for garganm@hobbsltd.ca
Successfully tested Autodiscover
Test Steps
Attempting each method of contacting the AutoDiscover Service
The AutoDiscover Service was successfully tested.
Test Steps
Attempting to test potential AutoDiscover URL https://hobbsltd.ca/AutoDiscover/AutoDiscover.xml
Failed testing this potential AutoDiscover URL
Test Steps
Attempting to resolve the host name hobbsltd.ca in DNS.
Host successfully resolved
Additional Details
IP(s) returned: 24.78.192.244
Testing TCP Port 443 on host hobbsltd.ca to ensure it is listening and open.
The port was opened successfully.
Testing SSL Certificate for validity.
The SSL Certificate failed one or more certificate validation checks.
Test Steps
Validating certificate name
Certificate name validation failed
 Tell me more about this issue and how to resolve it
Additional Details
Host name hobbsltd.ca does not match any name found on the server certificate CN=mail.hobbsltd.ca
 
 
Attempting to test potential AutoDiscover URL https://autodiscover.hobbsltd.ca/AutoDiscover/AutoDiscover.xml
Testing AutoDiscover URL succeeded
Test Steps
Attempting to resolve the host name autodiscover.hobbsltd.ca in DNS.
Host successfully resolved
Additional Details
IP(s) returned: 24.78.192.244
Testing TCP Port 443 on host autodiscover.hobbsltd.ca to ensure it is listening and open.
The port was opened successfully.
Testing SSL Certificate for validity.
The certificate passed all validation requirements.
Test Steps
Validating certificate name
Successfully validated the certificate name
Additional Details
Found hostname autodiscover.hobbsltd.ca in Certificate Subject Alternative Name entry
Testing certificate date to ensure validity
Date Validation passed. The certificate is not expired.
Additional Details
Certificate is valid: NotBefore = 9/18/2009 10:44:01 PM, NotAfter = 9/18/2014 10:44:01 PM"
 
Attempting to send AutoDiscover POST request to potential autodiscover URLs.
Successfully Retrieved AutoDiscover Settings by sending AutoDiscover POST.
Test Steps
Attempting to Retrieve XML AutoDiscover Response from url https://autodiscover.hobbsltd.ca/AutoDiscover/AutoDiscover.xml for user garganm@hobbsltd.ca
Successfully Retrieved AutoDiscover XML Response
Additional Details
AutoDiscover Account Settings
XML Response:
<?xml version="1.0"?>
<Autodiscover xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns:xsd="http://www.w3.org/2001/XMLSchema" xmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006">
<Response xmlns="http://schemas.microsoft.com/exchange/autodiscover/outlook/responseschema/2006a">
<User>
<DisplayName>Miranda D. Gargan</DisplayName>
<LegacyDN>/o=Hobbsltd/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=garganm</LegacyDN>
<DeploymentId>296637a8-8b0e-46df-9077-0a0f1071c646</DeploymentId>
</User>
<Account>
<AccountType>email</AccountType>
<Action>settings</Action>
<Protocol>
<Type>EXCH</Type>
<Server>exchange.hobbsltd.local</Server>
<ServerDN>/o=Hobbsltd/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=EXCHANGE</ServerDN>
<ServerVersion>720280B0</ServerVersion>
<MdbDN>/o=Hobbsltd/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=EXCHANGE/cn=Microsoft Private MDB</MdbDN>
<ASUrl>https://exchange.hobbsltd.local/EWS/Exchange.asmx</ASUrl>
<OOFUrl>https://exchange.hobbsltd.local/EWS/Exchange.asmx</OOFUrl>
<OABUrl>http://exchange.hobbsltd.local/OAB/74208662-d699-4511-96ca-dfb70b3df6bd/</OABUrl>
<UMUrl>https://exchange.hobbsltd.local/UnifiedMessaging/Service.asmx</UMUrl>
<Port>0</Port>
<DirectoryPort>0</DirectoryPort>
<ReferralPort>0</ReferralPort>
<PublicFolderServer>exchange.hobbsltd.local</PublicFolderServer>
<AD>exchange.hobbsltd.local</AD>
<EwsUrl>https://exchange.hobbsltd.local/EWS/Exchange.asmx</EwsUrl>
</Protocol>
<Protocol>
<Type>EXPR</Type>
<Server>mail.hobbsltd.ca</Server>
<Port>0</Port>
<DirectoryPort>0</DirectoryPort>
<ReferralPort>0</ReferralPort>
<SSL>On</SSL>
<AuthPackage>Basic</AuthPackage>
</Protocol>
<Protocol>
<Type>WEB</Type>
<Port>0</Port>
<DirectoryPort>0</DirectoryPort>
<ReferralPort>0</ReferralPort>
<External>
<OWAUrl AuthenticationMethod="Fba">http://webmail.hobbsltd.ca/</OWAUrl>
</External>
<Internal>
<OWAUrl AuthenticationMethod="Basic, Fba">https://exchange.hobbsltd.local/owa</OWAUrl>
<Protocol>
<Type>EXCH</Type>
<ASUrl>https://exchange.hobbsltd.local/EWS/Exchange.asmx</ASUrl>
</Protocol>
</Internal>
</Protocol>
</Account>
</Response>
</Autodiscover>

When I run outlook with RPC diag, the microsoft exchange connection status just sits at status=connecting unless i enter Administrator username and password.

Here is the test results from the Outlook anywhere test using the standard user.

Testing RPC/HTTP connectivity
RPC/HTTP test failed
Test Steps
Attempting to resolve the host name mail.hobbsltd.ca in DNS.
Host successfully resolved
Additional Details
IP(s) returned: 24.78.192.244
Testing TCP Port 443 on host mail.hobbsltd.ca to ensure it is listening and open.
The port was opened successfully.
Testing SSL Certificate for validity.
The SSL Certificate failed one or more certificate validation checks.
Test Steps
Validating certificate name
Successfully validated the certificate name
Additional Details
Found hostname mail.hobbsltd.ca in Certificate Subject Common name
Validating certificate trust
Certificate trust validation failed
 Tell me more about this issue and how to resolve it
Additional Details
The certificate chain did not end in a trusted root. Root = CN=mail.hobbsltd.ca  

i see that the certificate in use is self signed certificate.
Please have valid certificate (SAN)

or export and install the certificate on the client machine and make sure you can open OWA without any certificate error
once you accomplish this then manually concfigure RPC-https profile on the machine and try to connect see if you can.

What is the principal name of your Cert?  I understand you have several alternates, but what is the main principal name?

OK, nevermind.  Now I see it.  Please disregard earlier post.

I believe that its mail.hobbsltd.ca.

As i said in the original post, when use Admin Credentials that have full access to his account, it connects perfectly, no issues at all.

How are you putting in the username?  UPN (user@domain.com) or domain\user?

domain\user

I found out what my issue is, and I would like to thank everyone who tried to help me. Unfortunately my issue was the evermentioned "User Error".  If anyone else has this issue, Please double\triple check the password that the user gives you. Sigh.

Thanks again.