troubleshooting Question

outlook exchange account iMac

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vsindelic asked on
ExchangeOutlookMac OS X
1 Comment1 Solution1252 ViewsLast Modified:
I have a user that it's using iMac. I created an ssl certificate from godaddy, and created an A record for autodiscover on godaddy and SRV record for autodiscover on godaddy with following settings:
_autodiscover
_tcp
@
priority:0
weight:0
port:443
target:server.contoso.com

On the server I've enabled outlook anywhere, and also did these commands:

Set-WebServicesVirtualDirectory -Identity "server\EWS (Default Web Site)" -InternalUrl https://server.contoso.com/ews/exchange.asmx -ExternalUrl https://mail.contoso.com/ews/exchange.asmx

Set-OabVirtualDirectory -Identity "server\OAB (Default Web Site)" -InternalUrl https://server.contoso.com/OAB -ExternalUrl https://mail.contoso.com/OAB -RequireSSL:$True

Set-ClientAccessServer -Identity server -AutodiscoverServiceInternalURI https://server.contoso.com/autodiscover/autodiscover.xml

set-autodiscovervirtualdirectory -identity 'autodiscover (default Web site)' -windowsauthentication $false -basicauthentication $true -digestauthentication $false

Enable-OutlookAnywhere -Server:server.contoso.com -ExternalHostname:mail.contoso.com -DefaultAuthenticationMethod:Basic -SSLOffloading:$false


Ive tested outlook anywhere on my outlook on win7 and it's working like a charm but problem is iMac. Resutlts from https://www.testexchangeconnectivity.com are the following:

Connectivity Test Failed
 Test Details

ExRCA is attempting to test Autodiscover for user@contoso.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 https://contoso.com/AutoDiscover/AutoDiscover.xml
Testing of this potential Autodiscover URL failed.
Test Steps
Attempting to resolve the host name contoso.com in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: x.x.x.x -- (this IP is the only different one then those two bellow that are the same; it's returning the IP of the godaddy)
Testing TCP port 443 on host contoso.com to ensure it's listening and open.
The port was opened successfully.
Testing the SSL certificate to make sure it's valid.
The SSL certificate failed one or more certificate validation checks.
Test Steps
ExRCA is attempting to obtain the SSL certificate from remote server contoso.com on port 443.
ExRCA wasn't able to obtain the remote SSL certificate.
Additional Details
The certificate couldn't be validated because SSL negotiation wasn't successful. This could have occurred as a result of a network error or because of a problem with the certificate installation.
Attempting to test potential Autodiscover URL https://autodiscover.contoso.com/AutoDiscover/AutoDiscover.xml
Testing of this potential Autodiscover URL failed.
Test Steps
Attempting to resolve the host name autodiscover.contoso.com in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: x.x.x.x
Testing TCP port 443 on host autodiscover.contoso.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.contoso.com on port 443.
ExRCA successfully obtained the remote SSL certificate.
Additional Details
removed for security reasons(by me)
Validating the certificate name.
The certificate name was validated successfully.
Additional Details
Host name autodiscover.contoso.com was found in the Certificate Subject Alternative Name entry.
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 = 7/9/2012 4:34:04 PM, NotAfter = 7/9/2013 4:34:04 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.contoso.com/AutoDiscover/AutoDiscover.xml for user user@contoss.com.
ExRCA failed to obtain an Autodiscover XML response.
Additional Details
An HTTP 500 response was returned 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.contoso.com in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: x.x.x.x
Testing TCP port 80 on host autodiscover.contoso.com to ensure it's listening and open.
The port was opened successfully.
ExRCA is checking the host autodiscover.contoso.com for an HTTP redirect to the Autodiscover service.
ExRCA failed to get an HTTP redirect response for Autodiscover.
Additional Details
An HTTP 403 forbidden response was received. The response appears to have come from Unknown. Body of the response: You do not have permission to view this directory or page.
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.contoso.com in DNS.
The Autodiscover SRV record was successfully retrieved from DNS.
Additional Details
The Service Location (SRV) record lookup returned host server.contoso.com.
Attempting to test potential Autodiscover URL https://server.contoso.com/Autodiscover/Autodiscover.xml
Testing of this potential Autodiscover URL failed.

Test Steps
Attempting to resolve the host name server.contoso.com in DNS.
The host name couldn't be resolved.
 Tell me more about this issue and how to resolve it
Additional Details
Host server.contoso.com couldn't be resolved in DNS InfoDomainNonexistent.

I've created A record on the server autodiscover.

All this came up with connecting through vpn on imac and creating exchange account that outlook asks me this:

outlook was redirected to the server to get the new setting bla bla do you want to allow? I check always trust and click allow about 10x times after creating an account and still get unexpected data was encountered when trying to send an email.

And for the last I can say, help me someone pls?

Thank you
ASKER CERTIFIED SOLUTION
vsindelic

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