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Outlook not syncing with exchange server 2003

I configure RPC over HTTPS on the Exchange server 2003 which is install on a SBS 2003.. Client from outside the domain can't get there emails. Outlook is not syncing with exchange server 2003.
Outlook inside the domain is working fine so is OWA.
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SambaCor
Asked:
SambaCor
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1 Solution
 
Alan HardistyCo-OwnerCommented:
What name is on your certificate and does that name resolve externally in DNS to the IP Address of your server?
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SambaCorAuthor Commented:
Yes, I can ping it with no problem and get the IP address of my server.
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madhatter5501Commented:
is it only one user, or everyone?
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SambaCorAuthor Commented:
Everyone!
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Alan HardistyCo-OwnerCommented:
What about the other half of my question?
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SambaCorAuthor Commented:
Which question? The certificate name?
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Alan HardistyCo-OwnerCommented:
Yep - that's the part you haven't answered.
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James HIT DirectorCommented:
Run this test and post results:

https://www.testexchangeconnectivity.com/
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Alan HardistyCo-OwnerCommented:
@Spartan_1337 - Which one specifically?  There are numerous tests on the site that are available.
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James HIT DirectorCommented:
Outlook Anywhere (RPC over HTTP)
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SambaCorAuthor Commented:
Ok, I will run the test, thanks. The name of the certificate is mail.domain.org.
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SambaCorAuthor Commented:
Do I have to run the test from a remote computer or from the server?
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James HIT DirectorCommented:
You can run the test from anywhere.
It will ask you to enter credentials to run the connectivity test.
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SambaCorAuthor Commented:
The test result:

Testing RPC/HTTP connectivity.
  The RPC/HTTP test failed.
   Test Steps
   Attempting to resolve the host name mail.domain.org in DNS.
  The host name resolved successfully.
   Additional Details
  IP addresses returned: 65.xxx.xxx.226
 
 Testing TCP port 443 on host mail.domain.org 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 mail.domain.org on port 443.
  ExRCA successfully obtained the remote SSL certificate.
   Additional Details
  Remote Certificate Subject: CN=mail.domain.org, OU=AFSCME Domain Name, O=AFSCME Domain Name, L=Oakland, S=California, C=US, Issuer: CN=mail.domain.org, DC=Domain, DC=local.
 
 Validating the certificate name.
  The certificate name was validated successfully.
   Additional Details
  Host name mail.domain.org was found in the Certificate Subject Common name.
 
 Certificate trust is being validated.
  Certificate trust validation failed.
   Test Steps
   ExRCA is attempting to build certificate chains for certificate CN=mail.domain.org, OU=AFSCME Domain Name, O=AFSCME Domain Name, L=Oakland, S=California, C=US.
  A certificate chain couldn't be constructed for the certificate.
   Additional Details
  The certificate chain couldn't be built. You may be missing required intermediate certificates.
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Alan HardistyCo-OwnerCommented:
You may well find that your IIS Authentication settings on the RPC Virtual Directory isn't set with Integrated & Basic Authentication.

Check in IIS Manager and if not set this way, please enable both and then run IISRESET, then test Outlook.
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Alan HardistyCo-OwnerCommented:
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Alan HardistyCo-OwnerCommented:
Also - your SSL Cert looks self-issued, so you will need to install the certificate on each and every RPC Client for the cert to be trusted:

To install the certificate, you need to export it first via IIS Manager on the server.

Open up IIS Manager, expand Web Sites, then right-click on your Default Web Site and choose properties, then click on the Directory Security Tab, then the View Certificate button, then on the Details Tab of the Certificate Windows.

On the Details Tab, click on Copy To File, click Next, Next, Next, Choose the name and location for the certificate file (Desktop should be easy to find and certificate.cer for the name) then click Next and then Finish.

Copy the certificate.cer file to the computer on a USB stick and then do the following:

Open up Internet Explorer, Click on Tools, Internet Options, Content Tab, Certificate Button, Trusted Root Certification Authorities Tab.  Click Import, Next, Browse to the certificate.cer file on the USB stick and click next, Select 'Place all certificates in the following store' and click Browse, check the Show Physical Stores Box and then select Trusted Root Certification Authorities Folder (Expand it) and then choose Registry and click OK.  Click Next and then Finish.  Click OK on the next prompt.
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SambaCorAuthor Commented:
Ok, I am going to work on these thinks and get back to you. Thanks!
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SambaCorAuthor Commented:
Question Closed!
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Alan HardistyCo-OwnerCommented:
If the question is closed, please either accept an expert's comment that helped you solve the problem, or accept multiple comments if more than one comment helped you.

If you solved the problem yourself, without assistance, please post your solution and accept that as the solution to the question.

Thanks

Alan
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