I know Microsoft has EOL'd 2003 server.

Server is used as local exchange server with some users accessing via OWA or MobileSync. Server had an old SSL cert long expired. Company would like to migrate to Office365 so was investigating a staged migration. Necessary to that is a proper SSL cert for Outlook Anywhere.

Created file, got cert from Comodo, installed it to the personal certificates section of the Certificates MMC. Went into IIS manager, OWA properties - Directory Security, replaced the certificate with the new one. Doing a view certificate shows the proper data good for another year, says it is OK. I also turned off the check for 'enable anonymous access' in the authentication methods tab. Integrated windows auth and basic auth are checked.

Problem is browsing to the url https://mail.domain.com comes up with connection refused. going to url http://mail.domain.com gives error stating that I need to use HTTPS.

Need advice to get this webmail working on https.

  • You may have issues with new certs and Win2k3. blogs.technet.com/b/pki/archive/2010/09/30/… & digicert.com/sha-2-compatibility.htm – Chase Oct 20 '15 at 20:48
  • hmm, the server had an expired godaddy cert that I replaced. It has proven to be able to handle certs of some fashion. I am more apt to believe I missed a necessary configuration. – Eric Oct 20 '15 at 21:10
  • that would do it too. ;-) – Chase Oct 20 '15 at 21:52
  • Is the new certificate a SHA256 cert? If so have you installed the Windows 2003 hotfix to allow SHA256 certs support.microsoft.com/en-us/kb/968730 – Mass Nerder Oct 20 '15 at 23:56
  • I think you might be onto something. The signature algorithm of the previous and expired cert is 'sha1RSA'. The signature algorithm of the new one is sha256RSA. I will read that hotfix info and see if that's the answer. Nice work. I discounted it yesterday but only now realized how to verify. be back soon to let you know. – Eric Oct 21 '15 at 20:57

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