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For example, does the same code NOT result in a blocking error on Windows due to some vagaries under the covers between the networking stack on Windows and OS X? Even if true, whose network stack is more "standards compliant"? Would be interesting to know the answer to those questions. Without more details, it's hard to be sure. Some Microsoft support personnel try to pass this off as an OS X issue. If like most orgs, you're hosting at a third-party provider and don't have a valid SSL certificate installed, Outlook for Mac (more specifically, the autodiscover code), will cause the cert error to appear. So if you have your email for domain xyz.com hosted at Office 365, Microsoft's autodiscover code for Macs will try to connect to. For some bizarre reason (bizarre in that it doesn't appear that Windows-based code runs into the same issue), autodiscover for Mac Outlook clients since Outlook 15.9 first tries to establish an https connection to an organization's root domain.
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