On Tue, 1 Sep 2020, Jeffrey McKay via curl-library wrote:

In my program, I can connect to my test server (outlook.office365.com), and if I use port 143, the insecure IMAP port, I can receive the response. But if I use secure port 993, the program hangs on the select() command, timing out after 60 seconds.

If you want TLS already in the connect procedure, you need to use a URL that says so. Your code:

    strcpy_s(imap_host, "outlook.office365.com");
    curl_easy_setopt(curl, CURLOPT_URL, imap_host);

... uses no protocol scheme at all which will make curl guess, and in this case it thinks it is "http" - in clear text. It won't try to do any TLS negotiation on a clear text connection.

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