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Set up a WinHTTP status callback; inspect the WinHTTP status for WINHTTP_CALLBACK_STATUS_SECURE_FAILURE, and convert the status code to a useful message for callers.
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When SSL fails for the WinHTTP transport, by default we set the error message to the most unhelpful "user cancelled certificate check", which is set when there is no giterr set, even when there is no user certificate check configured.
Instead, try to capture the SSL failure to provide a more helpful error message by setting a status callback and looking for security failures (WINHTTP_CALLBACK_STATUS_SECURE_FAILURE), and providing a helpful error message for them.
If the security failure is not reported, and there is no user certificate check, update the error message to not suggest that the (nonexistent) user certificate check is at fault.