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Since Windows Smartscreen is now marking downloaded files signed with SHA1 post 1/1/16 as potentially unsafe, we have had to get a new code-signing cert. With it being a new cert, it has no 'reputation' with Smartscreen, and our new builds are still being marked as potentially unsafe.

Is there any way to get more helpful information from Smartscreen to find out exactly WHY a particular download has been flagged? We would like to be sure that it is 'just' the code signing key's low reputation before we push it out to customers.

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The best starting point would be to investigate its logs and see if it gets you anywhere. By default, SmartScreen does not log events as per Microsoft's documentation:

Logging: By default, SmartScreen Filter does not log events. However, if you use the Application Compatibility Toolkit to enable logging for application compatibility events, SmartScreen Filter logs an event when a warning is shown for a website.

Here is the link to Microsoft Application Compatibility Toolkit 5.0

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