Hi,
I have do a lab test to install KB4586830 on one 2016 Server and remote connect to it. I got no issue. So, the issue should not be related to this KB.
After researching, I found KB4457127 which contains the information of your issue.
https://support.microsoft.com/en-us/help/4457127
Addresses an issue that causes printing to an open or existing file to fail without displaying an error message. This issue occurs when using Microsoft Print to PDF or XPS Document Writer.
Please run powershell command "get-hotfix" to show the KB list you have installed. And try to install KB4457127 to see if you could resolve the issue.
Thanks,
Eleven
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