May 26

Chances are you installed a windows update to your server that caused this to occur.  There was some in April and May 2016 time frame that were released.

Completing the post installation tasks will resolve the issue:

https://support.microsoft.com/en-us/kb/3159706

Microsoft Warns WSUS Users About Flawed KB3148812 Update

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Jan 17

The Kindle currently supports PDF files inherently, you can just copy them into /documents folder. Plug the kindle into a available usb port in your computer and then copy the file over to the folder /documents. Make sure it shows that its in USB storage mode on the kindle.

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