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Files dragged into WordPress Media Library don't show up. 500 internal server error

Hello. I have WordPress installed on a Windows Server 2012 R2 machine running IIS 8.5.   After I installed WordPress and began creating a website I was able to drag all my images and other media files into the Media Library.  It worked fine.  But now when I drag the files to the Medial Library they don't show up on my pages and when I try to navigate to the file using the url that goes directly to it I get the 500 - Internal server error.   I noticed that WordPress changed the file location.  I don't know why. But when I originally installed it, it created a file structure for the images something like this (C:\SocialSkillsGroupClinic\wp-content\uploads\2016) and withing that 2016 folder there are folders 02, 03 etc .... The only that will allow me to access any media files from my website is the 02 folder.  So I'm having to manually copy all my media files into this one folder and hardcode links to them.  There is no way I can drag and drop from within WordPress.   Is there some kind of special permission that I need to set on the 2016 folder that will allow me to continue to drag and drop files to the media library?
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Jason C. Levine
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Hello @Jason C. Levine.  Thank you for the response.  I went in and turned off the option to organize uploads into month-and year-based folders.  

Yes. I definitely agree with you on the permissions thing.  I did go in and look at the folder permissions but I didn't see anything different.  Also I tried to make the same permissions on the entire uploads folders so all folders contained in it would have those permissions but I obviously didn't do that right either.  The question now is how do I configure the folders to give permission to WordPress or whatever is pulling from them?
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There is no answer for this question.  I'm still having the same problem.
You haven't responded to the suggestion of looking in the error log though; did you do that? We can only help you find a solution when you respond to questions/suggestions. Would you like the question re-opened? I think that's the right thing to do given you haven't got a solution yet.
Hello @Terry Woods.  I'm sorry for not responding. Thanks for following up.  I had actually given up on this one and started copying and hard coding my media myself instead of using WordPress's interface.   Yes. I think I looked at the logs that you were talking about.  I went into Event Viewer and looked at the Application, Security, Setup, and System logs under the Windows logs folder.
Ok, well if you'd like to look into it further, do let us know.
Great. I'm sure I will. Should I start a new thread when I do? Or can I reopen this question?
Ok Thanks. I'll wait till I create another WordPress instance and begin uploading media.  Thanks for your help and advice.