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django - Set up two media directories

I am doing Django project. I installed django-watermark from PyPI to make watermarks on my pictures.
enter image description here
Here you see my media directory, when pictures are uploaded to django, they appear in Media root. Next, watermark library grabs those pictures, adds watermarks and drops them to "watermarked" folder. Eventually, pictures have to be fetched from "watermarked" directory.

Website works perfectly when debug=True, however on my server (I use AWS, IIS Windows for hosting), when I set debug=False, instead of pictures I get 404 error.

My virtual directory for IIS is set to be my Media root directory
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enter image description here
these are my settings and url files


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After 48 hours of research I finally found the solution. There is no issue with my settings.py or the way I have configured Media_root or URL, nor there is need for usage of os.path.join or anything else....

It was all about IIS, even though I have had configured virtual directories, I haven't configured their handlers. Apparently, I have had to open virtual directory for media files --> double click on "handlers" --> View ordered list --> move "static" at the top of the list, that was all.


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