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Directions for using the drag & drop are in How To Upload Writing from Writing.Com 101 .
The red X shows an error message if you hover your mouse over it - Upload failed.
I tried it a few times. It uploaded a 5KB .docx file, taking longer than usual. Then it failed to load a 10KB .docx file, a 16 KB .rtf file, a 7KB .rtf file, or a 5KB .rtf file, some of which I've successfully uploaded before for testing. Tried the 5KB .docx file again, and that uploaded successfully again, but still slow. Tried the 16KB .rtf file, and that worked. Then the 10KB .docx file didn't work again. ... The StoryMaster?
Possible workarounds --
If the system is slow and/or timing out, you might be able to drag & drop smaller (5K?) pieces at a time, which if you use the Simple option, can be copy/pasted serially from a temporary 'upload' create item page to another create item page for actually submitting to create your item.
If it depends on which server you hit, which might be the issue since Whata got a 33KB text to load, trying it multiple times (starting from a fresh page load of the create a new item page) might help.
Or using the copy/paste method from the 101 entry above.
Hope that helps.