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It should work, but maybe there is a bug when askbot is set up on windows.

Will you be able to debug it? I do not have a windows system here...

The upload function is upload in askbot/views/writers. What is the value of file_url variable in the end of the function?

The debugging can be done for example with pdb, - insert lines somewhere in the function:

import pdb
pdb.set_trace()

Then try to upload attachment, the debugger will pause in the shell and you'll be able to step through the instructions by typing "n" and to find what is the value of the variable - just type the variable name.

Sorry, going in detail, because I don't know if you are familiar with pdb.

Also, could you try checking which directory is used on your system to store uploaded files:

python manage.py shell
>>>from django.conf.import settings
>>>settings.ASKBOT_FILE_UPLOAD_DIR

It should print a path to a directory which must be writable by the server.