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Mass uploading (Software)
Ixô released a software that enables multi-image uploading.

http://www2.kawaiyume.net/~jDanbooru/jDanbooru_v1.4.7z

USAGE:
Decompress with 7zip.
Enter on /dist/
Edit config propieties:
- login: Your username
- password: Your password
- salt: So-I-Heard-You-Like-Mupkids-?
- server: http://konachan.com
Open jDanbooru.jar, select a folder and tag
Example of config.propieties
<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE properties SYSTEM "http://java.sun.com/dtd/properties.dtd">
<properties>
<comment>Configution file for jDanbooru</comment>
<entry key="login">Oyashiro</entry>
<entry key="password">PassWorded</entry>
<entry key="salt">So-I-Heard-You-Like-Mupkids-?</entry>
<entry key="server">http://konachan.com</entry>
<entry key="upload_default_value">true</entry>
<entry key="file_renaming">true</entry>
</properties>
NOTE: flooding crap is not allowed, and upload it with at least one tag
After getting through maybe 3-5 images, it just simply froze for me.
It happened to me too on the first run, then it got solved without touching anything
http://www2.kawaiyume.net/~jDanbooru/jDanbooru_v1.6.7z

That's a newer version, so the config.propieties file should be a little different (new options)
New version if anybody is interested
http://www2.kawaiyume.net/~jDanbooru/jDanbooru_v1.7.7z

Has some progress bars