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The following Java applet allows you to easily upload many files to a confluence page. Download this jar file. On most operating systems you can execute it simply by double-clicking. You can also run it from the command line using:

java -jar ConfluenceFileUploaderExecutable.jar

Once you run this file a dialog like this should appear:

Click "Add files" and select the files you want to attach. Then click next:

For more information see:

http://confluence.atlassian.com/display/CONFEXT/Confluence+File+Uploader

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