There are a couple of ways to upload images. One is to use the document library portlet. The other is when you are editing web content within the WYSIWYG editor you click on the image icon. Here are details on the second option:
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Click on the image icon within the WYSIWGY
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Click on the "Browse Server" button
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Select the "YOUR COMMUNITY NAME" folder
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Select the "User Guide" folder -- if one doesn't exist you might want to create it using "Create New Folder" at the bottom of the GUI.
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Select the "Images" folder -- again you may need to create this folder the first time -- I think it makes sense to organize the content
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Click on the "Choose File" button at the bottom of the dialog to upload your image to the server -- this can be done more than once
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Click on the "Upload" button to upload the files to the server
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Select the uploaded image from the list
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Click OK -- if you need to change the size of the image you can change the width or height prior to clicking "OK"
