To attach a file:
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Edit something. (This can be anything, including a newsletter. It can be new, too.)
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Scroll to the bottom of the edit page.
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Click on the "File attachments" tab. It will look like this:

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Click on the "Choose File" button, and choose a file from your computer. (It can be from your hard drive or the shared drive.)
Note: You are limited to files 1 MB in size. If you need to upload something larger, ask Jordan.
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Click "Attach." Wait for the file to upload (shouldn't take more than a minute).
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Once the file is uploaded, you have the following options:
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Decide whether the file should show up in a "list" at the bottom of the page. For newsletters, this is the easiest way to attach the file. Alternatively, you can create a custom link to the item using the full url.
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You can also change the "description" of the item, which will show up if the item is listed.
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To delete the item, check the box under the word "delete" and save/preview your changes.
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Upload additional files if you want.
Note: You can upload photos using this method, and then embed them using the picture button. This is an alternative to the standard method for inserting photos.