First, navigate to your resident dashboard by following the steps in the help guide:

Resident Dashboard Overview

Learn how to access and navigate your Resident Dashboard for the first time with ease.
From your dashboard, select the work order where you need to add a file.
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On the Work Order Details page, click Provide Work Order Update.
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Then select Add Images and Files.
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Next, click Choose Images/Files. Depending on your computer’s settings, your drive folders will pop up on your screen.
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Afterward, select the file or image that you want to upload from your computer to the work order. Click Open to upload the file.
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Finally, click Upload File to upload the images or files you’ve selected. A confirmation message at the top of the next page will show that the image/file is uploaded. 
You can also add videos to a work order at any time except when the work order is completed/cancelled.
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And that’s it! Congratulations on uploading your images or files for your work order!