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You are able to upload documents from the Apple Finder to Wise Owl Legal on the upload documents page.
Below is the screen at https://demo.wols.com.au/Document/Upload/, you would replace <demo.wols.com.au> with your unique URL.
You can nominate your matter and other metadata fields before or after uploading documents. If you choose to upload a document with out a matter number, you can update it in the subsequent screen, allocate documents.
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How to save an email attachment from Outlook into Wise Owl Legal
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How to access documents to Email from Wise Owl Legal
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