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Is there any way with WordPress that a user could upload a file (pdf or jpg, for example) and have that image 'attached' to their account?

Ultimately, I'd like to be able to have a Gravity Forms form that automatically populates the user's name, contact info and this file, kind of like a job site where you can send all your info and your uploaded resume with one click.

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you can create a single page that doesn't let them register and then asking their First Name, Last Name and other details.

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And then use the field upload in the advance fields

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on the backend view you will be able to see the submission together with their name, address and other details and the file they included in their attachment.

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