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I have a community page which consist of a lightning-datatable filled with Opportunity records. As an action of the table I need to add Add Files action. Onclick of this action, user should see the standard Select Files modal.

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Is this something possible to achieve with the current capabilities?

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I don't believe there is a standard way of doing this. I had raised a case with Salesforce with a similar issue and I ended up using a custom component using lightning-file-upload. I believe you need to recreate a similar modal in LWC. For now I didn't include all the bells and whistle as the standard modal, but I'm working on it for the next project as an enhancement.

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