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In Magento, is it possible to display the simple product custom options (including file upload field) on the Grouped Product Page?

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No, not out of the box. Using anything else but simple products without custom options in a a grouped (or bundle) product needs an insane amount of customization to make it work right. It's unfortunately not intended by design at all.

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I have just submitted an extension to Magento Connect for Magento CE 2.1.0 which will allow custom options to be displayed on grouped product pages. This includes the file upload field among the other available types.

I'm not sure how long the approval process takes, but the extension will hopefully be available in the near future.

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