I doubt this, but is it possible to have multiple file upload fields that can each have multiple file attachments on a single node?

Comments

it should be possible, you just need to add multiple fields

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Actually you can also add a single file field set to allow multiple values.

Filefield works perfect for this. I wish I used it originally rather than the native file attachment... Now I have a bunch of work ahead moving files from the native attachment field to a newly created filefield replacement... I could just add more filefield upload fields and leave the existing file attachment field, but filefield lists the uploaded files much nicer (with file type icons etc), and file attachments are just a bulleted list... Unless there is a way to export the attachments to a new filefield... will give that a search...
Thanks again

I found this a little late, after adding an additional file upload field and people already uploading files to it. If you add a custom file field to your content type, set the file field Number of Values to something greater than 1, or unlimited. When a file is uploaded, another instance will appear allowing the user to upload another one.