Unable to add files to sets

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Hello: We are running Concrete5 version 5.6.2.1 and for the past 2 months I have been unable to associate any image file (existing or new) to an image set. I have tried creating new image sets and re-using existing image sets that have files associated with them, but none of this works.

I would also like someone to help us update to 5.6.3.3, but I need help from a consultant who can speak in layman terms and has good English language proficiency.

Can someone please help? Thanks.