Edit: I think I found the problem: Acrobat needs the Catalog dictionary to be an indirect reference that is not in an object streams.
- good3.pdf: PDF encrypted with (A)RC4 using V=4, PDF version 1.5, cross-reference and object streams, Catalog dictionary not in the object stream.
These files were generated with HexaPDF and work fine in all viewers except Adobe Acrobat Reader. They seem to be valid PDFs but Acrobat doesn't like them...
All files use the password 'test'.
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good1.pdf: PDF encrypted with (A)RC4 using V=2, PDF version 1.5, cross-reference and no object streams.
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good2.pdf: PDF encrypted with (A)RC4 using V=4, PDF version 1.5, cross-reference and no object streams.
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qpdf-good1.pdf: Using qpdf instead of HexaPDF, PDF encrypted with (A)RC4 using V=2, PDF version 1.5, cross-reference and object streams.
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bad1.pdf: PDF encrypted with (A)RC4 using V=2, PDF version 1.5, cross-reference and object streams.
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bad2.pdf: PDF encrypted with (A)RC4 using V=4, PDF version 1.5, cross-reference and object streams.