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How to Break Pdf Security Your refund is: $ 1,000,000,000 (One Trillion USD) HOW TO BREAK PDF SECURITY How to Break PDF Signature / How to Break PDF Encryption Karsten Meyer zu Selhausen Jens Müller, Christian Mainka, Fabian Ising, Sebastian Schinzel Vladislav Mladenov, Martin Grothe, Jörg Schwenk This Talk Digital Signature Encryption Signature Validation Panel Signature Form Field 27.12.2019 How To Break PDF Security 2 PDF Basics “Everything you need to spoof PDF Signatures” 27.12.2019 How To Break PDF Security 3 Portable Document Format (PDF) FIRST VERSION RELEASED IN 1.6 BILLION PDF DOCUMENTS ON THE WEB IN 2015 1993 USED BY BY ADOBE ~99% COMPANIES AND GOVERNMENTAL PDF-2.0 INSTITUTIONS WORLDWIDE RELEASED IN 2017, LAST VERSION FROM ADOBE 27.12.2019 How To Break PDF Security 4 Portable Document Format (PDF) 27.12.2019 How To Break PDF Security 6 PDF File Structure 27.12.2019 How To Break PDF Security 7 PDF File Structure 27.12.2019 PDF File Structure %PDF-1.4 Header 1 0 obj << /Type /Catalog /Pages 2 0 R >> endobj 2 0 obj << /Count 1 /Type /Pages /Kids [3 0 R] >> Body endobj 3 0 obj << /Type /Page /Parent 2 0 R /Contents 4 0 R >> endobj XRef Section 4 0 obj (Hello World) endobj Trailer xref First Object with ID 0 0 5 5 entries 000000000 00000 f 000000009 00000 n 000000058 00000 n Object 4 0 is located at byte 000000121 00000 n offset 184 is in use „n“ 000000184 00000 n trailer << /Root 1 0 R /Size 5 >> startxref 275 %%EOF 27.12.2019 How To Break PDF Security 9 Incremental Update Header • Prominent example: PDF Annotations Body XRef Section Trailer Body Updates Updated Xref Section Updated Trailer 27.12.2019 How To Break PDF Security 10 Incremental Update %PDF-1.4 Header 1 0 obj (/Catalog) endobj 2 0 obj (/Pages) endobj 3 0 obj (/Page) endobj 4 0 obj … (Hello World) Body endobj xref 0 5 Trailer XRef Section … %%EOF 4 1 obj Trailer … (Hello 36C3!) endobj xref Body Updates 4 1 00000300 00001 n trailer << /Root 1 0 R /Size 5 /Prev 275 >> Updated Xref Section startxref 375 %%EOF Updated Trailer 27.12.2019 How To Break PDF Security 11 PDF Signatures 27.12.2019 How To Break PDF Security 12 This talk is about PDF Digital Signatures This talk Electronic Signature Digital Signature Electronic Signature Signature Validation Panel Signature Form Field 27.12.2019 How To Break PDF Security 13 How to create a PDF Signature %PDF-1.4 Header Header 1 0 obj (/Catalog) endobj Body Body 2 0 obj (/Pages) endobj 3 0 obj (/Page) endobj 4 0 obj XRef Section XRef Section signature … (Hello World) endobj Trailer Trailer the by xref Body Updates 0 5 Trailer Updated Xref Section … Protected %%EOF Updated Trailer New Catalog PDF Signature Objects xref 6 5 ..... trailer … Signed PDF %%EOF 27.12.2019 How To Break PDF Security 14 PDF Signature Spoofing Goals and Prerequisites 27.12.2019 How To Break PDF Security 15 PDF Signature Spoofing Attacker Victim ManipulatedSigned SignedPDF PDF Manipulated Signed PDF Indistinguishable Sig. Details INVOICE Your refund is: Seller: Amazon EU S.à r.l $ 1,000,000,000 Date: 12.11.2019 Amount: 123,99 € (One Trillion USD) Different Content 27.12.2019 How To Break PDF Security 16 PDF Signature Spoofing Three novel attack classes • Attack Class #1: Incremental Saving Attacks • Attack Class #2: Signature Wrapping Attacks • Attack Class #3: Universal Signature Forgery 27.12.2019 How To Break PDF Security 17 Attack Class #1/3: Incremental Saving Attack Abuse „Incremental Saving“ • Add/remove content • Keep signature valid 27.12.2019 How To Break PDF Security 18 Incremental Saving Attack Header Body Xref Table signature Trailer the by Body Updates Xref Table Protected Trailer Body Updates Xref Table Apply “trivial” Update Trailer 27.12.2019 How To Break PDF Security 19 Incremental Saving Attack Header Header Header Header Body Body Body Body signature signature signature Xref Table Xref Table Xref Table signature Xref Table the the the Trailer Trailer Trailer the Trailer by by by by Body Updates Body Updates Body Updates Body Updates Xref Table Xref Table Xref Table Xref Table Protected Protected Protected Protected Trailer Trailer Trailer Trailer Body Updates Body Updates Body Updates Body Updates + Signature Object Xref Table Trailer Trailer 27.12.2019 How To Break PDF Security 20 Inc. Saving Attack: 11/22 Apps are Vulnerable Product ISA Adobe Reader DC ○ Evaluation results Adobe Reader 9 ○ ● Full Signature Bypass Adobe Reader XI ○ eXpert PDF 12 Ultimate ○ ◐ Limited Signature Bypass Expert PDF Reader ○ ○ Foxit Reader ● Not vulnerable LibreOffice (Draw) ◐ Master PDF Editor ● Nitro Pro ◐ Nitro Reader ◐ Nuance Power PDF Standard ○ PDF Architect 6 ○ PDF Editor 6 Pro ◐ PDFelement 6 Pro ◐ PDF Studio Viewer 2018 ● PDF Studio Pro ● PDF-Xchange Editor ○ PDF-Xchange Viewer ○ Perfect PDF 10 Premium ● Perfect PDF Reader ● Soda PDF Desktop ○ Soda PDF ○ Total 11/22 21 Attack Class #2/3: Signature Wrapping Attack Manipulate the signed ByteRange values Allocate space to inject malicious content 27.12.2019 How To Break PDF Security 22 Signature Wrapping Attack a %PDF-1.7 Original Document 1 0 obj Catalog b Further Objects 5 0 obj Signature /Contents <324d3 ….770000000000000000 00000000000000000000 0000000000000000000> c /ByteRange [a b c d] xref d trailer %%EOF 27.12.2019 How To Break PDF Security 23 Signature Wrapping Attack a a %PDF-1.7 %PDF-1.7 Original Document Original Document 1 0 obj Catalog 1 0 obj Catalog b b Further Objects Further Objects 5 0 obj Signature 5 0 obj Signature /Contents <324d3 /Contents <324d3 ….770000000000000000 ….770000000000000000 00000000000000000000 00000000000000000000 0000000000000000000> 0000000000000000000> c c /ByteRange [a b c d] /ByteRange [a b c d] xref xref d trailer d trailer %%EOF %%EOF 27.12.2019 How To Break PDF Security 24 Signature Wrapping Attack a a %PDF-1.7 %PDF-1.7 Original Document Original Document 1 0 obj Catalog 1 0 obj Catalog b b Further Objects Further Objects 5 0 obj Signature 5 0 obj Signature /Contents <324d3 /Contents <324d3 ….770000000000000000 ….770000000000000000 00000000000000000000 00000000000000000000 0000000000000000000> 0000000000000000000> c /ByteRange [a b c d] xref c d trailer /ByteRange [a b c d] %%EOF xref d trailer %%EOF 27.12.2019 How To Break PDF Security 25 Signature Wrapping Attack a a %PDF-1.7 %PDF-1.7 Original Document Original Document 1 0 obj Catalog 1 0 obj Catalog b b Further Objects Further Objects 5 0 obj Signature 5 0 obj Signature /Contents <324d3 /Contents/Contents <324d3<324d3 ….77> ….770000000000000000 ….770000000000000000/ByteRange [a b c* d] 00000000000000000000 00000000000000000000 0000000000000000000> 0000000000000000000>Malicious Objects c /ByteRange [a b c d] Padding xref Malicious xref c*c d trailer /ByteRange [a b c d] %%EOF xref trailer d %%EOF 27.12.2019 How To Break PDF Security 26 Signature Wrapping: 17/22 Apps are Vulnerable Product ISA SWA Adobe Reader DC ○ ○ Evaluation results Adobe Reader 9 ○ ○ ● Full Signature Bypass Adobe Reader XI ○ ● eXpert PDF 12 Ultimate ○ ● ◐ Limited Signature Bypass Expert PDF Reader ○ ● ○ Foxit Reader ● ● Not vulnerable LibreOffice (Draw) ◐ ○ Master PDF Editor ● ○ Nitro Pro ◐ ● Nitro Reader ◐ ● Nuance Power PDF Standard ○ ● PDF Architect 6 ○ ● PDF Editor 6 Pro ◐ ● PDFelement 6 Pro ◐ ● PDF Studio Viewer 2018 ● ● PDF Studio Pro ● ● PDF-Xchange Editor ○ ● PDF-Xchange Viewer ○ ● Perfect PDF 10 Premium ● ● Perfect PDF Reader ● ● Soda PDF Desktop ○ ● Soda PDF ○ ● Total 11/22 17/22 27 Attack Class #3/3: Universal Signature Forgery Disable signature validation But show „PDF is validly signed“ 27.12.2019 How To Break PDF Security 28 Universal Signature Forgery 10 0 obj (Signature) /Contents <PKCS7-encodedSignature+Certificate> Signature Value /ByteRange [0 177777 188000 999] Hash computed over these endobj Bytes 10 0 obj (Signature) 10 0 obj (Signature) 10 0 obj (Signature) 10 0 obj (Signature) ____ /Contents ____ /Contents null /Contents 0x00 /ByteRange [a b c d] /ByteRange [a b c d] /ByteRange [a b c d] /ByteRange [a b c d] 10 0 obj (Signature) 10 0 obj (Signature) 10 0 obj (Signature) 10 0 obj (Signature) /Contents sig.value /Contents sig.value /Contents sig.value /Contents sig.value ____ /ByteRange ____ /ByteRange null /ByteRange [a –b c d] 27.12.2019 How To Break PDF Security 29 Universal Sig. Forgery: 4/22 Apps are Vulnerable Product ISA SWA USF Adobe Reader DC ○ ○ ● Evaluation results Adobe Reader 9 ○ ○ ○ ● Full Signature Bypass Adobe Reader XI ○ ○ ● eXpert PDF 12 Ultimate ○ ● ○ ◐ Limited Signature Bypass Expert PDF Reader ○ ● ○ ○ Foxit Reader ● ● ○ Not vulnerable LibreOffice (Draw) ◐ ○ ○ Master PDF Editor ● ○ ○ Nitro Pro ◐ ● ○ Nitro Reader ◐ ● ○ Nuance Power PDF Standard ○ ● ○ PDF Architect 6 ○ ● ○ PDF Editor 6 Pro ◐ ● ◐ PDFelement 6 Pro ◐ ● ◐ PDF Studio Viewer 2018 ● ● ○ PDF Studio Pro ● ● ○ PDF-Xchange Editor ○ ● ○ PDF-Xchange Viewer ○ ● ○ Perfect PDF 10 Premium ● ● ○ Perfect PDF Reader ● ● ○ Soda PDF Desktop ○ ● ○ Soda PDF ○ ● ○ Total 11/22 17/22 4/22 31 Evaluation Summary: 21/22 Apps are Vulnerable Product ISA SWA USF Summary Adobe Reader DC ○ ○ ● ● Evaluation results Adobe Reader 9 ○ ○ ○ ○ ● Full Signature Bypass Adobe Reader XI ○ ● ● ● eXpert PDF 12 Ultimate ○ ● ○ ● ◐ Limited Signature Bypass Expert PDF Reader ○ ● ○ ● ○ Foxit Reader ● ● ○ ● Not vulnerable LibreOffice (Draw) ◐ ○ ○ ● Master PDF Editor ● ○ ○ ● Nitro Pro ◐ ● ○ ● Nitro Reader ◐ ● ○ ● Nuance Power PDF Standard ○ ● ○ ● PDF Architect 6 ○ ● ○ ● PDF Editor 6 Pro ◐ ● ◐ ● PDFelement 6 Pro ◐ ● ◐ ● PDF Studio Viewer 2018 ● ● ○ ● PDF Studio Pro ● ● ○ ● PDF-Xchange Editor ○ ● ○ ● PDF-Xchange Viewer ○ ● ○ ● Perfect PDF 10 Premium ● ● ○ ● Perfect PDF Reader ● ● ○ ● Soda PDF Desktop ○ ● ○ ● Soda PDF ○ ● ○ ● Total 11/22 17/22 4/22 21/22 32 PDF Encryption 27.12.2019 How To Break PDF Security 33 PDFex • Attack with a logo • Novel attack techniques targeting PDF encryption • Direct exfiltration • Malleability gadgets 27.12.2019 How To Break PDF Security 34 PDF: the de-facto standard for office documents SUPPORTS AES ENCRYPTION USES AES is good.
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