Analyzing Malicious Documents Cheat Sheet

This cheat sheet outlines tips and tools for analyzing malicious documents, such as Microsoft Office, RTF and Adobe Acrobat (PDF) files. To print it, use the one-page PDF version; you can also edit the Word version to customize it for you own needs.

General Approach to Document Analysis

  1. Examine the document for anomalies, such as risky tags, scripts, or other anomalous aspects.
  2. Locate embedded code, such as shellcode, VBA macros, JavaScript or other suspicious objects.
  3. Extract suspicious code or object from the file.
  4. If relevant, deobfuscate and examine JavaScript or macro code.
  5. If relevant, disassemble and/or debug shellcode.
  6. Understand the next steps in the infection chain.

Microsoft Office Format Notes

  • Binary document files supported by Microsoft Office use the OLE2 (a.k.a. Structured Storage) format.
  • SRP streams in OLE2 documents sometimes store a cached version of earlier macro code.
  • OOXML documents (.docx, .xlsm, etc.) supported by MS Office use zip compression to store contents.
  • Macros embedded in OOXML files are stored inside the OLE2 binary file, which is within the zip archive.
  • RTF documents don’t support macros, but can contain other files embedded as OLE1 objects.

Useful MS Office File Analysis Commands

unzip file.pptxExtract contents of OOXML file file.pptx. file.xlsm file.doc
Locate and extract macros from file.xlsm or file.doc. file.xlsList all OLE2 streams present in file.xls. -s 3 -v file.xlsExtract macros stored inside stream 3 in file.xls. file.xls -p plugin_http_heuristics Find obfuscated URLs in file.xls macros.
 msoffice-crypt -d -p pass file.docm file2.docm Decrypt OOXML file file.docm using password pass to create file2.docm. -d file.doc Disassemble p-code macro code from file.doc. file.rtf Extract objects embedded into RTF-formatted file.rtf. file.rtf List groups and structure of RTF-formatted file.rtf. file.rtf -f O List groups in file.rtf that enclose an object. file.rtf -s 5 -H -d > out.bin Extract object from group 5 and save it into out.bin. -xo file.doc Extract Flash (SWF) objects from OLE2 file file.doc.

Risky PDF Format Tags

  • /OpenAction and /AA specify the script or action to run automatically.
  • /JavaScript and /JS specify JavaScript to run.
  • /GoTo changes the view to a specified destination within the PDF or in another PDF file.
  • /Launch can launch a program or open a document.
  • /URI accesses a resource by its URL.
  • /SubmitForm and /GoToR can send data to URL.
  • /RichMedia can be used to embed Flash in a PDF.
  • /ObjStm can hide objects inside an Object Stream.
  • Be mindful of obfuscation with hex codes, such as /JavaScript vs. /J#61vaScript. (See examples.)

Useful PDF File Analysis Commands file.pdfScan file.pdf for risky keywords and dictionary entries. -fl file.pdfExamine file.pdf for risky tags and malformed objects. --object id file.pdfDisplay contents of object id in file.pdf. Add “--filter --raw” to decode the object’s stream.
qpdf --password=pass --decrypt infile.pdf outfile.pdfDecrypt infile.pdf using password pass to create outfile.pdf. -f file.pdf -o outExtract Flash (SWF) objects from file.pdf into the out directory.

Shellcode and Other Analysis Commands

xorsearch -W -d 3 file.binLocate shellcode patterns inside the binary file file.bin.
scdbg file.bin /foff 0x2BEmulate execution of shellcode in file.bin starting at offset 0x2B.
shellcode2exe file.binGenerate PE executable file.exe that runs shellcode from file.bin.
jmp2it file.bin 0x2B Execute shellcode in file file.bin starting at offset 0x2B. file.txtList Base64-encoded strings present in file file.txt. file.txt -e bu -s 2 -d > file.binConvert backslash Unicode-encoded Base64 string #2 from file.txt as file.bin file.

 Additional Document Analysis Tools


Special thanks for feedback to Pedro Bueno and Didier Stevens. If you have suggestions for improving this cheat sheet, please let me know. Creative Commons v3 “Attribution” License for this cheat sheet version 3.0.


About the Author

Lenny Zeltser develops products and programs that use security to achieve business results. He is the CISO at Axonius and Faculty Fellow at SANS Institute. Lenny has been leading efforts to establish resilient security practices and solve hard security problems for over two decades. A respected author and practitioner, he has been advancing tradecraft and contributing to the community. His insights build upon real-world experience, a Computer Science degree from the University of Pennsylvania, and an MBA degree from MIT Sloan.

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