File Transfer Cheat Sheet: The Practical Hacking Cheatsheet Series

File transfers are one of those skills that seem simple until you land on a machine where the tool you normally rely on simply isn’t available.

During Hack The Box machines, CTFs, ProLabs, penetration tests, and red team assessments, you’ll constantly encounter situations where you need to move a file between your attacker machine, a compromised host, or an internal system.

Maybe wget is missing.

Maybe curl is unavailable.

Maybe PowerShell is your only option on Windows.

Maybe outbound connections are restricted.

Or maybe you’re sitting behind a pivot and need to move files through an internal network.

That’s why the Practical Hacking Cheatsheet Series includes a dedicated:

File Transfer Cheat Sheet

This cheatsheet is designed as a practical reference for moving files between attacker and target machines across common Linux and Windows environments. Instead of relying on a single technique, it covers multiple approaches so you can quickly adapt when your preferred method doesn’t work.

The full File Transfer Cheat Sheet covers topics like:

• Python HTTP servers
• wget and curl
• Netcat file transfers
• Bash /dev/tcp
• SCP
• Base64 transfers
• PowerShell downloads
• Invoke-WebRequest
• Windows certutil
• BITSAdmin
• Windows curl.exe
• SMB file transfers
• Authenticated SMB shares
• HTTP POST file transfers
• File exfiltration
• SSH port forwarding
• SSH SOCKS proxies
• Chisel
• Ligolo-ng
• File integrity verification
• Transfer troubleshooting

Whether you’re transferring tools to a Linux target, downloading files onto Windows, exfiltrating data back to your attacker machine, or moving files through a pivoted network, the goal is the same: have a reliable method ready when you need it.

For example:

• How do I transfer a file when wget and curl aren’t installed?
• How do I download a file using PowerShell?
• How can I use certutil for a file transfer?
• How do I create a temporary SMB share?
• How do I transfer a binary file with Netcat?
• How can I move files through an SSH tunnel?
• How do I transfer files through a Chisel pivot?
• When should I use Ligolo-ng?
• How can I transfer a file using only Base64?
• How do I verify that a transferred file wasn’t corrupted?

The main idea is simple: don’t depend on a single file-transfer technique.

A good penetration tester knows how to adapt to the environment. If HTTP is blocked, try SMB. If common download utilities are missing, look at PowerShell, Netcat, or other available mechanisms. If the target sits behind a pivot, use the appropriate tunneling technique.

This cheatsheet puts those methods into a single practical reference that you can keep open while working through an HTB machine or authorized security assessment.

Full Cheatsheet Series

This is part of the complete Practical Hacking Cheatsheet Series:

Cheatsheet	Focus
Active Directory	AD attack methodology and commands
Web Application	Web exploitation techniques and payloads
Linux Privilege Escalation	Linux privilege escalation vectors
Windows Privilege Escalation	Windows privilege escalation vectors
Reverse Shells	Reverse shell one-liners and shell upgrades
File Transfers	Methods to transfer files between machines
Pivoting	SSH tunneling, Chisel, Ligolo, SOCKS
Password Attacks	Cracking, spraying, and brute-force techniques
Linux Enumeration	Post-exploitation Linux enumeration
Windows Enumeration	Post-exploitation Windows enumeration

Each cheatsheet is designed to be practical, concise, and easy to reference while solving machines, conducting authorized penetration tests, or preparing for certifications such as OSCP, CPTS, PNPT, and CRTO.

Who This Is For

This cheatsheet is made for:

• Hack The Box players
• CTF enthusiasts
• ProLab students
• Beginner and intermediate penetration testers
• Red team learners
• OSCP, CPTS, PNPT, and CRTO students
• Active Directory learners
• Cybersecurity students
• Anyone building a practical offensive security knowledge base

If you regularly work with compromised hosts or lab environments, this File Transfer Cheat Sheet gives you a quick reference for moving files across Linux and Windows systems, handling restricted environments, transferring data through pivots, and choosing the right technique when your first option doesn’t work.