PFX to PEM: Extract Certificate Private Key | OpenSSL & PowerShell (WSL)
Learn how to convert PFX to PEM, securely extract private keys, and manage SSL/TLS certificates using OpenSSL and PowerShell in Windows, WSL, Linux, and macOS. This step‑by‑step tutorial covers essential commands, certificate formats (PKCS#12, PEM, CRT, CER, X.509), and practical tips for managing SSL/TLS certificates across IIS, Nginx, Apache, and Azure. Perfect for sysadmins, IT pros, and developers who need secure, cross‑platform certificate workflows.
#PFXtoPEM #OpenSSL #PowerShell #WSL #CertificateManagement
You’ll learn
• How to convert PFX to PEM and extract the certificate private key securely
• Step‑by‑step OpenSSL commands for managing PKCS#12, PEM, CRT, CER, and X.509 formats
• Using PowerShell and WSL (Windows Subsystem for Linux) for cross‑platform certificate workflows
• Best practices for securing private PEM keys with permissions and passphrases
Applies to:
✅ Certificates: PKCS#12 .pfx/.p12 with an exportable private key; outputs as PEM (key, cert, CA chain).
✅ Windows 10/11 with WSL 2 with OpenSSL 3.x
✅ Windows Server 2022/2025 with WSL 2 with OpenSSL 3.x
✅ Linux/macOS with OpenSSL 3.x
Targets:
• Firewalls/VPNs: pfSense, FortiGate, Cisco ASA/FTD, Palo Alto, Sophos
• web/proxy: Nginx, Apache, HAProxy, Traefik
• Load Balancers: Azure App Gateway, AWS ALB/ELB
• Azure Key Vault import
Audience:
• SysAdmins
• Network/Security Engineers
• PKI/CA admins
• Developers working with SSL/TLS
Commands and Scripts (PowerShell/CMD/BASH) GitHub:
https://github.com/DariensTips/PFX-to...
Chapters:
0:00 Introduction
0:28 Export PFX (MMC and PowerShell)
1:42 Convert PFX to PEM using OpenSSL
3:11 Why WSL?
3:47 Security
5:59 Thank you for watching
6:22 Links & Resources
Links & Resources:
https://campus.barracuda.com/product/...
https://docs.openssl.org/3.0/man1/ope...
https://github.com/openssl/openssl/re...
https://knowledge.digicert.com/genera...
https://learn.microsoft.com/en-us/pow...
https://learn.microsoft.com/en-us/win...
https://learn.microsoft.com/en-us/win...
https://openssl.org/
Glossary:
PFX = Personal Information Exchange
PEM = Privacy-Enhanced Mail (Base64 certificate/key format)
TLS = Transport Layer Security
SSL = Secure Sockets Layer (legacy term still widely searched)
CA = Certificate Authority
RSA = Rivest-Shamir-Adleman (public-key algorithm)
WSL = Windows Subsystem for Linux
ICACLS = (Windows tool) manages file/folder ACLs and permissions
Related videos and Playlists:
• Active Directory Certificate Services (ADCS)
• WSL