OpenVPN 1.0 - open-source VPN 1.0

What is OpenVPN?

OpenVPN is an open-source VPN (Virtual Private Network) protocol that creates secure, encrypted tunnels between devices over the internet. It allows users to access private networks securely and anonymously.

Why is OpenVPN important?

  • Ensures confidentiality, integrity, and authentication of data.

  • Supports strong encryption (e.g., AES), TLS-based key exchange, and certificate-based authentication.

  • Highly configurable and works across platforms and network types.

How OpenVPN works (in simple steps):

  • You start the OpenVPN client and connect to a VPN server.

  • The client and server perform a TLS handshake to authenticate and exchange encryption keys.

  • A secure tunnel is established using protocols like UDP or TCP.

  • Your internet traffic is encrypted and routed through the VPN server.

  • The server decrypts the traffic and forwards it to the destination.

Where is OpenVPN used?

  • Remote work – Secure access to corporate networks.

  • Privacy protection – Hiding IP addresses and encrypting traffic on public Wi-Fi.

  • Bypass geo-restrictions – Accessing region-locked content.

  • Enterprise VPNs – Secure site-to-site or client-to-site connections.

  • Cloud and hybrid networks – Secure communication between cloud and on-prem systems.

Which OSI Layer does this protocol belong to?

  • OpenVPN operates primarily at the Network Layer (Layer 3) by routing IP packets.

  • It also uses the Transport Layer (Layer 4) via UDP or TCP to transmit data.

  • Unlike PPTP or L2TP, it uses SSL/TLS for encryption and authentication instead of GRE or IPsec.

  • In this section, you are going to learn

  • Terminology

  • Version Info

OpenVPN 1.0 Version

RFC

Year

Core Idea / Contribution

OpenVPN 0.91

Internal Docs

26-Dec-01

First public beta release. Introduced basic SSL/TLS tunneling using OpenSSL 0.9.6. Very limited configuration and no GUI.

OpenVPN 0.92 0.99

Internal Docs

Early 2002 (unofficial)

Experimental builds with incremental improvements. These

versions were not widely documented but served as stepping stones to 1.0.

OpenVPN v1.0

Internal Docs

2002

Initial release by James Yonan. Introduced SSL/TLS-based VPN tunneling using OpenSSL. Basic point-to-point tunneling with static keys. No compression, no client-server mode. Focused on simplicity and portability.

OpenVPN v1.5

Internal Docs

2003

Enhanced stability, better key handling, and configuration

flexibility.

OpenVPN v2.0

Internal Docs

2005

Major rewrite. Introduced client-server mode, TLS authentication, and better NAT traversal.

OpenVPN v2.1

Internal Docs

2009

Added IPv6 support, Windows UAC compatibility, and better

crypto options.

OpenVPN v2.3

Internal Docs

2013

Introduced PolarSSL support, ECC crypto, and IPv6

transport.

OpenVPN v2.4

OpenVPN 2.4 Manual

2017

Added AEAD ciphers (GCM), improved TLS negotiation, and

better mobile support.

OpenVPN v2.5

Internal Docs

2020

Enhanced crypto (ChaCha20-Poly1305), improved

multi-platform support.

OpenVPN v2.6

Internal Docs

2023

Added Data Channel Offload (DCO) support for performance.

OpenVPN RFC Draft

GitHub Draft

Ongoing

Work in progress to formally document the OpenVPN wire

protocol as an RFC.

Setup

Setup

OpenVPN Control Packet

S.No

Protocol Packets

Description

Size(Bytes)

1

OpenVPN Control Packet

Used for session initiation, TLS handshake, and key exchange.

~60300+

Packet Type

Indicates control type (e.g., handshake, key exchange) P_CONTROL_HARD_RESET_CLIENT_V1=Initiates a new session from the client side. P_CONTROL_HARD_RESET_SERVER_V1=Server response to clients hard reset. P_CONTROL_SOFT_RESET_V1=Used for renegotiation without full session reset. P_CONTROL_V1=Carries TLS handshake messages (e.g., ClientHello, ServerHello). P_ACK_V1=Acknowledges receipt of control packets.

1

Session ID

Identifies the VPN session

8

Message Type

TLS handshake, certificate exchange, etc.

Variable

Payload Length

Length of the control message

2

TLS Payload

Contains TLS handshake data (ClientHello, ServerHello, etc.)

Variable

OpenVPN Data Packet

S.No

Protocol Packets

Description

Size(Bytes)

2

OpenVPN Data Packet

Carries encrypted user data through the VPN tunnel.

Variable

Packet Type

Indicates this is a data packet P_DATA_V1=Encrypted payload (e.g., IP packets) with optional compression and HMAC. P_DATA_V2 (later)=Enhanced version with better replay protection and metadata (not in 1.0).

1

Session ID

Identifies the VPN session

8

Key ID

Identifies the encryption key used

1

Sequence Number

Ensures packet ordering and replay protection

4

Encrypted Payload

Encrypted IP packet or PPP frame

Variable

HMAC (optional)

Message authentication code for integrity

1632

Padding (optional)

Used for block cipher alignment

Variable

S.no

Use Case

Description

1

Secure Remote Access

Enables encrypted remote access to private networks over the

public internet.

2

Point-to-Point Tunneling

Establishes secure tunnels between two endpoints using SSL/TLS.

3

Static Key VPN

Uses pre-shared static keys for encryption and authentication.

4

Cross-Platform VPN

Supports Linux, Windows, and macOS for secure connectivity.

5

NAT Traversal

Operates over UDP/TCP, allowing VPN traffic to pass through NAT devices.

6

Lightweight Deployment

Minimal dependencies and configuration for quick setup.

7

Encrypted File Transfers

Secures file transfers between remote systems using the VPN tunnel.

8

Remote Shell Access

Protects remote shell sessions (e.g., SSH) by routing them through

the VPN.

S.no

Feature

Description

1

SSL/TLS Tunneling

Uses OpenSSL to create secure VPN tunnels over TCP or UDP.

2

Static Key Encryption

Supports pre-shared static keys for encryption and authentication.

3

Point-to-Point Mode

Operates in a simple peer-to-peer configuration (no client-server

model yet).

4

TUN/TAP Interface Support

Supports both TUN (IP-level) and TAP (Ethernet-level) virtual interfaces.

5

Cross-Platform Compatibility

Runs on Linux, Windows, and other Unix-like systems.

6

Portability

Designed to be lightweight and portable with minimal dependencies.

7

Basic Configuration Files

Uses simple text-based configuration files for setup.

8

No Compression

Compression (like LZO) was not yet implemented in version 1.0.

9

No Client-Server Mode

All peers were equal; client-server architecture came in later versions.

10

OpenSSL Integration

Relied on OpenSSL 0.9.6 for cryptographic functions.

SSL/TLS Tunneling - Testcases

#

Test Case

Description

Expected Result

1

VPN Client Start

Launch OpenVPN client

Client initializes

2

VPN Server Start

Launch OpenVPN server

Server listens on configured port

3

TLS Handshake Initiation

Client initiates TLS handshake

Server responds with certificate

4

Certificate Validation

Validate server certificate

Certificate accepted

5

Invalid Certificate

Use expired/invalid cert

Connection rejected

6

Mutual TLS Authentication

Use client and server certs

Both sides authenticated

7

TLS Version Compatibility

Use supported TLS version

Handshake succeeds

8

TLS Version Mismatch

Use unsupported TLS version

Handshake fails

9

Cipher Suite Negotiation

Negotiate cipher suite

Strongest common cipher selected

10

Weak Cipher Rejection

Use weak cipher

Connection rejected

11

VPN Tunnel Establishment

Complete handshake and start tunnel

Tunnel established

12

Data Transfer Through Tunnel

Send data over tunnel

Data encrypted and delivered

13

Tunnel Teardown

Disconnect VPN

Tunnel closed gracefully

14

Reconnect After Drop

Drop connection and reconnect

Tunnel re-established

15

UDP Transport Mode

Use UDP for transport

Tunnel established

16

TCP Transport Mode

Use TCP for transport

Tunnel established

17

NAT Traversal

Connect behind NAT

Tunnel established

18

Firewall Traversal

Connect through firewall

Tunnel established

19

Port Blocking

Block OpenVPN port

Connection fails

20

Compression Enabled

Enable LZO compression

Data compressed

21

Compression Disabled

Disable compression

Data uncompressed

22

Keepalive Mechanism

Enable keepalive

Tunnel remains active

23

TLS Renegotiation

Trigger TLS renegotiation

Tunnel remains secure

24

Replay Protection

Replay old packet

Packet dropped

25

Packet Fragmentation

Send large packets

Packets reassembled

26

IPv4 Tunnel Test

Use IPv4 for tunnel

Tunnel established

27

IPv6 Tunnel Test

Use IPv6 for tunnel

Tunnel established

28

DNS Leak Test

Check DNS resolution path

No DNS leak

29

Split Tunneling

Route only specific traffic

Only selected traffic tunneled

30

Full Tunneling

Route all traffic through VPN

All traffic tunneled

31

Authentication with Username/Pass

Use credentials for auth

Tunnel established

32

Authentication Failure

Use wrong credentials

Connection rejected

33

Static Key Mode

Use static key instead of TLS

Tunnel established

34

TLS-Auth HMAC Test

Use tls-auth key

HMAC verified

35

TLS-Crypt Test

Use tls-crypt key

Encrypted control channel

36

Log File Generation

Enable logging

Logs created

37

Verbosity Level Test

Change log verbosity

Logs reflect level

38

VPN with Mobile Client

Connect from mobile device

Tunnel established

39

VPN with Desktop Client

Connect from desktop

Tunnel established

40

VPN with Virtual Machine

Connect from VM

Tunnel established

41

VPN with Container

Connect from container

Tunnel established

42

VPN with Roaming

Roam between networks

Tunnel persists

43

VPN with Failover

Failover to backup link

Tunnel re-established

44

VPN with Load Balancer

Use load balancer

Tunnel established

45

VPN with Proxy

Connect via HTTP/SOCKS proxy

Tunnel established

46

VPN with Monitoring Tools

Monitor tunnel traffic

Traffic visible

47

VPN with IDS/IPS

Detect VPN traffic

Traffic detected

48

VPN with ACLs

Apply access control

Unauthorized traffic blocked

49

VPN with Policy Enforcement

Apply routing/firewall policies

Policies enforced

50

VPN with Analytics

Analyze VPN usage

Metrics collected

Static Key Encryption - Testcases

#

Test Case

Description

Expected Result

1

Static Key File Presence

Check if static key file exists

File found

2

Static Key Format Validation

Validate key file format

Format correct

3

Static Key Length Validation

Check key length

Length matches expected size

4

Static Key Permissions

Check file permissions

Permissions are secure

5

Static Key Encryption Enabled

Enable static key encryption

Tunnel established

6

Static Key Encryption Disabled

Disable static key encryption

Tunnel fails or unencrypted

7

Tunnel Establishment with Key

Establish tunnel using static key

Tunnel established

8

Tunnel Establishment without Key

Attempt tunnel without key

Tunnel fails

9

Key Mismatch Test

Use mismatched keys on client/server

Tunnel fails

10

Key Rotation Test

Replace static key and reconnect

Tunnel re-established

11

Key Corruption Test

Corrupt key file

Tunnel fails

12

Key Replay Protection

Replay encrypted packet

Packet dropped

13

Key with UDP Transport

Use static key over UDP

Tunnel established

14

Key with TCP Transport

Use static key over TCP

Tunnel established

15

Key with IPv4

Use static key over IPv4

Tunnel established

16

Key with IPv6

Use static key over IPv6

Tunnel established

17

Key with NAT Traversal

Use static key behind NAT

Tunnel established

18

Key with Firewall Traversal

Use static key through firewall

Tunnel established

19

Key with Compression

Enable compression with static key

Tunnel established

20

Key with Fragmentation

Send large packets

Packets reassembled

21

Key with Roaming

Roam between networks

Tunnel persists

22

Key with Failover

Failover to backup link

Tunnel re-established

23

Key with Load Balancer

Use load balancer

Tunnel established

24

Key with Proxy

Use proxy with static key

Tunnel established

25

Key with Mobile Client

Connect from mobile device

Tunnel established

26

Key with Desktop Client

Connect from desktop

Tunnel established

27

Key with Virtual Machine

Connect from VM

Tunnel established

28

Key with Container

Connect from container

Tunnel established

29

Key with DNS Leak Test

Check DNS resolution path

No DNS leak

30

Key with Split Tunneling

Route specific traffic

Only selected traffic tunneled

31

Key with Full Tunneling

Route all traffic

All traffic tunneled

32

Key with Logging Enabled

Enable logs

Logs show encrypted session

33

Key with Monitoring Tools

Monitor encrypted traffic

Traffic visible as encrypted

34

Key with IDS/IPS

Detect encrypted traffic

Traffic detected

35

Key with ACLs

Apply access control

Unauthorized traffic blocked

36

Key with Policy Enforcement

Apply routing/firewall policies

Policies enforced

37

Key with Replay Attack

Replay old encrypted packet

Packet dropped

38

Key with Packet Loss

Simulate packet loss

Tunnel remains stable

39

Key with Jitter

Introduce jitter

Tunnel remains stable

40

Key with Delay

Introduce delay

Tunnel remains stable

41

Key with Performance Benchmark

Measure throughput and latency

Metrics recorded

42

Key with Encryption Validation

Validate encryption using packet capture

Data is encrypted

43

Key with Static IP

Use static IP address

Tunnel established

44

Key with Dynamic IP

Use dynamic IP address

Tunnel established

45

Key with Port Forwarding

Use port forwarding

Tunnel established

46

Key with Port Blocking

Block VPN port

Tunnel fails

47

Key with Custom Port

Use non-default port

Tunnel established

48

Key with TLS Disabled

Use static key without TLS

Tunnel established

49

Key with TLS Enabled

Use static key with TLS

Tunnel established securely

50

Key with Session Multiplexing

Use multiple sessions over one tunnel

Sessions isolated and encrypted

Point-to-Point Mode - Testcases

#

Test Case

Description

Expected Result

1

Basic Tunnel Setup

Establish point-to-point tunnel

Tunnel established

2

Peer-to-Peer Connection

Connect two endpoints directly

Connection successful

3

IP Address Assignment

Assign IPs to both ends

IPs assigned correctly

4

Static IP Configuration

Use static IPs for both peers

Tunnel established

5

Dynamic IP Configuration

Use dynamic IPs

Tunnel established

6

Authentication with Pre-shared Key

Use PSK for authentication

Tunnel established

7

Authentication with Certificates

Use certificates for authentication

Tunnel established

8

Authentication Failure

Use invalid credentials

Tunnel fails

9

Encryption Enabled

Enable encryption

Data encrypted

10

Encryption Disabled

Disable encryption

Data sent in plaintext

11

Data Transfer Test

Send data through tunnel

Data delivered

12

Tunnel Teardown

Disconnect tunnel

Tunnel closed gracefully

13

Reconnect After Drop

Drop and re-establish tunnel

Tunnel re-established

14

Keepalive Mechanism

Enable keepalive

Tunnel remains active

15

NAT Traversal

Connect behind NAT

Tunnel established

16

Firewall Traversal

Connect through firewall

Tunnel established

17

Port Blocking

Block tunnel port

Tunnel fails

18

IPv4 Support

Use IPv4 for tunnel

Tunnel established

19

IPv6 Support

Use IPv6 for tunnel

Tunnel established

20

MTU Size Test

Vary MTU size

Tunnel adapts or fragments

21

Fragmentation Support

Send large packets

Packets reassembled

22

Compression Enabled

Enable compression

Data compressed

23

Compression Disabled

Disable compression

Data uncompressed

24

Replay Protection

Replay old packets

Packets dropped

25

Packet Loss Simulation

Drop packets

Tunnel remains stable

26

Jitter Simulation

Introduce jitter

Tunnel remains stable

27

Delay Simulation

Introduce delay

Tunnel remains stable

28

Performance Benchmark

Measure throughput and latency

Metrics recorded

29

Logging Enabled

Enable logging

Logs created

30

Monitoring Enabled

Monitor tunnel traffic

Traffic visible

31

ACL Enforcement

Apply access control

Unauthorized traffic blocked

32

Policy Enforcement

Apply routing/firewall policies

Policies enforced

33

DNS Leak Test

Check DNS resolution path

No DNS leak

34

Split Tunneling

Route specific traffic

Only selected traffic tunneled

35

Full Tunneling

Route all traffic

All traffic tunneled

36

Mobile Client Support

Connect from mobile device

Tunnel established

37

Desktop Client Support

Connect from desktop

Tunnel established

38

VM Support

Connect from virtual machine

Tunnel established

39

Container Support

Connect from container

Tunnel established

40

Roaming Support

Roam between networks

Tunnel persists

41

Failover Support

Failover to backup link

Tunnel re-established

42

Load Balancer Compatibility

Use load balancer

Tunnel established

43

Proxy Compatibility

Use proxy

Tunnel established

44

Custom Port Configuration

Use non-default port

Tunnel established

45

Port Forwarding

Use port forwarding

Tunnel established

46

Session Multiplexing

Attempt multiple sessions

Only one session allowed

47

Tunnel ID Assignment

Assign unique tunnel ID

ID assigned

48

Session ID Assignment

Assign unique session ID

ID assigned

49

Error Handling

Send malformed packet

Error logged

50

Protocol Compatibility

Use with different protocols (e.g., PPP, IP)

Tunnel supports protocol

TUN/TAP Interface Support - Testcases

#

Test Case

Description

Expected Result

1

TUN Interface Creation

Create a TUN interface

Interface appears in system

2

TAP Interface Creation

Create a TAP interface

Interface appears in system

3

TUN Interface Configuration

Assign IP to TUN interface

IP assigned successfully

4

TAP Interface Configuration

Assign MAC/IP to TAP interface

Configuration successful

5

TUN Interface Packet Routing

Route IP packets through TUN

Packets routed correctly

6

TAP Interface Frame Forwarding

Forward Ethernet frames through TAP

Frames forwarded correctly

7

TUN Interface with IPv4

Use IPv4 over TUN

Traffic delivered

8

TUN Interface with IPv6

Use IPv6 over TUN

Traffic delivered

9

TAP Interface with Bridging

Bridge TAP with physical NIC

Bridge works correctly

10

TUN Interface with NAT

Use NAT with TUN

Traffic translated correctly

11

TAP Interface with NAT

Use NAT with TAP

Traffic translated correctly

12

TUN Interface with Firewall

Apply firewall rules

Rules enforced

13

TAP Interface with Firewall

Apply firewall rules

Rules enforced

14

TUN Interface with VPN

Use TUN in VPN tunnel

Tunnel established

15

TAP Interface with VPN

Use TAP in VPN tunnel

Tunnel established

16

TUN Interface with Encryption

Encrypt traffic over TUN

Traffic encrypted

17

TAP Interface with Encryption

Encrypt traffic over TAP

Traffic encrypted

18

TUN Interface with Compression

Enable compression

Traffic compressed

19

TAP Interface with Compression

Enable compression

Traffic compressed

20

TUN Interface with MTU Test

Vary MTU size

Traffic adapts or fragments

21

TAP Interface with MTU Test

Vary MTU size

Traffic adapts or fragments

22

TUN Interface with Packet Loss

Simulate packet loss

Tunnel remains stable

23

TAP Interface with Packet Loss

Simulate packet loss

Tunnel remains stable

24

TUN Interface with Jitter

Introduce jitter

Tunnel remains stable

25

TAP Interface with Jitter

Introduce jitter

Tunnel remains stable

26

TUN Interface with Delay

Introduce delay

Tunnel remains stable

27

TAP Interface with Delay

Introduce delay

Tunnel remains stable

28

TUN Interface with Logging

Enable logging

Logs show TUN activity

29

TAP Interface with Logging

Enable logging

Logs show TAP activity

30

TUN Interface with Monitoring

Monitor TUN traffic

Traffic visible

31

TAP Interface with Monitoring

Monitor TAP traffic

Traffic visible

32

TUN Interface with ACLs

Apply ACLs

Unauthorized traffic blocked

33

TAP Interface with ACLs

Apply ACLs

Unauthorized traffic blocked

34

TUN Interface with Policy Routing

Apply routing policies

Policies enforced

35

TAP Interface with Policy Routing

Apply routing policies

Policies enforced

36

TUN Interface with Virtual Machine

Use TUN in VM

Tunnel works

37

TAP Interface with Virtual Machine

Use TAP in VM

Tunnel works

38

TUN Interface with Container

Use TUN in container

Tunnel works

39

TAP Interface with Container

Use TAP in container

Tunnel works

40

TUN Interface with Roaming

Roam between networks

Tunnel persists

41

TAP Interface with Roaming

Roam between networks

Tunnel persists

42

TUN Interface with Failover

Failover to backup link

Tunnel re-established

43

TAP Interface with Failover

Failover to backup link

Tunnel re-established

44

TUN Interface with Load Balancer

Use load balancer

Tunnel established

45

TAP Interface with Load Balancer

Use load balancer

Tunnel established

46

TUN Interface with Proxy

Use proxy

Tunnel established

47

TAP Interface with Proxy

Use proxy

Tunnel established

48

TUN Interface with Custom Routing

Apply custom routes

Routes applied

49

TAP Interface with Bridged Network

Bridge TAP to LAN

LAN access granted

50

TUN/TAP Interface Cleanup

Remove interface

Interface removed successfully

Cross-Platform Compatibility - Testcases

#

Test Case

Description

Expected Result

1

Windows Client to Linux Server

Connect from Windows to Linux VPN server

Tunnel established

2

Linux Client to Windows Server

Connect from Linux to Windows VPN server

Tunnel established

3

macOS Client to Linux Server

Connect from macOS to Linux VPN server

Tunnel established

4

Linux Client to macOS Server

Connect from Linux to macOS VPN server

Tunnel established

5

Android Client to Linux Server

Connect from Android device

Tunnel established

6

iOS Client to Linux Server

Connect from iOS device

Tunnel established

7

Windows Client to macOS Server

Connect from Windows to macOS VPN server

Tunnel established

8

macOS Client to Windows Server

Connect from macOS to Windows VPN server

Tunnel established

9

Android Client to Windows Server

Connect from Android to Windows VPN server

Tunnel established

10

iOS Client to Windows Server

Connect from iOS to Windows VPN server

Tunnel established

11

Windows Client to Android Server

Connect from Windows to Android-based VPN server

Tunnel established

12

Linux Client to Android Server

Connect from Linux to Android-based VPN server

Tunnel established

13

iOS Client to macOS Server

Connect from iOS to macOS VPN server

Tunnel established

14

Android Client to macOS Server

Connect from Android to macOS VPN server

Tunnel established

15

Cross-Platform Certificate Auth

Use same certificate on different OS

Auth succeeds

16

Cross-Platform PSK Auth

Use pre-shared key on different OS

Auth succeeds

17

GUI Client on Windows

Use GUI VPN client

Tunnel established

18

CLI Client on Linux

Use command-line VPN client

Tunnel established

19

Mobile App on Android

Use Android VPN app

Tunnel established

20

Mobile App on iOS

Use iOS VPN app

Tunnel established

21

VPN with Windows Firewall

Use VPN with Windows firewall enabled

Tunnel established

22

VPN with Linux iptables

Use VPN with iptables configured

Tunnel established

23

VPN with macOS PF Firewall

Use VPN with macOS firewall

Tunnel established

24

VPN with Android VPN API

Use Android native VPN API

Tunnel established

25

VPN with iOS VPN Framework

Use iOS VPN framework

Tunnel established

26

VPN with Docker Container

Run VPN client in Docker

Tunnel established

27

VPN with VirtualBox VM

Run VPN in VirtualBox

Tunnel established

28

VPN with VMware VM

Run VPN in VMware

Tunnel established

29

VPN with WSL on Windows

Use VPN in Windows Subsystem for Linux

Tunnel established

30

VPN with ARM-based Device

Use VPN on Raspberry Pi or similar

Tunnel established

31

VPN with Intel-based Device

Use VPN on Intel-based system

Tunnel established

32

VPN with M1/M2 Mac

Use VPN on Apple Silicon

Tunnel established

33

VPN with Chromebook

Use VPN on ChromeOS

Tunnel established

34

VPN with Smart TV (Android TV)

Use VPN on Android TV

Tunnel established

35

VPN with Router Firmware

Use VPN on OpenWRT/DD-WRT router

Tunnel established

36

VPN with IoT Device

Use VPN on IoT device (e.g., camera)

Tunnel established

37

VPN with NAS Device

Use VPN on Synology/QNAP NAS

Tunnel established

38

VPN with Gaming Console

Use VPN via shared connection

Console traffic tunneled

39

VPN with USB Tethering

Share VPN via USB tethering

Tunnel works

40

VPN with Hotspot Sharing

Share VPN via Wi-Fi hotspot

Tunnel works

41

VPN with Dual Boot System

Use VPN on both OSes

Tunnel works on both

42

VPN with Cross-Platform Config

Use same config file across OSes

Config loads successfully

43

VPN with Cross-Platform Scripts

Use platform-agnostic scripts

Scripts execute correctly

44

VPN with Cross-Platform Logging

Check logs on different OSes

Logs generated correctly

45

VPN with Cross-Platform Updates

Update VPN software on all platforms

Updates applied successfully

46

VPN with Cross-Platform Monitoring

Monitor VPN from different OSes

Monitoring works

47

VPN with Cross-Platform Debugging

Debug VPN issues across OSes

Issues identified

48

VPN with Cross-Platform UI

Use consistent UI across platforms

UI behaves similarly

49

VPN with Cross-Platform Performance

Measure performance on different OSes

Comparable metrics

50

VPN with Cross-Platform Security

Validate security posture across OSes

Security consistent

Portability - Testcases

#

Test Case

Description

Expected Result

1

Install on Windows

Install VPN client on Windows

Installation successful

2

Install on Linux

Install VPN client on Linux

Installation successful

3

Install on macOS

Install VPN client on macOS

Installation successful

4

Install on Android

Install VPN app on Android

App runs correctly

5

Install on iOS

Install VPN app on iOS

App runs correctly

6

Install on Raspberry Pi

Install VPN on ARM-based device

VPN runs successfully

7

Install on Docker Container

Deploy VPN in Docker

Container runs VPN

8

Install on Virtual Machine

Deploy VPN in VM

VPN runs successfully

9

Install on Chromebook

Install VPN on ChromeOS

VPN runs successfully

10

Install on Smart TV

Install VPN on Android TV

VPN runs successfully

11

Install on NAS Device

Install VPN on Synology/QNAP

VPN runs successfully

12

Install on Router Firmware

Install VPN on OpenWRT/DD-WRT

VPN runs successfully

13

Install on Gaming Console

Share VPN to console

Console traffic tunneled

14

Install via Package Manager

Install using apt/yum/brew

Package installs correctly

15

Install via Binary

Install using precompiled binary

Binary runs successfully

16

Install via Source Code

Compile and install from source

VPN runs successfully

17

Config File Portability

Use same config across platforms

Config loads correctly

18

Script Portability

Use same script across platforms

Script executes correctly

19

UI Portability

Use GUI across platforms

UI behaves consistently

20

CLI Portability

Use CLI across platforms

Commands execute correctly

21

Log Format Portability

Check log format across platforms

Logs readable and consistent

22

Certificate Portability

Use same certs across platforms

Certs validated

23

Key File Portability

Use same key files across platforms

Keys accepted

24

Portability with IPv4

Use IPv4 across platforms

Traffic routed correctly

25

Portability with IPv6

Use IPv6 across platforms

Traffic routed correctly

26

Portability with UDP

Use UDP transport across platforms

Tunnel established

27

Portability with TCP

Use TCP transport across platforms

Tunnel established

28

Portability with TLS

Use TLS encryption across platforms

Tunnel secured

29

Portability with DTLS

Use DTLS encryption across platforms

Tunnel secured

30

Portability with NAT

Use NAT traversal across platforms

Tunnel established

31

Portability with Firewall

Use firewall rules across platforms

Tunnel allowed

32

Portability with Proxy

Use proxy across platforms

Tunnel established

33

Portability with Split Tunneling

Configure split tunneling

Traffic routed correctly

34

Portability with Full Tunneling

Configure full tunneling

All traffic tunneled

35

Portability with Roaming

Roam between networks

Tunnel persists

36

Portability with Failover

Failover to backup link

Tunnel re-established

37

Portability with Load Balancer

Use load balancer

Tunnel established

38

Portability with Monitoring Tools

Use monitoring tools across platforms

Traffic visible

39

Portability with Logging Tools

Use logging tools across platforms

Logs generated

40

Portability with Performance Tools

Use performance tools across platforms

Metrics collected

41

Portability with Security Tools

Use security tools across platforms

Traffic analyzed

42

Portability with VPN Analytics

Use analytics tools across platforms

Insights generated

43

Portability with ACLs

Apply ACLs across platforms

Access controlled

44

Portability with Policy Enforcement

Apply policies across platforms

Policies enforced

45

Portability with TUN Interface

Use TUN interface across platforms

Interface created

46

Portability with TAP Interface

Use TAP interface across platforms

Interface created

47

Portability with GUI Clients

Use GUI clients across platforms

GUI behaves consistently

48

Portability with CLI Clients

Use CLI clients across platforms

CLI behaves consistently

49

Portability with VPN Libraries

Use VPN libraries in different environments

Libraries function correctly

50

Portability with VPN APIs

Use VPN APIs across platforms

APIs respond correctly

Basic Configuration Files - Testcases

#

Test Case

Description

Expected Result

1

Config File Presence

Check if config file exists

File found

2

Config File Format Validation

Validate syntax and structure

Format correct

3

Config File Extension Check

Verify file uses correct extension (e.g., .conf)

Extension valid

4

Config File Permissions

Check file permissions

Permissions secure

5

Load Config File

Load config into VPN client

Config loaded successfully

6

Invalid Config File

Use malformed config

Error reported

7

Missing Required Fields

Remove required fields

Config rejected

8

Optional Fields Handling

Include optional fields

Config accepted

9

Config with Comments

Add comments to config

Comments ignored

10

Config with Inline Comments

Use inline comments

Parsed correctly

11

Config with Extra Whitespace

Add extra spaces/tabs

Parsed correctly

12

Config with Environment Variables

Use env vars in config

Variables resolved

13

Config with Includes

Include external config files

Included successfully

14

Config with Paths

Use absolute/relative paths

Paths resolved correctly

15

Config with IP Address

Set local/remote IPs

IPs applied

16

Config with Port Number

Set custom port

Port used correctly

17

Config with Protocol

Set protocol (UDP/TCP)

Protocol applied

18

Config with Encryption Settings

Set encryption options

Settings applied

19

Config with Authentication

Set auth method (cert/PSK)

Auth succeeds

20

Config with Compression

Enable/disable compression

Setting applied

21

Config with Keepalive

Set keepalive options

Tunnel remains active

22

Config with DNS Options

Set DNS servers

DNS used correctly

23

Config with Routing Rules

Add static routes

Routes applied

24

Config with Split Tunneling

Configure split tunneling

Only selected traffic tunneled

25

Config with Full Tunneling

Route all traffic

All traffic tunneled

26

Config with Logging Options

Set log level and file

Logs generated

27

Config with Debug Mode

Enable debug mode

Detailed logs created

28

Config with Proxy Settings

Set proxy options

Proxy used

29

Config with NAT Traversal

Enable NAT-T

Tunnel established

30

Config with MTU Settings

Set MTU size

MTU applied

31

Config with Fragmentation

Enable fragmentation

Packets reassembled

32

Config with Replay Protection

Enable replay protection

Replays dropped

33

Config with TLS Settings

Set TLS version/ciphers

TLS handshake succeeds

34

Config with Static Key

Use static key file

Tunnel established

35

Config with Certificate Paths

Set cert/key file paths

Files loaded

36

Config with Username/Password

Set credentials

Auth succeeds

37

Config with Interface Binding

Bind to specific interface

Interface used

38

Config with IPv6 Support

Enable IPv6

IPv6 traffic routed

39

Config with IPv4 Support

Enable IPv4

IPv4 traffic routed

40

Config with TUN Interface

Use TUN mode

Interface created

41

Config with TAP Interface

Use TAP mode

Interface created

42

Config with Custom Scripts

Run up/down scripts

Scripts executed

43

Config with Multiple Profiles

Define multiple profiles

Profiles selectable

44

Config with Backup Server

Set fallback server

Fallback used on failure

45

Config with Load Balancing

Configure multiple servers

Load distributed

46

Config with Session Timeout

Set session timeout

Session ends as expected

47

Config with Reconnect Options

Enable auto-reconnect

Tunnel re-established

48

Config with Platform Portability

Use same config on different OS

Config works across platforms

49

Config with Version Compatibility

Use config with older/newer client

Config parsed correctly

50

Config Backup and Restore

Backup and restore config file

Settings restored

No Compression - Testcases

#

Test Case

Description

Expected Result

1

Compression Disabled in Config

Set compression to off in config

Compression disabled

2

Compression Option Not Present

Omit compression option

No compression applied

3

Compression Explicitly Set to None

Set compression to none

No compression applied

4

Compression Disabled by Default

Use default config with no compression

No compression applied

5

Compression Flag Ignored

Use unsupported compression flag

Ignored or error shown

6

Compression Disabled on Client

Disable compression on client side

No compression

7

Compression Disabled on Server

Disable compression on server side

No compression

8

Compression Mismatch

Enable on one side, disable on other

Tunnel fails or no compression

9

Compression with Legacy Client

Connect legacy client with no compression support

Tunnel established

10

Compression with Legacy Server

Connect to legacy server with no compression support

Tunnel established

11

Compression with IPv4

Use IPv4 with no compression

Data uncompressed

12

Compression with IPv6

Use IPv6 with no compression

Data uncompressed

13

Compression with UDP

Use UDP transport

Data uncompressed

14

Compression with TCP

Use TCP transport

Data uncompressed

15

Compression with TLS

Use TLS encryption

Data uncompressed

16

Compression with Static Key

Use static key encryption

Data uncompressed

17

Compression with Certificate Auth

Use cert-based auth

Data uncompressed

18

Compression with PSK Auth

Use pre-shared key auth

Data uncompressed

19

Compression with NAT

Use NAT traversal

Data uncompressed

20

Compression with Firewall

Pass through firewall

Data uncompressed

21

Compression with Proxy

Use proxy

Data uncompressed

22

Compression with Split Tunneling

Route partial traffic

Data uncompressed

23

Compression with Full Tunneling

Route all traffic

Data uncompressed

24

Compression with DNS Leak Test

Check DNS resolution path

No DNS leak

25

Compression with Packet Loss

Simulate packet loss

Tunnel stable, no compression

26

Compression with Jitter

Introduce jitter

Tunnel stable, no compression

27

Compression with Delay

Introduce delay

Tunnel stable, no compression

28

Compression with Logging Enabled

Enable logs

Logs show no compression

29

Compression with Monitoring Tools

Monitor traffic

Data appears uncompressed

30

Compression with IDS/IPS

Analyze traffic

Data visible to IDS/IPS

31

Compression with ACLs

Apply access control

Rules enforced

32

Compression with Policy Enforcement

Apply routing/firewall policies

Policies enforced

33

Compression with Performance Test

Measure throughput

Raw data rate observed

34

Compression with Large Files

Transfer large files

File size unchanged

35

Compression with Small Packets

Send small packets

No compression applied

36

Compression with VoIP

Use VoIP over tunnel

Voice quality unaffected

37

Compression with Video Streaming

Stream video

Stream quality unaffected

38

Compression with File Transfer

Transfer files

File integrity preserved

39

Compression with Email

Send/receive email

Email content unchanged

40

Compression with Web Browsing

Browse websites

Pages load normally

41

Compression with SSH

Use SSH over tunnel

Session stable, no compression

42

Compression with RDP

Use Remote Desktop

Session stable, no compression

43

Compression with SMB

Access shared folders

File access normal

44

Compression with FTP

Transfer files via FTP

Files uncompressed

45

Compression with VPN Reconnect

Reconnect after drop

Compression remains disabled

46

Compression with Failover

Failover to backup link

Compression remains disabled

47

Compression with Roaming

Roam between networks

Compression remains disabled

48

Compression with Load Balancer

Use load balancer

Compression remains disabled

49

Compression with Custom Scripts

Run up/down scripts

Scripts execute, compression off

50

Compression with Config Reload

Reload config during session

Compression remains disabled

No Client-Server Mode - Testcases

#

Test Case

Description

Expected Result

1

Peer A Initiates Tunnel

Peer A starts connection

Tunnel established

2

Peer B Initiates Tunnel

Peer B starts connection

Tunnel established

3

Simultaneous Initiation

Both peers initiate at once

One tunnel established

4

No Server Configuration

No server IP configured

Tunnel still works

5

Static Peer IPs

Use static IPs for both peers

Tunnel established

6

Dynamic Peer IPs

Use dynamic IPs

Tunnel established

7

NAT Traversal

Peers behind NAT

Tunnel established

8

Firewall Traversal

Peers behind firewall

Tunnel established

9

Port Forwarding

Use port forwarding

Tunnel established

10

No Central Authority

No central server present

Tunnel established

11

Peer Authentication

Use mutual authentication

Peers authenticated

12

Pre-shared Key Auth

Use PSK for both peers

Tunnel established

13

Certificate-based Auth

Use certificates on both peers

Tunnel established

14

Peer Role Symmetry

Both peers have equal roles

Tunnel functions bidirectionally

15

Peer Role Switching

Switch initiator/responder roles

Tunnel still works

16

Peer Discovery via Config

Use static config for peer discovery

Tunnel established

17

Peer Discovery via Broadcast

Use broadcast/multicast

Peers discover each other

18

Peer Discovery via DNS

Use DNS to resolve peer

Tunnel established

19

Peer Discovery via mDNS

Use mDNS for local discovery

Tunnel established

20

Peer Discovery Failure

Peer not reachable

Tunnel not established

21

Peer Reconnect

Peer reconnects after drop

Tunnel re-established

22

Peer Failover

Switch to backup peer

Tunnel re-established

23

Peer Load Balancing

Distribute traffic across peers

Load balanced

24

Peer-to-Peer Encryption

Encrypt traffic between peers

Data secured

25

Peer-to-Peer Compression

Compress traffic between peers

Data compressed

26

Peer-to-Peer Replay Protection

Replay old packets

Packets dropped

27

Peer-to-Peer Logging

Enable logs on both peers

Logs generated

28

Peer-to-Peer Monitoring

Monitor traffic on both peers

Traffic visible

29

Peer-to-Peer ACLs

Apply ACLs on both peers

Access controlled

30

Peer-to-Peer Policy Enforcement

Apply policies on both peers

Policies enforced

31

Peer-to-Peer IPv4

Use IPv4 between peers

Tunnel established

32

Peer-to-Peer IPv6

Use IPv6 between peers

Tunnel established

33

Peer-to-Peer UDP

Use UDP transport

Tunnel established

34

Peer-to-Peer TCP

Use TCP transport

Tunnel established

35

Peer-to-Peer TLS

Use TLS encryption

Tunnel secured

36

Peer-to-Peer DTLS

Use DTLS encryption

Tunnel secured

37

Peer-to-Peer TUN Interface

Use TUN interface

Interface created

38

Peer-to-Peer TAP Interface

Use TAP interface

Interface created

39

Peer-to-Peer Routing

Add static routes

Traffic routed correctly

40

Peer-to-Peer Bridging

Bridge TAP interfaces

LAN access granted

41

Peer-to-Peer Roaming

Roam between networks

Tunnel persists

42

Peer-to-Peer Failover

Failover to backup link

Tunnel re-established

43

Peer-to-Peer Load Testing

Send high traffic volume

Tunnel remains stable

44

Peer-to-Peer Performance Benchmark

Measure latency and throughput

Metrics recorded

45

Peer-to-Peer Debugging

Enable debug mode

Detailed logs available

46

Peer-to-Peer Config Portability

Use same config on both peers

Config works

47

Peer-to-Peer Platform Independence

Use different OS on each peer

Tunnel established

48

Peer-to-Peer Certificate Rotation

Rotate certificates

Tunnel re-established

49

Peer-to-Peer Key Rotation

Rotate PSK

Tunnel re-established

50

Peer-to-Peer Session Timeout

Let session idle

Tunnel times out

OpenSSL Integration - Testcases

#

Test Case

Description

Expected Result

1

OpenSSL Library Detection

Check if OpenSSL is installed

Library detected

2

OpenSSL Version Compatibility

Verify supported OpenSSL version

Compatible version found

3

OpenSSL Initialization

Initialize OpenSSL context

Initialization successful

4

OpenSSL Cleanup

Clean up OpenSSL context

Cleanup successful

5

TLS Handshake with OpenSSL

Perform TLS handshake using OpenSSL

Handshake successful

6

Certificate Loading

Load X.509 certificate

Certificate loaded

7

Private Key Loading

Load private key

Key loaded successfully

8

Certificate Validation

Validate peer certificate

Certificate valid

9

Invalid Certificate Handling

Use expired/invalid certificate

Connection rejected

10

CA Bundle Verification

Verify certificate chain

Chain validated

11

Cipher Suite Negotiation

Negotiate cipher suite using OpenSSL

Cipher selected

12

Unsupported Cipher Handling

Use unsupported cipher

Connection fails

13

TLS Version Negotiation

Negotiate TLS version

Version agreed

14

TLS 1.3 Support

Use TLS 1.3

Handshake successful

15

TLS 1.2 Support

Use TLS 1.2

Handshake successful

16

TLS Downgrade Protection

Attempt downgrade attack

Attack blocked

17

Session Resumption

Resume TLS session

Session resumed

18

OpenSSL Error Handling

Trigger OpenSSL error

Error logged

19

OpenSSL Logging

Enable OpenSSL debug logs

Logs generated

20

OpenSSL with UDP

Use OpenSSL with DTLS

Secure tunnel established

21

OpenSSL with TCP

Use OpenSSL with TLS

Secure tunnel established

22

OpenSSL with IPv4

Use OpenSSL over IPv4

Tunnel secured

23

OpenSSL with IPv6

Use OpenSSL over IPv6

Tunnel secured

24

OpenSSL with NAT

Use OpenSSL behind NAT

Tunnel established

25

OpenSSL with Firewall

Use OpenSSL through firewall

Tunnel established

26

OpenSSL with Proxy

Use OpenSSL through proxy

Tunnel established

27

OpenSSL with Certificate Revocation

Check CRL/OCSP status

Revoked cert rejected

28

OpenSSL with Mutual TLS

Use client and server certificates

Both authenticated

29

OpenSSL with PSK

Use pre-shared key with OpenSSL

Tunnel established

30

OpenSSL with DH Key Exchange

Use Diffie-Hellman

Key exchange successful

31

OpenSSL with ECDH Key Exchange

Use Elliptic Curve DH

Key exchange successful

32

OpenSSL with RSA Key Exchange

Use RSA for key exchange

Key exchange successful

33

OpenSSL with AES Encryption

Use AES cipher

Data encrypted

34

OpenSSL with ChaCha20

Use ChaCha20 cipher

Data encrypted

35

OpenSSL with SHA-256

Use SHA-256 for integrity

Hash verified

36

OpenSSL with SHA-512

Use SHA-512 for integrity

Hash verified

37

OpenSSL with HMAC

Use HMAC for message authentication

HMAC verified

38

OpenSSL with Compression Disabled

Ensure compression is off

No compression applied

39

OpenSSL with Custom Cipher List

Use custom cipher list

Cipher selected from list

40

OpenSSL with Certificate Pinning

Pin server certificate

Connection accepted only if matched

41

OpenSSL with Session Timeout

Let session idle

Session times out

42

OpenSSL with Session Renegotiation

Trigger renegotiation

Session renegotiated

43

OpenSSL with Load Balancer

Use OpenSSL behind load balancer

Tunnel established

44

OpenSSL with Roaming

Roam between networks

Tunnel persists

45

OpenSSL with Failover

Failover to backup server

Tunnel re-established

46

OpenSSL with Logging Tools

Use external logging tools

OpenSSL events logged

47

OpenSSL with Monitoring Tools

Monitor OpenSSL traffic

Traffic visible

48

OpenSSL with Performance Benchmark

Measure handshake and throughput

Metrics recorded

49

OpenSSL with Platform Portability

Use OpenSSL on different OS

Tunnel established

50

OpenSSL with Version Upgrade

Upgrade OpenSSL version

VPN still functions correctly

  • Reference links