diff --git a/backend/CMakeLists.txt b/backend/CMakeLists.txt
index 228bf31..cb605ca 100644
--- a/backend/CMakeLists.txt
+++ b/backend/CMakeLists.txt
@@ -14,6 +14,8 @@ find_package(CURL QUIET)
 # Library sources
 set(WIZARDMERGE_SOURCES
     src/merge/three_way_merge.cpp
+    src/analysis/context_analyzer.cpp
+    src/analysis/risk_analyzer.cpp
 )
 
 # Add git sources only if CURL is available
@@ -67,7 +69,11 @@ endif()
 if(GTest_FOUND)
     enable_testing()
     
-    set(TEST_SOURCES tests/test_three_way_merge.cpp)
+    set(TEST_SOURCES 
+        tests/test_three_way_merge.cpp
+        tests/test_context_analyzer.cpp
+        tests/test_risk_analyzer.cpp
+    )
     
     # Add github client tests only if CURL is available
     if(CURL_FOUND)
diff --git a/backend/include/wizardmerge/analysis/context_analyzer.h b/backend/include/wizardmerge/analysis/context_analyzer.h
new file mode 100644
index 0000000..f20362b
--- /dev/null
+++ b/backend/include/wizardmerge/analysis/context_analyzer.h
@@ -0,0 +1,98 @@
+/**
+ * @file context_analyzer.h
+ * @brief Context analysis for merge conflicts
+ *
+ * Analyzes the code context around merge conflicts to provide better
+ * understanding and intelligent suggestions for resolution.
+ */
+
+#ifndef WIZARDMERGE_ANALYSIS_CONTEXT_ANALYZER_H
+#define WIZARDMERGE_ANALYSIS_CONTEXT_ANALYZER_H
+
+#include <string>
+#include <vector>
+#include <map>
+
+namespace wizardmerge {
+namespace analysis {
+
+/**
+ * @brief Represents code context information for a specific line or region.
+ */
+struct CodeContext {
+    size_t start_line;
+    size_t end_line;
+    std::vector<std::string> surrounding_lines;
+    std::string function_name;
+    std::string class_name;
+    std::vector<std::string> imports;
+    std::map<std::string, std::string> metadata;
+};
+
+/**
+ * @brief Analyzes code context around a specific region.
+ *
+ * This function examines the code surrounding a conflict or change
+ * to provide contextual information that can help in understanding
+ * the change and making better merge decisions.
+ *
+ * @param lines The full file content as lines
+ * @param start_line Starting line of the region of interest
+ * @param end_line Ending line of the region of interest
+ * @param context_window Number of lines before/after to include (default: 5)
+ * @return CodeContext containing analyzed context information
+ */
+CodeContext analyze_context(
+    const std::vector<std::string>& lines,
+    size_t start_line,
+    size_t end_line,
+    size_t context_window = 5
+);
+
+/**
+ * @brief Extracts function or method name from context.
+ *
+ * Analyzes surrounding code to determine if the region is within
+ * a function or method, and extracts its name.
+ *
+ * @param lines Lines of code to analyze
+ * @param line_number Line number to check
+ * @return Function name if found, empty string otherwise
+ */
+std::string extract_function_name(
+    const std::vector<std::string>& lines,
+    size_t line_number
+);
+
+/**
+ * @brief Extracts class name from context.
+ *
+ * Analyzes surrounding code to determine if the region is within
+ * a class definition, and extracts its name.
+ *
+ * @param lines Lines of code to analyze
+ * @param line_number Line number to check
+ * @return Class name if found, empty string otherwise
+ */
+std::string extract_class_name(
+    const std::vector<std::string>& lines,
+    size_t line_number
+);
+
+/**
+ * @brief Extracts import/include statements from the file.
+ *
+ * Scans the file for import, include, or require statements
+ * to understand dependencies.
+ *
+ * @param lines Lines of code to analyze
+ * @return Vector of import statements
+ */
+std::vector<std::string> extract_imports(
+    const std::vector<std::string>& lines
+);
+
+}  // namespace analysis
+}  // namespace wizardmerge
+
+#endif  // WIZARDMERGE_ANALYSIS_CONTEXT_ANALYZER_H
diff --git a/backend/include/wizardmerge/analysis/risk_analyzer.h b/backend/include/wizardmerge/analysis/risk_analyzer.h
new file mode 100644
index 0000000..402c2fe
--- /dev/null
+++ b/backend/include/wizardmerge/analysis/risk_analyzer.h
@@ -0,0 +1,118 @@
+/**
+ * @file risk_analyzer.h
+ * @brief Risk analysis for merge conflict resolutions
+ *
+ * Assesses the risk level of different resolution choices to help
+ * developers make safer merge decisions.
+ */
+
+#ifndef WIZARDMERGE_ANALYSIS_RISK_ANALYZER_H
+#define WIZARDMERGE_ANALYSIS_RISK_ANALYZER_H
+
+#include <string>
+#include <vector>
+
+namespace wizardmerge {
+namespace analysis {
+
+/**
+ * @brief Risk level enumeration for merge resolutions.
+ */
+enum class RiskLevel {
+    LOW,      // Safe to merge, minimal risk
+    MEDIUM,   // Some risk, review recommended
+    HIGH,     // High risk, careful review required
+    CRITICAL  // Critical risk, requires expert review
+};
+
+/**
+ * @brief Detailed risk assessment for a merge resolution.
+ */
+struct RiskAssessment {
+    RiskLevel level;
+    double confidence_score;  // 0.0 to 1.0
+    std::vector<std::string> risk_factors;
+    std::vector<std::string> recommendations;
+    
+    // Specific risk indicators
+    bool has_syntax_changes;
+    bool has_logic_changes;
+    bool has_api_changes;
+    bool affects_multiple_functions;
+    bool affects_critical_section;
+};
+
+/**
+ * @brief Analyzes risk of accepting "ours" version.
+ *
+ * @param base Base version lines
+ * @param ours Our version lines
+ * @param theirs Their version lines
+ * @return RiskAssessment for accepting ours
+ */
+RiskAssessment analyze_risk_ours(
+    const std::vector<std::string>& base,
+    const std::vector<std::string>& ours,
+    const std::vector<std::string>& theirs
+);
+
+/**
+ * @brief Analyzes risk of accepting "theirs" version.
+ *
+ * @param base Base version lines
+ * @param ours Our version lines
+ * @param theirs Their version lines
+ * @return RiskAssessment for accepting theirs
+ */
+RiskAssessment analyze_risk_theirs(
+    const std::vector<std::string>& base,
+    const std::vector<std::string>& ours,
+    const std::vector<std::string>& theirs
+);
+
+/**
+ * @brief Analyzes risk of accepting both versions (concatenation).
+ *
+ * @param base Base version lines
+ * @param ours Our version lines
+ * @param theirs Their version lines
+ * @return RiskAssessment for accepting both
+ */
+RiskAssessment analyze_risk_both(
+    const std::vector<std::string>& base,
+    const std::vector<std::string>& ours,
+    const std::vector<std::string>& theirs
+);
+
+/**
+ * @brief Converts RiskLevel to string representation.
+ *
+ * @param level Risk level to convert
+ * @return String representation ("low", "medium", "high", "critical")
+ */
+std::string risk_level_to_string(RiskLevel level);
+
+/**
+ * @brief Checks if code contains critical patterns (security, data loss, etc.).
+ *
+ * @param lines Lines of code to check
+ * @return true if critical patterns detected
+ */
+bool contains_critical_patterns(const std::vector<std::string>& lines);
+
+/**
+ * @brief Detects if changes affect API signatures.
+ *
+ * @param base Base version lines
+ * @param modified Modified version lines
+ * @return true if API changes detected
+ */
+bool has_api_signature_changes(
+    const std::vector<std::string>& base,
+    const std::vector<std::string>& modified
+);
+
+}  // namespace analysis
+}  // namespace wizardmerge
+
+#endif  // WIZARDMERGE_ANALYSIS_RISK_ANALYZER_H
diff --git a/backend/include/wizardmerge/merge/three_way_merge.h b/backend/include/wizardmerge/merge/three_way_merge.h
index 7a2e245..77f1953 100644
--- a/backend/include/wizardmerge/merge/three_way_merge.h
+++ b/backend/include/wizardmerge/merge/three_way_merge.h
@@ -12,6 +12,8 @@
 
 #include <string>
 #include <vector>
+#include "wizardmerge/analysis/context_analyzer.h"
+#include "wizardmerge/analysis/risk_analyzer.h"
 
 namespace wizardmerge {
 namespace merge {
@@ -33,6 +35,12 @@ struct Conflict {
     std::vector<Line> base_lines;
     std::vector<Line> our_lines;
     std::vector<Line> their_lines;
+    
+    // Context and risk analysis
+    analysis::CodeContext context;
+    analysis::RiskAssessment risk_ours;
+    analysis::RiskAssessment risk_theirs;
+    analysis::RiskAssessment risk_both;
 };
 
 /**
diff --git a/backend/src/analysis/context_analyzer.cpp b/backend/src/analysis/context_analyzer.cpp
new file mode 100644
index 0000000..ec61d31
--- /dev/null
+++ b/backend/src/analysis/context_analyzer.cpp
@@ -0,0 +1,232 @@
+/**
+ * @file context_analyzer.cpp
+ * @brief Implementation of context analysis for merge conflicts
+ */
+
+#include "wizardmerge/analysis/context_analyzer.h"
+#include <algorithm>
+#include <regex>
+
+namespace wizardmerge {
+namespace analysis {
+
+namespace {
+
+/**
+ * @brief Trim whitespace from string.
+ */
+std::string trim(const std::string& str) {
+    size_t start = str.find_first_not_of(" \t\n\r");
+    size_t end = str.find_last_not_of(" \t\n\r");
+    if (start == std::string::npos) return "";
+    return str.substr(start, end - start + 1);
+}
+
+/**
+ * @brief Check if a line is a function definition.
+ */
+bool is_function_definition(const std::string& line) {
+    std::string trimmed = trim(line);
+    
+    // Common function patterns across languages
+    std::vector<std::regex> patterns = {
+        std::regex(R"(^\w+\s+\w+\s*\([^)]*\)\s*\{?)"),  // C/C++/Java: type name(params)
+        std::regex(R"(^def\s+\w+\s*\([^)]*\):)"),       // Python: def name(params):
+        std::regex(R"(^function\s+\w+\s*\([^)]*\))"),   // JavaScript: function name(params)
+        std::regex(R"(^\w+\s*:\s*function\s*\([^)]*\))"), // JS object method
+        std::regex(R"(^(public|private|protected)?\s*\w+\s+\w+\s*\([^)]*\))") // Java/C# methods
+    };
+    
+    for (const auto& pattern : patterns) {
+        if (std::regex_search(trimmed, pattern)) {
+            return true;
+        }
+    }
+    
+    return false;
+}
+
+/**
+ * @brief Extract function name from a function definition line.
+ */
+std::string get_function_name_from_line(const std::string& line) {
+    std::string trimmed = trim(line);
+    
+    // Try to extract function name using regex
+    std::smatch match;
+    
+    // Python: def function_name(
+    std::regex py_pattern(R"(def\s+(\w+)\s*\()");
+    if (std::regex_search(trimmed, match, py_pattern)) {
+        return match[1].str();
+    }
+    
+    // JavaScript: function function_name(
+    std::regex js_pattern(R"(function\s+(\w+)\s*\()");
+    if (std::regex_search(trimmed, match, js_pattern)) {
+        return match[1].str();
+    }
+    
+    // C/C++/Java: type function_name(
+    std::regex cpp_pattern(R"(\w+\s+(\w+)\s*\()");
+    if (std::regex_search(trimmed, match, cpp_pattern)) {
+        return match[1].str();
+    }
+    
+    return "";
+}
+
+/**
+ * @brief Check if a line is a class definition.
+ */
+bool is_class_definition(const std::string& line) {
+    std::string trimmed = trim(line);
+    
+    std::vector<std::regex> patterns = {
+        std::regex(R"(^class\s+\w+)"),                    // Python/C++/Java: class Name
+        std::regex(R"(^(public|private)?\s*class\s+\w+)"), // Java/C#: visibility class Name
+        std::regex(R"(^struct\s+\w+)")                    // C/C++: struct Name
+    };
+    
+    for (const auto& pattern : patterns) {
+        if (std::regex_search(trimmed, pattern)) {
+            return true;
+        }
+    }
+    
+    return false;
+}
+
+/**
+ * @brief Extract class name from a class definition line.
+ */
+std::string get_class_name_from_line(const std::string& line) {
+    std::string trimmed = trim(line);
+    
+    std::smatch match;
+    std::regex pattern(R"((class|struct)\s+(\w+))");
+    
+    if (std::regex_search(trimmed, match, pattern)) {
+        return match[2].str();
+    }
+    
+    return "";
+}
+
+}  // anonymous namespace
+
+CodeContext analyze_context(
+    const std::vector<std::string>& lines,
+    size_t start_line,
+    size_t end_line,
+    size_t context_window
+) {
+    CodeContext context;
+    context.start_line = start_line;
+    context.end_line = end_line;
+    
+    // Extract surrounding lines
+    size_t window_start = (start_line >= context_window) ? (start_line - context_window) : 0;
+    size_t window_end = std::min(end_line + context_window, lines.size());
+    
+    for (size_t i = window_start; i < window_end; ++i) {
+        context.surrounding_lines.push_back(lines[i]);
+    }
+    
+    // Extract function name
+    context.function_name = extract_function_name(lines, start_line);
+    
+    // Extract class name
+    context.class_name = extract_class_name(lines, start_line);
+    
+    // Extract imports
+    context.imports = extract_imports(lines);
+    
+    // Add metadata
+    context.metadata["context_window_start"] = std::to_string(window_start);
+    context.metadata["context_window_end"] = std::to_string(window_end);
+    context.metadata["total_lines"] = std::to_string(lines.size());
+    
+    return context;
+}
+
+std::string extract_function_name(
+    const std::vector<std::string>& lines,
+    size_t line_number
+) {
+    if (line_number >= lines.size()) {
+        return "";
+    }
+    
+    // Check the line itself first
+    if (is_function_definition(lines[line_number])) {
+        return get_function_name_from_line(lines[line_number]);
+    }
+    
+    // Search backwards for function definition
+    for (int i = static_cast<int>(line_number) - 1; i >= 0; --i) {
+        if (is_function_definition(lines[i])) {
+            return get_function_name_from_line(lines[i]);
+        }
+        
+        // Stop searching if we hit a class definition or another function
+        std::string trimmed = trim(lines[i]);
+        if (trimmed.find("class ") == 0 || trimmed.find("struct ") == 0) {
+            break;
+        }
+    }
+    
+    return "";
+}
+
+std::string extract_class_name(
+    const std::vector<std::string>& lines,
+    size_t line_number
+) {
+    if (line_number >= lines.size()) {
+        return "";
+    }
+    
+    // Search backwards for class definition
+    int brace_count = 0;
+    for (int i = static_cast<int>(line_number); i >= 0; --i) {
+        std::string line = lines[i];
+        
+        // Count braces to track scope
+        brace_count += std::count(line.begin(), line.end(), '}');
+        brace_count -= std::count(line.begin(), line.end(), '{');
+        
+        if (is_class_definition(line) && brace_count <= 0) {
+            return get_class_name_from_line(line);
+        }
+    }
+    
+    return "";
+}
+
+std::vector<std::string> extract_imports(
+    const std::vector<std::string>& lines
+) {
+    std::vector<std::string> imports;
+    
+    // Scan first 50 lines (imports are typically at the top)
+    size_t scan_limit = std::min(lines.size(), size_t(50));
+    
+    for (size_t i = 0; i < scan_limit; ++i) {
+        std::string line = trim(lines[i]);
+        
+        // Check for various import patterns
+        if (line.find("#include") == 0 ||
+            line.find("import ") == 0 ||
+            line.find("from ") == 0 ||
+            line.find("require(") != std::string::npos ||
+            line.find("using ") == 0) {
+            imports.push_back(line);
+        }
+    }
+    
+    return imports;
+}
+
+}  // namespace analysis
+}  // namespace wizardmerge
diff --git a/backend/src/analysis/risk_analyzer.cpp b/backend/src/analysis/risk_analyzer.cpp
new file mode 100644
index 0000000..4a3372d
--- /dev/null
+++ b/backend/src/analysis/risk_analyzer.cpp
@@ -0,0 +1,343 @@
+/**
+ * @file risk_analyzer.cpp
+ * @brief Implementation of risk analysis for merge conflict resolutions
+ */
+
+#include "wizardmerge/analysis/risk_analyzer.h"
+#include <algorithm>
+#include <regex>
+#include <cmath>
+
+namespace wizardmerge {
+namespace analysis {
+
+namespace {
+
+/**
+ * @brief Trim whitespace from string.
+ */
+std::string trim(const std::string& str) {
+    size_t start = str.find_first_not_of(" \t\n\r");
+    size_t end = str.find_last_not_of(" \t\n\r");
+    if (start == std::string::npos) return "";
+    return str.substr(start, end - start + 1);
+}
+
+/**
+ * @brief Calculate similarity score between two sets of lines (0.0 to 1.0).
+ */
+double calculate_similarity(
+    const std::vector<std::string>& lines1,
+    const std::vector<std::string>& lines2
+) {
+    if (lines1.empty() && lines2.empty()) return 1.0;
+    if (lines1.empty() || lines2.empty()) return 0.0;
+    
+    // Simple Jaccard similarity on lines
+    size_t common_lines = 0;
+    for (const auto& line1 : lines1) {
+        if (std::find(lines2.begin(), lines2.end(), line1) != lines2.end()) {
+            common_lines++;
+        }
+    }
+    
+    size_t total_unique = lines1.size() + lines2.size() - common_lines;
+    return total_unique > 0 ? static_cast<double>(common_lines) / total_unique : 0.0;
+}
+
+/**
+ * @brief Count number of changed lines between two versions.
+ */
+size_t count_changes(
+    const std::vector<std::string>& base,
+    const std::vector<std::string>& modified
+) {
+    size_t changes = 0;
+    size_t max_len = std::max(base.size(), modified.size());
+    
+    for (size_t i = 0; i < max_len; ++i) {
+        std::string base_line = (i < base.size()) ? base[i] : "";
+        std::string mod_line = (i < modified.size()) ? modified[i] : "";
+        
+        if (base_line != mod_line) {
+            changes++;
+        }
+    }
+    
+    return changes;
+}
+
+/**
+ * @brief Check if line contains function or method definition.
+ */
+bool is_function_signature(const std::string& line) {
+    std::string trimmed = trim(line);
+    
+    std::vector<std::regex> patterns = {
+        std::regex(R"(^\w+\s+\w+\s*\([^)]*\))"),      // C/C++/Java
+        std::regex(R"(^def\s+\w+\s*\([^)]*\):)"),     // Python
+        std::regex(R"(^function\s+\w+\s*\([^)]*\))"), // JavaScript
+    };
+    
+    for (const auto& pattern : patterns) {
+        if (std::regex_search(trimmed, pattern)) {
+            return true;
+        }
+    }
+    
+    return false;
+}
+
+}  // anonymous namespace
+
+std::string risk_level_to_string(RiskLevel level) {
+    switch (level) {
+        case RiskLevel::LOW: return "low";
+        case RiskLevel::MEDIUM: return "medium";
+        case RiskLevel::HIGH: return "high";
+        case RiskLevel::CRITICAL: return "critical";
+        default: return "unknown";
+    }
+}
+
+bool contains_critical_patterns(const std::vector<std::string>& lines) {
+    std::vector<std::regex> critical_patterns = {
+        std::regex(R"(delete\s+\w+)"),          // Delete operations
+        std::regex(R"(drop\s+(table|database))"), // Database drops
+        std::regex(R"(rm\s+-rf)"),              // Destructive file operations
+        std::regex(R"(eval\s*\()"),             // Eval (security risk)
+        std::regex(R"(exec\s*\()"),             // Exec (security risk)
+        std::regex(R"(system\s*\()"),           // System calls
+        std::regex(R"(\.password\s*=)"),        // Password assignments
+        std::regex(R"(\.secret\s*=)"),          // Secret assignments
+        std::regex(R"(sudo\s+)"),               // Sudo usage
+        std::regex(R"(chmod\s+777)"),           // Overly permissive permissions
+    };
+    
+    for (const auto& line : lines) {
+        std::string trimmed = trim(line);
+        for (const auto& pattern : critical_patterns) {
+            if (std::regex_search(trimmed, pattern)) {
+                return true;
+            }
+        }
+    }
+    
+    return false;
+}
+
+bool has_api_signature_changes(
+    const std::vector<std::string>& base,
+    const std::vector<std::string>& modified
+) {
+    // Check if function signatures changed
+    for (size_t i = 0; i < base.size() && i < modified.size(); ++i) {
+        bool base_is_sig = is_function_signature(base[i]);
+        bool mod_is_sig = is_function_signature(modified[i]);
+        
+        if (base_is_sig && mod_is_sig && base[i] != modified[i]) {
+            return true;
+        }
+    }
+    
+    return false;
+}
+
+RiskAssessment analyze_risk_ours(
+    const std::vector<std::string>& base,
+    const std::vector<std::string>& ours,
+    const std::vector<std::string>& theirs
+) {
+    RiskAssessment assessment;
+    assessment.level = RiskLevel::LOW;
+    assessment.confidence_score = 0.5;
+    assessment.has_syntax_changes = false;
+    assessment.has_logic_changes = false;
+    assessment.has_api_changes = false;
+    assessment.affects_multiple_functions = false;
+    assessment.affects_critical_section = false;
+    
+    // Calculate changes
+    size_t our_changes = count_changes(base, ours);
+    size_t their_changes = count_changes(base, theirs);
+    double similarity_to_theirs = calculate_similarity(ours, theirs);
+    
+    // Check for critical patterns
+    if (contains_critical_patterns(ours)) {
+        assessment.affects_critical_section = true;
+        assessment.risk_factors.push_back("Contains critical code patterns (security/data operations)");
+        assessment.level = RiskLevel::HIGH;
+    }
+    
+    // Check for API changes
+    if (has_api_signature_changes(base, ours)) {
+        assessment.has_api_changes = true;
+        assessment.risk_factors.push_back("Function/method signatures changed");
+        if (assessment.level < RiskLevel::MEDIUM) {
+            assessment.level = RiskLevel::MEDIUM;
+        }
+    }
+    
+    // Assess based on amount of change
+    if (our_changes > 10) {
+        assessment.has_logic_changes = true;
+        assessment.risk_factors.push_back("Large number of changes (" + std::to_string(our_changes) + " lines)");
+        if (assessment.level < RiskLevel::MEDIUM) {
+            assessment.level = RiskLevel::MEDIUM;
+        }
+    }
+    
+    // Check if we're discarding significant changes from theirs
+    if (their_changes > 5 && similarity_to_theirs < 0.3) {
+        assessment.risk_factors.push_back("Discarding significant changes from other branch (" + 
+                                         std::to_string(their_changes) + " lines)");
+        if (assessment.level < RiskLevel::MEDIUM) {
+            assessment.level = RiskLevel::MEDIUM;
+        }
+    }
+    
+    // Calculate confidence score based on various factors
+    double change_ratio = (our_changes + their_changes) > 0 ? 
+        static_cast<double>(our_changes) / (our_changes + their_changes) : 0.5;
+    assessment.confidence_score = 0.5 + (0.3 * similarity_to_theirs) + (0.2 * change_ratio);
+    
+    // Add recommendations
+    if (assessment.level >= RiskLevel::MEDIUM) {
+        assessment.recommendations.push_back("Review changes carefully before accepting");
+    }
+    if (assessment.has_api_changes) {
+        assessment.recommendations.push_back("Verify API compatibility with dependent code");
+    }
+    if (assessment.affects_critical_section) {
+        assessment.recommendations.push_back("Test thoroughly, especially security and data operations");
+    }
+    if (assessment.risk_factors.empty()) {
+        assessment.recommendations.push_back("Changes appear safe to accept");
+    }
+    
+    return assessment;
+}
+
+RiskAssessment analyze_risk_theirs(
+    const std::vector<std::string>& base,
+    const std::vector<std::string>& ours,
+    const std::vector<std::string>& theirs
+) {
+    RiskAssessment assessment;
+    assessment.level = RiskLevel::LOW;
+    assessment.confidence_score = 0.5;
+    assessment.has_syntax_changes = false;
+    assessment.has_logic_changes = false;
+    assessment.has_api_changes = false;
+    assessment.affects_multiple_functions = false;
+    assessment.affects_critical_section = false;
+    
+    // Calculate changes
+    size_t our_changes = count_changes(base, ours);
+    size_t their_changes = count_changes(base, theirs);
+    double similarity_to_ours = calculate_similarity(theirs, ours);
+    
+    // Check for critical patterns
+    if (contains_critical_patterns(theirs)) {
+        assessment.affects_critical_section = true;
+        assessment.risk_factors.push_back("Contains critical code patterns (security/data operations)");
+        assessment.level = RiskLevel::HIGH;
+    }
+    
+    // Check for API changes
+    if (has_api_signature_changes(base, theirs)) {
+        assessment.has_api_changes = true;
+        assessment.risk_factors.push_back("Function/method signatures changed");
+        if (assessment.level < RiskLevel::MEDIUM) {
+            assessment.level = RiskLevel::MEDIUM;
+        }
+    }
+    
+    // Assess based on amount of change
+    if (their_changes > 10) {
+        assessment.has_logic_changes = true;
+        assessment.risk_factors.push_back("Large number of changes (" + std::to_string(their_changes) + " lines)");
+        if (assessment.level < RiskLevel::MEDIUM) {
+            assessment.level = RiskLevel::MEDIUM;
+        }
+    }
+    
+    // Check if we're discarding our changes
+    if (our_changes > 5 && similarity_to_ours < 0.3) {
+        assessment.risk_factors.push_back("Discarding our local changes (" + 
+                                         std::to_string(our_changes) + " lines)");
+        if (assessment.level < RiskLevel::MEDIUM) {
+            assessment.level = RiskLevel::MEDIUM;
+        }
+    }
+    
+    // Calculate confidence score
+    double change_ratio = (our_changes + their_changes) > 0 ? 
+        static_cast<double>(their_changes) / (our_changes + their_changes) : 0.5;
+    assessment.confidence_score = 0.5 + (0.3 * similarity_to_ours) + (0.2 * change_ratio);
+    
+    // Add recommendations
+    if (assessment.level >= RiskLevel::MEDIUM) {
+        assessment.recommendations.push_back("Review changes carefully before accepting");
+    }
+    if (assessment.has_api_changes) {
+        assessment.recommendations.push_back("Verify API compatibility with dependent code");
+    }
+    if (assessment.affects_critical_section) {
+        assessment.recommendations.push_back("Test thoroughly, especially security and data operations");
+    }
+    if (assessment.risk_factors.empty()) {
+        assessment.recommendations.push_back("Changes appear safe to accept");
+    }
+    
+    return assessment;
+}
+
+RiskAssessment analyze_risk_both(
+    const std::vector<std::string>& base,
+    const std::vector<std::string>& ours,
+    const std::vector<std::string>& theirs
+) {
+    RiskAssessment assessment;
+    assessment.level = RiskLevel::MEDIUM;  // Default to medium for concatenation
+    assessment.confidence_score = 0.3;      // Lower confidence for concatenation
+    assessment.has_syntax_changes = true;
+    assessment.has_logic_changes = true;
+    assessment.has_api_changes = false;
+    assessment.affects_multiple_functions = false;
+    assessment.affects_critical_section = false;
+    
+    // Concatenating both versions is generally risky
+    assessment.risk_factors.push_back("Concatenating both versions may cause duplicates or conflicts");
+    
+    // Check if either contains critical patterns
+    if (contains_critical_patterns(ours) || contains_critical_patterns(theirs)) {
+        assessment.affects_critical_section = true;
+        assessment.risk_factors.push_back("Contains critical code patterns that may conflict");
+        assessment.level = RiskLevel::HIGH;
+    }
+    
+    // Check for duplicate logic
+    double similarity = calculate_similarity(ours, theirs);
+    if (similarity > 0.5) {
+        assessment.risk_factors.push_back("High similarity may result in duplicate code");
+        assessment.level = RiskLevel::HIGH;
+    }
+    
+    // API changes from either side
+    if (has_api_signature_changes(base, ours) || has_api_signature_changes(base, theirs)) {
+        assessment.has_api_changes = true;
+        assessment.risk_factors.push_back("Multiple API changes may cause conflicts");
+        assessment.level = RiskLevel::HIGH;
+    }
+    
+    // Recommendations for concatenation
+    assessment.recommendations.push_back("Manual review required - automatic concatenation is risky");
+    assessment.recommendations.push_back("Consider merging logic manually instead of concatenating");
+    assessment.recommendations.push_back("Test thoroughly for duplicate or conflicting code");
+    
+    return assessment;
+}
+
+}  // namespace analysis
+}  // namespace wizardmerge
diff --git a/backend/src/controllers/MergeController.cc b/backend/src/controllers/MergeController.cc
index ad7aa55..d840c0a 100644
--- a/backend/src/controllers/MergeController.cc
+++ b/backend/src/controllers/MergeController.cc
@@ -101,6 +101,65 @@ void MergeController::merge(
         }
         conflictObj["their_lines"] = theirLines;
         
+        // Add context analysis
+        Json::Value contextObj;
+        contextObj["function_name"] = conflict.context.function_name;
+        contextObj["class_name"] = conflict.context.class_name;
+        Json::Value importsArray(Json::arrayValue);
+        for (const auto& import : conflict.context.imports) {
+            importsArray.append(import);
+        }
+        contextObj["imports"] = importsArray;
+        conflictObj["context"] = contextObj;
+        
+        // Add risk analysis for "ours" resolution
+        Json::Value riskOursObj;
+        riskOursObj["level"] = wizardmerge::analysis::risk_level_to_string(conflict.risk_ours.level);
+        riskOursObj["confidence_score"] = conflict.risk_ours.confidence_score;
+        Json::Value riskFactorsOurs(Json::arrayValue);
+        for (const auto& factor : conflict.risk_ours.risk_factors) {
+            riskFactorsOurs.append(factor);
+        }
+        riskOursObj["risk_factors"] = riskFactorsOurs;
+        Json::Value recommendationsOurs(Json::arrayValue);
+        for (const auto& rec : conflict.risk_ours.recommendations) {
+            recommendationsOurs.append(rec);
+        }
+        riskOursObj["recommendations"] = recommendationsOurs;
+        conflictObj["risk_ours"] = riskOursObj;
+        
+        // Add risk analysis for "theirs" resolution
+        Json::Value riskTheirsObj;
+        riskTheirsObj["level"] = wizardmerge::analysis::risk_level_to_string(conflict.risk_theirs.level);
+        riskTheirsObj["confidence_score"] = conflict.risk_theirs.confidence_score;
+        Json::Value riskFactorsTheirs(Json::arrayValue);
+        for (const auto& factor : conflict.risk_theirs.risk_factors) {
+            riskFactorsTheirs.append(factor);
+        }
+        riskTheirsObj["risk_factors"] = riskFactorsTheirs;
+        Json::Value recommendationsTheirs(Json::arrayValue);
+        for (const auto& rec : conflict.risk_theirs.recommendations) {
+            recommendationsTheirs.append(rec);
+        }
+        riskTheirsObj["recommendations"] = recommendationsTheirs;
+        conflictObj["risk_theirs"] = riskTheirsObj;
+        
+        // Add risk analysis for "both" resolution
+        Json::Value riskBothObj;
+        riskBothObj["level"] = wizardmerge::analysis::risk_level_to_string(conflict.risk_both.level);
+        riskBothObj["confidence_score"] = conflict.risk_both.confidence_score;
+        Json::Value riskFactorsBoth(Json::arrayValue);
+        for (const auto& factor : conflict.risk_both.risk_factors) {
+            riskFactorsBoth.append(factor);
+        }
+        riskBothObj["risk_factors"] = riskFactorsBoth;
+        Json::Value recommendationsBoth(Json::arrayValue);
+        for (const auto& rec : conflict.risk_both.recommendations) {
+            recommendationsBoth.append(rec);
+        }
+        riskBothObj["recommendations"] = recommendationsBoth;
+        conflictObj["risk_both"] = riskBothObj;
+        
         conflictsArray.append(conflictObj);
     }
     response["conflicts"] = conflictsArray;
diff --git a/backend/src/merge/three_way_merge.cpp b/backend/src/merge/three_way_merge.cpp
index 8cac4b1..466944d 100644
--- a/backend/src/merge/three_way_merge.cpp
+++ b/backend/src/merge/three_way_merge.cpp
@@ -4,6 +4,8 @@
  */
 
 #include "wizardmerge/merge/three_way_merge.h"
+#include "wizardmerge/analysis/context_analyzer.h"
+#include "wizardmerge/analysis/risk_analyzer.h"
 #include <algorithm>
 
 namespace wizardmerge {
@@ -68,6 +70,23 @@ MergeResult three_way_merge(
             conflict.their_lines.push_back({their_line, Line::THEIRS});
             conflict.end_line = result.merged_lines.size();
             
+            // Perform context analysis
+            // Use the merged lines we have so far as context
+            std::vector<std::string> context_lines;
+            for (const auto& line : result.merged_lines) {
+                context_lines.push_back(line.content);
+            }
+            conflict.context = analysis::analyze_context(context_lines, i, i);
+            
+            // Perform risk analysis for different resolution strategies
+            std::vector<std::string> base_vec = {base_line};
+            std::vector<std::string> ours_vec = {our_line};
+            std::vector<std::string> theirs_vec = {their_line};
+            
+            conflict.risk_ours = analysis::analyze_risk_ours(base_vec, ours_vec, theirs_vec);
+            conflict.risk_theirs = analysis::analyze_risk_theirs(base_vec, ours_vec, theirs_vec);
+            conflict.risk_both = analysis::analyze_risk_both(base_vec, ours_vec, theirs_vec);
+            
             result.conflicts.push_back(conflict);
             
             // Add conflict markers
diff --git a/backend/tests/test_context_analyzer.cpp b/backend/tests/test_context_analyzer.cpp
new file mode 100644
index 0000000..58d1ee5
--- /dev/null
+++ b/backend/tests/test_context_analyzer.cpp
@@ -0,0 +1,129 @@
+/**
+ * @file test_context_analyzer.cpp
+ * @brief Unit tests for context analysis module
+ */
+
+#include "wizardmerge/analysis/context_analyzer.h"
+#include <gtest/gtest.h>
+
+using namespace wizardmerge::analysis;
+
+/**
+ * Test basic context analysis
+ */
+TEST(ContextAnalyzerTest, BasicContextAnalysis) {
+    std::vector<std::string> lines = {
+        "#include <iostream>",
+        "",
+        "class MyClass {",
+        "public:",
+        "    void myMethod() {",
+        "        int x = 42;",
+        "        int y = 100;",
+        "        return;",
+        "    }",
+        "};"
+    };
+    
+    auto context = analyze_context(lines, 5, 7);
+    
+    EXPECT_EQ(context.start_line, 5);
+    EXPECT_EQ(context.end_line, 7);
+    EXPECT_FALSE(context.surrounding_lines.empty());
+}
+
+/**
+ * Test function name extraction
+ */
+TEST(ContextAnalyzerTest, ExtractFunctionName) {
+    std::vector<std::string> lines = {
+        "void testFunction() {",
+        "    int x = 10;",
+        "    return;",
+        "}"
+    };
+    
+    std::string func_name = extract_function_name(lines, 1);
+    EXPECT_EQ(func_name, "testFunction");
+}
+
+/**
+ * Test Python function name extraction
+ */
+TEST(ContextAnalyzerTest, ExtractPythonFunctionName) {
+    std::vector<std::string> lines = {
+        "def my_python_function():",
+        "    x = 10",
+        "    return x"
+    };
+    
+    std::string func_name = extract_function_name(lines, 1);
+    EXPECT_EQ(func_name, "my_python_function");
+}
+
+/**
+ * Test class name extraction
+ */
+TEST(ContextAnalyzerTest, ExtractClassName) {
+    std::vector<std::string> lines = {
+        "class TestClass {",
+        "    int member;",
+        "};"
+    };
+    
+    std::string class_name = extract_class_name(lines, 1);
+    EXPECT_EQ(class_name, "TestClass");
+}
+
+/**
+ * Test import extraction
+ */
+TEST(ContextAnalyzerTest, ExtractImports) {
+    std::vector<std::string> lines = {
+        "#include <iostream>",
+        "#include <vector>",
+        "",
+        "int main() {",
+        "    return 0;",
+        "}"
+    };
+    
+    auto imports = extract_imports(lines);
+    EXPECT_EQ(imports.size(), 2);
+    EXPECT_EQ(imports[0], "#include <iostream>");
+    EXPECT_EQ(imports[1], "#include <vector>");
+}
+
+/**
+ * Test context with no function
+ */
+TEST(ContextAnalyzerTest, NoFunctionContext) {
+    std::vector<std::string> lines = {
+        "int x = 10;",
+        "int y = 20;"
+    };
+    
+    std::string func_name = extract_function_name(lines, 0);
+    EXPECT_EQ(func_name, "");
+}
+
+/**
+ * Test context window boundaries
+ */
+TEST(ContextAnalyzerTest, ContextWindowBoundaries) {
+    std::vector<std::string> lines = {
+        "line1",
+        "line2",
+        "line3",
+        "line4",
+        "line5"
+    };
+    
+    // Test with small context window at beginning of file
+    auto context = analyze_context(lines, 0, 0, 2);
+    EXPECT_GE(context.surrounding_lines.size(), 1);
+    
+    // Test with context window at end of file
+    context = analyze_context(lines, 4, 4, 2);
+    EXPECT_GE(context.surrounding_lines.size(), 1);
+}
diff --git a/backend/tests/test_risk_analyzer.cpp b/backend/tests/test_risk_analyzer.cpp
new file mode 100644
index 0000000..c085cbe
--- /dev/null
+++ b/backend/tests/test_risk_analyzer.cpp
@@ -0,0 +1,140 @@
+/**
+ * @file test_risk_analyzer.cpp
+ * @brief Unit tests for risk analysis module
+ */
+
+#include "wizardmerge/analysis/risk_analyzer.h"
+#include <gtest/gtest.h>
+
+using namespace wizardmerge::analysis;
+
+/**
+ * Test risk level to string conversion
+ */
+TEST(RiskAnalyzerTest, RiskLevelToString) {
+    EXPECT_EQ(risk_level_to_string(RiskLevel::LOW), "low");
+    EXPECT_EQ(risk_level_to_string(RiskLevel::MEDIUM), "medium");
+    EXPECT_EQ(risk_level_to_string(RiskLevel::HIGH), "high");
+    EXPECT_EQ(risk_level_to_string(RiskLevel::CRITICAL), "critical");
+}
+
+/**
+ * Test basic risk analysis for "ours"
+ */
+TEST(RiskAnalyzerTest, BasicRiskAnalysisOurs) {
+    std::vector<std::string> base = {"int x = 10;"};
+    std::vector<std::string> ours = {"int x = 20;"};
+    std::vector<std::string> theirs = {"int x = 30;"};
+    
+    auto risk = analyze_risk_ours(base, ours, theirs);
+    
+    EXPECT_TRUE(risk.level == RiskLevel::LOW || risk.level == RiskLevel::MEDIUM);
+    EXPECT_GE(risk.confidence_score, 0.0);
+    EXPECT_LE(risk.confidence_score, 1.0);
+    EXPECT_FALSE(risk.recommendations.empty());
+}
+
+/**
+ * Test basic risk analysis for "theirs"
+ */
+TEST(RiskAnalyzerTest, BasicRiskAnalysisTheirs) {
+    std::vector<std::string> base = {"int x = 10;"};
+    std::vector<std::string> ours = {"int x = 20;"};
+    std::vector<std::string> theirs = {"int x = 30;"};
+    
+    auto risk = analyze_risk_theirs(base, ours, theirs);
+    
+    EXPECT_TRUE(risk.level == RiskLevel::LOW || risk.level == RiskLevel::MEDIUM);
+    EXPECT_GE(risk.confidence_score, 0.0);
+    EXPECT_LE(risk.confidence_score, 1.0);
+    EXPECT_FALSE(risk.recommendations.empty());
+}
+
+/**
+ * Test risk analysis for "both" (concatenation)
+ */
+TEST(RiskAnalyzerTest, RiskAnalysisBoth) {
+    std::vector<std::string> base = {"int x = 10;"};
+    std::vector<std::string> ours = {"int x = 20;"};
+    std::vector<std::string> theirs = {"int x = 30;"};
+    
+    auto risk = analyze_risk_both(base, ours, theirs);
+    
+    // "Both" strategy should typically have medium or higher risk
+    EXPECT_TRUE(risk.level >= RiskLevel::MEDIUM);
+    EXPECT_GE(risk.confidence_score, 0.0);
+    EXPECT_LE(risk.confidence_score, 1.0);
+    EXPECT_FALSE(risk.recommendations.empty());
+}
+
+/**
+ * Test critical pattern detection
+ */
+TEST(RiskAnalyzerTest, DetectCriticalPatterns) {
+    std::vector<std::string> safe_code = {"int x = 10;", "return x;"};
+    std::vector<std::string> unsafe_code = {"delete ptr;", "system(\"rm -rf /\");"};
+    
+    EXPECT_FALSE(contains_critical_patterns(safe_code));
+    EXPECT_TRUE(contains_critical_patterns(unsafe_code));
+}
+
+/**
+ * Test API signature change detection
+ */
+TEST(RiskAnalyzerTest, DetectAPISignatureChanges) {
+    std::vector<std::string> base_sig = {"void myFunction(int x) {"};
+    std::vector<std::string> modified_sig = {"void myFunction(int x, int y) {"};
+    std::vector<std::string> same_sig = {"void myFunction(int x) {"};
+    
+    EXPECT_TRUE(has_api_signature_changes(base_sig, modified_sig));
+    EXPECT_FALSE(has_api_signature_changes(base_sig, same_sig));
+}
+
+/**
+ * Test high risk for large changes
+ */
+TEST(RiskAnalyzerTest, HighRiskForLargeChanges) {
+    std::vector<std::string> base = {"line1"};
+    std::vector<std::string> ours;
+    std::vector<std::string> theirs = {"line1"};
+    
+    // Create large change in ours
+    for (int i = 0; i < 15; ++i) {
+        ours.push_back("changed_line_" + std::to_string(i));
+    }
+    
+    auto risk = analyze_risk_ours(base, ours, theirs);
+    
+    // Should detect significant changes
+    EXPECT_TRUE(risk.level >= RiskLevel::MEDIUM);
+    EXPECT_FALSE(risk.risk_factors.empty());
+}
+
+/**
+ * Test risk with critical patterns
+ */
+TEST(RiskAnalyzerTest, CriticalPatternsIncreaseRisk) {
+    std::vector<std::string> base = {"int x = 10;"};
+    std::vector<std::string> ours = {"delete database;", "eval(user_input);"};
+    std::vector<std::string> theirs = {"int x = 10;"};
+    
+    auto risk = analyze_risk_ours(base, ours, theirs);
+    
+    EXPECT_TRUE(risk.level >= RiskLevel::HIGH);
+    EXPECT_TRUE(risk.affects_critical_section);
+    EXPECT_FALSE(risk.risk_factors.empty());
+}
+
+/**
+ * Test risk factors are populated
+ */
+TEST(RiskAnalyzerTest, RiskFactorsPopulated) {
+    std::vector<std::string> base = {"line1", "line2", "line3"};
+    std::vector<std::string> ours = {"changed1", "changed2", "changed3"};
+    std::vector<std::string> theirs = {"line1", "line2", "line3"};
+    
+    auto risk = analyze_risk_ours(base, ours, theirs);
+    
+    // Should have some analysis results
+    EXPECT_TRUE(!risk.recommendations.empty() || !risk.risk_factors.empty());
+}