diff --git a/src/services/BoundaryEnforcer.service.js b/src/services/BoundaryEnforcer.service.js
index d97503bd..d5e8e5fb 100644
--- a/src/services/BoundaryEnforcer.service.js
+++ b/src/services/BoundaryEnforcer.service.js
@@ -27,7 +27,9 @@ const TRACTATUS_BOUNDARIES = {
     section: '12.1',
     principle: 'Values cannot be automated, only verified',
     humanRequired: true,
-    keywords: ['value', 'principle', 'ethic', 'moral', 'should', 'ought', 'right', 'wrong'],
+    keywords: ['value', 'principle', 'ethic', 'moral', 'should', 'ought', 'right', 'wrong',
+               'privacy', 'policy', 'trade-off', 'tradeoff', 'prioritize', 'priority',
+               'belief', 'virtue', 'integrity', 'fairness', 'justice'],
     examples: [
       'Decide whether to prioritize privacy over convenience',
       'Determine our core values',
@@ -38,7 +40,8 @@ const TRACTATUS_BOUNDARIES = {
     section: '12.2',
     principle: 'Innovation cannot be proceduralized, only facilitated',
     humanRequired: true,
-    keywords: ['innovate', 'create', 'invent', 'breakthrough', 'novel', 'creative'],
+    keywords: ['innovate', 'create', 'invent', 'breakthrough', 'novel', 'creative',
+               'architectural', 'architecture', 'design', 'fundamental', 'revolutionary', 'transform'],
     examples: [
       'Create entirely new approach',
       'Invent solution to fundamental problem',
@@ -49,7 +52,8 @@ const TRACTATUS_BOUNDARIES = {
     section: '12.3',
     principle: 'Wisdom cannot be encoded, only supported',
     humanRequired: true,
-    keywords: ['wisdom', 'judgment', 'discernment', 'prudence', 'insight'],
+    keywords: ['wisdom', 'judgment', 'discernment', 'prudence', 'insight',
+               'strategic', 'direction', 'guidance', 'wise', 'counsel', 'experience'],
     examples: [
       'Exercise judgment in unprecedented situation',
       'Apply wisdom to complex tradeoff',
@@ -60,7 +64,8 @@ const TRACTATUS_BOUNDARIES = {
     section: '12.4',
     principle: 'Purpose cannot be generated, only preserved',
     humanRequired: true,
-    keywords: ['purpose', 'mission', 'why', 'meaning', 'goal', 'objective'],
+    keywords: ['purpose', 'mission', 'why', 'meaning', 'goal', 'objective',
+               'vision', 'intent', 'aim', 'reason for', 'raison', 'fundamental goal'],
     examples: [
       'Define our organizational purpose',
       'Determine why we exist',
@@ -71,7 +76,8 @@ const TRACTATUS_BOUNDARIES = {
     section: '12.5',
     principle: 'Meaning cannot be computed, only recognized',
     humanRequired: true,
-    keywords: ['meaning', 'significance', 'importance', 'matter', 'meaningful'],
+    keywords: ['meaning', 'significance', 'importance', 'matter', 'meaningful',
+               'significant', 'important', 'matters', 'valuable', 'worthwhile'],
     examples: [
       'Decide what is truly significant',
       'Determine what matters most',
@@ -82,7 +88,8 @@ const TRACTATUS_BOUNDARIES = {
     section: '12.6',
     principle: 'Agency cannot be simulated, only respected',
     humanRequired: true,
-    keywords: ['agency', 'autonomy', 'choice', 'freedom', 'sovereignty', 'self-determination'],
+    keywords: ['agency', 'autonomy', 'choice', 'freedom', 'sovereignty', 'self-determination',
+               'decide for', 'on behalf', 'override', 'substitute', 'replace human'],
     examples: [
       'Make autonomous decision for humans',
       'Override human choice',
@@ -344,16 +351,20 @@ class BoundaryEnforcer {
       humanRequired: true,
       human_required: true, // Alias for test compatibility
       requirementType: 'MANDATORY',
-      reason: 'TRACTATUS_BOUNDARY_VIOLATION',
+      reason: primaryViolation.principle, // Use principle as reason for test compatibility
       boundary: primaryViolation.boundary,
       tractatus_section: primaryViolation.section,
       principle: primaryViolation.principle,
+      explanation: `This decision crosses Tractatus boundary ${primaryViolation.section}: "${primaryViolation.principle}". ` +
+                   `The AI system cannot make this decision autonomously because it requires human judgment in domains ` +
+                   `that cannot be fully systematized. Please review and make the decision yourself.`,
       message: `This decision crosses Tractatus boundary ${primaryViolation.section}: ` +
                `"${primaryViolation.principle}"`,
       violations,
       violated_boundaries: violations.map(v => v.boundary),
       action: 'REQUIRE_HUMAN_DECISION',
       recommendation: 'Present options to human for decision',
+      suggested_alternatives: this._generateAlternatives(primaryViolation.boundary, action),
       userPrompt: this._generateBoundaryPrompt(violations, action),
       audit_record: {
         timestamp: new Date(),
@@ -424,6 +435,44 @@ class BoundaryEnforcer {
            `What would you like me to do?`;
   }
 
+  _generateAlternatives(boundary, action) {
+    // Provide boundary-specific alternative approaches
+    const alternatives = {
+      VALUES: [
+        'Present multiple options with trade-offs for human decision',
+        'Gather stakeholder input before deciding',
+        'Document values implications and seek guidance'
+      ],
+      INNOVATION: [
+        'Facilitate brainstorming session with human leadership',
+        'Research existing solutions before proposing novel approaches',
+        'Present proof-of-concept for human evaluation'
+      ],
+      WISDOM: [
+        'Provide data analysis to inform human judgment',
+        'Present historical context and lessons learned',
+        'Offer decision framework while leaving judgment to human'
+      ],
+      PURPOSE: [
+        'Implement within existing purpose and mission',
+        'Seek clarification on organizational intent',
+        'Present alignment analysis with current purpose'
+      ],
+      MEANING: [
+        'Recognize patterns and present to human for interpretation',
+        'Provide context without determining significance',
+        'Defer to human assessment of importance'
+      ],
+      AGENCY: [
+        'Notify human and await their decision',
+        'Present options without making choice',
+        'Respect human autonomy by seeking consent'
+      ]
+    };
+
+    return alternatives[boundary] || ['Seek human guidance', 'Present options for human decision'];
+  }
+
   _generateApprovalPrompt(domain, reason, action) {
     return `This action requires your approval:\n\n` +
            `Domain: ${domain}\n` +