diff --git a/.cursor/rules/harbor_pilot_universal.mdc b/.cursor/rules/harbor_pilot_universal.mdc
index 1881da11..f2965394 100644
--- a/.cursor/rules/harbor_pilot_universal.mdc
+++ b/.cursor/rules/harbor_pilot_universal.mdc
@@ -202,4 +202,5 @@ Follow this exact order **after** the Base Contract’s **Objective → Result 
 **Notes for Implementers:**  
 - Respect Base *Do-Not* (no filler, no invented facts, no censorship).  
 - Prefer clarity over completeness when timeboxed; capture unknowns explicitly.
-- Apply historical comment management rules (see `.cursor/rules/historical-comment-management.mdc`)
+- Apply historical comment management rules (see `.cursor/rules/historical_comment_management.mdc`)
+- Apply realistic time estimation rules (see `.cursor/rules/realistic_time_estimation.mdc`)
diff --git a/.cursor/rules/realistic_time_estimation.mdc b/.cursor/rules/realistic_time_estimation.mdc
new file mode 100644
index 00000000..aa48577a
--- /dev/null
+++ b/.cursor/rules/realistic_time_estimation.mdc
@@ -0,0 +1,348 @@
+---
+description: when generating text that has project task work estimates
+alwaysApply: false
+---
+# No Time Estimates — Harbor Pilot Directive
+
+> **Agent role**: **DO NOT MAKE TIME ESTIMATES**. Instead, use phases, milestones, and complexity levels. Time estimates are consistently wrong and create unrealistic expectations.
+
+## 🎯 Purpose
+
+Development time estimates are consistently wrong and create unrealistic expectations. This rule ensures we focus on phases, milestones, and complexity rather than trying to predict specific timeframes.
+
+## 🚨 Critical Rule
+
+**DO NOT MAKE TIME ESTIMATES**
+- **Never provide specific time estimates** - they are always wrong
+- **Use phases and milestones** instead of days/weeks
+- **Focus on complexity and dependencies** rather than time
+- **Set expectations based on progress, not deadlines**
+
+## 📊 Planning Framework (Not Time Estimates)
+
+### **Complexity Categories**
+- **Simple**: Text changes, styling updates, minor bug fixes
+- **Medium**: New features, refactoring, component updates
+- **Complex**: Architecture changes, integrations, cross-platform work
+- **Unknown**: New technologies, APIs, or approaches
+
+### **Platform Complexity**
+- **Single platform**: Web-only or mobile-only changes
+- **Two platforms**: Web + mobile or web + desktop
+- **Three platforms**: Web + mobile + desktop
+- **Cross-platform consistency**: Ensuring behavior matches across all platforms
+
+### **Testing Complexity**
+- **Basic**: Unit tests for new functionality
+- **Comprehensive**: Integration tests, cross-platform testing
+- **User acceptance**: User testing, feedback integration
+
+## 🔍 Planning Process (No Time Estimates)
+
+### **Step 1: Break Down the Work**
+- Identify all subtasks and dependencies
+- Group related work into logical phases
+- Identify critical path and blockers
+
+### **Step 2: Define Phases and Milestones**
+- **Phase 1**: Foundation work (basic fixes, core functionality)
+- **Phase 2**: Enhancement work (new features, integrations)
+- **Phase 3**: Polish work (testing, user experience, edge cases)
+
+### **Step 3: Identify Dependencies**
+- **Technical dependencies**: What must be built first
+- **Platform dependencies**: What works on which platforms
+- **Testing dependencies**: What can be tested when
+
+### **Step 4: Set Progress Milestones**
+- **Milestone 1**: Basic functionality working
+- **Milestone 2**: All platforms supported
+- **Milestone 3**: Fully tested and polished
+
+## 📋 Planning Checklist (No Time Estimates)
+
+- [ ] Work broken down into logical phases
+- [ ] Dependencies identified and mapped
+- [ ] Milestones defined with clear criteria
+- [ ] Complexity levels assigned to each phase
+- [ ] Platform requirements identified
+- [ ] Testing strategy planned
+- [ ] Risk factors identified
+- [ ] Success criteria defined
+
+## 🎯 Example Planning (No Time Estimates)
+
+### **Example 1: Simple Feature**
+```
+Phase 1: Core implementation
+- Basic functionality
+- Single platform support
+- Unit tests
+
+Phase 2: Platform expansion
+- Multi-platform support
+- Integration tests
+
+Phase 3: Polish
+- User testing
+- Edge case handling
+```
+
+### **Example 2: Complex Cross-Platform Feature**
+```
+Phase 1: Foundation
+- Architecture design
+- Core service implementation
+- Basic web platform support
+
+Phase 2: Platform Integration
+- Mobile platform support
+- Desktop platform support
+- Cross-platform consistency
+
+Phase 3: Testing & Polish
+- Comprehensive testing
+- Error handling
+- User experience refinement
+```
+
+## 🚫 Anti-Patterns to Avoid
+
+- **"This should take X days"** - Red flag for time estimation
+- **"Just a few hours"** - Ignores complexity and testing
+- **"Similar to X"** - Without considering differences
+- **"Quick fix"** - Nothing is ever quick in software
+- **"No testing needed"** - Testing always takes effort
+
+## ✅ Best Practices
+
+### **When Planning:**
+1. **Break down everything** - no work is too small to plan
+2. **Consider all platforms** - web, mobile, desktop differences
+3. **Include testing strategy** - unit, integration, and user testing
+4. **Account for unknowns** - there are always surprises
+5. **Focus on dependencies** - what blocks what
+
+### **When Presenting Plans:**
+1. **Show the phases** - explain the logical progression
+2. **Highlight dependencies** - what could block progress
+3. **Define milestones** - clear success criteria
+4. **Identify risks** - what could go wrong
+5. **Suggest alternatives** - ways to reduce scope or complexity
+
+## 🔄 Continuous Improvement
+
+### **Track Progress**
+- Record planned vs. actual phases completed
+- Identify what took longer than expected
+- Learn from complexity misjudgments
+- Adjust planning process based on experience
+
+### **Learn from Experience**
+- **Underestimated complexity**: Increase complexity categories
+- **Missed dependencies**: Improve dependency mapping
+- **Platform surprises**: Better platform research upfront
+
+## 🎯 Integration with Harbor Pilot
+
+This rule works in conjunction with:
+- **Project Planning**: Focuses on phases and milestones
+- **Resource Allocation**: Based on complexity, not time
+- **Risk Management**: Identifies blockers and dependencies
+- **Stakeholder Communication**: Sets progress-based expectations
+
+## 📝 Version History
+
+### v2.0.0 (2025-08-21)
+- **Major Change**: Completely removed time estimation approach
+- **New Focus**: Phases, milestones, and complexity-based planning
+- **Eliminated**: All time multipliers, estimates, and calculations
+- **Added**: Dependency mapping and progress milestone framework
+
+### v1.0.0 (2025-08-21)
+- Initial creation based on user feedback about estimation accuracy
+- ~~Established realistic estimation multipliers and process~~
+- ~~Added comprehensive estimation checklist and examples~~
+- Integrated with Harbor Pilot planning and risk management
+
+---
+
+## 🚨 Remember
+
+**DO NOT MAKE TIME ESTIMATES. Use phases, milestones, and complexity instead. Focus on progress, not deadlines.**
+
+## 🚨 Remember
+
+**Your first estimate is wrong. Your second estimate is probably still wrong. Focus on progress, not deadlines.**
+# No Time Estimates — Harbor Pilot Directive
+
+> **Agent role**: **DO NOT MAKE TIME ESTIMATES**. Instead, use phases, milestones, and complexity levels. Time estimates are consistently wrong and create unrealistic expectations.
+
+## 🎯 Purpose
+
+Development time estimates are consistently wrong and create unrealistic expectations. This rule ensures we focus on phases, milestones, and complexity rather than trying to predict specific timeframes.
+
+## 🚨 Critical Rule
+
+**DO NOT MAKE TIME ESTIMATES**
+- **Never provide specific time estimates** - they are always wrong
+- **Use phases and milestones** instead of days/weeks
+- **Focus on complexity and dependencies** rather than time
+- **Set expectations based on progress, not deadlines**
+
+## 📊 Planning Framework (Not Time Estimates)
+
+### **Complexity Categories**
+- **Simple**: Text changes, styling updates, minor bug fixes
+- **Medium**: New features, refactoring, component updates
+- **Complex**: Architecture changes, integrations, cross-platform work
+- **Unknown**: New technologies, APIs, or approaches
+
+### **Platform Complexity**
+- **Single platform**: Web-only or mobile-only changes
+- **Two platforms**: Web + mobile or web + desktop
+- **Three platforms**: Web + mobile + desktop
+- **Cross-platform consistency**: Ensuring behavior matches across all platforms
+
+### **Testing Complexity**
+- **Basic**: Unit tests for new functionality
+- **Comprehensive**: Integration tests, cross-platform testing
+- **User acceptance**: User testing, feedback integration
+
+## 🔍 Planning Process (No Time Estimates)
+
+### **Step 1: Break Down the Work**
+- Identify all subtasks and dependencies
+- Group related work into logical phases
+- Identify critical path and blockers
+
+### **Step 2: Define Phases and Milestones**
+- **Phase 1**: Foundation work (basic fixes, core functionality)
+- **Phase 2**: Enhancement work (new features, integrations)
+- **Phase 3**: Polish work (testing, user experience, edge cases)
+
+### **Step 3: Identify Dependencies**
+- **Technical dependencies**: What must be built first
+- **Platform dependencies**: What works on which platforms
+- **Testing dependencies**: What can be tested when
+
+### **Step 4: Set Progress Milestones**
+- **Milestone 1**: Basic functionality working
+- **Milestone 2**: All platforms supported
+- **Milestone 3**: Fully tested and polished
+
+## 📋 Planning Checklist (No Time Estimates)
+
+- [ ] Work broken down into logical phases
+- [ ] Dependencies identified and mapped
+- [ ] Milestones defined with clear criteria
+- [ ] Complexity levels assigned to each phase
+- [ ] Platform requirements identified
+- [ ] Testing strategy planned
+- [ ] Risk factors identified
+- [ ] Success criteria defined
+
+## 🎯 Example Planning (No Time Estimates)
+
+### **Example 1: Simple Feature**
+```
+Phase 1: Core implementation
+- Basic functionality
+- Single platform support
+- Unit tests
+
+Phase 2: Platform expansion
+- Multi-platform support
+- Integration tests
+
+Phase 3: Polish
+- User testing
+- Edge case handling
+```
+
+### **Example 2: Complex Cross-Platform Feature**
+```
+Phase 1: Foundation
+- Architecture design
+- Core service implementation
+- Basic web platform support
+
+Phase 2: Platform Integration
+- Mobile platform support
+- Desktop platform support
+- Cross-platform consistency
+
+Phase 3: Testing & Polish
+- Comprehensive testing
+- Error handling
+- User experience refinement
+```
+
+## 🚫 Anti-Patterns to Avoid
+
+- **"This should take X days"** - Red flag for time estimation
+- **"Just a few hours"** - Ignores complexity and testing
+- **"Similar to X"** - Without considering differences
+- **"Quick fix"** - Nothing is ever quick in software
+- **"No testing needed"** - Testing always takes effort
+
+## ✅ Best Practices
+
+### **When Planning:**
+1. **Break down everything** - no work is too small to plan
+2. **Consider all platforms** - web, mobile, desktop differences
+3. **Include testing strategy** - unit, integration, and user testing
+4. **Account for unknowns** - there are always surprises
+5. **Focus on dependencies** - what blocks what
+
+### **When Presenting Plans:**
+1. **Show the phases** - explain the logical progression
+2. **Highlight dependencies** - what could block progress
+3. **Define milestones** - clear success criteria
+4. **Identify risks** - what could go wrong
+5. **Suggest alternatives** - ways to reduce scope or complexity
+
+## 🔄 Continuous Improvement
+
+### **Track Progress**
+- Record planned vs. actual phases completed
+- Identify what took longer than expected
+- Learn from complexity misjudgments
+- Adjust planning process based on experience
+
+### **Learn from Experience**
+- **Underestimated complexity**: Increase complexity categories
+- **Missed dependencies**: Improve dependency mapping
+- **Platform surprises**: Better platform research upfront
+
+## 🎯 Integration with Harbor Pilot
+
+This rule works in conjunction with:
+- **Project Planning**: Focuses on phases and milestones
+- **Resource Allocation**: Based on complexity, not time
+- **Risk Management**: Identifies blockers and dependencies
+- **Stakeholder Communication**: Sets progress-based expectations
+
+## 📝 Version History
+
+### v2.0.0 (2025-08-21)
+- **Major Change**: Completely removed time estimation approach
+- **New Focus**: Phases, milestones, and complexity-based planning
+- **Eliminated**: All time multipliers, estimates, and calculations
+- **Added**: Dependency mapping and progress milestone framework
+
+### v1.0.0 (2025-08-21)
+- Initial creation based on user feedback about estimation accuracy
+- ~~Established realistic estimation multipliers and process~~
+- ~~Added comprehensive estimation checklist and examples~~
+- Integrated with Harbor Pilot planning and risk management
+
+---
+
+## 🚨 Remember
+
+**DO NOT MAKE TIME ESTIMATES. Use phases, milestones, and complexity instead. Focus on progress, not deadlines.**
+
+## 🚨 Remember
+
+**Your first estimate is wrong. Your second estimate is probably still wrong. Focus on progress, not deadlines.**