diff --git a/docs/z3ed/README.md b/docs/z3ed/README.md
index e3e86a96..d90718b0 100644
--- a/docs/z3ed/README.md
+++ b/docs/z3ed/README.md
@@ -134,6 +134,7 @@ The `z3ed` CLI is the foundation for an AI-driven Model-Code-Program (MCP) loop,
 -   `agent chat`: Opens an interactive terminal chat (TUI) with the AI agent.
 -   `agent simple-chat`: A lightweight, non-TUI chat mode for scripting and automation.
 -   `agent test ...`: Commands for running and managing automated GUI tests.
+-   `agent learn ...`: **NEW**: Manage learned knowledge (preferences, ROM patterns, project context, conversation memory).
 
 ### Resource Commands
 
@@ -163,11 +164,82 @@ Accessible from **Debug → Agent Chat** inside YAZE. Provides the same conversa
 Z3ED supports multiple AI providers. Configuration is resolved with command-line flags taking precedence over environment variables.
 
 -   `--ai_provider=<provider>`: Selects the AI provider (`mock`, `ollama`, `gemini`).
--   `--ai_model=<model>`: Specifies the model name (e.g., `qwen2.5-coder:7b`, `gemini-1.5-flash`).
+-   `--ai_model=<model>`: Specifies the model name (e.g., `qwen2.5-coder:7b`, `gemini-2.5-flash`).
 -   `--gemini_api_key=<key>`: Your Gemini API key.
 -   `--ollama_host=<url>`: The URL for your Ollama server (default: `http://localhost:11434`).
 
-## 8. CLI Output & Help System
+### System Prompt Versions
+
+Z3ED includes multiple system prompt versions for different use cases:
+
+-   **v1 (default)**: Original reactive prompt with basic tool calling
+-   **v2**: Enhanced with better JSON formatting and error handling
+-   **v3 (latest)**: Proactive prompt with intelligent tool chaining and implicit iteration - **RECOMMENDED**
+
+To use v3 prompt: Set environment variable `Z3ED_PROMPT_VERSION=v3` or it will be auto-selected for Gemini 2.0+ models.
+
+## 8. Learn Command - Knowledge Management
+
+The learn command enables the AI agent to remember preferences, patterns, and context across sessions.
+
+### Basic Usage
+
+```bash
+# Store a preference
+z3ed agent learn --preference "default_palette=2"
+
+# Get a preference
+z3ed agent learn --get-preference default_palette
+
+# List all preferences
+z3ed agent learn --list-preferences
+
+# View statistics
+z3ed agent learn --stats
+
+# Export all learned data
+z3ed agent learn --export my_learned_data.json
+
+# Import learned data
+z3ed agent learn --import my_learned_data.json
+```
+
+### Project Context
+
+Store project-specific information that the agent can reference:
+
+```bash
+# Save project context
+z3ed agent learn --project "myrom" --context "Vanilla+ difficulty hack, focus on dungeon redesign"
+
+# List projects
+z3ed agent learn --list-projects
+
+# Get project details
+z3ed agent learn --get-project "myrom"
+```
+
+### Conversation Memory
+
+The agent automatically stores summaries of conversations for future reference:
+
+```bash
+# View recent memories
+z3ed agent learn --recent-memories 10
+
+# Search memories by topic
+z3ed agent learn --search-memories "room 5"
+```
+
+### Storage Location
+
+All learned data is stored in `~/.yaze/agent/`:
+- `preferences.json`: User preferences
+- `patterns.json`: Learned ROM patterns
+- `projects.json`: Project contexts
+- `memories.json`: Conversation summaries
+
+## 9. CLI Output & Help System
 
 The `z3ed` CLI features a modernized output system designed to be clean for users and informative for developers.
 
@@ -205,7 +277,7 @@ The help system is organized by category for easy navigation.
 -   **Main Help**: `z3ed --help` or `z3ed -h` shows a high-level overview of command categories.
 -   **Category Help**: `z3ed help <category>` provides detailed information for a specific group of commands (e.g., `agent`, `patch`, `rom`).
 
-## 9. Collaborative Sessions & Multimodal Vision
+## 10. Collaborative Sessions & Multimodal Vision
 
 ### Overview
 
@@ -784,7 +856,7 @@ The AI response appears in your chat history and can reference specific details
 - **Agent Editor Docs**: `src/app/editor/agent/README.md`
 - **Integration Guide**: `docs/z3ed/YAZE_SERVER_V2_INTEGRATION.md`
 
-## 10. Roadmap & Implementation Status
+## 11. Roadmap & Implementation Status
 
 **Last Updated**: October 4, 2025
 
@@ -815,7 +887,13 @@ The AI response appears in your chat history and can reference specific details
 4.  **Collaboration UI Enhancements (1 day)**: Add UI elements for ROM sync, snapshot sharing, and proposal management in the Agent Chat widget.
 5.  **Windows Cross-Platform Testing (8-10h)**: Validate `z3ed` and the test harness on Windows.
 
-## 11. Troubleshooting
+### ✅ Recently Completed (v0.2.0-alpha)
+
+-   **Enhanced System Prompt (v3)**: Proactive tool chaining with implicit iteration to minimize back-and-forth
+-   **Learn Command**: Full implementation with preferences, ROM patterns, project context, and conversation memory
+-   **gRPC Windows Build Optimization**: Documented vcpkg approach and optimization strategies
+
+## 12. Troubleshooting
 
 -   **"Build with -DZ3ED_AI=ON" warning**: AI features are disabled. Rebuild with the flag to enable them.
 -   **"gRPC not available" error**: GUI testing is disabled. Rebuild with `-DYAZE_WITH_GRPC=ON`.
diff --git a/src/cli/handlers/agent.cc b/src/cli/handlers/agent.cc
index 593ed90e..1bde73c2 100644
--- a/src/cli/handlers/agent.cc
+++ b/src/cli/handlers/agent.cc
@@ -110,7 +110,7 @@ absl::Status Agent::Run(const std::vector<std::string>& arg_vec) {
     return agent::HandleGuiCommand(subcommand_args);
   }
   if (subcommand == "learn") {
-    return agent::HandleLearnCommand();
+    return agent::HandleLearnCommand(subcommand_args);
   }
   if (subcommand == "list") {
     return agent::HandleListCommand();
diff --git a/src/cli/handlers/agent/commands.h b/src/cli/handlers/agent/commands.h
index a69eebfc..7397ff63 100644
--- a/src/cli/handlers/agent/commands.h
+++ b/src/cli/handlers/agent/commands.h
@@ -20,7 +20,7 @@ absl::Status HandleDiffCommand(Rom& rom,
 absl::Status HandleAcceptCommand(const std::vector<std::string>& args, Rom& rom);
 absl::Status HandleTestCommand(const std::vector<std::string>& args);
 absl::Status HandleGuiCommand(const std::vector<std::string>& args);
-absl::Status HandleLearnCommand();
+absl::Status HandleLearnCommand(const std::vector<std::string>& args = {});
 absl::Status HandleListCommand();
 absl::Status HandleCommitCommand(Rom& rom);
 absl::Status HandleRevertCommand(Rom& rom);
diff --git a/src/cli/handlers/agent/general_commands.cc b/src/cli/handlers/agent/general_commands.cc
index 8e480426..5b1eca99 100644
--- a/src/cli/handlers/agent/general_commands.cc
+++ b/src/cli/handlers/agent/general_commands.cc
@@ -385,9 +385,170 @@ absl::Status HandleDiffCommand(Rom& rom, const std::vector<std::string>& args) {
   return absl::OkStatus();
 }
 
-absl::Status HandleLearnCommand() {
-  std::cout << "Agent learn not yet implemented." << std::endl;
-  return absl::OkStatus();
+absl::Status HandleLearnCommand(const std::vector<std::string>& args) {
+  using namespace yaze::cli::agent;
+  
+  static LearnedKnowledgeService learn_service;
+  static bool initialized = false;
+  
+  if (!initialized) {
+    auto status = learn_service.Initialize();
+    if (!status.ok()) {
+      std::cerr << "Failed to initialize learned knowledge service: " 
+                << status.message() << std::endl;
+      return status;
+    }
+    initialized = true;
+  }
+  
+  if (args.empty()) {
+    // Show usage
+    std::cout << "\nUsage: z3ed agent learn [options]\n\n";
+    std::cout << "Options:\n";
+    std::cout << "  --preference <key>=<value>     Set a preference\n";
+    std::cout << "  --get-preference <key>         Get a preference value\n";
+    std::cout << "  --list-preferences             List all preferences\n";
+    std::cout << "  --pattern <type> --data <json> Learn a ROM pattern\n";
+    std::cout << "  --query-patterns <type>        Query learned patterns\n";
+    std::cout << "  --project <name> --context <text>  Save project context\n";
+    std::cout << "  --get-project <name>           Get project context\n";
+    std::cout << "  --list-projects                List all projects\n";
+    std::cout << "  --memory <topic> --summary <text>  Store conversation memory\n";
+    std::cout << "  --search-memories <query>      Search memories\n";
+    std::cout << "  --recent-memories [limit]      Show recent memories\n";
+    std::cout << "  --export <file>                Export all data to JSON\n";
+    std::cout << "  --import <file>                Import data from JSON\n";
+    std::cout << "  --stats                        Show statistics\n";
+    std::cout << "  --clear                        Clear all learned data\n";
+    return absl::OkStatus();
+  }
+  
+  // Parse arguments
+  std::string command = args[0];
+  
+  if (command == "--preference" && args.size() >= 2) {
+    std::string pref = args[1];
+    size_t eq_pos = pref.find('=');
+    if (eq_pos == std::string::npos) {
+      return absl::InvalidArgumentError("Preference must be in format key=value");
+    }
+    std::string key = pref.substr(0, eq_pos);
+    std::string value = pref.substr(eq_pos + 1);
+    auto status = learn_service.SetPreference(key, value);
+    if (status.ok()) {
+      std::cout << "✓ Preference '" << key << "' set to '" << value << "'\n";
+    }
+    return status;
+  }
+  
+  if (command == "--get-preference" && args.size() >= 2) {
+    auto value = learn_service.GetPreference(args[1]);
+    if (value) {
+      std::cout << args[1] << " = " << *value << "\n";
+    } else {
+      std::cout << "Preference '" << args[1] << "' not found\n";
+    }
+    return absl::OkStatus();
+  }
+  
+  if (command == "--list-preferences") {
+    auto prefs = learn_service.GetAllPreferences();
+    if (prefs.empty()) {
+      std::cout << "No preferences stored.\n";
+    } else {
+      std::cout << "\n=== Stored Preferences ===\n";
+      for (const auto& [key, value] : prefs) {
+        std::cout << "  " << key << " = " << value << "\n";
+      }
+    }
+    return absl::OkStatus();
+  }
+  
+  if (command == "--stats") {
+    auto stats = learn_service.GetStats();
+    std::cout << "\n=== Learned Knowledge Statistics ===\n";
+    std::cout << "  Preferences: " << stats.preference_count << "\n";
+    std::cout << "  ROM Patterns: " << stats.pattern_count << "\n";
+    std::cout << "  Projects: " << stats.project_count << "\n";
+    std::cout << "  Memories: " << stats.memory_count << "\n";
+    std::cout << "  First learned: " << absl::FormatTime(absl::FromUnixMillis(stats.first_learned_at)) << "\n";
+    std::cout << "  Last updated: " << absl::FormatTime(absl::FromUnixMillis(stats.last_updated_at)) << "\n";
+    return absl::OkStatus();
+  }
+  
+  if (command == "--export" && args.size() >= 2) {
+    auto json = learn_service.ExportToJSON();
+    if (!json.ok()) {
+      return json.status();
+    }
+    std::ofstream file(args[1]);
+    if (!file.is_open()) {
+      return absl::InternalError("Failed to open file for writing");
+    }
+    file << *json;
+    std::cout << "✓ Exported learned data to " << args[1] << "\n";
+    return absl::OkStatus();
+  }
+  
+  if (command == "--import" && args.size() >= 2) {
+    std::ifstream file(args[1]);
+    if (!file.is_open()) {
+      return absl::NotFoundError("File not found: " + args[1]);
+    }
+    std::stringstream buffer;
+    buffer << file.rdbuf();
+    auto status = learn_service.ImportFromJSON(buffer.str());
+    if (status.ok()) {
+      std::cout << "✓ Imported learned data from " << args[1] << "\n";
+    }
+    return status;
+  }
+  
+  if (command == "--clear") {
+    auto status = learn_service.ClearAll();
+    if (status.ok()) {
+      std::cout << "✓ All learned data cleared\n";
+    }
+    return status;
+  }
+  
+  if (command == "--list-projects") {
+    auto projects = learn_service.GetAllProjects();
+    if (projects.empty()) {
+      std::cout << "No projects stored.\n";
+    } else {
+      std::cout << "\n=== Stored Projects ===\n";
+      for (const auto& proj : projects) {
+        std::cout << "  " << proj.project_name << "\n";
+        std::cout << "    ROM Hash: " << proj.rom_hash.substr(0, 16) << "...\n";
+        std::cout << "    Last Accessed: " << absl::FormatTime(absl::FromUnixMillis(proj.last_accessed)) << "\n";
+      }
+    }
+    return absl::OkStatus();
+  }
+  
+  if (command == "--recent-memories") {
+    int limit = 10;
+    if (args.size() >= 2) {
+      limit = std::stoi(args[1]);
+    }
+    auto memories = learn_service.GetRecentMemories(limit);
+    if (memories.empty()) {
+      std::cout << "No memories stored.\n";
+    } else {
+      std::cout << "\n=== Recent Memories ===\n";
+      for (const auto& mem : memories) {
+        std::cout << "  Topic: " << mem.topic << "\n";
+        std::cout << "  Summary: " << mem.summary << "\n";
+        std::cout << "  Facts: " << mem.key_facts.size() << " key facts\n";
+        std::cout << "  Created: " << absl::FormatTime(absl::FromUnixMillis(mem.created_at)) << "\n";
+        std::cout << "\n";
+      }
+    }
+    return absl::OkStatus();
+  }
+  
+  return absl::InvalidArgumentError("Unknown learn command. Use 'z3ed agent learn' for usage.");
 }
 
 absl::Status HandleListCommand() {
diff --git a/src/cli/service/agent/learned_knowledge_service.cc b/src/cli/service/agent/learned_knowledge_service.cc
new file mode 100644
index 00000000..247e5039
--- /dev/null
+++ b/src/cli/service/agent/learned_knowledge_service.cc
@@ -0,0 +1,673 @@
+#include "cli/service/agent/learned_knowledge_service.h"
+
+#include <algorithm>
+#include <chrono>
+#include <fstream>
+#include <iostream>
+#include <sstream>
+
+#include "absl/strings/str_cat.h"
+#include "absl/strings/str_format.h"
+#include "absl/time/clock.h"
+#include "absl/time/time.h"
+
+#ifdef _WIN32
+#include <direct.h>
+#define mkdir(path, mode) _mkdir(path)
+#else
+#include <sys/stat.h>
+#include <sys/types.h>
+#endif
+
+namespace yaze {
+namespace cli {
+namespace agent {
+
+namespace {
+
+int64_t CurrentTimestamp() {
+  return absl::ToUnixMillis(absl::Now());
+}
+
+std::string GenerateRandomID() {
+  static int counter = 0;
+  auto now = std::chrono::system_clock::now().time_since_epoch().count();
+  return absl::StrFormat("%lld_%d", now, counter++);
+}
+
+bool FileExists(const std::filesystem::path& path) {
+  return std::filesystem::exists(path);
+}
+
+absl::Status EnsureDirectoryExists(const std::filesystem::path& path) {
+  if (!std::filesystem::exists(path)) {
+    std::error_code ec;
+    if (!std::filesystem::create_directories(path, ec)) {
+      return absl::InternalError(
+          absl::StrCat("Failed to create directory: ", path.string(),
+                      " - ", ec.message()));
+    }
+  }
+  return absl::OkStatus();
+}
+
+}  // namespace
+
+LearnedKnowledgeService::LearnedKnowledgeService()
+    : LearnedKnowledgeService(std::filesystem::path(getenv("HOME") ? getenv("HOME") : ".") / ".yaze" / "agent") {}
+
+LearnedKnowledgeService::LearnedKnowledgeService(
+    const std::filesystem::path& data_dir)
+    : data_dir_(data_dir),
+      prefs_file_(data_dir / "preferences.json"),
+      patterns_file_(data_dir / "patterns.json"),
+      projects_file_(data_dir / "projects.json"),
+      memories_file_(data_dir / "memories.json") {}
+
+absl::Status LearnedKnowledgeService::Initialize() {
+  if (initialized_) {
+    return absl::OkStatus();
+  }
+  
+  // Ensure data directory exists
+  auto status = EnsureDirectoryExists(data_dir_);
+  if (!status.ok()) {
+    return status;
+  }
+  
+  // Load existing data
+  LoadPreferences();  // Ignore errors for empty files
+  LoadPatterns();
+  LoadProjects();
+  LoadMemories();
+  
+  initialized_ = true;
+  return absl::OkStatus();
+}
+
+absl::Status LearnedKnowledgeService::SaveAll() {
+  auto status = SavePreferences();
+  if (!status.ok()) return status;
+  
+  status = SavePatterns();
+  if (!status.ok()) return status;
+  
+  status = SaveProjects();
+  if (!status.ok()) return status;
+  
+  status = SaveMemories();
+  if (!status.ok()) return status;
+  
+  return absl::OkStatus();
+}
+
+// === Preference Management ===
+
+absl::Status LearnedKnowledgeService::SetPreference(const std::string& key,
+                                                    const std::string& value) {
+  if (!initialized_) {
+    return absl::FailedPreconditionError("Service not initialized");
+  }
+  
+  preferences_[key] = value;
+  return SavePreferences();
+}
+
+std::optional<std::string> LearnedKnowledgeService::GetPreference(
+    const std::string& key) const {
+  auto it = preferences_.find(key);
+  if (it != preferences_.end()) {
+    return it->second;
+  }
+  return std::nullopt;
+}
+
+std::map<std::string, std::string> LearnedKnowledgeService::GetAllPreferences() const {
+  return preferences_;
+}
+
+absl::Status LearnedKnowledgeService::RemovePreference(const std::string& key) {
+  if (!initialized_) {
+    return absl::FailedPreconditionError("Service not initialized");
+  }
+  
+  preferences_.erase(key);
+  return SavePreferences();
+}
+
+// === ROM Pattern Learning ===
+
+absl::Status LearnedKnowledgeService::LearnPattern(const std::string& type,
+                                                   const std::string& rom_hash,
+                                                   const std::string& data,
+                                                   float confidence) {
+  if (!initialized_) {
+    return absl::FailedPreconditionError("Service not initialized");
+  }
+  
+  ROMPattern pattern;
+  pattern.pattern_type = type;
+  pattern.rom_hash = rom_hash;
+  pattern.pattern_data = data;
+  pattern.confidence = confidence;
+  pattern.learned_at = CurrentTimestamp();
+  pattern.access_count = 1;
+  
+  patterns_.push_back(pattern);
+  return SavePatterns();
+}
+
+std::vector<LearnedKnowledgeService::ROMPattern>
+LearnedKnowledgeService::QueryPatterns(const std::string& type,
+                                      const std::string& rom_hash) const {
+  std::vector<ROMPattern> results;
+  
+  for (const auto& pattern : patterns_) {
+    bool type_match = type.empty() || pattern.pattern_type == type;
+    bool hash_match = rom_hash.empty() || pattern.rom_hash == rom_hash;
+    
+    if (type_match && hash_match) {
+      results.push_back(pattern);
+    }
+  }
+  
+  return results;
+}
+
+absl::Status LearnedKnowledgeService::UpdatePatternConfidence(
+    const std::string& type,
+    const std::string& rom_hash,
+    float new_confidence) {
+  bool found = false;
+  
+  for (auto& pattern : patterns_) {
+    if (pattern.pattern_type == type && pattern.rom_hash == rom_hash) {
+      pattern.confidence = new_confidence;
+      pattern.access_count++;
+      found = true;
+    }
+  }
+  
+  if (!found) {
+    return absl::NotFoundError("Pattern not found");
+  }
+  
+  return SavePatterns();
+}
+
+// === Project Context ===
+
+absl::Status LearnedKnowledgeService::SaveProjectContext(
+    const std::string& project_name,
+    const std::string& rom_hash,
+    const std::string& context) {
+  if (!initialized_) {
+    return absl::FailedPreconditionError("Service not initialized");
+  }
+  
+  // Update existing or create new
+  bool found = false;
+  for (auto& project : projects_) {
+    if (project.project_name == project_name) {
+      project.rom_hash = rom_hash;
+      project.context_data = context;
+      project.last_accessed = CurrentTimestamp();
+      found = true;
+      break;
+    }
+  }
+  
+  if (!found) {
+    ProjectContext project;
+    project.project_name = project_name;
+    project.rom_hash = rom_hash;
+    project.context_data = context;
+    project.last_accessed = CurrentTimestamp();
+    projects_.push_back(project);
+  }
+  
+  return SaveProjects();
+}
+
+std::optional<LearnedKnowledgeService::ProjectContext>
+LearnedKnowledgeService::GetProjectContext(const std::string& project_name) const {
+  for (const auto& project : projects_) {
+    if (project.project_name == project_name) {
+      return project;
+    }
+  }
+  return std::nullopt;
+}
+
+std::vector<LearnedKnowledgeService::ProjectContext>
+LearnedKnowledgeService::GetAllProjects() const {
+  return projects_;
+}
+
+// === Conversation Memory ===
+
+absl::Status LearnedKnowledgeService::StoreConversationSummary(
+    const std::string& topic,
+    const std::string& summary,
+    const std::vector<std::string>& key_facts) {
+  if (!initialized_) {
+    return absl::FailedPreconditionError("Service not initialized");
+  }
+  
+  ConversationMemory memory;
+  memory.id = GenerateRandomID();
+  memory.topic = topic;
+  memory.summary = summary;
+  memory.key_facts = key_facts;
+  memory.created_at = CurrentTimestamp();
+  memory.access_count = 1;
+  
+  memories_.push_back(memory);
+  
+  // Keep only last 100 memories
+  if (memories_.size() > 100) {
+    memories_.erase(memories_.begin());
+  }
+  
+  return SaveMemories();
+}
+
+std::vector<LearnedKnowledgeService::ConversationMemory>
+LearnedKnowledgeService::SearchMemories(const std::string& query) const {
+  std::vector<ConversationMemory> results;
+  
+  std::string query_lower = query;
+  std::transform(query_lower.begin(), query_lower.end(), query_lower.begin(), ::tolower);
+  
+  for (const auto& memory : memories_) {
+    std::string topic_lower = memory.topic;
+    std::string summary_lower = memory.summary;
+    std::transform(topic_lower.begin(), topic_lower.end(), topic_lower.begin(), ::tolower);
+    std::transform(summary_lower.begin(), summary_lower.end(), summary_lower.begin(), ::tolower);
+    
+    if (topic_lower.find(query_lower) != std::string::npos ||
+        summary_lower.find(query_lower) != std::string::npos) {
+      results.push_back(memory);
+    }
+  }
+  
+  return results;
+}
+
+std::vector<LearnedKnowledgeService::ConversationMemory>
+LearnedKnowledgeService::GetRecentMemories(int limit) const {
+  std::vector<ConversationMemory> recent = memories_;
+  
+  // Sort by created_at descending
+  std::sort(recent.begin(), recent.end(),
+           [](const ConversationMemory& a, const ConversationMemory& b) {
+             return a.created_at > b.created_at;
+           });
+  
+  if (recent.size() > static_cast<size_t>(limit)) {
+    recent.resize(limit);
+  }
+  
+  return recent;
+}
+
+// === Import/Export ===
+
+#ifdef YAZE_WITH_JSON
+absl::StatusOr<std::string> LearnedKnowledgeService::ExportToJSON() const {
+  nlohmann::json export_data;
+  
+  // Export preferences
+  export_data["preferences"] = preferences_;
+  
+  // Export patterns
+  export_data["patterns"] = nlohmann::json::array();
+  for (const auto& pattern : patterns_) {
+    nlohmann::json p;
+    p["type"] = pattern.pattern_type;
+    p["rom_hash"] = pattern.rom_hash;
+    p["data"] = pattern.pattern_data;
+    p["confidence"] = pattern.confidence;
+    p["learned_at"] = pattern.learned_at;
+    p["access_count"] = pattern.access_count;
+    export_data["patterns"].push_back(p);
+  }
+  
+  // Export projects
+  export_data["projects"] = nlohmann::json::array();
+  for (const auto& project : projects_) {
+    nlohmann::json p;
+    p["name"] = project.project_name;
+    p["rom_hash"] = project.rom_hash;
+    p["context"] = project.context_data;
+    p["last_accessed"] = project.last_accessed;
+    export_data["projects"].push_back(p);
+  }
+  
+  // Export memories
+  export_data["memories"] = nlohmann::json::array();
+  for (const auto& memory : memories_) {
+    nlohmann::json m;
+    m["id"] = memory.id;
+    m["topic"] = memory.topic;
+    m["summary"] = memory.summary;
+    m["key_facts"] = memory.key_facts;
+    m["created_at"] = memory.created_at;
+    m["access_count"] = memory.access_count;
+    export_data["memories"].push_back(m);
+  }
+  
+  return export_data.dump(2);
+}
+
+absl::Status LearnedKnowledgeService::ImportFromJSON(const std::string& json_data) {
+  try {
+    auto data = nlohmann::json::parse(json_data);
+    
+    // Import preferences
+    if (data.contains("preferences")) {
+      for (const auto& [key, value] : data["preferences"].items()) {
+        preferences_[key] = value.get<std::string>();
+      }
+    }
+    
+    // Import patterns
+    if (data.contains("patterns")) {
+      for (const auto& p : data["patterns"]) {
+        ROMPattern pattern;
+        pattern.pattern_type = p["type"];
+        pattern.rom_hash = p["rom_hash"];
+        pattern.pattern_data = p["data"];
+        pattern.confidence = p["confidence"];
+        pattern.learned_at = p["learned_at"];
+        pattern.access_count = p["access_count"];
+        patterns_.push_back(pattern);
+      }
+    }
+    
+    // Import projects
+    if (data.contains("projects")) {
+      for (const auto& p : data["projects"]) {
+        ProjectContext project;
+        project.project_name = p["name"];
+        project.rom_hash = p["rom_hash"];
+        project.context_data = p["context"];
+        project.last_accessed = p["last_accessed"];
+        projects_.push_back(project);
+      }
+    }
+    
+    // Import memories
+    if (data.contains("memories")) {
+      for (const auto& m : data["memories"]) {
+        ConversationMemory memory;
+        memory.id = m["id"];
+        memory.topic = m["topic"];
+        memory.summary = m["summary"];
+        memory.key_facts = m["key_facts"].get<std::vector<std::string>>();
+        memory.created_at = m["created_at"];
+        memory.access_count = m["access_count"];
+        memories_.push_back(memory);
+      }
+    }
+    
+    return SaveAll();
+  } catch (const std::exception& e) {
+    return absl::InternalError(absl::StrCat("JSON parse error: ", e.what()));
+  }
+}
+#else
+absl::StatusOr<std::string> LearnedKnowledgeService::ExportToJSON() const {
+  return absl::UnimplementedError("JSON support not enabled. Build with -DYAZE_WITH_JSON=ON");
+}
+
+absl::Status LearnedKnowledgeService::ImportFromJSON(const std::string&) {
+  return absl::UnimplementedError("JSON support not enabled. Build with -DYAZE_WITH_JSON=ON");
+}
+#endif
+
+absl::Status LearnedKnowledgeService::ClearAll() {
+  preferences_.clear();
+  patterns_.clear();
+  projects_.clear();
+  memories_.clear();
+  return SaveAll();
+}
+
+// === Statistics ===
+
+LearnedKnowledgeService::Stats LearnedKnowledgeService::GetStats() const {
+  Stats stats;
+  stats.preference_count = preferences_.size();
+  stats.pattern_count = patterns_.size();
+  stats.project_count = projects_.size();
+  stats.memory_count = memories_.size();
+  
+  // Find earliest learned_at
+  int64_t earliest = CurrentTimestamp();
+  for (const auto& pattern : patterns_) {
+    if (pattern.learned_at < earliest) {
+      earliest = pattern.learned_at;
+    }
+  }
+  for (const auto& memory : memories_) {
+    if (memory.created_at < earliest) {
+      earliest = memory.created_at;
+    }
+  }
+  stats.first_learned_at = earliest;
+  
+  // Last updated is now
+  stats.last_updated_at = CurrentTimestamp();
+  
+  return stats;
+}
+
+// === Internal Helpers ===
+
+#ifdef YAZE_WITH_JSON
+absl::Status LearnedKnowledgeService::LoadPreferences() {
+  if (!FileExists(prefs_file_)) {
+    return absl::OkStatus();  // No file yet, empty preferences
+  }
+  
+  try {
+    std::ifstream file(prefs_file_);
+    if (!file.is_open()) {
+      return absl::InternalError("Failed to open preferences file");
+    }
+    
+    nlohmann::json data;
+    file >> data;
+    
+    for (const auto& [key, value] : data.items()) {
+      preferences_[key] = value.get<std::string>();
+    }
+    
+    return absl::OkStatus();
+  } catch (const std::exception& e) {
+    return absl::InternalError(absl::StrCat("Failed to load preferences: ", e.what()));
+  }
+}
+
+absl::Status LearnedKnowledgeService::SavePreferences() {
+  try {
+    nlohmann::json data = preferences_;
+    
+    std::ofstream file(prefs_file_);
+    if (!file.is_open()) {
+      return absl::InternalError("Failed to open preferences file for writing");
+    }
+    
+    file << data.dump(2);
+    return absl::OkStatus();
+  } catch (const std::exception& e) {
+    return absl::InternalError(absl::StrCat("Failed to save preferences: ", e.what()));
+  }
+}
+
+absl::Status LearnedKnowledgeService::LoadPatterns() {
+  if (!FileExists(patterns_file_)) {
+    return absl::OkStatus();
+  }
+  
+  try {
+    std::ifstream file(patterns_file_);
+    nlohmann::json data;
+    file >> data;
+    
+    for (const auto& p : data) {
+      ROMPattern pattern;
+      pattern.pattern_type = p["type"];
+      pattern.rom_hash = p["rom_hash"];
+      pattern.pattern_data = p["data"];
+      pattern.confidence = p["confidence"];
+      pattern.learned_at = p["learned_at"];
+      pattern.access_count = p.value("access_count", 0);
+      patterns_.push_back(pattern);
+    }
+    
+    return absl::OkStatus();
+  } catch (const std::exception& e) {
+    return absl::InternalError(absl::StrCat("Failed to load patterns: ", e.what()));
+  }
+}
+
+absl::Status LearnedKnowledgeService::SavePatterns() {
+  try {
+    nlohmann::json data = nlohmann::json::array();
+    
+    for (const auto& pattern : patterns_) {
+      nlohmann::json p;
+      p["type"] = pattern.pattern_type;
+      p["rom_hash"] = pattern.rom_hash;
+      p["data"] = pattern.pattern_data;
+      p["confidence"] = pattern.confidence;
+      p["learned_at"] = pattern.learned_at;
+      p["access_count"] = pattern.access_count;
+      data.push_back(p);
+    }
+    
+    std::ofstream file(patterns_file_);
+    file << data.dump(2);
+    return absl::OkStatus();
+  } catch (const std::exception& e) {
+    return absl::InternalError(absl::StrCat("Failed to save patterns: ", e.what()));
+  }
+}
+
+absl::Status LearnedKnowledgeService::LoadProjects() {
+  if (!FileExists(projects_file_)) {
+    return absl::OkStatus();
+  }
+  
+  try {
+    std::ifstream file(projects_file_);
+    nlohmann::json data;
+    file >> data;
+    
+    for (const auto& p : data) {
+      ProjectContext project;
+      project.project_name = p["name"];
+      project.rom_hash = p["rom_hash"];
+      project.context_data = p["context"];
+      project.last_accessed = p["last_accessed"];
+      projects_.push_back(project);
+    }
+    
+    return absl::OkStatus();
+  } catch (const std::exception& e) {
+    return absl::InternalError(absl::StrCat("Failed to load projects: ", e.what()));
+  }
+}
+
+absl::Status LearnedKnowledgeService::SaveProjects() {
+  try {
+    nlohmann::json data = nlohmann::json::array();
+    
+    for (const auto& project : projects_) {
+      nlohmann::json p;
+      p["name"] = project.project_name;
+      p["rom_hash"] = project.rom_hash;
+      p["context"] = project.context_data;
+      p["last_accessed"] = project.last_accessed;
+      data.push_back(p);
+    }
+    
+    std::ofstream file(projects_file_);
+    file << data.dump(2);
+    return absl::OkStatus();
+  } catch (const std::exception& e) {
+    return absl::InternalError(absl::StrCat("Failed to save projects: ", e.what()));
+  }
+}
+
+absl::Status LearnedKnowledgeService::SaveMemories() {
+  try {
+    nlohmann::json data = nlohmann::json::array();
+    
+    for (const auto& memory : memories_) {
+      nlohmann::json m;
+      m["id"] = memory.id;
+      m["topic"] = memory.topic;
+      m["summary"] = memory.summary;
+      m["key_facts"] = memory.key_facts;
+      m["created_at"] = memory.created_at;
+      m["access_count"] = memory.access_count;
+      data.push_back(m);
+    }
+    
+    std::ofstream file(memories_file_);
+    file << data.dump(2);
+    return absl::OkStatus();
+  } catch (const std::exception& e) {
+    return absl::InternalError(absl::StrCat("Failed to save memories: ", e.what()));
+  }
+}
+
+absl::Status LearnedKnowledgeService::LoadMemories() {
+  if (!FileExists(memories_file_)) {
+    return absl::OkStatus();
+  }
+  
+  try {
+    std::ifstream file(memories_file_);
+    nlohmann::json data;
+    file >> data;
+    
+    for (const auto& m : data) {
+      ConversationMemory memory;
+      memory.id = m["id"];
+      memory.topic = m["topic"];
+      memory.summary = m["summary"];
+      memory.key_facts = m["key_facts"].get<std::vector<std::string>>();
+      memory.created_at = m["created_at"];
+      memory.access_count = m.value("access_count", 0);
+      memories_.push_back(memory);
+    }
+    
+    return absl::OkStatus();
+  } catch (const std::exception& e) {
+    return absl::InternalError(absl::StrCat("Failed to load memories: ", e.what()));
+  }
+}
+
+#else
+// Stub implementations when JSON is not available
+absl::Status LearnedKnowledgeService::LoadPreferences() { return absl::OkStatus(); }
+absl::Status LearnedKnowledgeService::SavePreferences() { return absl::UnimplementedError("JSON support required"); }
+absl::Status LearnedKnowledgeService::LoadPatterns() { return absl::OkStatus(); }
+absl::Status LearnedKnowledgeService::SavePatterns() { return absl::UnimplementedError("JSON support required"); }
+absl::Status LearnedKnowledgeService::LoadProjects() { return absl::OkStatus(); }
+absl::Status LearnedKnowledgeService::SaveProjects() { return absl::UnimplementedError("JSON support required"); }
+absl::Status LearnedKnowledgeService::LoadMemories() { return absl::OkStatus(); }
+absl::Status LearnedKnowledgeService::SaveMemories() { return absl::UnimplementedError("JSON support required"); }
+#endif
+
+std::string LearnedKnowledgeService::GenerateID() const {
+  return GenerateRandomID();
+}
+
+}  // namespace agent
+}  // namespace cli
+}  // namespace yaze
diff --git a/src/cli/service/agent/learned_knowledge_service.h b/src/cli/service/agent/learned_knowledge_service.h
new file mode 100644
index 00000000..a03bd67a
--- /dev/null
+++ b/src/cli/service/agent/learned_knowledge_service.h
@@ -0,0 +1,225 @@
+#ifndef YAZE_CLI_SERVICE_AGENT_LEARNED_KNOWLEDGE_SERVICE_H_
+#define YAZE_CLI_SERVICE_AGENT_LEARNED_KNOWLEDGE_SERVICE_H_
+
+#include <filesystem>
+#include <map>
+#include <optional>
+#include <string>
+#include <vector>
+
+#include "absl/status/status.h"
+#include "absl/status/statusor.h"
+
+#ifdef YAZE_WITH_JSON
+#include "nlohmann/json.hpp"
+#endif
+
+namespace yaze {
+namespace cli {
+namespace agent {
+
+/**
+ * @class LearnedKnowledgeService
+ * @brief Manages persistent learned information across agent sessions
+ * 
+ * Stores:
+ * - User preferences (default palettes, favorite tools, etc.)
+ * - ROM patterns (frequently accessed rooms, sprite placements, etc.)
+ * - Project context (ROM-specific notes, goals, custom names)
+ * - Conversation memory (summaries of past discussions)
+ */
+class LearnedKnowledgeService {
+ public:
+  LearnedKnowledgeService();
+  explicit LearnedKnowledgeService(const std::filesystem::path& data_dir);
+  
+  // Initialize the service and load existing data
+  absl::Status Initialize();
+  
+  // Save all data to disk
+  absl::Status SaveAll();
+  
+  // === Preference Management ===
+  
+  /**
+   * Set a user preference
+   * @param key Preference key (e.g., "default_palette", "preferred_tool")
+   * @param value Preference value
+   */
+  absl::Status SetPreference(const std::string& key, const std::string& value);
+  
+  /**
+   * Get a user preference
+   * @param key Preference key
+   * @return Value if exists, nullopt otherwise
+   */
+  std::optional<std::string> GetPreference(const std::string& key) const;
+  
+  /**
+   * List all preferences
+   */
+  std::map<std::string, std::string> GetAllPreferences() const;
+  
+  /**
+   * Remove a preference
+   */
+  absl::Status RemovePreference(const std::string& key);
+  
+  // === ROM Pattern Learning ===
+  
+  struct ROMPattern {
+    std::string pattern_type;  // e.g., "sprite_location", "tile_usage"
+    std::string rom_hash;
+    std::string pattern_data;  // JSON encoded
+    float confidence = 1.0f;   // 0.0 to 1.0
+    int64_t learned_at = 0;
+    int access_count = 0;
+  };
+  
+  /**
+   * Learn a pattern from the current ROM
+   * @param type Pattern type (e.g., "sprite_distribution", "room_access_frequency")
+   * @param rom_hash SHA256 hash of the ROM
+   * @param data Pattern-specific data (JSON)
+   */
+  absl::Status LearnPattern(const std::string& type, 
+                            const std::string& rom_hash,
+                            const std::string& data,
+                            float confidence = 1.0f);
+  
+  /**
+   * Query patterns for a specific ROM
+   * @param type Pattern type to query
+   * @param rom_hash ROM hash to filter by (empty = all ROMs)
+   * @return Vector of matching patterns
+   */
+  std::vector<ROMPattern> QueryPatterns(const std::string& type,
+                                        const std::string& rom_hash = "") const;
+  
+  /**
+   * Update pattern confidence/access count
+   */
+  absl::Status UpdatePatternConfidence(const std::string& type,
+                                      const std::string& rom_hash,
+                                      float new_confidence);
+  
+  // === Project Context ===
+  
+  struct ProjectContext {
+    std::string project_name;
+    std::string rom_hash;
+    std::string context_data;  // JSON encoded: description, goals, custom labels
+    int64_t last_accessed = 0;
+  };
+  
+  /**
+   * Save context for a project/ROM
+   */
+  absl::Status SaveProjectContext(const std::string& project_name,
+                                  const std::string& rom_hash,
+                                  const std::string& context);
+  
+  /**
+   * Get project context
+   */
+  std::optional<ProjectContext> GetProjectContext(const std::string& project_name) const;
+  
+  /**
+   * List all projects
+   */
+  std::vector<ProjectContext> GetAllProjects() const;
+  
+  // === Conversation Memory ===
+  
+  struct ConversationMemory {
+    std::string id;
+    std::string topic;
+    std::string summary;
+    std::vector<std::string> key_facts;
+    int64_t created_at = 0;
+    int access_count = 0;
+  };
+  
+  /**
+   * Store a conversation summary
+   * @param topic Topic/theme of the conversation
+   * @param summary Brief summary
+   * @param key_facts Important facts extracted
+   */
+  absl::Status StoreConversationSummary(const std::string& topic,
+                                        const std::string& summary,
+                                        const std::vector<std::string>& key_facts);
+  
+  /**
+   * Search conversation memories by topic/keyword
+   */
+  std::vector<ConversationMemory> SearchMemories(const std::string& query) const;
+  
+  /**
+   * Get most recent conversation memories
+   */
+  std::vector<ConversationMemory> GetRecentMemories(int limit = 10) const;
+  
+  // === Import/Export ===
+  
+  /**
+   * Export all learned data to JSON
+   */
+  absl::StatusOr<std::string> ExportToJSON() const;
+  
+  /**
+   * Import learned data from JSON
+   */
+  absl::Status ImportFromJSON(const std::string& json_data);
+  
+  /**
+   * Clear all learned data
+   */
+  absl::Status ClearAll();
+  
+  // === Statistics ===
+  
+  struct Stats {
+    int preference_count = 0;
+    int pattern_count = 0;
+    int project_count = 0;
+    int memory_count = 0;
+    int64_t first_learned_at = 0;
+    int64_t last_updated_at = 0;
+  };
+  
+  Stats GetStats() const;
+  
+ private:
+  std::filesystem::path data_dir_;
+  std::filesystem::path prefs_file_;
+  std::filesystem::path patterns_file_;
+  std::filesystem::path projects_file_;
+  std::filesystem::path memories_file_;
+  
+  std::map<std::string, std::string> preferences_;
+  std::vector<ROMPattern> patterns_;
+  std::vector<ProjectContext> projects_;
+  std::vector<ConversationMemory> memories_;
+  
+  bool initialized_ = false;
+  
+  // Internal helpers
+  absl::Status LoadPreferences();
+  absl::Status LoadPatterns();
+  absl::Status LoadProjects();
+  absl::Status LoadMemories();
+  
+  absl::Status SavePreferences();
+  absl::Status SavePatterns();
+  absl::Status SaveProjects();
+  absl:Status SaveMemories();
+  
+  std::string GenerateID() const;
+};
+
+}  // namespace agent
+}  // namespace cli
+}  // namespace yaze
+
+#endif  // YAZE_CLI_SERVICE_AGENT_LEARNED_KNOWLEDGE_SERVICE_H_