diff --git a/CLAUDE.md b/CLAUDE.md
index 02308bc..08386ea 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -233,7 +233,7 @@ blocked_commands:
 - Scripts: `./scripts/build.sh` matches the script by name from any directory
 
 **Limits:**
-- Maximum 50 commands per project config
+- Maximum 100 commands per project config
 - Blocklisted commands (sudo, dd, shutdown, etc.) can NEVER be allowed
 - Org-level blocked commands cannot be overridden by project configs
 
diff --git a/examples/OPTIMIZE_CONFIG.md b/examples/OPTIMIZE_CONFIG.md
new file mode 100644
index 0000000..2fea54a
--- /dev/null
+++ b/examples/OPTIMIZE_CONFIG.md
@@ -0,0 +1,230 @@
+# How to Optimize Your allowed_commands.yaml
+
+## The Problem
+
+Your config might have redundant commands like this:
+
+```yaml
+commands:
+  - name: flutter
+  - name: flutter*           # ← This already covers EVERYTHING below!
+  - name: flutter test       # ← Redundant
+  - name: flutter test --coverage  # ← Redundant
+  - name: flutter build apk        # ← Redundant
+  - name: flutter build ios        # ← Redundant
+  # ... 20+ more flutter commands
+```
+
+**Result:** 65 commands when you only need ~10-15
+
+## How Wildcards Work
+
+When you have `flutter*`, it matches:
+- ✅ `flutter` (the base command)
+- ✅ `flutter test`
+- ✅ `flutter test --coverage`
+- ✅ `flutter build apk`
+- ✅ `flutter build ios`
+- ✅ `flutter run`
+- ✅ **ANY command starting with "flutter"**
+
+**You don't need to list every subcommand separately!**
+
+## Example: GOD-APP Optimization
+
+### Before (65 commands)
+```yaml
+commands:
+  # Flutter
+  - name: flutter
+  - name: flutter*
+  - name: flutter test
+  - name: flutter test --coverage
+  - name: flutter test --exclude-tags=golden,integration
+  - name: flutter test --tags=golden
+  - name: flutter test --tags=golden --update-goldens
+  - name: flutter test --verbose
+  - name: flutter drive
+  - name: flutter test integration_test/
+  - name: flutter build apk
+  - name: flutter build apk --debug
+  - name: flutter build apk --release
+  - name: flutter build appbundle
+  - name: flutter build ios
+  - name: flutter build ios --debug
+  - name: flutter build ipa
+  - name: flutter build web
+  - name: flutter pub get
+  - name: flutter pub upgrade
+  - name: flutter doctor
+  - name: flutter clean
+  # ... and more
+
+  # Dart
+  - name: dart
+  - name: dartfmt
+  - name: dartanalyzer
+  - name: dart format
+  - name: dart analyze
+  - name: dart fix
+  - name: dart pub
+```
+
+### After (15 commands) ✨
+```yaml
+commands:
+  # Flutter & Dart (wildcards cover all subcommands)
+  - name: flutter*
+    description: All Flutter SDK commands
+
+  - name: dart*
+    description: All Dart language tools
+
+  # Testing tools
+  - name: patrol
+    description: Patrol integration testing (if needed separately)
+
+  # Coverage tools
+  - name: lcov
+    description: Code coverage tool
+
+  - name: genhtml
+    description: Generate HTML coverage reports
+
+  # Android tools
+  - name: adb*
+    description: Android Debug Bridge commands
+
+  - name: gradle*
+    description: Gradle build system
+
+  # iOS tools (macOS only)
+  - name: xcrun*
+    description: Xcode developer tools
+
+  - name: xcodebuild
+    description: Xcode build system
+
+  - name: simctl
+    description: iOS Simulator control
+
+  - name: ios-deploy
+    description: Deploy to iOS devices
+
+  # Project scripts
+  - name: ./scripts/*.sh
+    description: All project build/test scripts
+```
+
+**Reduced from 65 → 15 commands (77% reduction!)**
+
+## Optimization Checklist
+
+For each group of commands, ask:
+
+### ❓ "Do I have the base command AND a wildcard?"
+```yaml
+# Bad (redundant)
+- name: flutter
+- name: flutter*
+
+# Good (just the wildcard)
+- name: flutter*
+```
+
+The wildcard already matches the base command!
+
+### ❓ "Am I listing subcommands individually?"
+```yaml
+# Bad (verbose)
+- name: flutter test
+- name: flutter test --coverage
+- name: flutter build apk
+- name: flutter run
+
+# Good (one wildcard)
+- name: flutter*
+```
+
+### ❓ "Can I group multiple scripts?"
+```yaml
+# If you can't use wildcards for scripts, at least group them logically
+- name: ./scripts/test.sh
+- name: ./scripts/build.sh
+- name: ./scripts/integration_test.sh
+```
+
+These are fine - scripts need explicit paths. But if you have 20+ scripts, consider if they're all necessary.
+
+## Common Wildcards
+
+| Instead of... | Use... | Covers |
+|---------------|--------|--------|
+| flutter, flutter test, flutter build, flutter run | `flutter*` | All flutter commands |
+| dart, dart format, dart analyze, dart pub | `dart*` | All dart commands |
+| npm, npm install, npm run, npm test | `npm*` | All npm commands |
+| cargo, cargo build, cargo test, cargo run | `cargo*` | All cargo commands |
+| git, git status, git commit, git push | Just `git` | Git is in global defaults |
+
+## When NOT to Optimize
+
+Keep separate entries when:
+1. **Different base commands:** `swift` and `swiftc` are different (though `swift*` covers both)
+2. **Documentation clarity:** Sometimes listing helps future developers understand what's needed
+3. **Argument restrictions (Phase 3):** If you'll add argument validation later
+
+## Quick Optimization Script
+
+To see what you can reduce:
+
+```bash
+# Count commands by prefix
+grep "^  - name:" .autocoder/allowed_commands.yaml | \
+  sed 's/^  - name: //' | \
+  cut -d' ' -f1 | \
+  sort | uniq -c | sort -rn
+```
+
+If you see multiple commands with the same prefix, use a wildcard!
+
+## UI Feedback (Future Enhancement)
+
+Great suggestion! Here's what a UI could show:
+
+```
+⚠️  Config Optimization Available
+
+Your config has 65 commands. We detected opportunities to reduce it:
+
+• 25 flutter commands → Use flutter* (saves 24 entries)
+• 8 dart commands → Use dart* (saves 7 entries)
+• 12 adb commands → Use adb* (saves 11 entries)
+
+[Optimize Automatically] [Keep As-Is]
+
+Potential reduction: 65 → 23 commands
+```
+
+Or during config editing:
+
+```
+📊 Command Usage Stats
+
+flutter*        : 25 subcommands detected
+dart*           : 8 subcommands detected
+./scripts/*.sh  : 7 scripts detected
+
+💡 Tip: Using wildcards covers all subcommands automatically
+```
+
+**This would be a great addition to Phase 3 or beyond!**
+
+## Your GOD-APP Optimization
+
+Here's what you could do:
+
+**Current:** 65 commands (exceeds 50 limit, config rejected!)
+
+**Optimized:** ~15 commands using wildcards
+
+Would you like me to create an optimized version of your GOD-APP config?
diff --git a/examples/README.md b/examples/README.md
index b995f5e..4f228db 100644
--- a/examples/README.md
+++ b/examples/README.md
@@ -72,7 +72,7 @@ commands:
 - ✅ Temporary tools needed during development
 
 **Limits:**
-- Maximum 50 commands per project
+- Maximum 100 commands per project
 - Cannot override org-level blocked commands
 - Cannot allow hardcoded blocklist commands (sudo, dd, etc.)
 
@@ -321,13 +321,13 @@ blocked_commands: []  # Rely on hardcoded blocklist only
    - Bad: Adding `xcodebuild` to org config when only one project uses it
    - Good: Add `xcodebuild` to that project's config
 
-4. **Don't exceed the 50 command limit per project**
-   - If you need more, you're probably being too specific
-   - Use wildcards instead: `npm-*` covers many npm tools
+4. **Don't exceed the 100 command limit per project**
+   - If you need more, you're probably listing subcommands unnecessarily
+   - Use wildcards instead: `flutter*` covers all flutter commands, not just the base
 
 5. **Don't ignore validation errors**
    - If your YAML is rejected, fix the structure
-   - Common issues: missing `version`, malformed lists, over 50 commands
+   - Common issues: missing `version`, malformed lists, over 100 commands
 
 ---
 
diff --git a/examples/project_allowed_commands.yaml b/examples/project_allowed_commands.yaml
index 48b8bd6..2a3bdf5 100644
--- a/examples/project_allowed_commands.yaml
+++ b/examples/project_allowed_commands.yaml
@@ -113,7 +113,7 @@ commands: []
 #   - Scripts: "./scripts/build.sh" matches the script by name
 #
 # Limits:
-#   - Maximum 50 commands per project
+#   - Maximum 100 commands per project
 #   - Commands in the blocklist (sudo, dd, shutdown, etc.) can NEVER be allowed
 #   - Org-level blocked commands (see ~/.autocoder/config.yaml) cannot be overridden
 #
diff --git a/security.py b/security.py
index a73a2e9..17f9ee2 100644
--- a/security.py
+++ b/security.py
@@ -491,8 +491,8 @@ def load_project_commands(project_dir: Path) -> Optional[dict]:
         if not isinstance(commands, list):
             return None
 
-        # Enforce 50 command limit
-        if len(commands) > 50:
+        # Enforce 100 command limit
+        if len(commands) > 100:
             return None
 
         # Validate each command entry
diff --git a/test_security.py b/test_security.py
index 3af10cf..8f1f757 100644
--- a/test_security.py
+++ b/test_security.py
@@ -263,8 +263,8 @@ commands:
             print(f"         Got: {config}")
             failed += 1
 
-        # Test 4: Over limit (50 commands)
-        commands = [f"  - name: cmd{i}\n    description: Command {i}" for i in range(51)]
+        # Test 4: Over limit (100 commands)
+        commands = [f"  - name: cmd{i}\n    description: Command {i}" for i in range(101)]
         config_path.write_text("version: 1\ncommands:\n" + "\n".join(commands))
         config = load_project_commands(project_dir)
         if config is None:
diff --git a/test_security_integration.py b/test_security_integration.py
index 4a13329..f4ded43 100644
--- a/test_security_integration.py
+++ b/test_security_integration.py
@@ -326,21 +326,21 @@ def test_invalid_yaml_ignored():
             return False
 
 
-def test_50_command_limit():
-    """Test that configs with >50 commands are rejected."""
+def test_100_command_limit():
+    """Test that configs with >100 commands are rejected."""
     print("\n" + "=" * 70)
-    print("TEST 9: 50 command limit enforced")
+    print("TEST 9: 100 command limit enforced")
     print("=" * 70)
 
     with tempfile.TemporaryDirectory() as tmpdir:
         project_dir = Path(tmpdir)
 
-        # Create config with 51 commands
+        # Create config with 101 commands
         autocoder_dir = project_dir / ".autocoder"
         autocoder_dir.mkdir()
 
         commands = [
-            f"  - name: cmd{i}\n    description: Command {i}" for i in range(51)
+            f"  - name: cmd{i}\n    description: Command {i}" for i in range(101)
         ]
         (autocoder_dir / "allowed_commands.yaml").write_text(
             "version: 1\ncommands:\n" + "\n".join(commands)
@@ -353,10 +353,10 @@ def test_50_command_limit():
         result = asyncio.run(bash_security_hook(input_data, context=context))
 
         if result.get("decision") == "block":
-            print("✅ PASS: Config with >50 commands rejected")
+            print("✅ PASS: Config with >100 commands rejected")
             return True
         else:
-            print("❌ FAIL: Config with >50 commands should be rejected")
+            print("❌ FAIL: Config with >100 commands should be rejected")
             return False
 
 
@@ -376,7 +376,7 @@ def main():
         test_org_blocklist_enforcement,
         test_org_allowlist_inheritance,
         test_invalid_yaml_ignored,
-        test_50_command_limit,
+        test_100_command_limit,
     ]
 
     passed = 0