diff --git a/apps/backend/cli/utils.py b/apps/backend/cli/utils.py
index 25b92ca2..b9969020 100644
--- a/apps/backend/cli/utils.py
+++ b/apps/backend/cli/utils.py
@@ -15,7 +15,46 @@ if str(_PARENT_DIR) not in sys.path:
     sys.path.insert(0, str(_PARENT_DIR))
 
 from core.auth import get_auth_token, get_auth_token_source
-from dotenv import load_dotenv
+
+
+def import_dotenv():
+    """
+    Import and return load_dotenv with helpful error message if not installed.
+
+    This centralized function ensures consistent error messaging across all
+    runner scripts when python-dotenv is not available.
+
+    Returns:
+        The load_dotenv function
+
+    Raises:
+        SystemExit: If dotenv cannot be imported, with helpful installation instructions.
+    """
+    try:
+        from dotenv import load_dotenv as _load_dotenv
+
+        return _load_dotenv
+    except ImportError:
+        sys.exit(
+            "Error: Required Python package 'python-dotenv' is not installed.\n"
+            "\n"
+            "This usually means you're not using the virtual environment.\n"
+            "\n"
+            "To fix this:\n"
+            "1. From the 'apps/backend/' directory, activate the venv:\n"
+            "   source .venv/bin/activate  # Linux/macOS\n"
+            "   .venv\\Scripts\\activate   # Windows\n"
+            "\n"
+            "2. Or install dependencies directly:\n"
+            "   pip install python-dotenv\n"
+            "   pip install -r requirements.txt\n"
+            "\n"
+            f"Current Python: {sys.executable}\n"
+        )
+
+
+# Load .env with helpful error if dependencies not installed
+load_dotenv = import_dotenv()
 from graphiti_config import get_graphiti_status
 from linear_integration import LinearManager
 from linear_updater import is_linear_enabled
diff --git a/apps/backend/runners/github/runner.py b/apps/backend/runners/github/runner.py
index 669030e4..b3934cdc 100644
--- a/apps/backend/runners/github/runner.py
+++ b/apps/backend/runners/github/runner.py
@@ -56,8 +56,10 @@ if sys.platform == "win32":
 # Add backend to path
 sys.path.insert(0, str(Path(__file__).parent.parent.parent))
 
-# Load .env file
-from dotenv import load_dotenv
+# Load .env file with centralized error handling
+from cli.utils import import_dotenv
+
+load_dotenv = import_dotenv()
 
 env_file = Path(__file__).parent.parent.parent / ".env"
 if env_file.exists():
diff --git a/apps/backend/runners/gitlab/runner.py b/apps/backend/runners/gitlab/runner.py
index c2a0be32..d4f61827 100644
--- a/apps/backend/runners/gitlab/runner.py
+++ b/apps/backend/runners/gitlab/runner.py
@@ -26,8 +26,10 @@ from pathlib import Path
 # Add backend to path
 sys.path.insert(0, str(Path(__file__).parent.parent.parent))
 
-# Load .env file
-from dotenv import load_dotenv
+# Load .env file with centralized error handling
+from cli.utils import import_dotenv
+
+load_dotenv = import_dotenv()
 
 env_file = Path(__file__).parent.parent.parent / ".env"
 if env_file.exists():
diff --git a/apps/backend/runners/ideation_runner.py b/apps/backend/runners/ideation_runner.py
index 4e74f683..9b914456 100644
--- a/apps/backend/runners/ideation_runner.py
+++ b/apps/backend/runners/ideation_runner.py
@@ -26,8 +26,10 @@ from pathlib import Path
 # Add auto-claude to path
 sys.path.insert(0, str(Path(__file__).parent.parent))
 
-# Load .env file from auto-claude/ directory
-from dotenv import load_dotenv
+# Load .env file with centralized error handling
+from cli.utils import import_dotenv
+
+load_dotenv = import_dotenv()
 
 env_file = Path(__file__).parent.parent / ".env"
 if env_file.exists():
diff --git a/apps/backend/runners/insights_runner.py b/apps/backend/runners/insights_runner.py
index 22c2d9ad..bd4bf362 100644
--- a/apps/backend/runners/insights_runner.py
+++ b/apps/backend/runners/insights_runner.py
@@ -15,8 +15,10 @@ from pathlib import Path
 # Add auto-claude to path
 sys.path.insert(0, str(Path(__file__).parent.parent))
 
-# Load .env file from auto-claude/ directory
-from dotenv import load_dotenv
+# Load .env file with centralized error handling
+from cli.utils import import_dotenv
+
+load_dotenv = import_dotenv()
 
 env_file = Path(__file__).parent.parent / ".env"
 if env_file.exists():
diff --git a/apps/backend/runners/roadmap_runner.py b/apps/backend/runners/roadmap_runner.py
index 4a31c025..06625add 100644
--- a/apps/backend/runners/roadmap_runner.py
+++ b/apps/backend/runners/roadmap_runner.py
@@ -20,8 +20,10 @@ from pathlib import Path
 # Add auto-claude to path
 sys.path.insert(0, str(Path(__file__).parent.parent))
 
-# Load .env file from auto-claude/ directory
-from dotenv import load_dotenv
+# Load .env file with centralized error handling
+from cli.utils import import_dotenv
+
+load_dotenv = import_dotenv()
 
 env_file = Path(__file__).parent.parent / ".env"
 if env_file.exists():
diff --git a/apps/backend/runners/spec_runner.py b/apps/backend/runners/spec_runner.py
index 0bda6db1..4c5a4bba 100644
--- a/apps/backend/runners/spec_runner.py
+++ b/apps/backend/runners/spec_runner.py
@@ -26,11 +26,11 @@ The AI considers:
 - Risk factors and edge cases
 
 Usage:
-    python auto-claude/spec_runner.py --task "Add user authentication"
-    python auto-claude/spec_runner.py --interactive
-    python auto-claude/spec_runner.py --continue 001-feature
-    python auto-claude/spec_runner.py --task "Fix button color" --complexity simple
-    python auto-claude/spec_runner.py --task "Simple fix" --no-ai-assessment
+    python runners/spec_runner.py --task "Add user authentication"
+    python runners/spec_runner.py --interactive
+    python runners/spec_runner.py --continue 001-feature
+    python runners/spec_runner.py --task "Fix button color" --complexity simple
+    python runners/spec_runner.py --task "Simple fix" --no-ai-assessment
 """
 
 import sys
@@ -81,8 +81,10 @@ if sys.platform == "win32":
 # Add auto-claude to path (parent of runners/)
 sys.path.insert(0, str(Path(__file__).parent.parent))
 
-# Load .env file
-from dotenv import load_dotenv
+# Load .env file with centralized error handling
+from cli.utils import import_dotenv
+
+load_dotenv = import_dotenv()
 
 env_file = Path(__file__).parent.parent / ".env"
 dev_env_file = Path(__file__).parent.parent.parent / "dev" / "auto-claude" / ".env"
diff --git a/guides/CLI-USAGE.md b/guides/CLI-USAGE.md
index c0c50785..dd41f507 100644
--- a/guides/CLI-USAGE.md
+++ b/guides/CLI-USAGE.md
@@ -74,16 +74,16 @@ All commands below should be run from the `apps/backend/` directory:
 source .venv/bin/activate
 
 # Create a spec interactively
-python spec_runner.py --interactive
+python runners/spec_runner.py --interactive
 
 # Or with a task description
-python spec_runner.py --task "Add user authentication with OAuth"
+python runners/spec_runner.py --task "Add user authentication with OAuth"
 
 # Force a specific complexity level
-python spec_runner.py --task "Fix button color" --complexity simple
+python runners/spec_runner.py --task "Fix button color" --complexity simple
 
 # Continue an interrupted spec
-python spec_runner.py --continue 001-feature
+python runners/spec_runner.py --continue 001-feature
 ```
 
 ### Complexity Tiers