diff --git a/Makefile b/Makefile
index 828b8837..9d06b8d6 100644
--- a/Makefile
+++ b/Makefile
@@ -93,10 +93,10 @@ dev: install
 test: $(VENV)/bin/activate
 	@echo "🧪 Running tests..."
 	@if [ -f $(VENV)/bin/pytest ]; then \
-		$(VENV)/bin/pytest tests/ -v; \
+		PYTHONPATH=. $(VENV)/bin/pytest tests/ -v; \
 	else \
-		$(VENV_PYTHON) -m pytest tests/ -v 2>/dev/null || \
-		$(VENV_PYTHON) -m unittest discover tests/ -v; \
+		PYTHONPATH=. $(VENV_PYTHON) -m pytest tests/ -v 2>/dev/null || \
+		PYTHONPATH=. $(VENV_PYTHON) -m unittest discover tests/ -v; \
 	fi
 
 # Build the package
@@ -229,20 +229,20 @@ WORKSPACE_DIR := .markitect_workspace
 CURRENT_ISSUE_FILE := $(WORKSPACE_DIR)/current_issue.json
 
 # List all gitea issues
-list-issues:
-	@python3 tddai_cli.py list-issues
+list-issues: $(VENV)/bin/activate
+	@PYTHONPATH=. $(VENV_PYTHON) tddai_cli.py list-issues
 
 # Show detailed view of a specific issue
-show-issue:
+show-issue: $(VENV)/bin/activate
 	@if [ -z "$(NUM)" ]; then \
 		echo "❌ Please specify issue number: make show-issue NUM=5"; \
 		exit 1; \
 	fi
-	@python3 tddai_cli.py show-issue $(NUM)
+	@PYTHONPATH=. $(VENV_PYTHON) tddai_cli.py show-issue $(NUM)
 
 # List only open issues (active backlog)
-list-open-issues:
-	@python3 tddai_cli.py list-open-issues
+list-open-issues: $(VENV)/bin/activate
+	@PYTHONPATH=. $(VENV_PYTHON) tddai_cli.py list-open-issues
 
 # Generate test skeleton from gitea issue (requires Claude Code)
 test-from-issue:
@@ -268,21 +268,21 @@ test-from-issue:
 	@curl -s "$(ISSUES_API)/$(NUM)" | jq -r 'if .title then "✅ Issue #$(NUM): " + .title + "\n\n🧪 Generating test skeleton...\n   Please ask Claude Code to generate a test for this issue:\n\n   Command: '"'"'Generate a test skeleton for issue #$(NUM)'"'"'\n\n📋 Issue Details:\n   Title: " + .title + "\n   Description: " + .body + "\n\n📝 Test Requirements:\n   - Follow TDD principles (test first, then implementation)\n   - Use pytest framework (existing project convention)\n   - Place test in tests/ directory\n   - Name test file: test_issue_$(NUM)_*.py\n   - Include docstring referencing issue #$(NUM)\n   - Test should initially fail (red state)\n\n💡 After generation, run '"'"'make test'"'"' to verify test fails initially" else "❌ Issue #$(NUM) not found or API error\n   Use '"'"'make list-open-issues'"'"' to see available issues" end' 2>/dev/null || echo "❌ Issue #$(NUM) not found or API error"
 
 # Start working on an issue (creates workspace)
-start-issue:
+start-issue: $(VENV)/bin/activate
 	@if [ -z "$(NUM)" ]; then \
 		echo "❌ Please specify issue number: make start-issue NUM=1"; \
 		exit 1; \
 	fi
-	@python3 tddai_cli.py start-issue $(NUM)
+	@PYTHONPATH=. $(VENV_PYTHON) tddai_cli.py start-issue $(NUM)
 
 # Add test to current issue workspace
-add-test:
-	@python3 tddai_cli.py add-test
+add-test: $(VENV)/bin/activate
+	@PYTHONPATH=. $(VENV_PYTHON) tddai_cli.py add-test
 
 # Show current workspace status
-workspace-status:
-	@python3 tddai_cli.py workspace-status
+workspace-status: $(VENV)/bin/activate
+	@PYTHONPATH=. $(VENV_PYTHON) tddai_cli.py workspace-status
 
 # Complete issue work (move tests to main and cleanup)
-finish-issue:
-	@python3 tddai_cli.py finish-issue
+finish-issue: $(VENV)/bin/activate
+	@PYTHONPATH=. $(VENV_PYTHON) tddai_cli.py finish-issue