diff --git a/pyrit/cli/frontend_core.py b/pyrit/cli/frontend_core.py
index 5ff336c18..f6a55d84f 100644
--- a/pyrit/cli/frontend_core.py
+++ b/pyrit/cli/frontend_core.py
@@ -20,6 +20,7 @@
 import json
 import logging
 import sys
+from collections.abc import Callable
 from pathlib import Path
 from typing import TYPE_CHECKING, Any, Optional
 
@@ -895,36 +896,51 @@ def parse_run_arguments(*, args_string: str) -> dict[str, Any]:
         "max_dataset_size": None,
     }
 
+    def _collect_list_values(
+        *,
+        flag: str,
+        start_index: int,
+        parse_value: Optional[Callable[[str], Any]] = None,
+        stop_on_short_strategy_flag: bool = False,
+    ) -> tuple[list[Any], int]:
+        values: list[Any] = []
+        index = start_index + 1
+
+        while index < len(parts) and not parts[index].startswith("--"):
+            if stop_on_short_strategy_flag and parts[index] == "-s":
+                break
+            values.append(parse_value(parts[index]) if parse_value else parts[index])
+            index += 1
+
+        if not values:
+            raise ValueError(f"{flag} requires at least one value")
+
+        return values, index
+
     i = 1
     while i < len(parts):
         if parts[i] == "--initializers":
-            # Collect initializers until next flag, parsing name:key=val syntax
-            result["initializers"] = []
-            i += 1
-            while i < len(parts) and not parts[i].startswith("--"):
-                result["initializers"].append(_parse_initializer_arg(parts[i]))
-                i += 1
+            result["initializers"], i = _collect_list_values(
+                flag="--initializers",
+                start_index=i,
+                parse_value=_parse_initializer_arg,
+            )
         elif parts[i] == "--initialization-scripts":
-            # Collect script paths until next flag
-            result["initialization_scripts"] = []
-            i += 1
-            while i < len(parts) and not parts[i].startswith("--"):
-                result["initialization_scripts"].append(parts[i])
-                i += 1
+            result["initialization_scripts"], i = _collect_list_values(
+                flag="--initialization-scripts",
+                start_index=i,
+            )
         elif parts[i] == "--env-files":
-            # Collect env file paths until next flag
-            result["env_files"] = []
-            i += 1
-            while i < len(parts) and not parts[i].startswith("--"):
-                result["env_files"].append(parts[i])
-                i += 1
+            result["env_files"], i = _collect_list_values(
+                flag="--env-files",
+                start_index=i,
+            )
         elif parts[i] in ("--strategies", "-s"):
-            # Collect strategies until next flag
-            result["scenario_strategies"] = []
-            i += 1
-            while i < len(parts) and not parts[i].startswith("--") and parts[i] != "-s":
-                result["scenario_strategies"].append(parts[i])
-                i += 1
+            result["scenario_strategies"], i = _collect_list_values(
+                flag=parts[i],
+                start_index=i,
+                stop_on_short_strategy_flag=True,
+            )
         elif parts[i] == "--max-concurrency":
             i += 1
             if i >= len(parts):
@@ -956,12 +972,10 @@ def parse_run_arguments(*, args_string: str) -> dict[str, Any]:
             result["log_level"] = validate_log_level(log_level=parts[i])
             i += 1
         elif parts[i] == "--dataset-names":
-            # Collect dataset names until next flag
-            result["dataset_names"] = []
-            i += 1
-            while i < len(parts) and not parts[i].startswith("--"):
-                result["dataset_names"].append(parts[i])
-                i += 1
+            result["dataset_names"], i = _collect_list_values(
+                flag="--dataset-names",
+                start_index=i,
+            )
         elif parts[i] == "--max-dataset-size":
             i += 1
             if i >= len(parts):
diff --git a/tests/unit/cli/test_frontend_core.py b/tests/unit/cli/test_frontend_core.py
index 7c040deb5..6042a393b 100644
--- a/tests/unit/cli/test_frontend_core.py
+++ b/tests/unit/cli/test_frontend_core.py
@@ -684,6 +684,22 @@ def test_parse_run_arguments_missing_value(self):
         with pytest.raises(ValueError, match="requires a value"):
             frontend_core.parse_run_arguments(args_string="test_scenario --max-concurrency")
 
+    @pytest.mark.parametrize(
+        ("args_string", "flag"),
+        [
+            ("test_scenario --initializers --max-retries 2", "--initializers"),
+            ("test_scenario --initialization-scripts --max-retries 2", "--initialization-scripts"),
+            ("test_scenario --env-files --database InMemory", "--env-files"),
+            ("test_scenario --strategies --max-retries 2", "--strategies"),
+            ("test_scenario -s --max-retries 2", "-s"),
+            ("test_scenario --dataset-names --max-dataset-size 5", "--dataset-names"),
+        ],
+    )
+    def test_parse_run_arguments_list_flags_require_values(self, args_string: str, flag: str):
+        """Test list-style arguments require at least one value."""
+        with pytest.raises(ValueError, match=rf"{flag} requires at least one value"):
+            frontend_core.parse_run_arguments(args_string=args_string)
+
 
 @pytest.mark.asyncio
 @pytest.mark.usefixtures("patch_central_database")