diff --git a/flytekit/clis/sdk_in_container/run.py b/flytekit/clis/sdk_in_container/run.py
index eb8164f2b0..39d0135f44 100644
--- a/flytekit/clis/sdk_in_container/run.py
+++ b/flytekit/clis/sdk_in_container/run.py
@@ -17,6 +17,7 @@
 from mashumaro.codecs.json import JSONEncoder
 from rich.progress import Progress, TextColumn, TimeElapsedColumn
 from typing_extensions import get_origin
+from typing_inspect import is_optional_type
 
 from flytekit import Annotations, FlyteContext, FlyteContextManager, Labels, LaunchPlan, Literal, WorkflowExecutionPhase
 from flytekit.clis.sdk_in_container.helpers import (
@@ -696,9 +697,16 @@ def _run(*args, **kwargs):
             inputs = {}
             for input_name, v in entity.python_interface.inputs_with_defaults.items():
                 processed_click_value = kwargs.get(input_name)
+                skip_default_value_selection = False
+                if (
+                    is_optional_type(v[0])
+                    and isinstance(processed_click_value, str)
+                    and processed_click_value.lower() == "none"
+                ):
+                    processed_click_value = None
+                    skip_default_value_selection = True
                 optional_v = False
 
-                skip_default_value_selection = False
                 if processed_click_value is None and isinstance(v, typing.Tuple):
                     if entity_type == "workflow" and hasattr(v[0], "__args__"):
                         origin_base_type = get_origin(v[0])
@@ -730,6 +738,8 @@ def _run(*args, **kwargs):
                     inputs[input_name] = processed_click_value
                 if processed_click_value is None and v[0] == bool:
                     inputs[input_name] = False
+                if processed_click_value is None and is_optional(v[0]):
+                    inputs[input_name] = None
 
             if not run_level_params.is_remote:
                 with FlyteContextManager.with_context(_update_flyte_context(run_level_params)):
diff --git a/flytekit/interaction/click_types.py b/flytekit/interaction/click_types.py
index 056fa2db61..0efc821a75 100644
--- a/flytekit/interaction/click_types.py
+++ b/flytekit/interaction/click_types.py
@@ -19,6 +19,7 @@
 from dataclasses_json import DataClassJsonMixin, dataclass_json
 from packaging.version import Version
 from pytimeparse import parse
+from typing_inspect import is_optional_type
 
 from flytekit import BlobType, FlyteContext, Literal, LiteralType, StructuredDataset
 from flytekit.core.artifact import ArtifactQuery
@@ -572,6 +573,8 @@ def convert(
             if not self._is_remote:
                 return value
 
+            if is_optional_type(self._python_type) and isinstance(value, str) and value.lower() == "none":
+                value = None
             lit = TypeEngine.to_literal(self._flyte_ctx, value, self._python_type, self._literal_type)
             return lit
         except click.BadParameter:
@@ -581,3 +584,10 @@ def convert(
                 f"Failed to convert param: {param if param else 'NA'}, value: {value} to type: {self._python_type}."
                 f" Reason {e}"
             ) from e
+
+
+def is_optional(_type):
+    """
+    Checks if the given type is Optional Type
+    """
+    return typing.get_origin(_type) is typing.Union and type(None) in typing.get_args(_type)