diff --git a/lib/galaxy/tools/parameters/dynamic_options.py b/lib/galaxy/tools/parameters/dynamic_options.py
index 14360f3c666..ef4cbabd063 100644
--- a/lib/galaxy/tools/parameters/dynamic_options.py
+++ b/lib/galaxy/tools/parameters/dynamic_options.py
@@ -14,10 +14,6 @@ from galaxy.model import (
     MetadataFile,
     User,
 )
-from galaxy.tools.wrappers import (
-    DatasetFilenameWrapper,
-    DatasetListWrapper,
-)
 from galaxy.util import string_as_bool
 from . import validation
 
@@ -467,6 +463,8 @@ class RemoveValueFilter(Filter):
         self.separator = elem.get("separator", ",")
 
     def filter_options(self, options, trans, other_values):
+        from galaxy.tools.wrappers import DatasetFilenameWrapper
+
         if trans is not None and trans.workflow_building_mode:
             return options
 
@@ -803,6 +801,11 @@ def _get_ref_data(other_values, ref_name):
     - a KeyError is raised if no such element exists
     - a ValueError is raised if the element is not of the type DatasetFilenameWrapper, HistoryDatasetAssociation, DatasetListWrapper, HistoryDatasetCollectionAssociation, list
     """
+    from galaxy.tools.wrappers import (
+        DatasetFilenameWrapper,
+        DatasetListWrapper,
+    )
+
     ref = other_values[ref_name]
     if not isinstance(
         ref,
diff --git a/lib/galaxy/tools/wrappers.py b/lib/galaxy/tools/wrappers.py
index ecc26378775..528bee38085 100644
--- a/lib/galaxy/tools/wrappers.py
+++ b/lib/galaxy/tools/wrappers.py
@@ -27,13 +27,18 @@ from galaxy.model import (
     HasTags,
     HistoryDatasetCollectionAssociation,
 )
+from galaxy.model.metadata import FileParameter
 from galaxy.model.none_like import NoneDataset
 from galaxy.security.object_wrapper import wrap_with_safe_string
+from galaxy.tools.parameters.basic import BooleanToolParameter
 from galaxy.tools.parameters.wrapped_json import (
     data_collection_input_to_staging_path_and_source_path,
     data_input_to_staging_path_and_source_path,
 )
-from galaxy.util import filesystem_safe_string
+from galaxy.util import (
+    filesystem_safe_string,
+    string_as_bool,
+)
 
 if TYPE_CHECKING:
     from galaxy.datatypes.registry import Registry
@@ -121,25 +126,29 @@ class InputValueWrapper(ToolParameterValueWrapper):
         self.value = value
         self._other_values: Dict[str, str] = other_values or {}
 
-    def _get_cast_value(self, other: Any) -> Union[str, int, float, bool, None]:
-        if self.input.type == "boolean" and isinstance(other, str):
-            return str(self)
+    def _get_cast_values(self, other: Any) -> Tuple[Union[str, int, float, bool, None], Any]:
+        if isinstance(self.input, BooleanToolParameter) and isinstance(other, str):
+            if other in (self.input.truevalue, self.input.falsevalue):
+                return str(self), other
+            else:
+                return bool(self), string_as_bool(other)
         # For backward compatibility, allow `$wrapper != ""` for optional non-text param
         if self.input.optional and self.value is None:
             if isinstance(other, str):
-                return str(self)
+                return str(self), other
             else:
-                return None
+                return None, other
         cast_table = {
             "text": str,
             "integer": int,
             "float": float,
             "boolean": bool,
         }
-        return cast(Union[str, int, float, bool], cast_table.get(self.input.type, str)(self))
+        return cast(Union[str, int, float, bool], cast_table.get(self.input.type, str)(self)), other
 
     def __eq__(self, other: Any) -> bool:
-        return bool(self._get_cast_value(other) == other)
+        casted_self, casted_other = self._get_cast_values(other)
+        return casted_self == casted_other
 
     def __ne__(self, other: Any) -> bool:
         return not self == other
@@ -162,7 +171,8 @@ class InputValueWrapper(ToolParameterValueWrapper):
         return getattr(self.value, key)
 
     def __gt__(self, other: Any) -> bool:
-        return bool(self._get_cast_value(other) > other)
+        casted_self, casted_other = self._get_cast_values(other)
+        return casted_self > casted_other
 
     def __int__(self) -> int:
         return int(float(self))
@@ -290,7 +300,6 @@ class DatasetFilenameWrapper(ToolParameterValueWrapper):
                 if rval is None:
                     rval = self.metadata.spec[name].no_value
                 metadata_param = self.metadata.spec[name].param
-                from galaxy.model.metadata import FileParameter
 
                 rval = metadata_param.to_safe_string(rval)
                 if isinstance(metadata_param, FileParameter) and self.compute_environment:
diff --git a/test/unit/app/tools/test_wrappers.py b/test/unit/app/tools/test_wrappers.py
index d094aaec5a3..c9a20f12e39 100644
--- a/test/unit/app/tools/test_wrappers.py
+++ b/test/unit/app/tools/test_wrappers.py
@@ -160,10 +160,12 @@ def test_input_value_wrapper_comparison(tool):
     assert bool(wrapper) is True, wrapper
     assert str(wrapper) == "truevalue"
     assert wrapper == "truevalue"
+    assert wrapper == "true"
     wrapper = valuewrapper(tool, False, "boolean")
     assert bool(wrapper) is False, wrapper
     assert str(wrapper) == "falsevalue"
     assert wrapper == "falsevalue"
+    assert wrapper == "false"
 
 
 @with_mock_tool