diff --git a/lib/galaxy/tools/wrappers.py b/lib/galaxy/tools/wrappers.py
index a7425d50472..89776480080 100644
--- a/lib/galaxy/tools/wrappers.py
+++ b/lib/galaxy/tools/wrappers.py
@@ -83,7 +83,7 @@ class InputValueWrapper(ToolParameterValueWrapper):
         if self.input.type == 'boolean' and isinstance(other, string_types):
             return str(self)
         # For backward compatibility, allow `$wrapper != ""` for optional non-text param
-        if self.input.optional and self.value is None and isinstance(other, string_types):
+        if self.input.optional and self.value is None and self.input.type != 'boolean':
             return str(self)
         cast = {
             'text': str,
diff --git a/test/unit/tools/test_wrappers.py b/test/unit/tools/test_wrappers.py
index 9bb9bb53a18..b1567be682c 100644
--- a/test/unit/tools/test_wrappers.py
+++ b/test/unit/tools/test_wrappers.py
@@ -108,15 +108,19 @@ def test_raw_object_wrapper():
     assert not false_wrapper
 
 
-def valuewrapper(tool, value, paramtype):
+def valuewrapper(tool, value, paramtype, optional=False):
     if paramtype == "integer":
-        parameter = IntegerToolParameter(tool, XML('<param name="blah" type="integer" value="10" min="0" />'))
+        optional = 'optional="true"' if optional else 'value="10"'
+        parameter = IntegerToolParameter(tool, XML('<param name="blah" type="integer" %s min="0" />' % optional))
     elif paramtype == "text":
-        parameter = TextToolParameter(tool, XML('<param name="blah" type="text" value="foo"/>'))
+        optional = 'optional="true"' if optional else 'value="foo"'
+        parameter = TextToolParameter(tool, XML('<param name="blah" type="text" %s/>' % optional))
     elif paramtype == "float":
-        parameter = FloatToolParameter(tool, XML('<param name="blah" type="float" value="10.0"/>'))
+        optional = 'optional="true"' if optional else 'value="10.0"'
+        parameter = FloatToolParameter(tool, XML('<param name="blah" type="float" %s/>' % optional))
     elif paramtype == "boolean":
-        parameter = BooleanToolParameter(tool, XML('<param name="blah" type="boolean" truevalue="truevalue" falsevalue="falsevalue"/>'))
+        optional = 'optional="true"' if optional else 'value=""'
+        parameter = BooleanToolParameter(tool, XML('<param name="blah" type="boolean" truevalue="truevalue" falsevalue="falsevalue" %s/>' % optional))
     return InputValueWrapper(parameter, value)
 
 
@@ -143,19 +147,23 @@ def test_input_value_wrapper_comparison(tool):
 
 @with_mock_tool
 def test_input_value_wrapper_comparison_optional(tool):
-    parameter = IntegerToolParameter(tool, XML('<param name="blah" type="integer" min="0" optional="true"/>'))
-    wrapper = InputValueWrapper(parameter, None)
+    wrapper = valuewrapper(tool, None, 'integer', optional=True)
     assert not wrapper
     with pytest.raises(ValueError):
         int(wrapper)
     assert str(wrapper) == ""
     assert wrapper == ""  # for backward-compatibility
-    parameter = IntegerToolParameter(tool, XML('<param name="blah" type="integer" min="0" optional="true"/>'))
-    wrapper = InputValueWrapper(parameter, 0)
+    wrapper = valuewrapper(tool, 0, 'integer', optional=True)
     assert wrapper == 0
     assert int(wrapper) == 0
     assert str(wrapper)
     assert wrapper != ""  # for backward-compatibility, the correct way to check if an optional integer param is not empty is to use str(wrapper)
+    wrapper = valuewrapper(tool, None, 'integer', optional=True)
+    assert wrapper != 1
+    assert str(wrapper) == ""
+    wrapper = valuewrapper(tool, None, "boolean")
+    assert bool(wrapper) is False, wrapper
+    assert str(wrapper) == 'falsevalue'
 
 
 @with_mock_tool