diff --git a/ci/linting_requirements.txt b/ci/linting_requirements.txt
index 85a3cc97a3a..5c5a75ff7b5 100644
--- a/ci/linting_requirements.txt
+++ b/ci/linting_requirements.txt
@@ -11,7 +11,7 @@ flake8-mutable==1.2.0
 flake8-pep3101==1.3.0
 flake8-print==4.0.0
 flake8-quotes==3.2.0
-flake8-simplify==0.12.0
+flake8-simplify==0.14.0
 pep8-naming==0.11.1
 
 flake8-rst-docstrings==0.0.14
diff --git a/tests/test_xarray.py b/tests/test_xarray.py
index b849424be42..b51982b6086 100644
--- a/tests/test_xarray.py
+++ b/tests/test_xarray.py
@@ -376,12 +376,12 @@ def test_resolve_axis_conflict_double_lonlat(test_ds_generic):
     test_ds_generic['d'].attrs['_CoordinateAxisType'] = 'Lat'
     test_ds_generic['e'].attrs['_CoordinateAxisType'] = 'Lon'
 
-    with pytest.warns(UserWarning, match='More than one x coordinate'):
-        with pytest.raises(AttributeError):
-            test_ds_generic['test'].metpy.x
-    with pytest.warns(UserWarning, match='More than one y coordinate'):
-        with pytest.raises(AttributeError):
-            test_ds_generic['test'].metpy.y
+    with pytest.warns(UserWarning, match='More than one x coordinate'),\
+            pytest.raises(AttributeError):
+        test_ds_generic['test'].metpy.x
+    with pytest.warns(UserWarning, match='More than one y coordinate'),\
+            pytest.raises(AttributeError):
+        test_ds_generic['test'].metpy.y
 
 
 def test_resolve_axis_conflict_double_xy(test_ds_generic):
@@ -391,12 +391,12 @@ def test_resolve_axis_conflict_double_xy(test_ds_generic):
     test_ds_generic['d'].attrs['standard_name'] = 'projection_x_coordinate'
     test_ds_generic['e'].attrs['standard_name'] = 'projection_y_coordinate'
 
-    with pytest.warns(UserWarning, match='More than one x coordinate'):
-        with pytest.raises(AttributeError):
-            test_ds_generic['test'].metpy.x
-    with pytest.warns(UserWarning, match='More than one y coordinate'):
-        with pytest.raises(AttributeError):
-            test_ds_generic['test'].metpy.y
+    with pytest.warns(UserWarning, match='More than one x coordinate'),\
+            pytest.raises(AttributeError):
+        test_ds_generic['test'].metpy.x
+    with pytest.warns(UserWarning, match='More than one y coordinate'),\
+            pytest.raises(AttributeError):
+        test_ds_generic['test'].metpy.y
 
 
 def test_resolve_axis_conflict_double_x_with_single_dim(test_ds_generic):
@@ -413,9 +413,9 @@ def test_resolve_axis_conflict_double_vertical(test_ds_generic):
     test_ds_generic['b'].attrs['units'] = 'hPa'
     test_ds_generic['c'].attrs['units'] = 'Pa'
 
-    with pytest.warns(UserWarning, match='More than one vertical coordinate'):
-        with pytest.raises(AttributeError):
-            test_ds_generic['test'].metpy.vertical
+    with pytest.warns(UserWarning, match='More than one vertical coordinate'),\
+            pytest.raises(AttributeError):
+        test_ds_generic['test'].metpy.vertical
 
 
 criterion_matches = [