diff --git a/tests/test_appctx.py b/tests/test_appctx.py
index b9ed29b515..aeb75a55c0 100644
--- a/tests/test_appctx.py
+++ b/tests/test_appctx.py
@@ -120,7 +120,7 @@ def cleanup(exception):
     def index():
         raise Exception("dummy")
 
-    with pytest.raises(Exception):
+    with pytest.raises(Exception, match="dummy"):
         with app.app_context():
             client.get("/")
 
diff --git a/tests/test_basic.py b/tests/test_basic.py
index 2a177e9a70..3dc3a0e9a7 100644
--- a/tests/test_basic.py
+++ b/tests/test_basic.py
@@ -150,10 +150,7 @@ def more():
 
 def test_disallow_string_for_allowed_methods(app):
     with pytest.raises(TypeError):
-
-        @app.route("/", methods="GET POST")
-        def index():
-            return "Hey"
+        app.add_url_rule("/", methods="GET POST", endpoint="test")
 
 
 def test_url_mapping(app, client):
@@ -937,8 +934,9 @@ def test_baseexception_error_handling(app, client):
     def broken_func():
         raise KeyboardInterrupt()
 
-    with pytest.raises(KeyboardInterrupt):
-        client.get("/")
+    with client:
+        with pytest.raises(KeyboardInterrupt):
+            client.get("/")
 
         ctx = flask._request_ctx_stack.top
         assert ctx.preserved
@@ -1243,20 +1241,25 @@ def from_bad_wsgi():
 
     with pytest.raises(TypeError) as e:
         c.get("/none")
-        assert "returned None" in str(e.value)
-        assert "from_none" in str(e.value)
+
+    assert "returned None" in str(e.value)
+    assert "from_none" in str(e.value)
 
     with pytest.raises(TypeError) as e:
         c.get("/small_tuple")
-        assert "tuple must have the form" in str(e.value)
 
-    pytest.raises(TypeError, c.get, "/large_tuple")
+    assert "tuple must have the form" in str(e.value)
+
+    with pytest.raises(TypeError):
+        c.get("/large_tuple")
 
     with pytest.raises(TypeError) as e:
         c.get("/bad_type")
-        assert "it was a bool" in str(e.value)
 
-    pytest.raises(TypeError, c.get, "/bad_wsgi")
+    assert "it was a bool" in str(e.value)
+
+    with pytest.raises(TypeError):
+        c.get("/bad_wsgi")
 
 
 def test_make_response(app, req_ctx):
@@ -1674,11 +1677,9 @@ def index():
 
     assert not app.got_first_request
     assert client.get("/").data == b"Awesome"
-    with pytest.raises(AssertionError) as e:
 
-        @app.route("/foo")
-        def broken():
-            return "Meh"
+    with pytest.raises(AssertionError) as e:
+        app.add_url_rule("/foo", endpoint="late")
 
     assert "A setup function was called" in str(e.value)
 
diff --git a/tests/test_cli.py b/tests/test_cli.py
index f9f3673a67..6e8b57f05a 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -305,9 +305,9 @@ def bad_load():
 
     lazy = DispatchingApp(bad_load, use_eager_loading=False)
 
-    with pytest.raises(BadExc):
-        # reduce flakiness by waiting for the internal loading lock
-        with lazy._lock:
+    # reduce flakiness by waiting for the internal loading lock
+    with lazy._lock:
+        with pytest.raises(BadExc):
             lazy._flush_bg_loading_exception()
 
 
diff --git a/tests/test_config.py b/tests/test_config.py
index bbe4f1e2d3..944b93d7c0 100644
--- a/tests/test_config.py
+++ b/tests/test_config.py
@@ -133,9 +133,11 @@ class Test(Base):
 def test_config_from_envvar(monkeypatch):
     monkeypatch.setattr("os.environ", {})
     app = flask.Flask(__name__)
+
     with pytest.raises(RuntimeError) as e:
         app.config.from_envvar("FOO_SETTINGS")
-        assert "'FOO_SETTINGS' is not set" in str(e.value)
+
+    assert "'FOO_SETTINGS' is not set" in str(e.value)
     assert not app.config.from_envvar("FOO_SETTINGS", silent=True)
 
     monkeypatch.setattr(
@@ -147,8 +149,8 @@ def test_config_from_envvar(monkeypatch):
 
 def test_config_from_envvar_missing(monkeypatch):
     monkeypatch.setattr("os.environ", {"FOO_SETTINGS": "missing.cfg"})
+    app = flask.Flask(__name__)
     with pytest.raises(IOError) as e:
-        app = flask.Flask(__name__)
         app.config.from_envvar("FOO_SETTINGS")
     msg = str(e.value)
     assert msg.startswith(