diff --git a/tests/unit/test_route.py b/tests/unit/test_route.py
index 645698b..839f897 100644
--- a/tests/unit/test_route.py
+++ b/tests/unit/test_route.py
@@ -62,6 +62,54 @@ CONFIG_WITH_TLS = {
     }
 }
 
+CONFIG_MIDDLEWARE = {
+    "http": {
+        "middlewares": {
+            "custom-headers-http": {
+                "headers": {
+                    "customRequestHeaders": {
+                        "X-Forwarded-Proto": "http"
+                    }
+                }
+            },
+            "custom-headers-https": {
+                "headers": {
+                    "customRequestHeaders": {
+                        "X-Forwarded-Proto": "https"
+                    }
+                }
+            },
+        },
+        "routers": {
+            "juju-foo-router": {
+                "entryPoints": ["web"],
+                "middlewares": ["custom-headers-http"],
+                "rule": "PathPrefix(`/path`)",
+                "service": "juju-foo-service",
+            },
+            "juju-foo-router-tls": {
+                "entryPoints": ["websecure"],
+                "middlewares": ["custom-headers-https"],
+                "rule": "PathPrefix(`/path`)",
+                "service": "juju-foo-service",
+                "tls": {
+                    "domains": [
+                        {
+                            "main": "testhostname",
+                            "sans": ["*.testhostname"],
+                        },
+                    ],
+                },
+            },
+        },
+        "services": {
+            "juju-foo-service": {
+                "loadBalancer": {"servers": [{"url": "http://foo.testmodel-endpoints.local:8080"}]}
+            }
+        },
+    }
+}
+
 
 @pytest.fixture(scope="function")
 def harness() -> Harness[TraefikIngressCharm]:
@@ -280,3 +328,15 @@ def test_static_config_partially_broken(harness: Harness[TraefikIngressCharm]):
     assert generated_config["barbaras"] == {"rhabarber": "bar"}
     assert generated_config["entryPoints"]["shondaland"]["address"] == ":6767"
     assert generated_config["foo"] == {"bar": "baz"}
+
+def test_middleware(harness: Harness[TraefikIngressCharm]):
+    tr_relation_id, relation = initialize_and_setup_tr_relation(harness)
+    charm = harness.charm
+    config = yaml.dump(CONFIG_MIDDLEWARE)
+    harness.update_relation_data(tr_relation_id, REMOTE_APP_NAME, {"config": config})
+
+    assert charm.traefik_route.is_ready(relation)
+    assert charm.traefik_route.get_config(relation) == config
+    file = f"/opt/traefik/juju/juju_ingress_{relation.name}_{relation.id}_{relation.app.name}.yaml"
+    conf = yaml.safe_load(charm.container.pull(file).read())
+    assert conf == CONFIG_MIDDLEWARE
diff --git a/tox.ini b/tox.ini
index 596356a..2e9d47b 100644
--- a/tox.ini
+++ b/tox.ini
@@ -14,7 +14,8 @@ all_path = {[vars]src_path} {[vars]tst_path} {[vars]lib_path}
 
 [testenv]
 setenv =
-  JUJU_VERSION=3.0.3 # fix ops borkiness
+  # fix ops borkiness
+  JUJU_VERSION=3.0.3
   PYTHONPATH = {toxinidir}:{toxinidir}/lib:{[vars]src_path}
   PYTHONBREAKPOINT=ipdb.set_trace
   PY_COLORS=1