diff --git a/test/test_events.py b/test/test_events.py
index 201917f..b5da3dd 100644
--- a/test/test_events.py
+++ b/test/test_events.py
@@ -29,13 +29,36 @@ def web1(docker_compose):
     except NotFound:
         pass
 
+@pytest.fixture()
+def web2(docker_compose):
+    """
+    pytest fixture creating a web container with `VIRTUAL_HOST=nginx-proxy`, `VIRTUAL_PATH=/web2/` and `VIRTUAL_DEST=/` listening on port 82.
+    """
+    container = docker_compose.containers.run(
+        name="web2",
+        image="web",
+        detach=True,
+        environment={
+            "WEB_PORTS": "82",
+            "VIRTUAL_HOST": "nginx-proxy",
+            "VIRTUAL_PATH": "/web2/",
+            "VIRTUAL_DEST": "/",
+        },
+        ports={"82/tcp": None}
+    )
+    sleep(2)  # give it some time to initialize and for docker-gen to detect it
+    yield container
+    try:
+        docker_compose.containers.get("web2").remove(force=True)
+    except NotFound:
+        pass
 
 def test_nginx_proxy_behavior_when_alone(docker_compose, nginxproxy):
     r = nginxproxy.get("http://nginx-proxy/")
     assert r.status_code == 503
 
 
-def test_new_container_is_detected(web1, nginxproxy):
+def test_new_container_is_detected_vhost(web1, nginxproxy):
     r = nginxproxy.get("http://web1.nginx-proxy/port")
     assert r.status_code == 200
     assert "answer from port 81\n" == r.text
@@ -44,3 +67,16 @@ def test_new_container_is_detected(web1, nginxproxy):
     sleep(2)
     r = nginxproxy.get("http://web1.nginx-proxy/port")
     assert r.status_code == 503
+
+def test_new_container_is_detected_vpath(web2, nginxproxy):
+    r = nginxproxy.get("http://nginx-proxy/web2/port")
+    assert r.status_code == 200
+    assert "answer from port 82\n" == r.text
+    r = nginxproxy.get("http://nginx-proxy/port")
+    assert r.status_code in [404, 503]
+
+    web2.remove(force=True)
+    sleep(2)
+    r = nginxproxy.get("http://nginx-proxy/web2/port")
+    assert r.status_code == 503
+
diff --git a/test/test_virtual-path/test_virtual_paths.py b/test/test_virtual-path/test_virtual_paths.py
new file mode 100644
index 0000000..115d47f
--- /dev/null
+++ b/test/test_virtual-path/test_virtual_paths.py
@@ -0,0 +1,59 @@
+from time import sleep
+
+import pytest
+from docker.errors import NotFound
+
+@pytest.mark.parametrize("stub,expected_port", [
+    ("nginx-proxy.test/web1", 81),
+    ("nginx-proxy.test/web2", 82),
+    ("nginx-proxy.test", 83),
+    ("foo.nginx-proxy.test", 42),
+])
+def test_valid_path(docker_compose, nginxproxy, stub, expected_port):
+    r = nginxproxy.get(f"http://{stub}/port")
+    assert r.status_code == 200
+    assert r.text == f"answer from port {expected_port}\n"
+
+@pytest.mark.parametrize("stub", [
+    "nginx-proxy.test/foo",
+    "bar.nginx-proxy.test",
+])
+def test_invalid_path(docker_compose, nginxproxy, stub):
+    r = nginxproxy.get(f"http://{stub}/port")
+    assert r.status_code in [404, 503]
+
+@pytest.fixture()
+def web4(docker_compose):
+    """
+    pytest fixture creating a web container with `VIRTUAL_HOST=nginx-proxy.test`, `VIRTUAL_PATH=/web4/` and `VIRTUAL_DEST=/` listening on port 84.
+    """
+    container = docker_compose.containers.run(
+        name="web4",
+        image="web",
+        detach=True,
+        environment={
+            "WEB_PORTS": "84",
+            "VIRTUAL_HOST": "nginx-proxy.test",
+            "VIRTUAL_PATH": "/web4/",
+            "VIRTUAL_DEST": "/",
+        },
+        ports={"84/tcp": None}
+    )
+    sleep(2)  # give it some time to initialize and for docker-gen to detect it
+    yield container
+    try:
+        docker_compose.containers.get("web4").remove(force=True)
+    except NotFound:
+        pass
+
+"""
+Test if we can add and remove a single virtual_path from multiple ones on the same subdomain.
+"""
+def test_container_hotplug(web4, nginxproxy):
+    r = nginxproxy.get(f"http://nginx-proxy.test/web4/port")
+    assert r.status_code == 200
+    assert r.text == f"answer from port 84\n"
+    web4.remove(force=True)
+    sleep(2)
+    r = nginxproxy.get(f"http://nginx-proxy.test/web4/port")
+    assert r.status_code == 404
diff --git a/test/test_virtual-path/test_virtual_paths.yml b/test/test_virtual-path/test_virtual_paths.yml
new file mode 100644
index 0000000..ca688eb
--- /dev/null
+++ b/test/test_virtual-path/test_virtual_paths.yml
@@ -0,0 +1,42 @@
+
+foo:
+  image: web
+  expose:
+    - "42"
+  environment:
+    WEB_PORTS: "42"
+    VIRTUAL_HOST: "foo.nginx-proxy.test"
+
+web1:
+  image: web
+  expose:
+    - "81"
+  environment:
+    WEB_PORTS: "81"
+    VIRTUAL_HOST: "nginx-proxy.test"
+    VIRTUAL_PATH: "/web1/"
+
+web2:
+  image: web
+  expose:
+    - "82"
+  environment:
+    WEB_PORTS: "82"
+    VIRTUAL_HOST: "nginx-proxy.test"
+    VIRTUAL_PATH: "/web2/"
+
+web3:
+  image: web
+  expose:
+    - "83"
+  environment:
+    WEB_PORTS: "83"
+    VIRTUAL_HOST: "nginx-proxy.test"
+    VIRTUAL_PATH: "/"
+
+sut:
+  image: nginxproxy/nginx-proxy:test
+  volumes:
+    - /var/run/docker.sock:/tmp/docker.sock:ro
+    - ../lib/ssl/dhparam.pem:/etc/nginx/dhparam/dhparam.pem:ro
+