diff --git a/test/test_debug/test_proxy-debug-flag.py b/test/test_debug/test_proxy-debug-flag.py
new file mode 100644
index 0000000..b99ccef
--- /dev/null
+++ b/test/test_debug/test_proxy-debug-flag.py
@@ -0,0 +1,12 @@
+import pytest
+import re
+
+def test_debug_info_is_present_in_nginx_generated_conf(docker_compose, nginxproxy):
+    conf = nginxproxy.get_conf().decode('ASCII')
+    assert re.search(r"# Exposed ports: \[\{\d+\.\d+\.\d+\.\d+\s+80\s+tcp \} \{\d+\.\d+\.\d+\.\d+\s+81\s+tcp \}\]", conf) or \
+           re.search(r"# Exposed ports: \[\{\d+\.\d+\.\d+\.\d+\s+81\s+tcp \} \{\d+\.\d+\.\d+\.\d+\s+80\s+tcp \}\]", conf)
+    assert re.search(r"# Exposed ports: \[\{\d+\.\d+\.\d+\.\d+\s+82\s+tcp \} \{\d+\.\d+\.\d+\.\d+\s+83\s+tcp \}\]", conf) or \
+           re.search(r"# Exposed ports: \[\{\d+\.\d+\.\d+\.\d+\s+83\s+tcp \} \{\d+\.\d+\.\d+\.\d+\s+82\s+tcp \}\]", conf)
+    assert "# Default virtual port: 80" in conf
+    assert "# VIRTUAL_PORT: 82" in conf
+    assert conf.count("# /!\ Virtual port not exposed") == 1
diff --git a/test/test_debug/test_proxy-debug-flag.yml b/test/test_debug/test_proxy-debug-flag.yml
new file mode 100644
index 0000000..e7af54c
--- /dev/null
+++ b/test/test_debug/test_proxy-debug-flag.yml
@@ -0,0 +1,27 @@
+web1:
+  image: web
+  expose:
+    - "80"
+    - "81"
+  environment:
+    WEB_PORTS: "80 81"
+    VIRTUAL_HOST: "web1.nginx-proxy.tld"
+    VIRTUAL_PORT: "82"
+
+web2:
+  image: web
+  expose:
+    - "82"
+    - "83"
+  environment:
+    WEB_PORTS: "82 83"
+    VIRTUAL_HOST: "web2.nginx-proxy.tld"
+    VIRTUAL_PORT: "82"
+
+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
+  environment:
+    DEBUG: "true"
diff --git a/test/test_debug/test_server-debug-flag.py b/test/test_debug/test_server-debug-flag.py
new file mode 100644
index 0000000..50ae737
--- /dev/null
+++ b/test/test_debug/test_server-debug-flag.py
@@ -0,0 +1,8 @@
+import pytest
+import re
+
+def test_debug_info_is_present_in_nginx_generated_conf(docker_compose, nginxproxy):
+    conf = nginxproxy.get_conf().decode('ASCII')
+    assert re.search(r"# Exposed ports: \[\{\d+\.\d+\.\d+\.\d+\s+80\s+tcp \} \{\d+\.\d+\.\d+\.\d+\s+81\s+tcp \}\]", conf) or \
+           re.search(r"# Exposed ports: \[\{\d+\.\d+\.\d+\.\d+\s+81\s+tcp \} \{\d+\.\d+\.\d+\.\d+\s+80\s+tcp \}\]", conf)
+    assert conf.count("# Exposed ports: [{") == 1
diff --git a/test/test_debug/test_server-debug-flag.yml b/test/test_debug/test_server-debug-flag.yml
new file mode 100644
index 0000000..0256cf8
--- /dev/null
+++ b/test/test_debug/test_server-debug-flag.yml
@@ -0,0 +1,26 @@
+web1:
+  image: web
+  expose:
+    - "80"
+    - "81"
+  environment:
+    WEB_PORTS: "80 81"
+    VIRTUAL_HOST: "web1.nginx-proxy.tld"
+    VIRTUAL_PORT: "82"
+    DEBUG: "true"
+
+web2:
+  image: web
+  expose:
+    - "82"
+    - "83"
+  environment:
+    WEB_PORTS: "82 83"
+    VIRTUAL_HOST: "web2.nginx-proxy.tld"
+    VIRTUAL_PORT: "82"
+
+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