diff --git a/bootstrap/bootstrap.py b/bootstrap/bootstrap.py
index 3a42fb2..70bdbf8 100644
--- a/bootstrap/bootstrap.py
+++ b/bootstrap/bootstrap.py
@@ -16,6 +16,7 @@ import os
 import subprocess
 import sys
 import logging
+import shutil
 
 
 def get_os_release_variable(key):
@@ -31,8 +32,10 @@ def get_os_release_variable(key):
         "source /etc/os-release && echo ${{{key}}}".format(key=key)
     ]).decode().strip()
 
-def main():
-
+def validate_host():
+    """
+    Make sure TLJH is installable in current host
+    """
     # Support only Ubuntu 18.04+
     distro = get_os_release_variable('ID')
     version = float(get_os_release_variable('VERSION_ID'))
@@ -43,6 +46,21 @@ def main():
         print('The Littlest JupyterHub requires Ubuntu 18.04 or higher')
         sys.exit(1)
 
+    if sys.version_info < (3, 5):
+        print("bootstrap.py must be run with at least Python 3.5")
+        sys.exit(1)
+
+    if not (shutil.which('systemd') and shutil.which('systemctl')):
+        print("Systemd is required to run TLJH")
+        # Only fail running inside docker if systemd isn't present
+        if os.path.exists('/.dockerenv'):
+            print("Running inside a docker container without systemd isn't supported")
+            print("We recommend against running a production TLJH instance inside a docker container")
+            print("For local development, see http://tljh.jupyter.org/en/latest/contributing/dev-setup.html")
+        sys.exit(1)
+
+def main():
+    validate_host()
     install_prefix = os.environ.get('TLJH_INSTALL_PREFIX', '/opt/tljh')
     hub_prefix = os.path.join(install_prefix, 'hub')
 
diff --git a/integration-tests/test_bootstrap.py b/integration-tests/test_bootstrap.py
index 5bf143f..fa02b68 100644
--- a/integration-tests/test_bootstrap.py
+++ b/integration-tests/test_bootstrap.py
@@ -2,14 +2,9 @@
 Test running bootstrap script in different circumstances
 """
 import subprocess
+from textwrap import dedent
 
-
-def test_ubuntu_too_old():
-    """
-    Error with a useful message when running in older Ubuntu
-    """
-    container_name = 'old-distro-test'
-
+def run_bootstrap(container_name, image):
     # stop container if it is already running
     subprocess.run([
         'docker', 'rm', '-f', container_name
@@ -17,7 +12,7 @@ def test_ubuntu_too_old():
     
     # Start a detached Ubuntu 16.04 container
     subprocess.check_call([
-        'docker', 'run', '--detach', '--name', container_name, 'ubuntu:16.04', 
+        'docker', 'run', '--detach', '--name', container_name, image,
         '/bin/bash', '-c', 'sleep 1000s'
     ])
     # Install python3 inside the ubuntu container
@@ -35,10 +30,27 @@ def test_ubuntu_too_old():
         'bootstrap/', f'{container_name}:/srv'
     ])
 
-    # Run bootstrap script, validate that it fails appropriately
-    output = subprocess.run([
+    # Run bootstrap script, return the output
+    return subprocess.run([
         'docker', 'exec', '-i', container_name,
         'python3', '/srv/bootstrap/bootstrap.py'
     ], check=False, stdout=subprocess.PIPE, encoding='utf-8')
+
+def test_ubuntu_too_old():
+    """
+    Error with a useful message when running in older Ubuntu
+    """
+    output = run_bootstrap('old-distro-test', 'ubuntu:16.04')
     assert output.stdout == 'The Littlest JupyterHub requires Ubuntu 18.04 or higher\n'
-    assert output.returncode == 1
\ No newline at end of file
+    assert output.returncode == 1
+
+
+def test_inside_no_systemd_docker():
+    output = run_bootstrap('plain-docker-test', 'ubuntu:18.04')
+    assert output.stdout.strip() == dedent("""
+        Systemd is required to run TLJH
+        Running inside a docker container without systemd isn't supported
+        We recommend against running a production TLJH instance inside a docker container
+        For local development, see http://tljh.jupyter.org/en/latest/contributing/dev-setup.html
+    """).strip()
+    assert output.returncode == 1