diff --git a/changelog.d/5005.misc b/changelog.d/5005.misc
new file mode 100644
index 0000000000..f74147b352
--- /dev/null
+++ b/changelog.d/5005.misc
@@ -0,0 +1 @@
+Convert SYNAPSE_NO_TLS Docker variable to boolean for user friendliness. Contributed by Gabriel Eckerson.
diff --git a/docker/README.md b/docker/README.md
index b48d74e09c..b27a692d5b 100644
--- a/docker/README.md
+++ b/docker/README.md
@@ -102,8 +102,9 @@ when ``SYNAPSE_CONFIG_PATH`` is not set.
 * ``SYNAPSE_SERVER_NAME`` (mandatory), the server public hostname.
 * ``SYNAPSE_REPORT_STATS``, (mandatory, ``yes`` or ``no``), enable anonymous
   statistics reporting back to the Matrix project which helps us to get funding.
-* ``SYNAPSE_NO_TLS``, set this variable to disable TLS in Synapse (use this if
-  you run your own TLS-capable reverse proxy).
+* `SYNAPSE_NO_TLS`, (accepts `true`, `false`, `on`, `off`, `1`, `0`, `yes`, `no`]): disable
+  TLS in Synapse (use this if you run your own TLS-capable reverse proxy). Defaults
+  to `false` (ie, TLS is enabled by default).
 * ``SYNAPSE_ENABLE_REGISTRATION``, set this variable to enable registration on
   the Synapse instance.
 * ``SYNAPSE_ALLOW_GUEST``, set this variable to allow guest joining this server.
diff --git a/docker/start.py b/docker/start.py
index 941d9996a8..2da555272a 100755
--- a/docker/start.py
+++ b/docker/start.py
@@ -59,6 +59,18 @@ else:
         if not os.path.exists("/compiled"): os.mkdir("/compiled")
 
         config_path = "/compiled/homeserver.yaml"
+        
+        # Convert SYNAPSE_NO_TLS to boolean if exists
+        if "SYNAPSE_NO_TLS" in environ:
+            tlsanswerstring = str.lower(environ["SYNAPSE_NO_TLS"])
+            if tlsanswerstring in ("true", "on", "1", "yes"):
+                environ["SYNAPSE_NO_TLS"] = True
+            else:
+                if tlsanswerstring in ("false", "off", "0", "no"):
+                    environ["SYNAPSE_NO_TLS"] = False
+                else:
+                    print("Environment variable \"SYNAPSE_NO_TLS\" found but value \"" + tlsanswerstring + "\" unrecognized; exiting.")
+                    sys.exit(2)
 
         convert("/conf/homeserver.yaml", config_path, environ)
         convert("/conf/log.config", "/compiled/log.config", environ)