diff --git a/CHANGELOG.md b/CHANGELOG.md
index 98148a7..fce6dfe 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,9 @@
 # Changelog
 
+## Latest
+
+- [Bugfix] Fix boolean configuration choices
+
 ## 3.3.9 (2019-05-13)
 
 - [Improvement] Add `local exec` command for running commands inside existing containers
diff --git a/tutor/config.py b/tutor/config.py
index 1db4fc9..6b52a6e 100644
--- a/tutor/config.py
+++ b/tutor/config.py
@@ -260,7 +260,7 @@ def load_interactive(config):
     ask_bool(
         (
             "Activate SSL/TLS certificates for HTTPS access? Important note:"
-            "this will NOT work in a development environment."
+            " this will NOT work in a development environment."
         ),
         "ACTIVATE_HTTPS",
         config,
@@ -298,7 +298,9 @@ def ask(question, key, config):
 
 
 def ask_bool(question, key, config):
-    return click.confirm(fmt.question(question), prompt_suffix=" ", default=config[key])
+    config[key] = click.confirm(
+        fmt.question(question), prompt_suffix=" ", default=config[key]
+    )
 
 
 def ask_choice(question, key, config, choices):