diff --git a/doc/installation.rst b/doc/installation.rst
index 875f7bae..cb24a860 100644
--- a/doc/installation.rst
+++ b/doc/installation.rst
@@ -190,6 +190,11 @@ not permitted" error when building. Add the line ::
 
 to your ``/etc/sysctl.conf`` (or wherever your distro stores that).
 
+Ubuntu is further restricting user namespaces through AppArmor. Either set
+``/proc/sys/kernel/apparmor_restrict_unprivileged_userns`` to ``0`` or create
+an AppArmor profile for the ``bob-namespace-sandbox`` binary that allows user
+namespaces for Bob.
+
 If you are using Docker, you must relax the security settings as they block
 nested containers by default. Adding ``--security-opt seccomp=unconfined
 --security-opt apparmor=unconfined`` to the ``docker run`` command should
diff --git a/pym/bob/invoker.py b/pym/bob/invoker.py
index fb5b0af9..63e7fefe 100644
--- a/pym/bob/invoker.py
+++ b/pym/bob/invoker.py
@@ -450,9 +450,23 @@ def ensureSandboxUsable():
             ret = subprocess.run([getSandboxHelperPath(), "-C"], stdout=subprocess.DEVNULL,
                                  stderr=subprocess.DEVNULL).returncode
             if ret != 0:
+                knobs = [("/proc/sys/kernel/unprivileged_userns_clone", "1"),
+                         ("/proc/sys/kernel/apparmor_restrict_unprivileged_userns", "0")]
+                for knob, expected_val in knobs:
+                    try:
+                        with open(knob) as f:
+                            if f.read().strip() != expected_val:
+                                msg = f"Make sure {knob} is {expected_val}."
+                                break
+                    except FileNotFoundError:
+                        pass
+                    except OSError:
+                        msg = f"Make sure {knob} is {expected_val}."
+                        break
+                else:
+                    msg = f"Not sure why that is exactly. Please consider opening a bug report at https://github.com/BobBuildTool/bob."
                 raise BuildError("Your system does not support unprivileged containers! You need to build without sandbox (--no-sandbox).",
-                                 help="Make sure /proc/sys/kernel/unprivileged_userns_clone is 1."
-                                      " In case you use Docker, consider using the 'unconfined' seccomp profile."
+                                 help=f"{msg} In case you use Docker, consider using the 'unconfined' seccomp profile."
                                       " See https://bob-build-tool.readthedocs.io/en/latest/installation.html#sandbox-capabilities for more details.",
                                  returncode=3)
         except OSError as e:
diff --git a/src/namespace-sandbox/namespace-sandbox.c b/src/namespace-sandbox/namespace-sandbox.c
index 763aa46e..ba0af0e9 100644
--- a/src/namespace-sandbox/namespace-sandbox.c
+++ b/src/namespace-sandbox/namespace-sandbox.c
@@ -74,7 +74,12 @@ struct Options {
 static int CreateTarget(const char *path, bool is_directory);
 
 // Child function used by CheckNamespacesSupported() in call to clone().
-static int CheckNamespacesSupportedChild(void *arg) { return 0; }
+static int CheckNamespacesSupportedChild(void *arg) {
+  // Check that we can make our mount namespace private. This fails on Ubuntu if
+  // /proc/sys/kernel/apparmor_restrict_unprivileged_userns_complain is enabled.
+  return mount("none", "/", NULL, MS_REC | MS_PRIVATE, NULL) == 0
+         ? EXIT_SUCCESS : EXIT_FAILURE;
+}
 
 // Check whether the required namespaces are supported.
 static int CheckNamespacesSupported() {
@@ -100,9 +105,13 @@ static int CheckNamespacesSupported() {
                          CLONE_NEWUSER | CLONE_NEWNS | CLONE_NEWUTS |
                              CLONE_NEWIPC | CLONE_NEWNET | SIGCHLD,
                          NULL));
-  CHECK_CALL(waitpid(pid, NULL, 0));
+  int status = 0;
+  CHECK_CALL(waitpid(pid, &status, 0));
 
-  return EXIT_SUCCESS;
+  if (WIFEXITED(status) && WEXITSTATUS(status) == 0)
+    return EXIT_SUCCESS;
+  else
+    return EXIT_FAILURE;
 }
 
 // Print out a usage error. argc and argv are the argument counter and vector,
diff --git a/test/run-tests.sh b/test/run-tests.sh
index 4e97f169..c7cff46c 100755
--- a/test/run-tests.sh
+++ b/test/run-tests.sh
@@ -227,6 +227,11 @@ if [[ -n $RUN_COVERAGE ]] ; then
     fi
 fi
 
+# Make sure sandbox helper is updated
+$RUN_PYTHON3 -c "from bob.develop.make import makeSandboxHelper
+makeSandboxHelper()
+"
+
 # execute everything if nothing was specified
 if [[ -z ${RUN_UNITTEST_PAT+isset} && -z ${RUN_BLACKBOX_PAT+isset} &&
       -z ${RUN_INTEGRATION_PAT+isset} ]] ; then