diff --git a/src/test/test-execute.c b/src/test/test-execute.c
index ea68225ad7..68166cf749 100644
--- a/src/test/test-execute.c
+++ b/src/test/test-execute.c
@@ -45,7 +45,7 @@ typedef void (*test_function_t)(Manager *m);
 static void check(Manager *m, Unit *unit, int status_expected, int code_expected) {
         Service *service = NULL;
         usec_t ts;
-        usec_t timeout = 2 * USEC_PER_SEC;
+        usec_t timeout = 2 * USEC_PER_MINUTE;
 
         assert_se(m);
         assert_se(unit);
@@ -317,6 +317,7 @@ static void test_exec_dynamic_user(Manager *m) {
         test(m, "exec-dynamicuser-fixeduser.service", 0, CLD_EXITED);
         test(m, "exec-dynamicuser-fixeduser-one-supplementarygroup.service", 0, CLD_EXITED);
         test(m, "exec-dynamicuser-supplementarygroups.service", 0, CLD_EXITED);
+        test(m, "exec-dynamicuser-state-dir.service", 0, CLD_EXITED);
 }
 
 static void test_exec_environment(Manager *m) {
@@ -500,7 +501,6 @@ int main(int argc, char *argv[]) {
                 test_exec_user,
                 test_exec_group,
                 test_exec_supplementary_groups,
-                test_exec_dynamic_user,
                 test_exec_environment,
                 test_exec_environmentfile,
                 test_exec_passenvironment,
@@ -517,6 +517,7 @@ int main(int argc, char *argv[]) {
         };
         static const test_function_t system_tests[] = {
                 test_exec_systemcall_system_mode_with_user,
+                test_exec_dynamic_user,
                 NULL,
         };
         int r;
diff --git a/test/meson.build b/test/meson.build
index 9fdcd2d8d2..991d3fcc92 100644
--- a/test/meson.build
+++ b/test/meson.build
@@ -64,6 +64,7 @@ test_data_files = '''
         test-execute/exec-dynamicuser-fixeduser.service
         test-execute/exec-dynamicuser-fixeduser-one-supplementarygroup.service
         test-execute/exec-dynamicuser-supplementarygroups.service
+        test-execute/exec-dynamicuser-state-dir.service
         test-execute/exec-ignoresigpipe-no.service
         test-execute/exec-ignoresigpipe-yes.service
         test-execute/exec-personality-x86-64.service
diff --git a/test/test-execute/exec-dynamicuser-state-dir.service b/test/test-execute/exec-dynamicuser-state-dir.service
new file mode 100644
index 0000000000..7e2d88450b
--- /dev/null
+++ b/test/test-execute/exec-dynamicuser-state-dir.service
@@ -0,0 +1,19 @@
+[Unit]
+Description=Test DynamicUser= with StateDirectory=
+
+[Service]
+ExecStart=/usr/bin/test -w /var/lib/waldo
+ExecStart=/usr/bin/test -w /var/lib/quux/pief
+ExecStart=/bin/touch /var/lib/waldo/yay
+ExecStart=/bin/touch /var/lib/quux/pief/yayyay
+ExecStart=/usr/bin/test -f /var/lib/waldo/yay
+ExecStart=/usr/bin/test -f /var/lib/quux/pief/yayyay
+ExecStart=/usr/bin/test -f /var/lib/private/waldo/yay
+ExecStart=/usr/bin/test -f /var/lib/private/quux/pief/yayyay
+
+# Make sure that /var/lib/private/waldo is really the only writable directory besides the obvious candidates
+ExecStart=/bin/sh -x -c 'test $$(find / -type d -writable 2> /dev/null | egrep -v -e \'^(/var/tmp$$|/tmp$$|/proc/|/dev/mqueue$$|/dev/shm$$)\' | sort -u | tr -d '\\\\n') = /var/lib/private/quux/pief/var/lib/private/waldo'
+
+Type=oneshot
+DynamicUser=yes
+StateDirectory=waldo quux/pief