diff --git a/src/test/test-execute.c b/src/test/test-execute.c
index 92efc09371..1ef6bb4efa 100644
--- a/src/test/test-execute.c
+++ b/src/test/test-execute.c
@@ -341,6 +341,13 @@ static void test_exec_dynamicuser(Manager *m) {
         test(m, "exec-dynamicuser-fixeduser-one-supplementarygroup.service", 0, CLD_EXITED);
         test(m, "exec-dynamicuser-supplementarygroups.service", 0, CLD_EXITED);
         test(m, "exec-dynamicuser-statedir.service", 0, CLD_EXITED);
+
+        test(m, "exec-dynamicuser-statedir-migrate-step1.service", 0, CLD_EXITED);
+        test(m, "exec-dynamicuser-statedir-migrate-step2.service", 0, CLD_EXITED);
+        (void) rm_rf("/var/lib/test-dynamicuser-migrate", REMOVE_ROOT|REMOVE_PHYSICAL);
+        (void) rm_rf("/var/lib/test-dynamicuser-migrate2", REMOVE_ROOT|REMOVE_PHYSICAL);
+        (void) rm_rf("/var/lib/private/test-dynamicuser-migrate", REMOVE_ROOT|REMOVE_PHYSICAL);
+        (void) rm_rf("/var/lib/private/test-dynamicuser-migrate2", REMOVE_ROOT|REMOVE_PHYSICAL);
 }
 
 static void test_exec_environment(Manager *m) {
diff --git a/test/meson.build b/test/meson.build
index cd00186266..c50757a46b 100644
--- a/test/meson.build
+++ b/test/meson.build
@@ -56,6 +56,8 @@ test_data_files = '''
         test-execute/exec-capabilityboundingset-simple.service
         test-execute/exec-dynamicuser-fixeduser-one-supplementarygroup.service
         test-execute/exec-dynamicuser-fixeduser.service
+        test-execute/exec-dynamicuser-statedir-migrate-step1.service
+        test-execute/exec-dynamicuser-statedir-migrate-step2.service
         test-execute/exec-dynamicuser-statedir.service
         test-execute/exec-dynamicuser-supplementarygroups.service
         test-execute/exec-environment-empty.service
diff --git a/test/test-execute/exec-dynamicuser-statedir-migrate-step1.service b/test/test-execute/exec-dynamicuser-statedir-migrate-step1.service
new file mode 100644
index 0000000000..83bdfb311a
--- /dev/null
+++ b/test/test-execute/exec-dynamicuser-statedir-migrate-step1.service
@@ -0,0 +1,16 @@
+[Unit]
+Description=Test DynamicUser= migrate StateDirectory= (preparation)
+
+[Service]
+ExecStart=/bin/sh -c 'test -w /var/lib/test-dynamicuser-migrate'
+ExecStart=/bin/sh -c 'test -w /var/lib/test-dynamicuser-migrate2/hoge'
+ExecStart=/bin/sh -c 'test ! -L /var/lib/test-dynamicuser-migrate'
+ExecStart=/bin/sh -c 'test ! -L /var/lib/test-dynamicuser-migrate2/hoge'
+ExecStart=/bin/sh -c 'test -d /var/lib/test-dynamicuser-migrate'
+ExecStart=/bin/sh -c 'test -d /var/lib/test-dynamicuser-migrate2/hoge'
+ExecStart=/bin/sh -c 'touch /var/lib/test-dynamicuser-migrate/yay'
+ExecStart=/bin/sh -c 'touch /var/lib/test-dynamicuser-migrate2/hoge/yayyay'
+
+Type=oneshot
+DynamicUser=no
+StateDirectory=test-dynamicuser-migrate test-dynamicuser-migrate2/hoge
diff --git a/test/test-execute/exec-dynamicuser-statedir-migrate-step2.service b/test/test-execute/exec-dynamicuser-statedir-migrate-step2.service
new file mode 100644
index 0000000000..8154922a2f
--- /dev/null
+++ b/test/test-execute/exec-dynamicuser-statedir-migrate-step2.service
@@ -0,0 +1,24 @@
+[Unit]
+Description=Test DynamicUser= migrate StateDirectory= (preparation)
+
+[Service]
+ExecStart=/bin/sh -c 'test -w /var/lib/test-dynamicuser-migrate'
+ExecStart=/bin/sh -c 'test -w /var/lib/test-dynamicuser-migrate2/hoge'
+ExecStart=/bin/sh -c 'test -L /var/lib/test-dynamicuser-migrate'
+ExecStart=/bin/sh -c 'test -L /var/lib/test-dynamicuser-migrate2/hoge'
+ExecStart=/bin/sh -c 'test -d /var/lib/test-dynamicuser-migrate'
+ExecStart=/bin/sh -c 'test -d /var/lib/test-dynamicuser-migrate2/hoge'
+ExecStart=/bin/sh -c 'test -f /var/lib/test-dynamicuser-migrate/yay'
+ExecStart=/bin/sh -c 'test -f /var/lib/test-dynamicuser-migrate2/hoge/yayyay'
+ExecStart=/bin/sh -c 'test -d /var/lib/private/test-dynamicuser-migrate'
+ExecStart=/bin/sh -c 'test -d /var/lib/private/test-dynamicuser-migrate2/hoge'
+ExecStart=/bin/sh -c 'test -f /var/lib/private/test-dynamicuser-migrate/yay'
+ExecStart=/bin/sh -c 'test -f /var/lib/private/test-dynamicuser-migrate2/hoge/yayyay'
+ExecStart=/bin/sh -c 'touch /var/lib/test-dynamicuser-migrate/yay'
+ExecStart=/bin/sh -c 'touch /var/lib/test-dynamicuser-migrate2/hoge/yayyay'
+ExecStart=/bin/sh -c 'touch /var/lib/private/test-dynamicuser-migrate/yay'
+ExecStart=/bin/sh -c 'touch /var/lib/private/test-dynamicuser-migrate2/hoge/yayyay'
+
+Type=oneshot
+DynamicUser=yes
+StateDirectory=test-dynamicuser-migrate test-dynamicuser-migrate2/hoge