diff --git a/test/TEST-34-DYNAMICUSERMIGRATE/Makefile b/test/TEST-34-DYNAMICUSERMIGRATE/Makefile
new file mode 120000
index 0000000000..e9f93b1104
--- /dev/null
+++ b/test/TEST-34-DYNAMICUSERMIGRATE/Makefile
@@ -0,0 +1 @@
+../TEST-01-BASIC/Makefile
\ No newline at end of file
diff --git a/test/TEST-34-DYNAMICUSERMIGRATE/test.sh b/test/TEST-34-DYNAMICUSERMIGRATE/test.sh
new file mode 100755
index 0000000000..8ef28b05f7
--- /dev/null
+++ b/test/TEST-34-DYNAMICUSERMIGRATE/test.sh
@@ -0,0 +1,48 @@
+#!/bin/bash
+set -e
+TEST_DESCRIPTION="test migrating state directory from DynamicUser=1 to DynamicUser=0 and back"
+
+. $TEST_BASE_DIR/test-functions
+
+test_setup() {
+    create_empty_image
+    mkdir -p $TESTDIR/root
+    mount ${LOOPDEV}p1 $TESTDIR/root
+
+    (
+        LOG_LEVEL=5
+        eval $(udevadm info --export --query=env --name=${LOOPDEV}p2)
+
+        setup_basic_environment
+
+        # mask some services that we do not want to run in these tests
+        ln -fs /dev/null $initdir/etc/systemd/system/systemd-hwdb-update.service
+        ln -fs /dev/null $initdir/etc/systemd/system/systemd-journal-catalog-update.service
+        ln -fs /dev/null $initdir/etc/systemd/system/systemd-networkd.service
+        ln -fs /dev/null $initdir/etc/systemd/system/systemd-networkd.socket
+        ln -fs /dev/null $initdir/etc/systemd/system/systemd-resolved.service
+        ln -fs /dev/null $initdir/etc/systemd/system/systemd-machined.service
+
+        # setup the testsuite service
+        cat >$initdir/etc/systemd/system/testsuite.service <<EOF
+[Unit]
+Description=Testsuite service
+
+[Service]
+ExecStart=/bin/bash -x /testsuite.sh
+Type=oneshot
+StandardOutput=tty
+StandardError=tty
+NotifyAccess=all
+EOF
+        cp testsuite.sh $initdir/
+
+        setup_testsuite
+    ) || return 1
+    setup_nspawn_root
+
+    ddebug "umount $TESTDIR/root"
+    umount $TESTDIR/root
+}
+
+do_test "$@"
diff --git a/test/TEST-34-DYNAMICUSERMIGRATE/testsuite.sh b/test/TEST-34-DYNAMICUSERMIGRATE/testsuite.sh
new file mode 100755
index 0000000000..8f5316e3e5
--- /dev/null
+++ b/test/TEST-34-DYNAMICUSERMIGRATE/testsuite.sh
@@ -0,0 +1,46 @@
+#!/bin/bash
+set -ex
+set -o pipefail
+
+systemd-analyze log-level debug
+systemd-analyze log-target console
+
+# Set everything up without DynamicUser=1
+
+systemd-run --wait -p DynamicUser=0 -p StateDirectory=zzz touch /var/lib/zzz/test
+systemd-run --wait -p DynamicUser=0 -p StateDirectory=zzz test -f /var/lib/zzz/test
+! systemd-run --wait -p DynamicUser=0 -p StateDirectory=zzz test -f /var/lib/zzz/test-missing
+
+test -d /var/lib/zzz
+! test -L /var/lib/zzz
+! test -e /var/lib/private/zzz
+test -f /var/lib/zzz/test
+! test -f /var/lib/zzz/test-missing
+
+# Convert to DynamicUser=1
+
+systemd-run --wait -p DynamicUser=1 -p StateDirectory=zzz test -f /var/lib/zzz/test
+! systemd-run --wait -p DynamicUser=1 -p StateDirectory=zzz test -f /var/lib/zzz/test-missing
+
+test -L /var/lib/zzz
+test -d /var/lib/private/zzz
+
+test -f /var/lib/zzz/test
+! test -f /var/lib/zzz/test-missing
+
+# Convert back
+
+systemd-run --wait -p DynamicUser=0 -p StateDirectory=zzz test -f /var/lib/zzz/test
+! systemd-run --wait -p DynamicUser=0 -p StateDirectory=zzz test -f /var/lib/zzz/test-missing
+
+test -d /var/lib/zzz
+! test -L /var/lib/zzz
+! test -e /var/lib/private/zzz
+test -f /var/lib/zzz/test
+! test -f /var/lib/zzz/test-missing
+
+systemd-analyze log-level info
+
+echo OK > /testok
+
+exit 0