diff --git a/src/core/manager-serialize.c b/src/core/manager-serialize.c
index 62dfce93a0..3f624619df 100644
--- a/src/core/manager-serialize.c
+++ b/src/core/manager-serialize.c
@@ -92,7 +92,6 @@ int manager_serialize(
         (void) serialize_item_format(f, "current-job-id", "%" PRIu32, m->current_job_id);
         (void) serialize_item_format(f, "n-installed-jobs", "%u", m->n_installed_jobs);
         (void) serialize_item_format(f, "n-failed-jobs", "%u", m->n_failed_jobs);
-        (void) serialize_bool(f, "ready-sent", m->ready_sent);
         (void) serialize_bool(f, "taint-logged", m->taint_logged);
         (void) serialize_bool(f, "service-watchdogs", m->service_watchdogs);
 
@@ -356,15 +355,6 @@ int manager_deserialize(Manager *m, FILE *f, FDSet *fds) {
                         else
                                 m->n_failed_jobs += n;
 
-                } else if ((val = startswith(l, "ready-sent="))) {
-                        int b;
-
-                        b = parse_boolean(val);
-                        if (b < 0)
-                                log_notice("Failed to parse ready-sent flag '%s', ignoring.", val);
-                        else
-                                m->ready_sent = m->ready_sent || b;
-
                 } else if ((val = startswith(l, "taint-logged="))) {
                         int b;
 
@@ -558,7 +548,7 @@ int manager_deserialize(Manager *m, FILE *f, FDSet *fds) {
 
                         if (q < _MANAGER_TIMESTAMP_MAX) /* found it */
                                 (void) deserialize_dual_timestamp(val, m->timestamps + q);
-                        else if (!STARTSWITH_SET(l, "kdbus-fd=", "honor-device-enumeration=")) /* ignore deprecated values */
+                        else if (!STARTSWITH_SET(l, "kdbus-fd=", "honor-device-enumeration=", "ready-sent=")) /* ignore deprecated values */
                                 log_notice("Unknown serialization item '%s', ignoring.", l);
                 }
         }
diff --git a/src/core/manager.c b/src/core/manager.c
index 2789f0e3d0..456ad46135 100644
--- a/src/core/manager.c
+++ b/src/core/manager.c
@@ -3885,7 +3885,7 @@ static void manager_notify_finished(Manager *m) {
         log_taint_string(m);
 }
 
-static void manager_send_ready_user_scope(Manager *m) {
+static void manager_send_ready_on_basic_target(Manager *m) {
         int r;
 
         assert(m);
@@ -3904,18 +3904,18 @@ static void manager_send_ready_user_scope(Manager *m) {
         m->status_ready = false;
 }
 
-static void manager_send_ready_system_scope(Manager *m) {
+static void manager_send_ready_on_idle(Manager *m) {
         int r;
 
         assert(m);
 
-        if (!MANAGER_IS_SYSTEM(m))
-                return;
-
         /* Skip the notification if nothing changed. */
         if (m->ready_sent && m->status_ready)
                 return;
 
+        /* Note that for user managers, we might have already sent READY=1 in manager_send_ready_user_scope().
+         * But we still need to flush STATUS=. The second READY=1 will be treated as a noop so it doesn't
+         * hurt to send it twice. */
         r = sd_notify(/* unset_environment= */ false,
                       "READY=1\n"
                       "STATUS=Ready.");
@@ -3940,7 +3940,7 @@ static void manager_check_basic_target(Manager *m) {
                 return;
 
         /* For user managers, send out READY=1 as soon as we reach basic.target */
-        manager_send_ready_user_scope(m);
+        manager_send_ready_on_basic_target(m);
 
         /* Log the taint string as soon as we reach basic.target */
         log_taint_string(m);
@@ -3971,7 +3971,7 @@ void manager_check_finished(Manager *m) {
         if (hashmap_buckets(m->jobs) > hashmap_size(m->units) / 10)
                 m->jobs = hashmap_free(m->jobs);
 
-        manager_send_ready_system_scope(m);
+        manager_send_ready_on_idle(m);
 
         /* Notify Type=idle units that we are done now */
         manager_close_idle_pipe(m);
diff --git a/src/rpm/systemd-update-helper.in b/src/rpm/systemd-update-helper.in
index c81e16c3d3..8af9149352 100755
--- a/src/rpm/systemd-update-helper.in
+++ b/src/rpm/systemd-update-helper.in
@@ -107,25 +107,13 @@ case "$command" in
 
         [ -d /run/systemd/system ] || exit 0
 
-        users=$(systemctl list-units 'user@*' --legend=no | sed -n -r 's/.*user@([0-9]+).service.*/\1/p')
-
-        if [[ "$command" =~ reexec ]]; then
-            for user in $users; do
-                SYSTEMD_BUS_TIMEOUT={{UPDATE_HELPER_USER_TIMEOUT_SEC}}s \
-                        systemctl --user -M "$user@" daemon-reexec &
-            done
-            wait
-        fi
-
-        if [[ "$command" =~ reload ]]; then
-            for user in $users; do
-                SYSTEMD_BUS_TIMEOUT={{UPDATE_HELPER_USER_TIMEOUT_SEC}}s \
-                        systemctl --user -M "$user@" daemon-reload &
-            done
-            wait
+        if [[ "$command" =~ reexec|reload ]]; then
+            SYSTEMD_BUS_TIMEOUT={{UPDATE_HELPER_USER_TIMEOUT_SEC}}s systemctl reload "user@*.service"
         fi
 
         if [[ "$command" =~ restart ]]; then
+            users=$(systemctl list-units 'user@*' --legend=no | sed -n -r 's/.*user@([0-9]+).service.*/\1/p')
+
             for user in $users; do
                 SYSTEMD_BUS_TIMEOUT={{UPDATE_HELPER_USER_TIMEOUT_SEC}}s \
                         systemctl --user -M "$user@" reload-or-restart --marked &
diff --git a/units/capsule@.service.in b/units/capsule@.service.in
index f2bb9e3a45..a64298786e 100644
--- a/units/capsule@.service.in
+++ b/units/capsule@.service.in
@@ -23,6 +23,10 @@ StateDirectory=capsules/%i
 RuntimeDirectory=capsules/%i
 LogExtraFields=CAPSULE=%i
 Slice=capsule.slice
+# Reexecute the manager on service reload, instead of reloading.
+# This provides a synchronous method for restarting all user manager
+# instances after upgrade.
+ReloadSignal=RTMIN+25
 KillMode=mixed
 Delegate=pids memory cpu
 DelegateSubgroup=init.scope
diff --git a/units/user@.service.in b/units/user@.service.in
index 5695465747..381ab2a0db 100644
--- a/units/user@.service.in
+++ b/units/user@.service.in
@@ -20,6 +20,10 @@ PAMName=systemd-user
 Type=notify-reload
 ExecStart={{LIBEXECDIR}}/systemd --user
 Slice=user-%i.slice
+# Reexecute the manager on service reload, instead of reloading.
+# This provides a synchronous method for restarting all user manager
+# instances after upgrade.
+ReloadSignal=RTMIN+25
 KillMode=mixed
 Delegate=pids memory cpu
 DelegateSubgroup=init.scope