diff --git a/src/core/transaction.c b/src/core/transaction.c
index bafbb80b47..982b6cf6dc 100644
--- a/src/core/transaction.c
+++ b/src/core/transaction.c
@@ -976,11 +976,11 @@ int transaction_add_job_and_dependencies(
         }
 
         if (is_new && !ignore_requirements && type != JOB_NOP) {
-                Set *following;
+                _cleanup_set_free_ Set *following = NULL;
 
                 /* If we are following some other unit, make sure we
                  * add all dependencies of everybody following. */
-                if (unit_following_set(ret->unit, &following) > 0) {
+                if (unit_following_set(ret->unit, &following) > 0)
                         SET_FOREACH(dep, following) {
                                 r = transaction_add_job_and_dependencies(tr, type, dep, ret, false, false, false, ignore_order, e);
                                 if (r < 0) {
@@ -991,16 +991,13 @@ int transaction_add_job_and_dependencies(
                                 }
                         }
 
-                        set_free(following);
-                }
-
                 /* Finally, recursively add in all dependencies. */
                 if (IN_SET(type, JOB_START, JOB_RESTART)) {
                         UNIT_FOREACH_DEPENDENCY(dep, ret->unit, UNIT_ATOM_PULL_IN_START) {
                                 r = transaction_add_job_and_dependencies(tr, JOB_START, dep, ret, true, false, false, ignore_order, e);
                                 if (r < 0) {
                                         if (r != -EBADR) /* job type not applicable */
-                                                goto fail;
+                                                return r;
 
                                         sd_bus_error_free(e);
                                 }
@@ -1022,7 +1019,7 @@ int transaction_add_job_and_dependencies(
                                 r = transaction_add_job_and_dependencies(tr, JOB_VERIFY_ACTIVE, dep, ret, true, false, false, ignore_order, e);
                                 if (r < 0) {
                                         if (r != -EBADR) /* job type not applicable */
-                                                goto fail;
+                                                return r;
 
                                         sd_bus_error_free(e);
                                 }
@@ -1032,7 +1029,7 @@ int transaction_add_job_and_dependencies(
                                 r = transaction_add_job_and_dependencies(tr, JOB_STOP, dep, ret, true, true, false, ignore_order, e);
                                 if (r < 0) {
                                         if (r != -EBADR) /* job type not applicable */
-                                                goto fail;
+                                                return r;
 
                                         sd_bus_error_free(e);
                                 }
@@ -1050,30 +1047,42 @@ int transaction_add_job_and_dependencies(
                 }
 
                 if (IN_SET(type, JOB_STOP, JOB_RESTART)) {
-                        UnitDependencyAtom atom;
-                        JobType ptype;
-
+                        _cleanup_set_free_ Set *propagated_restart = NULL;
                         /* We propagate STOP as STOP, but RESTART only as TRY_RESTART, in order not to start
                          * dependencies that are not around. */
-                        if (type == JOB_RESTART) {
-                                atom = UNIT_ATOM_PROPAGATE_RESTART;
-                                ptype = JOB_TRY_RESTART;
-                        } else {
-                                ptype = JOB_STOP;
-                                atom = UNIT_ATOM_PROPAGATE_STOP;
-                        }
 
-                        UNIT_FOREACH_DEPENDENCY(dep, ret->unit, atom) {
-                                JobType nt;
+                        if (type == JOB_RESTART)
+                                UNIT_FOREACH_DEPENDENCY(dep, ret->unit, UNIT_ATOM_PROPAGATE_RESTART) {
+                                        JobType nt;
 
-                                nt = job_type_collapse(ptype, dep);
-                                if (nt == JOB_NOP)
+                                        r = set_ensure_put(&propagated_restart, NULL, dep);
+                                        if (r < 0)
+                                                return r;
+
+                                        nt = job_type_collapse(JOB_TRY_RESTART, dep);
+                                        if (nt == JOB_NOP)
+                                                continue;
+
+                                        r = transaction_add_job_and_dependencies(tr, nt, dep, ret, true, false, false, ignore_order, e);
+                                        if (r < 0) {
+                                                if (r != -EBADR) /* job type not applicable */
+                                                        return r;
+
+                                                sd_bus_error_free(e);
+                                        }
+                                }
+
+                        /* The 'stop' part of a restart job is also propagated to
+                         * units with UNIT_ATOM_PROPAGATE_STOP */
+                        UNIT_FOREACH_DEPENDENCY(dep, ret->unit, UNIT_ATOM_PROPAGATE_STOP) {
+                                /* Units experienced restart propagation are skipped */
+                                if (set_contains(propagated_restart, dep))
                                         continue;
 
-                                r = transaction_add_job_and_dependencies(tr, nt, dep, ret, true, false, false, ignore_order, e);
+                                r = transaction_add_job_and_dependencies(tr, JOB_STOP, dep, ret, true, false, false, ignore_order, e);
                                 if (r < 0) {
                                         if (r != -EBADR) /* job type not applicable */
-                                                goto fail;
+                                                return r;
 
                                         sd_bus_error_free(e);
                                 }
@@ -1087,9 +1096,6 @@ int transaction_add_job_and_dependencies(
         }
 
         return 0;
-
-fail:
-        return r;
 }
 
 int transaction_add_isolate_jobs(Transaction *tr, Manager *m) {