diff --git a/src/network/networkd-address.c b/src/network/networkd-address.c
index 3164f82c304..63b40da4328 100644
--- a/src/network/networkd-address.c
+++ b/src/network/networkd-address.c
@@ -1295,7 +1295,7 @@ void address_cancel_request(Address *address) {
                 .address = address,
         };
 
-        request_drop(ordered_set_get(address->link->manager->request_queue, &req));
+        request_detach(address->link->manager, &req);
         address_cancel_requesting(address);
 }
 
diff --git a/src/network/networkd-link.c b/src/network/networkd-link.c
index 48f8e40fb40..e925739d06e 100644
--- a/src/network/networkd-link.c
+++ b/src/network/networkd-link.c
@@ -906,7 +906,7 @@ static void link_drop_requests(Link *link) {
 
         ORDERED_SET_FOREACH(req, link->manager->request_queue)
                 if (req->link == link)
-                        request_drop(req);
+                        request_detach(link->manager, req);
 }
 
 static Link *link_drop(Link *link) {
diff --git a/src/network/networkd-queue.c b/src/network/networkd-queue.c
index 06a0cb066e2..70edc27fcdf 100644
--- a/src/network/networkd-queue.c
+++ b/src/network/networkd-queue.c
@@ -81,25 +81,38 @@ static Request *request_free(Request *req) {
         if (!req)
                 return NULL;
 
-        if (req->link && req->link->manager)
-                /* To prevent from triggering assertions in hash functions, remove this request before
-                 * freeing object below. */
-                ordered_set_remove(req->link->manager->request_queue, req);
+        /* To prevent from triggering assertions in the hash and compare functions, remove this request
+         * before freeing userdata below. */
+        if (req->manager)
+                ordered_set_remove(req->manager->request_queue, req);
+
         if (req->consume_object)
                 request_free_object(req->type, req->object);
-        link_unref(req->link);
+
+        link_unref(req->link); /* link may be NULL, but link_unref() can handle it gracefully. */
 
         return mfree(req);
 }
 
 DEFINE_TRIVIAL_REF_UNREF_FUNC(Request, request, request_free);
 
-void request_drop(Request *req) {
+void request_detach(Manager *manager, Request *req) {
+        assert(manager);
+
         if (!req)
                 return;
 
-        if (req->message_counter)
+        req = ordered_set_remove(manager->request_queue, req);
+        if (!req)
+                return;
+
+        req->manager = NULL;
+
+        if (req->message_counter) {
+                assert(*req->message_counter > 0);
                 (*req->message_counter)--;
+                req->message_counter = NULL; /* To prevent double decrement. */
+        }
 
         request_unref(req);
 }
@@ -257,6 +270,7 @@ int netdev_queue_request(
 
         *req = (Request) {
                 .n_ref = 1,
+                .manager = netdev->manager,
                 .netdev = netdev_ref(netdev),
                 .type = REQUEST_TYPE_NETDEV_INDEPENDENT,
                 .consume_object = true,
@@ -264,9 +278,6 @@ int netdev_queue_request(
 
         existing = ordered_set_get(netdev->manager->request_queue, req);
         if (existing) {
-                /* To prevent from removing the existing request. */
-                req->netdev = netdev_unref(req->netdev);
-
                 if (ret)
                         *ret = existing;
                 return 0;
@@ -276,6 +287,8 @@ int netdev_queue_request(
         if (r < 0)
                 return r;
 
+        req->manager = netdev->manager;
+
         if (ret)
                 *ret = req;
 
@@ -336,9 +349,6 @@ int link_queue_request(
 
         existing = ordered_set_get(link->manager->request_queue, req);
         if (existing) {
-                /* To prevent from removing the existing request. */
-                req->link = link_unref(req->link);
-
                 if (ret)
                         *ret = existing;
                 return 0;
@@ -348,6 +358,7 @@ int link_queue_request(
         if (r < 0)
                 return r;
 
+        req->manager = link->manager;
         if (req->message_counter)
                 (*req->message_counter)++;
 
@@ -440,8 +451,8 @@ int manager_process_requests(sd_event_source *s, void *userdata) {
                                 if (req->link)
                                         link_enter_failed(req->link);
                         } else if (r > 0) {
-                                ordered_set_remove(manager->request_queue, req);
-                                request_unref(req);
+                                req->message_counter = NULL;
+                                request_detach(manager, req);
                                 processed = true;
                         }
                 }
diff --git a/src/network/networkd-queue.h b/src/network/networkd-queue.h
index 7410e5c8612..14403efdd08 100644
--- a/src/network/networkd-queue.h
+++ b/src/network/networkd-queue.h
@@ -46,7 +46,9 @@ typedef enum RequestType {
 typedef struct Request {
         unsigned n_ref;
 
-        Link *link;
+        Manager *manager; /* must be non-NULL */
+        Link *link; /* can be NULL */
+
         RequestType type;
         bool consume_object;
         union {
@@ -74,7 +76,7 @@ Request *request_ref(Request *req);
 Request *request_unref(Request *req);
 DEFINE_TRIVIAL_CLEANUP_FUNC(Request*, request_unref);
 
-void request_drop(Request *req);
+void request_detach(Manager *manager, Request *req);
 
 int netdev_queue_request(
                 NetDev *netdev,
diff --git a/src/network/networkd-route.c b/src/network/networkd-route.c
index 1c5ace643ed..9be1190655e 100644
--- a/src/network/networkd-route.c
+++ b/src/network/networkd-route.c
@@ -1560,7 +1560,7 @@ void route_cancel_request(Route *route, Link *link) {
                 .route = route,
         };
 
-        request_drop(ordered_set_get(link->manager->request_queue, &req));
+        request_detach(link->manager, &req);
         route_cancel_requesting(route);
 }