diff --git a/src/network/networkd-dhcp-prefix-delegation.c b/src/network/networkd-dhcp-prefix-delegation.c
index b8b03f6d3b..d8f9a2c053 100644
--- a/src/network/networkd-dhcp-prefix-delegation.c
+++ b/src/network/networkd-dhcp-prefix-delegation.c
@@ -176,8 +176,7 @@ int dhcp_pd_remove(Link *link, bool only_marked) {
 
                         link_remove_dhcp_pd_subnet_prefix(link, &route->dst.in6);
 
-                        RET_GATHER(ret, route_remove(route));
-                        route_cancel_request(route, link);
+                        RET_GATHER(ret, route_remove_and_cancel(route, link->manager));
                 }
         } else {
                 Address *address;
@@ -612,9 +611,7 @@ void dhcp_pd_prefix_lost(Link *uplink) {
                                           .address = route->dst }))
                         continue;
 
-                (void) route_remove(route);
-
-                route_cancel_request(route, uplink);
+                (void) route_remove_and_cancel(route, uplink->manager);
         }
 
         set_clear(uplink->dhcp_pd_prefixes);
diff --git a/src/network/networkd-dhcp4.c b/src/network/networkd-dhcp4.c
index be7abcf6f3..1a1836cf66 100644
--- a/src/network/networkd-dhcp4.c
+++ b/src/network/networkd-dhcp4.c
@@ -256,8 +256,7 @@ static int dhcp4_remove_address_and_routes(Link *link, bool only_marked) {
                 if (only_marked && !route_is_marked(route))
                         continue;
 
-                RET_GATHER(ret, route_remove(route));
-                route_cancel_request(route, link);
+                RET_GATHER(ret, route_remove_and_cancel(route, link->manager));
         }
 
         SET_FOREACH(address, link->addresses) {
diff --git a/src/network/networkd-dhcp6.c b/src/network/networkd-dhcp6.c
index 26ed034bbe..eb1420be5c 100644
--- a/src/network/networkd-dhcp6.c
+++ b/src/network/networkd-dhcp6.c
@@ -62,8 +62,7 @@ static int dhcp6_remove(Link *link, bool only_marked) {
                 if (only_marked && !route_is_marked(route))
                         continue;
 
-                RET_GATHER(ret, route_remove(route));
-                route_cancel_request(route, link);
+                RET_GATHER(ret, route_remove_and_cancel(route, link->manager));
         }
 
         SET_FOREACH(address, link->addresses) {
diff --git a/src/network/networkd-ndisc.c b/src/network/networkd-ndisc.c
index 7186187fd8..488c8c0294 100644
--- a/src/network/networkd-ndisc.c
+++ b/src/network/networkd-ndisc.c
@@ -1173,7 +1173,7 @@ static int ndisc_drop_outdated(Link *link, usec_t timestamp_usec) {
                 if (route->lifetime_usec >= timestamp_usec)
                         continue; /* the route is still valid */
 
-                r = route_remove_and_drop(route);
+                r = route_remove_and_cancel(route, link->manager);
                 if (r < 0)
                         RET_GATHER(ret, log_link_warning_errno(link, r, "Failed to remove outdated SLAAC route, ignoring: %m"));
         }
diff --git a/src/network/networkd-route.c b/src/network/networkd-route.c
index 3a33769f8b..efb121cb82 100644
--- a/src/network/networkd-route.c
+++ b/src/network/networkd-route.c
@@ -510,13 +510,13 @@ static int route_remove_handler(sd_netlink *rtnl, sd_netlink_message *m, Link *l
         return 1;
 }
 
-int route_remove(Route *route) {
+int route_remove(Route *route, Manager *manager) {
         _cleanup_(sd_netlink_message_unrefp) sd_netlink_message *m = NULL;
         Link *link = NULL;
         int r;
 
         assert(route);
-        Manager *manager = ASSERT_PTR(route->manager);
+        assert(manager);
 
         log_route_debug(route, "Removing", manager);
 
@@ -541,17 +541,27 @@ int route_remove(Route *route) {
         return 0;
 }
 
-int route_remove_and_drop(Route *route) {
-        if (!route)
-                return 0;
+int route_remove_and_cancel(Route *route, Manager *manager) {
+        bool waiting = false;
+        Request *req;
 
-        route_cancel_request(route, NULL);
+        assert(route);
+        assert(manager);
 
-        if (route_exists(route))
-                return route_remove(route);
+        /* If the route is remembered by the manager, then use the remembered object. */
+        (void) route_get(manager, route, &route);
 
-        if (route->state == 0)
-                route_free(route);
+        /* Cancel the request for the route. If the request is already called but we have not received the
+         * notification about the request, then explicitly remove the route. */
+        if (route_get_request(manager, route, &req) >= 0) {
+                waiting = req->waiting_reply;
+                request_detach(req);
+                route_cancel_requesting(route);
+        }
+
+        /* If we know that the route will come or already exists, remove it. */
+        if (waiting || (route->manager && route_exists(route)))
+                return route_remove(route, manager);
 
         return 0;
 }
@@ -562,7 +572,7 @@ static int route_expire_handler(sd_event_source *s, uint64_t usec, void *userdat
 
         assert(route->manager);
 
-        r = route_remove(route);
+        r = route_remove(route, route->manager);
         if (r < 0) {
                 Link *link = NULL;
                 (void) route_get_link(route->manager, route, &link);
@@ -944,20 +954,6 @@ int link_request_static_routes(Link *link, bool only_ipv4) {
         return 0;
 }
 
-void route_cancel_request(Route *route, Link *link) {
-        assert(route);
-        Manager *manager = ASSERT_PTR(route->manager ?: ASSERT_PTR(link)->manager);
-
-        if (!route_is_requesting(route))
-                return;
-
-        Request *req;
-        if (route_get_request(manager, route, &req) >= 0)
-                request_detach(req);
-
-        route_cancel_requesting(route);
-}
-
 static int process_route_one(
                 Manager *manager,
                 uint16_t type,
@@ -1376,7 +1372,7 @@ int link_drop_routes(Link *link, bool foreign) {
                 if (!route_is_marked(route))
                         continue;
 
-                RET_GATHER(r, route_remove(route));
+                RET_GATHER(r, route_remove(route, link->manager));
         }
 
         return r;
diff --git a/src/network/networkd-route.h b/src/network/networkd-route.h
index 090bf34a61..51a06dd0f1 100644
--- a/src/network/networkd-route.h
+++ b/src/network/networkd-route.h
@@ -88,8 +88,8 @@ int route_new_static(Network *network, const char *filename, unsigned section_li
 int route_dup(const Route *src, const RouteNextHop *nh, Route **ret);
 
 int route_configure_handler_internal(sd_netlink *rtnl, sd_netlink_message *m, Link *link, Route *route, const char *error_msg);
-int route_remove(Route *route);
-int route_remove_and_drop(Route *route);
+int route_remove(Route *route, Manager *manager);
+int route_remove_and_cancel(Route *route, Manager *manager);
 
 int route_get(Manager *manager, const Route *route, Route **ret);
 
@@ -102,7 +102,6 @@ static inline int link_drop_foreign_routes(Link *link) {
 }
 int link_foreignize_routes(Link *link);
 
-void route_cancel_request(Route *route, Link *link);
 int link_request_route(
                 Link *link,
                 const Route *route,