diff --git a/src/network/networkd-dhcp-prefix-delegation.c b/src/network/networkd-dhcp-prefix-delegation.c
index dc4868300a..24bafb8b4a 100644
--- a/src/network/networkd-dhcp-prefix-delegation.c
+++ b/src/network/networkd-dhcp-prefix-delegation.c
@@ -184,7 +184,7 @@ int dhcp6_pd_remove(Link *link, bool only_marked) {
                         if (k < 0)
                                 r = k;
 
-                        route_cancel_request(route);
+                        route_cancel_request(route, link);
                 }
         } else {
                 Address *address;
@@ -655,6 +655,7 @@ static int dhcp6_pd_finalize(Link *link) {
 }
 
 void dhcp6_pd_prefix_lost(Link *dhcp6_link) {
+        Route *route;
         Link *link;
         int r;
 
@@ -662,7 +663,7 @@ void dhcp6_pd_prefix_lost(Link *dhcp6_link) {
         assert(dhcp6_link->manager);
 
         HASHMAP_FOREACH(link, dhcp6_link->manager->links_by_index) {
-                if (link == dhcp6_link)
+                if (!dhcp6_pd_is_uplink(link, dhcp6_link, /* accept_auto = */ true))
                         continue;
 
                 r = dhcp6_pd_remove(link, /* only_marked = */ false);
@@ -670,6 +671,25 @@ void dhcp6_pd_prefix_lost(Link *dhcp6_link) {
                         link_enter_failed(link);
         }
 
+        SET_FOREACH(route, dhcp6_link->manager->routes) {
+                if (route->source != NETWORK_CONFIG_SOURCE_DHCP6)
+                        continue;
+                if (route->family != AF_INET6)
+                        continue;
+                if (route->type != RTN_UNREACHABLE)
+                        continue;
+                if (!set_contains(dhcp6_link->dhcp6_pd_prefixes,
+                                  &(struct in_addr_prefix) {
+                                          .family = AF_INET6,
+                                          .prefixlen = route->dst_prefixlen,
+                                          .address = route->dst }))
+                        continue;
+
+                (void) route_remove(route);
+
+                route_cancel_request(route, dhcp6_link);
+        }
+
         set_clear(dhcp6_link->dhcp6_pd_prefixes);
 }
 
diff --git a/src/network/networkd-dhcp4.c b/src/network/networkd-dhcp4.c
index 1ee0052a75..cd30cae7c9 100644
--- a/src/network/networkd-dhcp4.c
+++ b/src/network/networkd-dhcp4.c
@@ -71,7 +71,7 @@ static int dhcp4_remove_address_and_routes(Link *link, bool only_marked) {
                 if (k < 0)
                         r = k;
 
-                route_cancel_request(route);
+                route_cancel_request(route, link);
         }
 
         SET_FOREACH(address, link->addresses) {
diff --git a/src/network/networkd-dhcp6.c b/src/network/networkd-dhcp6.c
index f86efca5c7..b9831e7fa1 100644
--- a/src/network/networkd-dhcp6.c
+++ b/src/network/networkd-dhcp6.c
@@ -63,7 +63,7 @@ static int dhcp6_remove(Link *link, bool only_marked) {
                 if (k < 0)
                         r = k;
 
-                route_cancel_request(route);
+                route_cancel_request(route, link);
         }
 
         SET_FOREACH(address, link->addresses) {
diff --git a/src/network/networkd-ndisc.c b/src/network/networkd-ndisc.c
index 470c969329..df5e580aef 100644
--- a/src/network/networkd-ndisc.c
+++ b/src/network/networkd-ndisc.c
@@ -90,7 +90,7 @@ static int ndisc_remove(Link *link, struct in6_addr *router) {
                 if (k < 0)
                         r = k;
 
-                route_cancel_request(route);
+                route_cancel_request(route, link);
         }
 
         SET_FOREACH(address, link->addresses) {
diff --git a/src/network/networkd-route.c b/src/network/networkd-route.c
index 003c8dcde4..8e4081a8e3 100644
--- a/src/network/networkd-route.c
+++ b/src/network/networkd-route.c
@@ -1260,24 +1260,25 @@ static int route_configure(
         return 0;
 }
 
-void route_cancel_request(Route *route) {
+void route_cancel_request(Route *route, Link *link) {
         Request req;
 
         assert(route);
 
+        link = route->link ?: link;
+
+        assert(link);
+
         if (!route_is_requesting(route))
                 return;
 
-        if (!route->link)
-                return;
-
         req = (Request) {
-                .link = route->link,
+                .link = link,
                 .type = REQUEST_TYPE_ROUTE,
                 .route = route,
         };
 
-        request_drop(ordered_set_get(route->link->manager->request_queue, &req));
+        request_drop(ordered_set_get(link->manager->request_queue, &req));
         route_cancel_requesting(route);
 }
 
diff --git a/src/network/networkd-route.h b/src/network/networkd-route.h
index a3194de1ae..e3e22a5985 100644
--- a/src/network/networkd-route.h
+++ b/src/network/networkd-route.h
@@ -86,7 +86,7 @@ int link_drop_routes(Link *link);
 int link_drop_foreign_routes(Link *link);
 void link_foreignize_routes(Link *link);
 
-void route_cancel_request(Route *route);
+void route_cancel_request(Route *route, Link *link);
 int link_request_route(
                 Link *link,
                 Route *route,