diff --git a/src/network/networkd-address.c b/src/network/networkd-address.c
index b083b632b12..35142093ddb 100644
--- a/src/network/networkd-address.c
+++ b/src/network/networkd-address.c
@@ -848,10 +848,6 @@ int link_drop_foreign_addresses(Link *link) {
         assert(link);
         assert(link->network);
 
-        /* Keep all addresses when KeepConfiguration=yes. */
-        if (link->network->keep_configuration == KEEP_CONFIGURATION_YES)
-                return 0;
-
         /* First, mark all addresses. */
         SET_FOREACH(address, link->addresses) {
                 /* We consider IPv6LL addresses to be managed by the kernel, or dropped in link_drop_ipv6ll_addresses() */
diff --git a/src/network/networkd-link.c b/src/network/networkd-link.c
index de21343854d..238b68579c5 100644
--- a/src/network/networkd-link.c
+++ b/src/network/networkd-link.c
@@ -1240,10 +1240,13 @@ static int link_reconfigure_impl(Link *link, bool force) {
 
         link_drop_requests(link);
 
-        if (network && !force)
+        if (network && !force && network->keep_configuration != KEEP_CONFIGURATION_YES)
                 /* When a new/updated .network file is assigned, first make all configs (addresses,
                  * routes, and so on) foreign, and then drop unnecessary configs later by
-                 * link_drop_foreign_config() in link_configure(). */
+                 * link_drop_foreign_config() in link_configure().
+                 * Note, when KeepConfiguration=yes, link_drop_foreign_config() does nothing. Hence,
+                 * here we need to drop the configs such as addresses, routes, and so on configured by
+                 * the previously assigned .network file. */
                 link_foreignize_config(link);
         else {
                 /* Remove all managed configs. Note, foreign configs are removed in later by