diff --git a/src/core/devices/nm-device.c b/src/core/devices/nm-device.c
index 371145982..078dc16a5 100644
--- a/src/core/devices/nm-device.c
+++ b/src/core/devices/nm-device.c
@@ -833,7 +833,8 @@ static void _dev_ipshared4_spawn_dnsmasq(NMDevice *self);
 
 static void _dev_ipshared6_start(NMDevice *self);
 
-static void _cleanup_ip_pre(NMDevice *self, int addr_family, CleanupType cleanup_type);
+static void
+_cleanup_ip_pre(NMDevice *self, int addr_family, CleanupType cleanup_type, gboolean from_reapply);
 
 static void concheck_update_state(NMDevice *          self,
                                   int                 addr_family,
@@ -3246,10 +3247,6 @@ got_ip_state:
                                                       &may_fail_other)))
         combinedip_state = NM_DEVICE_IP_STATE_PENDING;
     else if (ip_state == NM_DEVICE_IP_STATE_READY
-             && NM_IN_SET(ip_state_other,
-                          NM_DEVICE_IP_STATE_PENDING,
-                          NM_DEVICE_IP_STATE_READY,
-                          NM_DEVICE_IP_STATE_FAILED)
              && _prop_get_ipvx_may_fail_cached(self,
                                                nm_utils_addr_family_other(addr_family),
                                                &may_fail_other))
@@ -3350,13 +3347,16 @@ _dev_ip_state_check_async(NMDevice *self, int addr_family)
 }
 
 static void
-_dev_ip_state_cleanup(NMDevice *self, int addr_family)
+_dev_ip_state_cleanup(NMDevice *self, int addr_family, gboolean from_reapply)
 {
     NMDevicePrivate *priv = NM_DEVICE_GET_PRIVATE(self);
     int              IS_IPv4;
 
     if (addr_family == AF_UNSPEC) {
-        _dev_ip_state_set_state(self, addr_family, NM_DEVICE_IP_STATE_NONE, "ip-state-clear");
+        _dev_ip_state_set_state(self,
+                                addr_family,
+                                from_reapply ? NM_DEVICE_IP_STATE_PENDING : NM_DEVICE_IP_STATE_NONE,
+                                "ip-state-clear");
         return;
     }
 
@@ -3364,7 +3364,10 @@ _dev_ip_state_cleanup(NMDevice *self, int addr_family)
 
     nm_clear_g_source_inst(&priv->ip_data_x[IS_IPv4].check_async_source);
     nm_clear_g_source_inst(&priv->ip_data_x[IS_IPv4].req_timeout_source);
-    _dev_ip_state_set_state(self, addr_family, NM_DEVICE_IP_STATE_NONE, "ip-state-clear");
+    _dev_ip_state_set_state(self,
+                            addr_family,
+                            from_reapply ? NM_DEVICE_IP_STATE_PENDING : NM_DEVICE_IP_STATE_NONE,
+                            "ip-state-clear");
     priv->ip_data_x[IS_IPv4].wait_for_carrier = FALSE;
     priv->ip_data_x[IS_IPv4].wait_for_ports   = FALSE;
     priv->ip_data_x[IS_IPv4].is_disabled      = FALSE;
@@ -11744,11 +11747,11 @@ activate_stage3_ip_config(NMDevice *self)
 
     if (priv->ip_data_4.do_reapply) {
         _LOGD_ip(AF_INET, "reapply...");
-        _cleanup_ip_pre(self, AF_INET, CLEANUP_TYPE_DECONFIGURE);
+        _cleanup_ip_pre(self, AF_INET, CLEANUP_TYPE_DECONFIGURE, TRUE);
     }
     if (priv->ip_data_6.do_reapply) {
         _LOGD_ip(AF_INET6, "reapply...");
-        _cleanup_ip_pre(self, AF_INET6, CLEANUP_TYPE_DECONFIGURE);
+        _cleanup_ip_pre(self, AF_INET6, CLEANUP_TYPE_DECONFIGURE, TRUE);
     }
 
     /* Add the interface to the specified firewall zone */
@@ -12247,7 +12250,7 @@ delete_on_deactivate_check_and_schedule(NMDevice *self)
 }
 
 static void
-_cleanup_ip_pre(NMDevice *self, int addr_family, CleanupType cleanup_type)
+_cleanup_ip_pre(NMDevice *self, int addr_family, CleanupType cleanup_type, gboolean from_reapply)
 {
     const int IS_IPv4 = NM_IS_IPv4(addr_family);
 
@@ -12265,8 +12268,8 @@ _cleanup_ip_pre(NMDevice *self, int addr_family, CleanupType cleanup_type)
 
     _dev_ipmanual_cleanup(self);
 
-    _dev_ip_state_cleanup(self, AF_UNSPEC);
-    _dev_ip_state_cleanup(self, addr_family);
+    _dev_ip_state_cleanup(self, AF_UNSPEC, from_reapply);
+    _dev_ip_state_cleanup(self, addr_family, from_reapply);
 }
 
 gboolean
@@ -14923,8 +14926,8 @@ _cleanup_generic_pre(NMDevice *self, CleanupType cleanup_type)
     for (i = 0; i < 2; i++)
         nm_clear_pointer(&priv->hostname_resolver_x[i], _hostname_resolver_free);
 
-    _cleanup_ip_pre(self, AF_INET, cleanup_type);
-    _cleanup_ip_pre(self, AF_INET6, cleanup_type);
+    _cleanup_ip_pre(self, AF_INET, cleanup_type, FALSE);
+    _cleanup_ip_pre(self, AF_INET6, cleanup_type, FALSE);
 
     _dev_ip_state_req_timeout_cancel(self, AF_UNSPEC);
 }
@@ -15424,8 +15427,8 @@ _set_state_full(NMDevice *self, NMDeviceState state, NMDeviceStateReason reason,
             /* Clean up any half-done IP operations if the device's layer2
              * finds out it needs authentication during IP config.
              */
-            _cleanup_ip_pre(self, AF_INET, CLEANUP_TYPE_DECONFIGURE);
-            _cleanup_ip_pre(self, AF_INET6, CLEANUP_TYPE_DECONFIGURE);
+            _cleanup_ip_pre(self, AF_INET, CLEANUP_TYPE_DECONFIGURE, FALSE);
+            _cleanup_ip_pre(self, AF_INET6, CLEANUP_TYPE_DECONFIGURE, FALSE);
         }
         break;
     default: