diff --git a/src/core/devices/nm-device.c b/src/core/devices/nm-device.c
index f8b0dad9c8..6e9b04b34f 100644
--- a/src/core/devices/nm-device.c
+++ b/src/core/devices/nm-device.c
@@ -17980,6 +17980,14 @@ _set_state_full(NMDevice *self, NMDeviceState state, NMDeviceStateReason reason,
             nm_device_cleanup(self, reason, CLEANUP_TYPE_DECONFIGURE);
         }
         break;
+    case NM_DEVICE_STATE_DEACTIVATING:
+        /* When deactivating, certain devices are removed/disconnected after the
+         * STATE_CHANGED signal is sent and before the DHCP release packet
+         * can be sent. To ensure the release packet is sent, we cleanup DHCP
+         * before the signal is emitted*/
+        _dev_ipdhcpx_cleanup(self, AF_INET, TRUE, FALSE);
+        _dev_ipdhcpx_cleanup(self, AF_INET6, TRUE, FALSE);
+        break;
     case NM_DEVICE_STATE_DISCONNECTED:
         if (old_state > NM_DEVICE_STATE_DISCONNECTED) {
             /* Ensure devices that previously assumed a connection now have
@@ -18029,6 +18037,7 @@ _set_state_full(NMDevice *self, NMDeviceState state, NMDeviceStateReason reason,
                                (guint32) state,
                                (guint32) old_state,
                                (guint32) reason);
+
     g_signal_emit(self,
                   signals[STATE_CHANGED],
                   0,
diff --git a/src/core/nm-manager.c b/src/core/nm-manager.c
index 87dde2c3af..ada26de1bd 100644
--- a/src/core/nm-manager.c
+++ b/src/core/nm-manager.c
@@ -8146,6 +8146,27 @@ nm_manager_start(NMManager *self, GError **error)
     return TRUE;
 }
 
+static int
+compare_device_remove_order(const CList *a, const CList *b, const void *user_data)
+{
+    NMDevice *dev_a = c_list_entry(a, NMDevice, devices_lst);
+    NMDevice *dev_b = c_list_entry(b, NMDevice, devices_lst);
+
+    gboolean a_has_dhcp =
+        nm_device_get_dhcp_config(dev_a, AF_INET) || nm_device_get_dhcp_config(dev_a, AF_INET6);
+    gboolean b_has_dhcp =
+        nm_device_get_dhcp_config(dev_b, AF_INET) || nm_device_get_dhcp_config(dev_b, AF_INET6);
+    gboolean a_is_software = nm_device_is_software(dev_a);
+    gboolean b_is_software = nm_device_is_software(dev_b);
+
+    /* priority: software AND dhcp first, then dhcp only
+     * then everything else,*/
+    uint a_score = a_has_dhcp ? (a_is_software ? 2 : 1) : 0;
+    uint b_score = b_has_dhcp ? (b_is_software ? 2 : 1) : 0;
+
+    return b_score - a_score;
+}
+
 void
 nm_manager_stop(NMManager *self)
 {
@@ -8167,6 +8188,12 @@ nm_manager_stop(NMManager *self)
 
     nm_dbus_manager_stop(nm_dbus_object_get_manager(NM_DBUS_OBJECT(self)));
 
+    /* When OVS internal interface or linux bridge holds DHCP, if we delete its
+     * physical interface first, then we cannot send out DHCP release request
+     * anymore. To fix that, we need to remove/deactivate software interfaces that
+     * holds DHCP config first.
+     */
+    c_list_sort(&priv->devices_lst_head, compare_device_remove_order, NULL);
     while ((device = c_list_first_entry(&priv->devices_lst_head, NMDevice, devices_lst)))
         remove_device(self, device, TRUE);