diff --git a/src/libsystemd-network/sd-dhcp-client.c b/src/libsystemd-network/sd-dhcp-client.c
index d27609655f..5064bf2b4f 100644
--- a/src/libsystemd-network/sd-dhcp-client.c
+++ b/src/libsystemd-network/sd-dhcp-client.c
@@ -1661,10 +1661,37 @@ static int client_handle_offer(sd_dhcp_client *client, DHCPMessage *message, siz
         return 0;
 }
 
+static int client_enter_requesting_now(sd_dhcp_client *client) {
+        assert(client);
+
+        client_set_state(client, DHCP_STATE_REQUESTING);
+        client->attempt = 0;
+
+        return event_reset_time(client->event, &client->timeout_resend,
+                                CLOCK_BOOTTIME, 0, 0,
+                                client_timeout_resend, client,
+                                client->event_priority, "dhcp4-resend-timer",
+                                /* force_reset = */ true);
+}
+
+static int client_enter_requesting_delayed(sd_event_source *s, uint64_t usec, void *userdata) {
+        sd_dhcp_client *client = ASSERT_PTR(userdata);
+        DHCP_CLIENT_DONT_DESTROY(client);
+        int r;
+
+        r = client_enter_requesting_now(client);
+        if (r < 0)
+                client_stop(client, r);
+
+        return 0;
+}
+
 static int client_enter_requesting(sd_dhcp_client *client) {
         assert(client);
         assert(client->lease);
 
+        (void) event_source_disable(client->timeout_resend);
+
         if (client->lease->ipv6_only_preferred_usec > 0) {
                 if (client->ipv6_acquired) {
                         log_dhcp_client(client,
@@ -1675,17 +1702,16 @@ static int client_enter_requesting(sd_dhcp_client *client) {
                 log_dhcp_client(client,
                                 "Received an OFFER with IPv6-only preferred option, delaying to send REQUEST with %s.",
                                 FORMAT_TIMESPAN(client->lease->ipv6_only_preferred_usec, USEC_PER_SEC));
+
+                return event_reset_time_relative(client->event, &client->timeout_ipv6_only_mode,
+                                                 CLOCK_BOOTTIME,
+                                                 client->lease->ipv6_only_preferred_usec, 0,
+                                                 client_enter_requesting_delayed, client,
+                                                 client->event_priority, "dhcp4-ipv6-only-mode-timer",
+                                                 /* force_reset = */ true);
         }
 
-        client_set_state(client, DHCP_STATE_REQUESTING);
-        client->attempt = 0;
-
-        return event_reset_time_relative(client->event, &client->timeout_resend,
-                                         CLOCK_BOOTTIME,
-                                         client->lease->ipv6_only_preferred_usec, 0,
-                                         client_timeout_resend, client,
-                                         client->event_priority, "dhcp4-resend-timer",
-                                         /* force_reset = */ true);
+        return client_enter_requesting_now(client);
 }
 
 static int client_handle_forcerenew(sd_dhcp_client *client, DHCPMessage *force, size_t len) {
@@ -1887,7 +1913,7 @@ static int client_enter_bound_now(sd_dhcp_client *client, int notify_event) {
         return 0;
 }
 
-static int client_timeout_ipv6_only_mode(sd_event_source *s, uint64_t usec, void *userdata) {
+static int client_enter_bound_delayed(sd_event_source *s, uint64_t usec, void *userdata) {
         sd_dhcp_client *client = ASSERT_PTR(userdata);
         DHCP_CLIENT_DONT_DESTROY(client);
         int r;
@@ -1927,7 +1953,7 @@ static int client_enter_bound(sd_dhcp_client *client, int notify_event) {
                 return event_reset_time_relative(client->event, &client->timeout_ipv6_only_mode,
                                                  CLOCK_BOOTTIME,
                                                  client->lease->ipv6_only_preferred_usec, 0,
-                                                 client_timeout_ipv6_only_mode, client,
+                                                 client_enter_bound_delayed, client,
                                                  client->event_priority, "dhcp4-ipv6-only-mode",
                                                  /* force_reset = */ true);
         }