diff --git a/protocols/gossipsub/CHANGELOG.md b/protocols/gossipsub/CHANGELOG.md
index 349defd9c20b..5d38d4c75bff 100644
--- a/protocols/gossipsub/CHANGELOG.md
+++ b/protocols/gossipsub/CHANGELOG.md
@@ -1,9 +1,13 @@
 # 0.44.0 [unreleased]
 
+- Update to the `libp2p_swarm::handler::ConnectionEvent` `DialTimeout` introduction and consequential changes. See [PR XXXX].
+
 - Update to `libp2p-core` `v0.39.0`.
 
 - Update to `libp2p-swarm` `v0.42.0`.
 
+[PR XXXX]: https://github.com/libp2p/rust-libp2p/pull/XXXX
+
 # 0.43.0
 
 - Update to `libp2p-core` `v0.38.0`.
diff --git a/protocols/gossipsub/src/handler.rs b/protocols/gossipsub/src/handler.rs
index dc695bf7df87..07a1bdaeb1a5 100644
--- a/protocols/gossipsub/src/handler.rs
+++ b/protocols/gossipsub/src/handler.rs
@@ -27,9 +27,8 @@ use futures::StreamExt;
 use instant::Instant;
 use libp2p_core::upgrade::{NegotiationError, UpgradeError};
 use libp2p_swarm::handler::{
-    ConnectionEvent, ConnectionHandler, ConnectionHandlerEvent, ConnectionHandlerUpgrErr,
-    DialUpgradeError, FullyNegotiatedInbound, FullyNegotiatedOutbound, KeepAlive,
-    SubstreamProtocol,
+    ConnectionEvent, ConnectionHandler, ConnectionHandlerEvent, DialUpgradeError,
+    FullyNegotiatedInbound, FullyNegotiatedOutbound, KeepAlive, SubstreamProtocol,
 };
 use libp2p_swarm::NegotiatedSubstream;
 use log::{error, trace, warn};
@@ -123,8 +122,15 @@ pub struct GossipsubHandler {
     /// The amount of time we allow idle connections before disconnecting.
     idle_timeout: Duration,
 
-    /// Collection of errors from attempting an upgrade.
-    upgrade_errors: VecDeque<ConnectionHandlerUpgrErr<GossipsubHandlerError>>,
+    /// Collection of pendings events to be returned.
+    pending_events: VecDeque<
+        ConnectionHandlerEvent<
+            <GossipsubHandler as ConnectionHandler>::OutboundProtocol,
+            <GossipsubHandler as ConnectionHandler>::OutboundOpenInfo,
+            <GossipsubHandler as ConnectionHandler>::OutEvent,
+            <GossipsubHandler as ConnectionHandler>::Error,
+        >,
+    >,
 
     /// Flag determining whether to maintain the connection to the peer.
     keep_alive: KeepAlive,
@@ -176,7 +182,7 @@ impl GossipsubHandler {
             peer_kind_sent: false,
             protocol_unsupported: false,
             idle_timeout,
-            upgrade_errors: VecDeque::new(),
+            pending_events: VecDeque::new(),
             keep_alive: KeepAlive::Until(Instant::now() + Duration::from_secs(INITIAL_KEEP_ALIVE)),
             in_mesh: false,
         }
@@ -243,6 +249,45 @@ impl GossipsubHandler {
             self.outbound_substream = Some(OutboundSubstreamState::PendingSend(substream, message));
         }
     }
+
+    fn on_dial_upgrade_error(
+        &mut self,
+        DialUpgradeError { error, .. }: DialUpgradeError<
+            <Self as ConnectionHandler>::OutboundOpenInfo,
+            <Self as ConnectionHandler>::OutboundProtocol,
+        >,
+    ) {
+        self.outbound_substream_establishing = false;
+        warn!("Dial upgrade error {:?}", error);
+        let reported_error = match error {
+            // There was an error post negotiation, close the connection.
+            UpgradeError::Apply(e) => ConnectionHandlerEvent::Close(e),
+            UpgradeError::Select(negotiation_error) => {
+                match negotiation_error {
+                    NegotiationError::Failed => {
+                        // The protocol is not supported
+                        self.protocol_unsupported = true;
+                        if !self.peer_kind_sent {
+                            self.peer_kind_sent = true;
+                            // clear all substreams so the keep alive returns false
+                            self.inbound_substream = None;
+                            self.outbound_substream = None;
+                            self.keep_alive = KeepAlive::No;
+                            ConnectionHandlerEvent::Custom(HandlerEvent::PeerKind(
+                                PeerKind::NotSupported,
+                            ))
+                        } else {
+                            return;
+                        }
+                    }
+                    NegotiationError::ProtocolError(e) => ConnectionHandlerEvent::Close(
+                        GossipsubHandlerError::NegotiationProtocolError(e),
+                    ),
+                }
+            }
+        };
+        self.pending_events.push_back(reported_error);
+    }
 }
 
 impl ConnectionHandler for GossipsubHandler {
@@ -291,44 +336,9 @@ impl ConnectionHandler for GossipsubHandler {
             Self::Error,
         >,
     > {
-        // Handle any upgrade errors
-        if let Some(error) = self.upgrade_errors.pop_front() {
-            let reported_error = match error {
-                // Timeout errors get mapped to NegotiationTimeout and we close the connection.
-                ConnectionHandlerUpgrErr::Timeout => {
-                    Some(GossipsubHandlerError::NegotiationTimeout)
-                }
-                // There was an error post negotiation, close the connection.
-                ConnectionHandlerUpgrErr::Upgrade(UpgradeError::Apply(e)) => Some(e),
-                ConnectionHandlerUpgrErr::Upgrade(UpgradeError::Select(negotiation_error)) => {
-                    match negotiation_error {
-                        NegotiationError::Failed => {
-                            // The protocol is not supported
-                            self.protocol_unsupported = true;
-                            if !self.peer_kind_sent {
-                                self.peer_kind_sent = true;
-                                // clear all substreams so the keep alive returns false
-                                self.inbound_substream = None;
-                                self.outbound_substream = None;
-                                self.keep_alive = KeepAlive::No;
-                                return Poll::Ready(ConnectionHandlerEvent::Custom(
-                                    HandlerEvent::PeerKind(PeerKind::NotSupported),
-                                ));
-                            } else {
-                                None
-                            }
-                        }
-                        NegotiationError::ProtocolError(e) => {
-                            Some(GossipsubHandlerError::NegotiationProtocolError(e))
-                        }
-                    }
-                }
-            };
-
-            // If there was a fatal error, close the connection.
-            if let Some(error) = reported_error {
-                return Poll::Ready(ConnectionHandlerEvent::Close(error));
-            }
+        // Handle pending events.
+        if let Some(event) = self.pending_events.pop_front() {
+            return Poll::Ready(event);
         }
 
         if !self.peer_kind_sent {
@@ -573,10 +583,14 @@ impl ConnectionHandler for GossipsubHandler {
             ConnectionEvent::FullyNegotiatedOutbound(fully_negotiated_outbound) => {
                 self.on_fully_negotiated_outbound(fully_negotiated_outbound)
             }
-            ConnectionEvent::DialUpgradeError(DialUpgradeError { error: e, .. }) => {
-                self.outbound_substream_establishing = false;
-                warn!("Dial upgrade error {:?}", e);
-                self.upgrade_errors.push_back(e);
+            ConnectionEvent::DialUpgradeError(dial_upgrade_error) => {
+                self.on_dial_upgrade_error(dial_upgrade_error)
+            }
+            ConnectionEvent::DialTimeout(_) => {
+                warn!("Dial upgrade timeout expired");
+                self.pending_events.push_back(ConnectionHandlerEvent::Close(
+                    GossipsubHandlerError::NegotiationTimeout,
+                ));
             }
             ConnectionEvent::AddressChange(_) | ConnectionEvent::ListenUpgradeError(_) => {}
         }