diff --git a/node/src/events.rs b/node/src/events.rs
index 2d7dcae3..17c458e2 100644
--- a/node/src/events.rs
+++ b/node/src/events.rs
@@ -167,6 +167,9 @@ pub struct NodeEventInfo {
 #[serde(tag = "type")]
 #[serde(rename_all = "snake_case")]
 pub enum NodeEvent {
+    /// Node is connecting to bootnodes
+    ConnectingToBootnodes,
+
     /// Peer just connected
     PeerConnected {
         #[serde(serialize_with = "serialize_as_string")]
@@ -295,7 +298,8 @@ impl NodeEvent {
             | NodeEvent::FatalSyncerError { .. }
             | NodeEvent::FetchingHeadersFailed { .. }
             | NodeEvent::NetworkCompromised => true,
-            NodeEvent::PeerConnected { .. }
+            NodeEvent::ConnectingToBootnodes
+            | NodeEvent::PeerConnected { .. }
             | NodeEvent::PeerDisconnected { .. }
             | NodeEvent::SamplingStarted { .. }
             | NodeEvent::ShareSamplingResult { .. }
@@ -312,6 +316,9 @@ impl NodeEvent {
 impl fmt::Display for NodeEvent {
     fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
         match self {
+            NodeEvent::ConnectingToBootnodes => {
+                write!(f, "Connecting to bootnodes")
+            }
             NodeEvent::PeerConnected { id, trusted } => {
                 if *trusted {
                     write!(f, "Trusted peer connected: {id}")
diff --git a/node/src/p2p.rs b/node/src/p2p.rs
index 22b46a34..fc9d718d 100644
--- a/node/src/p2p.rs
+++ b/node/src/p2p.rs
@@ -39,7 +39,10 @@ use libp2p::{
     kad,
     multiaddr::Protocol,
     ping,
-    swarm::{ConnectionId, NetworkBehaviour, NetworkInfo, Swarm, SwarmEvent},
+    swarm::{
+        dial_opts::{DialOpts, PeerCondition},
+        ConnectionId, NetworkBehaviour, NetworkInfo, Swarm, SwarmEvent,
+    },
     Multiaddr, PeerId,
 };
 use smallvec::SmallVec;
@@ -54,7 +57,7 @@ pub(crate) mod shwap;
 mod swarm;
 
 use crate::block_ranges::BlockRange;
-use crate::events::EventPublisher;
+use crate::events::{EventPublisher, NodeEvent};
 use crate::executor::{self, spawn, Interval};
 use crate::p2p::header_ex::{HeaderExBehaviour, HeaderExConfig};
 use crate::p2p::header_session::HeaderSession;
@@ -580,6 +583,8 @@ where
     bitswap_queries: HashMap<beetswap::QueryId, OneshotResultSender<Vec<u8>, P2pError>>,
     network_compromised_token: CancellationToken,
     store: Arc<S>,
+    event_pub: EventPublisher,
+    bootnodes: HashMap<PeerId, Vec<Multiaddr>>,
 }
 
 struct HeaderSubState {
@@ -639,15 +644,20 @@ where
             }
         }
 
+        let mut bootnodes = HashMap::<_, Vec<_>>::new();
+
         for addr in args.bootnodes {
-            // Bootstrap peers are always trusted
-            if let Some(peer_id) = addr.peer_id() {
-                peer_tracker.set_trusted(peer_id, true);
-            }
+            let peer_id = addr.peer_id().expect("multiaddr already validated");
+            bootnodes.entry(peer_id).or_default().push(addr);
+        }
 
-            if let Err(e) = swarm.dial(addr.clone()) {
-                error!("Failed to dial on {addr}: {e}");
-            }
+        for (peer_id, addrs) in bootnodes.iter_mut() {
+            addrs.sort();
+            addrs.dedup();
+            addrs.shrink_to_fit();
+
+            // Bootstrap peers are always trusted
+            peer_tracker.set_trusted(*peer_id, true);
         }
 
         Ok(Worker {
@@ -660,6 +670,8 @@ where
             bitswap_queries: HashMap::new(),
             network_compromised_token: CancellationToken::new(),
             store: args.store,
+            event_pub: args.event_pub,
+            bootnodes,
         })
     }
 
@@ -667,6 +679,8 @@ where
         let mut report_interval = Interval::new(Duration::from_secs(60)).await;
         let mut kademlia_interval = Interval::new(Duration::from_secs(30)).await;
 
+        self.dial_bootnodes();
+
         // Initiate discovery
         let _ = self.swarm.behaviour_mut().kademlia.bootstrap();
 
@@ -699,6 +713,26 @@ where
         }
     }
 
+    fn dial_bootnodes(&mut self) {
+        self.event_pub.send(NodeEvent::ConnectingToBootnodes);
+
+        for (peer_id, addrs) in &self.bootnodes {
+            let dial_opts = DialOpts::peer_id(*peer_id)
+                .addresses(addrs.clone())
+                // Without this set, `kademlia::Behaviour` won't be able to canonicalize
+                // `/tls/ws` to `/wss`.
+                .extend_addresses_through_behaviour()
+                // Tell Swarm not to dial if peer is already connected or there
+                // is an ongoing dialing.
+                .condition(PeerCondition::DisconnectedAndNotDialing)
+                .build();
+
+            if let Err(e) = self.swarm.dial(dial_opts) {
+                error!("Failed to dial on {addrs:?}: {e}");
+            }
+        }
+    }
+
     fn prune_canceled_bitswap_queries(&mut self) {
         let mut cancelled = SmallVec::<[_; 16]>::new();
 
diff --git a/node/src/syncer.rs b/node/src/syncer.rs
index 2262235e..449abe68 100644
--- a/node/src/syncer.rs
+++ b/node/src/syncer.rs
@@ -379,9 +379,11 @@ where
     fn spawn_try_init(&self) -> oneshot::Receiver<Result<(ExtendedHeader, Duration)>> {
         let p2p = self.p2p.clone();
         let store = self.store.clone();
+        let event_pub = self.event_pub.clone();
         let (tx, rx) = oneshot::channel();
 
         let fut = async move {
+            let mut event_reported = false;
             let now = Instant::now();
             let mut backoff = ExponentialBackoffBuilder::default()
                 .with_max_interval(TRY_INIT_BACKOFF_MAX_INTERVAL)
@@ -389,7 +391,7 @@ where
                 .build();
 
             loop {
-                match try_init(&p2p, &*store).await {
+                match try_init(&p2p, &*store, &event_pub, &mut event_reported).await {
                     Ok(network_head) => {
                         tx.maybe_send(Ok((network_head, now.elapsed())));
                         break;
@@ -410,8 +412,6 @@ where
             }
         };
 
-        self.event_pub.send(NodeEvent::FetchingHeadHeaderStarted);
-
         spawn_cancellable(
             self.cancellation_token.child_token(),
             fut.instrument(info_span!("try_init")),
@@ -603,12 +603,22 @@ fn in_syncing_window(header: &ExtendedHeader) -> bool {
     header.time().after(syncing_window_start)
 }
 
-async fn try_init<S>(p2p: &P2p, store: &S) -> Result<ExtendedHeader>
+async fn try_init<S>(
+    p2p: &P2p,
+    store: &S,
+    event_pub: &EventPublisher,
+    event_reported: &mut bool,
+) -> Result<ExtendedHeader>
 where
     S: Store,
 {
     p2p.wait_connected_trusted().await?;
 
+    if !*event_reported {
+        event_pub.send(NodeEvent::FetchingHeadHeaderStarted);
+        *event_reported = true;
+    }
+
     let network_head = p2p.get_head_header().await?;
 
     // If the network head and the store head have the same height,