diff --git a/src/node/handlers/rx_loop.rs b/src/node/handlers/rx_loop.rs
index fcee5f5..a88de14 100644
--- a/src/node/handlers/rx_loop.rs
+++ b/src/node/handlers/rx_loop.rs
@@ -80,6 +80,7 @@ impl Node {
                         .map(|d| d.as_millis() as u64)
                         .unwrap_or(0);
                     self.resend_pending_handshakes(now_ms).await;
+                    self.resend_pending_session_handshakes(now_ms).await;
                     self.purge_idle_sessions(now_ms);
                     self.process_pending_retries(now_ms).await;
                     self.check_tree_state().await;
diff --git a/src/node/handlers/session.rs b/src/node/handlers/session.rs
index 524ee13..b56869b 100644
--- a/src/node/handlers/session.rs
+++ b/src/node/handlers/session.rs
@@ -161,6 +161,7 @@ impl Node {
             entry.set_coords_warmup_remaining(self.config.node.session.coords_warmup_packets);
             entry.mark_established(Self::now_ms());
             entry.init_mmp(&self.config.node.session_mmp);
+            entry.clear_handshake_payload();
             info!(src = %self.peer_display_name(src_addr), "Session established (responder, on first encrypted message)");
         }
 
@@ -316,8 +317,18 @@ impl Node {
                     );
                 }
                 EndToEndState::Responding(_) => {
-                    // Duplicate setup while we already responded — drop
-                    debug!(src = %self.peer_display_name(src_addr), "Duplicate SessionSetup, already responding");
+                    // Duplicate setup while we already responded — resend stored ack
+                    if let Some(payload) = existing.handshake_payload() {
+                        debug!(src = %self.peer_display_name(src_addr), "Duplicate SessionSetup, resending SessionAck");
+                        let my_addr = *self.node_addr();
+                        let mut datagram = SessionDatagram::new(my_addr, *src_addr, payload.to_vec())
+                            .with_ttl(self.config.node.session.default_ttl);
+                        if let Err(e) = self.send_session_datagram(&mut datagram).await {
+                            debug!(error = %e, dest = %self.peer_display_name(src_addr), "Failed to resend SessionAck");
+                        }
+                    } else {
+                        debug!(src = %self.peer_display_name(src_addr), "Duplicate SessionSetup, no stored ack to resend");
+                    }
                     return;
                 }
                 EndToEndState::Established(_) => {
@@ -360,8 +371,9 @@ impl Node {
         // Build and send SessionAck
         let our_coords = self.tree_state.my_coords().clone();
         let ack = SessionAck::new(our_coords).with_handshake(msg2);
+        let ack_payload = ack.encode();
         let my_addr = *self.node_addr();
-        let mut datagram = SessionDatagram::new(my_addr, *src_addr, ack.encode())
+        let mut datagram = SessionDatagram::new(my_addr, *src_addr, ack_payload.clone())
             .with_ttl(self.config.node.session.default_ttl);
 
         // Route the ack back to the initiator
@@ -370,9 +382,11 @@ impl Node {
             return;
         }
 
-        // Store session entry in Responding state
+        // Store session entry in Responding state with ack payload for potential resend
         let now_ms = Self::now_ms();
-        let entry = SessionEntry::new(*src_addr, remote_pubkey, EndToEndState::Responding(handshake), now_ms, false);
+        let resend_interval = self.config.node.rate_limit.handshake_resend_interval_ms;
+        let mut entry = SessionEntry::new(*src_addr, remote_pubkey, EndToEndState::Responding(handshake), now_ms, false);
+        entry.set_handshake_payload(ack_payload, now_ms + resend_interval);
         self.sessions.insert(*src_addr, entry);
 
         debug!(src = %self.peer_display_name(src_addr), "SessionSetup processed, SessionAck sent");
@@ -433,6 +447,7 @@ impl Node {
         entry.set_coords_warmup_remaining(self.config.node.session.coords_warmup_packets);
         entry.mark_established(now_ms);
         entry.init_mmp(&self.config.node.session_mmp);
+        entry.clear_handshake_payload();
         entry.touch(now_ms);
         self.sessions.insert(*src_addr, entry);
         self.coord_cache.insert(*src_addr, ack.src_coords, now_ms);
@@ -723,10 +738,11 @@ impl Node {
         let dest_coords = self.get_dest_coords(&dest_addr);
         let setup = SessionSetup::new(our_coords, dest_coords)
             .with_handshake(msg1);
+        let setup_payload = setup.encode();
 
         // Wrap in SessionDatagram
         let my_addr = *self.node_addr();
-        let mut datagram = SessionDatagram::new(my_addr, dest_addr, setup.encode())
+        let mut datagram = SessionDatagram::new(my_addr, dest_addr, setup_payload.clone())
             .with_ttl(self.config.node.session.default_ttl);
 
         // Route toward destination
@@ -735,9 +751,11 @@ impl Node {
         // Register destination identity for TUN → session routing
         self.register_identity(dest_addr, dest_pubkey);
 
-        // Store session entry
+        // Store session entry with handshake payload for potential resend
         let now_ms = Self::now_ms();
-        let entry = SessionEntry::new(dest_addr, dest_pubkey, EndToEndState::Initiating(handshake), now_ms, true);
+        let resend_interval = self.config.node.rate_limit.handshake_resend_interval_ms;
+        let mut entry = SessionEntry::new(dest_addr, dest_pubkey, EndToEndState::Initiating(handshake), now_ms, true);
+        entry.set_handshake_payload(setup_payload, now_ms + resend_interval);
         self.sessions.insert(dest_addr, entry);
 
         info!(dest = %self.peer_display_name(&dest_addr), "Session initiation started");
@@ -1027,7 +1045,7 @@ impl Node {
     ///
     /// Finds the next hop for the destination, seeds path_mtu from the
     /// first-hop transport MTU, and sends as an encrypted link message.
-    async fn send_session_datagram(
+    pub(in crate::node) async fn send_session_datagram(
         &mut self,
         datagram: &mut SessionDatagram,
     ) -> Result<(), NodeError> {
diff --git a/src/node/handlers/timeout.rs b/src/node/handlers/timeout.rs
index 4e2bc0e..55b6382 100644
--- a/src/node/handlers/timeout.rs
+++ b/src/node/handlers/timeout.rs
@@ -151,6 +151,84 @@ impl Node {
         }
     }
 
+    /// Resend session-layer handshake messages and timeout stale handshakes.
+    ///
+    /// For sessions in Initiating or Responding state:
+    /// - If the handshake has exceeded the timeout window, remove the session.
+    /// - If a resend is due and under max resends, resend the stored payload
+    ///   wrapped in a fresh SessionDatagram (so routing can adapt).
+    pub(in crate::node) async fn resend_pending_session_handshakes(&mut self, now_ms: u64) {
+        if self.sessions.is_empty() {
+            return;
+        }
+
+        let timeout_ms = self.config.node.rate_limit.handshake_timeout_secs * 1000;
+        let max_resends = self.config.node.rate_limit.handshake_max_resends;
+        let interval_ms = self.config.node.rate_limit.handshake_resend_interval_ms;
+        let backoff = self.config.node.rate_limit.handshake_resend_backoff;
+        let ttl = self.config.node.session.default_ttl;
+
+        // First pass: find timed-out sessions to remove
+        let timed_out: Vec<crate::NodeAddr> = self.sessions.iter()
+            .filter(|(_, entry)| {
+                !entry.is_established()
+                    && now_ms.saturating_sub(entry.last_activity()) > timeout_ms
+            })
+            .map(|(addr, _)| *addr)
+            .collect();
+
+        for addr in &timed_out {
+            let name = self.peer_display_name(addr);
+            info!(dest = %name, "Session handshake timed out, removing");
+            self.sessions.remove(addr);
+            self.pending_tun_packets.remove(addr);
+        }
+
+        // Second pass: collect resend candidates
+        let my_addr = *self.node_addr();
+        let candidates: Vec<(crate::NodeAddr, Vec<u8>)> = self.sessions.iter()
+            .filter(|(_, entry)| {
+                !entry.is_established()
+                    && entry.handshake_payload().is_some()
+                    && entry.resend_count() < max_resends
+                    && entry.next_resend_at_ms() > 0
+                    && now_ms >= entry.next_resend_at_ms()
+            })
+            .map(|(addr, entry)| (*addr, entry.handshake_payload().unwrap().to_vec()))
+            .collect();
+
+        for (dest_addr, payload) in candidates {
+            use crate::protocol::SessionDatagram;
+
+            let mut datagram = SessionDatagram::new(my_addr, dest_addr, payload)
+                .with_ttl(ttl);
+            let sent = match self.send_session_datagram(&mut datagram).await {
+                Ok(_) => true,
+                Err(e) => {
+                    debug!(
+                        dest = %self.peer_display_name(&dest_addr),
+                        error = %e,
+                        "Session handshake resend failed"
+                    );
+                    false
+                }
+            };
+
+            if sent
+                && let Some(entry) = self.sessions.get_mut(&dest_addr)
+            {
+                let count = entry.resend_count() + 1;
+                let next = now_ms + (interval_ms as f64 * backoff.powi(count as i32)) as u64;
+                entry.record_resend(next);
+                debug!(
+                    dest = %self.peer_display_name(&dest_addr),
+                    resend = count,
+                    "Resent session handshake"
+                );
+            }
+        }
+    }
+
     /// Remove established sessions that have been idle too long.
     ///
     /// Only targets sessions in the Established state. Initiating/Responding
diff --git a/src/node/session.rs b/src/node/session.rs
index 6bc91fd..d8ac764 100644
--- a/src/node/session.rs
+++ b/src/node/session.rs
@@ -70,6 +70,15 @@ pub(crate) struct SessionEntry {
     is_initiator: bool,
     /// Session-layer MMP state. Initialized on Established transition.
     mmp: Option<MmpSessionState>,
+
+    // === Handshake Resend ===
+    /// Encoded session-layer payload for resend (SessionSetup or SessionAck).
+    /// Cleared on Established transition.
+    handshake_payload: Option<Vec<u8>>,
+    /// Number of resends performed.
+    resend_count: u32,
+    /// When the next resend should fire (Unix ms). 0 = no resend scheduled.
+    next_resend_at_ms: u64,
 }
 
 impl SessionEntry {
@@ -91,6 +100,9 @@ impl SessionEntry {
             coords_warmup_remaining: 0,
             is_initiator,
             mmp: None,
+            handshake_payload: None,
+            resend_count: 0,
+            next_resend_at_ms: 0,
         }
     }
 
@@ -193,4 +205,45 @@ impl SessionEntry {
     pub(crate) fn init_mmp(&mut self, config: &SessionMmpConfig) {
         self.mmp = Some(MmpSessionState::new(config, self.is_initiator));
     }
+
+    // === Handshake Resend ===
+
+    /// Store the encoded session-layer payload for potential resend.
+    ///
+    /// For initiators, this is the SessionSetup payload bytes.
+    /// For responders, this is the SessionAck payload bytes.
+    /// The payload is re-wrapped in a fresh SessionDatagram on each resend
+    /// so routing can adapt to topology changes.
+    pub(crate) fn set_handshake_payload(&mut self, payload: Vec<u8>, next_resend_at_ms: u64) {
+        self.handshake_payload = Some(payload);
+        self.resend_count = 0;
+        self.next_resend_at_ms = next_resend_at_ms;
+    }
+
+    /// Get the stored handshake payload for resend.
+    pub(crate) fn handshake_payload(&self) -> Option<&[u8]> {
+        self.handshake_payload.as_deref()
+    }
+
+    /// Clear the stored handshake payload (called on Established transition).
+    pub(crate) fn clear_handshake_payload(&mut self) {
+        self.handshake_payload = None;
+        self.next_resend_at_ms = 0;
+    }
+
+    /// Number of resends performed so far.
+    pub(crate) fn resend_count(&self) -> u32 {
+        self.resend_count
+    }
+
+    /// When the next resend should fire (Unix ms). 0 = no resend scheduled.
+    pub(crate) fn next_resend_at_ms(&self) -> u64 {
+        self.next_resend_at_ms
+    }
+
+    /// Record a resend and schedule the next one.
+    pub(crate) fn record_resend(&mut self, next_resend_at_ms: u64) {
+        self.resend_count += 1;
+        self.next_resend_at_ms = next_resend_at_ms;
+    }
 }
diff --git a/src/node/tests/session.rs b/src/node/tests/session.rs
index fd29991..74b3f32 100644
--- a/src/node/tests/session.rs
+++ b/src/node/tests/session.rs
@@ -1480,3 +1480,184 @@ fn test_identity_cache_lookup() {
     assert_eq!(addr, remote_addr);
     assert_eq!(pk, remote.pubkey_full());
 }
+
+// ============================================================================
+// Session-layer handshake resend tests
+// ============================================================================
+
+/// Test that SessionEntry handshake payload storage works correctly.
+#[test]
+fn test_session_entry_handshake_payload_storage() {
+    use crate::noise::HandshakeState;
+
+    let identity_a = Identity::generate();
+    let identity_b = Identity::generate();
+
+    let handshake = HandshakeState::new_initiator(
+        identity_a.keypair(),
+        identity_b.pubkey_full(),
+    );
+
+    let mut entry = crate::node::session::SessionEntry::new(
+        *identity_b.node_addr(),
+        identity_b.pubkey_full(),
+        EndToEndState::Initiating(handshake),
+        1000,
+        true,
+    );
+
+    // Initially no handshake payload
+    assert!(entry.handshake_payload().is_none());
+    assert_eq!(entry.resend_count(), 0);
+    assert_eq!(entry.next_resend_at_ms(), 0);
+
+    // Store a handshake payload
+    let payload = vec![0x01, 0x02, 0x03, 0x04];
+    entry.set_handshake_payload(payload.clone(), 2000);
+
+    assert_eq!(entry.handshake_payload().unwrap(), &payload);
+    assert_eq!(entry.resend_count(), 0);
+    assert_eq!(entry.next_resend_at_ms(), 2000);
+}
+
+/// Test that resend_count and next_resend_at_ms track correctly on SessionEntry.
+#[test]
+fn test_session_entry_resend_tracking() {
+    use crate::noise::HandshakeState;
+
+    let identity_a = Identity::generate();
+    let identity_b = Identity::generate();
+
+    let handshake = HandshakeState::new_initiator(
+        identity_a.keypair(),
+        identity_b.pubkey_full(),
+    );
+
+    let mut entry = crate::node::session::SessionEntry::new(
+        *identity_b.node_addr(),
+        identity_b.pubkey_full(),
+        EndToEndState::Initiating(handshake),
+        1000,
+        true,
+    );
+
+    entry.set_handshake_payload(vec![0x01], 2000);
+
+    // Record first resend
+    entry.record_resend(4000);
+    assert_eq!(entry.resend_count(), 1);
+    assert_eq!(entry.next_resend_at_ms(), 4000);
+
+    // Record second resend
+    entry.record_resend(8000);
+    assert_eq!(entry.resend_count(), 2);
+    assert_eq!(entry.next_resend_at_ms(), 8000);
+}
+
+/// Test that clear_handshake_payload clears payload and resets timer.
+#[test]
+fn test_session_entry_clear_handshake_payload() {
+    use crate::noise::HandshakeState;
+
+    let identity_a = Identity::generate();
+    let identity_b = Identity::generate();
+
+    let handshake = HandshakeState::new_initiator(
+        identity_a.keypair(),
+        identity_b.pubkey_full(),
+    );
+
+    let mut entry = crate::node::session::SessionEntry::new(
+        *identity_b.node_addr(),
+        identity_b.pubkey_full(),
+        EndToEndState::Initiating(handshake),
+        1000,
+        true,
+    );
+
+    entry.set_handshake_payload(vec![0x01, 0x02], 2000);
+    entry.record_resend(4000);
+    assert!(entry.handshake_payload().is_some());
+    assert_eq!(entry.resend_count(), 1);
+
+    // Clear on Established transition
+    entry.clear_handshake_payload();
+    assert!(entry.handshake_payload().is_none());
+    assert_eq!(entry.next_resend_at_ms(), 0);
+    // resend_count is NOT reset — it's a historical record
+    assert_eq!(entry.resend_count(), 1);
+}
+
+/// Test that session handshake timeout removes stale Initiating sessions.
+#[tokio::test]
+async fn test_session_handshake_timeout() {
+    use crate::noise::HandshakeState;
+
+    let mut node = make_node();
+
+    let identity_b = Identity::generate();
+    let handshake = HandshakeState::new_initiator(
+        node.identity.keypair(),
+        identity_b.pubkey_full(),
+    );
+
+    let dest_addr = *identity_b.node_addr();
+
+    // Create a session at time 1000
+    let entry = crate::node::session::SessionEntry::new(
+        dest_addr,
+        identity_b.pubkey_full(),
+        EndToEndState::Initiating(handshake),
+        1000,
+        true,
+    );
+    node.sessions.insert(dest_addr, entry);
+
+    assert!(node.sessions.contains_key(&dest_addr));
+
+    // Before timeout: session should remain
+    let timeout_secs = node.config.node.rate_limit.handshake_timeout_secs;
+    let before_timeout = 1000 + timeout_secs * 1000 - 1;
+    node.resend_pending_session_handshakes(before_timeout).await;
+    assert!(node.sessions.contains_key(&dest_addr), "Session should survive before timeout");
+
+    // After timeout: session should be removed
+    let after_timeout = 1000 + timeout_secs * 1000 + 1;
+    node.resend_pending_session_handshakes(after_timeout).await;
+    assert!(!node.sessions.contains_key(&dest_addr), "Timed-out session should be removed");
+}
+
+/// Test that session handshake timeout removes stale Responding sessions.
+#[tokio::test]
+async fn test_session_responding_timeout() {
+    use crate::noise::HandshakeState;
+
+    let mut node = make_node();
+
+    let identity_a = Identity::generate();
+    let identity_b = Identity::generate();
+
+    let handshake = HandshakeState::new_responder(
+        identity_b.keypair(),
+    );
+
+    let src_addr = *identity_a.node_addr();
+
+    // Create a Responding session at time 1000
+    let entry = crate::node::session::SessionEntry::new(
+        src_addr,
+        identity_a.pubkey_full(),
+        EndToEndState::Responding(handshake),
+        1000,
+        false,
+    );
+    node.sessions.insert(src_addr, entry);
+
+    assert!(node.sessions.contains_key(&src_addr));
+
+    // After timeout: session should be removed
+    let timeout_secs = node.config.node.rate_limit.handshake_timeout_secs;
+    let after_timeout = 1000 + timeout_secs * 1000 + 1;
+    node.resend_pending_session_handshakes(after_timeout).await;
+    assert!(!node.sessions.contains_key(&src_addr), "Timed-out Responding session should be removed");
+}