diff --git a/CHANGELOG.md b/CHANGELOG.md
index 299abca..d27e0ed 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,7 @@
 # Unreleased
 
+  * Fix DTLS 1.2 ClientHello retransmissions #160
+
 # 0.7.2
 
   * Stop advertising unsupported RSA signatures in DTLS 1.2 CertificateRequest #157
diff --git a/src/dtls12/engine.rs b/src/dtls12/engine.rs
index dd4b9c2..9310eb7 100644
--- a/src/dtls12/engine.rs
+++ b/src/dtls12/engine.rs
@@ -514,6 +514,13 @@ impl Engine {
         }
 
         match (self.connect_timeout, self.flight_timeout) {
+            // Keep this before the `(Armed, _)` arms. Starting a new flight resets its timer to
+            // `Unarmed`, but leaves the overall connection timer armed. If that mixed state
+            // returned the connection deadline, the caller would not drive `handle_timeout` to
+            // arm the flight timer until the whole handshake expired, so the flight would never
+            // be retransmitted. Returning `now` requests that immediate drive; the next poll sees
+            // both concrete deadlines and can return the earlier one.
+            (Timeout::Unarmed, _) | (_, Timeout::Unarmed) => now,
             (Timeout::Armed(c), Timeout::Armed(f)) => {
                 if c < f {
                     c
@@ -523,8 +530,6 @@ impl Engine {
             }
             (Timeout::Armed(c), _) => c,
             (_, Timeout::Armed(f)) => f,
-            // Both Unarmed or mixed Unarmed/Disabled: return current time
-            // to trigger handle_timeout on the next cycle.
             _ => now,
         }
     }
diff --git a/tests/dtls12/retransmit.rs b/tests/dtls12/retransmit.rs
index eb7a644..b1c9dde 100644
--- a/tests/dtls12/retransmit.rs
+++ b/tests/dtls12/retransmit.rs
@@ -155,6 +155,50 @@ fn first_record_matching(datagrams: &[Vec<u8>], content_type: u8, epoch: u16) ->
     None
 }
 
+#[test]
+#[cfg(feature = "rcgen")]
+fn dtls12_client_hello_retransmits_using_advertised_deadlines() {
+    use dimpl::certificate::generate_self_signed_certificate;
+
+    let now = Instant::now();
+    let certificate = generate_self_signed_certificate().expect("generate client certificate");
+    let mut client = Dtls::new_12(Arc::new(Config::default()), certificate, now);
+    client.set_active(true);
+
+    client.handle_timeout(now).expect("start client handshake");
+    let initial_output = drain_outputs(&mut client);
+    assert!(
+        !initial_output.packets.is_empty(),
+        "client should emit ClientHello"
+    );
+
+    // Drop the initial flight and handle the timeout.
+    let arm_at = initial_output
+        .timeout
+        .expect("client should advertise a deadline");
+    client
+        .handle_timeout(arm_at)
+        .expect("arm ClientHello retransmission");
+    let after_timer_arming = drain_outputs(&mut client);
+    assert!(
+        after_timer_arming.packets.is_empty(),
+        "arming should not retransmit early"
+    );
+
+    let retransmit_at = after_timer_arming
+        .timeout
+        .expect("client should advertise a retransmission deadline");
+    client
+        .handle_timeout(retransmit_at)
+        .expect("retransmit ClientHello");
+    let retransmission_output = drain_outputs(&mut client);
+
+    assert!(
+        !retransmission_output.packets.is_empty(),
+        "the dropped ClientHello flight was not retransmitted"
+    );
+}
+
 #[test]
 #[cfg(feature = "rcgen")]
 fn dtls12_resends_each_flight_epoch_and_sequence_increase() {