diff --git a/packages/cultnet-rs/src/rudp.rs b/packages/cultnet-rs/src/rudp.rs
index bf611a15..9e8c4a1c 100644
--- a/packages/cultnet-rs/src/rudp.rs
+++ b/packages/cultnet-rs/src/rudp.rs
@@ -574,6 +574,11 @@ impl CultNetRudpSession {
         payload: Vec<u8>,
         options: CultNetRudpSendOptions,
     ) -> Result<CultNetRudpPacket> {
+        // Measure the window as `send_many` will: without the deadline-passed
+        // sends it is about to reclaim.
+        if options.reliable {
+            self.purge_expired_reliable(options.now_ms);
+        }
         if options.reliable
             && (!self.queued_reliable.is_empty()
                 || !self.window_admits(self.next_sequence, payload.len()))
diff --git a/packages/cultnet-rs/tests/rudp_flow_window.rs b/packages/cultnet-rs/tests/rudp_flow_window.rs
index 85c7a864..58065970 100644
--- a/packages/cultnet-rs/tests/rudp_flow_window.rs
+++ b/packages/cultnet-rs/tests/rudp_flow_window.rs
@@ -249,3 +249,34 @@ fn acknowledged_bytes_stop_counting_when_the_lowest_unacked_packet_expires() ->
     }
     Ok(())
 }
+
+#[test]
+fn a_direct_send_is_not_refused_for_bytes_whose_lowest_packet_has_expired() -> Result<()> {
+    let mut sender = connected(1)?;
+    let expiring = CultNetRudpSendOptions {
+        reliable: true,
+        now_ms: 0,
+        reliable_expire_after_ms: Some(100),
+        ..Default::default()
+    };
+    let g = sender
+        .send_many("state", vec![7], expiring, None)?
+        .remove(0);
+    for offset in 1..=4u32 {
+        assert_eq!(send(&mut sender, MIB)?.len(), 1);
+        sender.receive(&ack_for(g.sequence + offset), 1)?;
+    }
+    assert!(sender.send("state", vec![7; MIB], reliable()).is_err());
+
+    // The first call after g's deadline is a direct send: it measures the
+    // window without g, as `send_many` would, and goes on the wire.
+    let at_200 = CultNetRudpSendOptions {
+        reliable: true,
+        now_ms: 200,
+        ..Default::default()
+    };
+    let sent = sender.send("state", vec![7; MIB], at_200)?;
+    assert_eq!(sent.sequence, g.sequence + 5);
+    assert_eq!(sender.outstanding_reliable_packet_count(), 1);
+    Ok(())
+}