diff --git a/veilid-core/src/network_manager/send_data.rs b/veilid-core/src/network_manager/send_data.rs
index 59ae1c7e..6a3f5720 100644
--- a/veilid-core/src/network_manager/send_data.rs
+++ b/veilid-core/src/network_manager/send_data.rs
@@ -276,7 +276,11 @@ impl NetworkManager {
                         connection_descriptor,
                     )));
                 }
-                Some(d) => d,
+                Some(d) => {
+                    // Connection couldn't send, kill it
+                    node_ref.clear_last_connection(connection_descriptor);
+                    d
+                }
             }
         } else {
             data
diff --git a/veilid-core/src/routing_table/bucket_entry.rs b/veilid-core/src/routing_table/bucket_entry.rs
index 39f7e9f4..e400875d 100644
--- a/veilid-core/src/routing_table/bucket_entry.rs
+++ b/veilid-core/src/routing_table/bucket_entry.rs
@@ -411,6 +411,13 @@ impl BucketEntryInner {
             .insert(key, (last_connection, timestamp));
     }
 
+     // Removes a connection descriptor in this entry's table of last connections
+     pub fn clear_last_connection(&mut self, last_connection: ConnectionDescriptor) {
+        let key = self.descriptor_to_key(last_connection);
+        self.last_connections
+            .remove(&key);
+    }
+
     // Clears the table of last connections to ensure we create new ones and drop any existing ones
     pub fn clear_last_connections(&mut self) {
         self.last_connections.clear();
diff --git a/veilid-core/src/routing_table/node_ref.rs b/veilid-core/src/routing_table/node_ref.rs
index a10dfecf..6580e171 100644
--- a/veilid-core/src/routing_table/node_ref.rs
+++ b/veilid-core/src/routing_table/node_ref.rs
@@ -308,6 +308,12 @@ pub trait NodeRefBase: Sized {
         })
     }
 
+    fn clear_last_connection(&self, connection_descriptor: ConnectionDescriptor) {
+        self.operate_mut(|rti, e| {
+            e.clear_last_connection(connection_descriptor);
+        })
+    }
+
     fn has_any_dial_info(&self) -> bool {
         self.operate(|_rti, e| {
             for rtd in RoutingDomain::all() {