diff --git a/coordinator/tributary/tendermint/src/block.rs b/coordinator/tributary/tendermint/src/block.rs
index 71dfb3cc..6dfacfdb 100644
--- a/coordinator/tributary/tendermint/src/block.rs
+++ b/coordinator/tributary/tendermint/src/block.rs
@@ -139,10 +139,8 @@ impl<N: Network> BlockData<N> {
     // 27, 33, 41, 46, 60, 64
     self.round_mut().step = data.step();
 
-    // Only return a message to if we're actually a current validator and haven't prior posted a
-    // message
+    // Only return a message to if we're actually a current validator
     let round_number = self.round().number;
-    let step = data.step();
     let res = self.validator_id.map(|validator_id| Message {
       sender: validator_id,
       block: self.number,
@@ -150,21 +148,59 @@ impl<N: Network> BlockData<N> {
       data,
     });
 
-    if res.is_some() {
+    if let Some(res) = res.as_ref() {
+      const LATEST_BLOCK_KEY: &[u8] = b"tendermint-machine-sent_block";
+      const LATEST_ROUND_KEY: &[u8] = b"tendermint-machine-sent_round";
+      const PROPOSE_KEY: &[u8] = b"tendermint-machine-sent_propose";
+      const PEVOTE_KEY: &[u8] = b"tendermint-machine-sent_prevote";
+      const PRECOMMIT_KEY: &[u8] = b"tendermint-machine-sent_commit";
+
+      let genesis = self.genesis;
+      let key = |prefix: &[u8]| [prefix, &genesis].concat();
+
       let mut txn = self.db.txn();
-      let key = [
-        b"tendermint-machine_already_sent_message".as_ref(),
-        &self.genesis,
-        &self.number.0.to_le_bytes(),
-        &round_number.0.to_le_bytes(),
-        &step.encode(),
-      ]
-      .concat();
-      // If we've already sent a message, return
-      if txn.get(&key).is_some() {
+
+      // Ensure we haven't prior sent a message for a future block/round
+      let last_block_or_round = |txn: &mut <N::Db as Db>::Transaction<'_>, prefix, current| {
+        let key = key(prefix);
+        let latest =
+          u64::from_le_bytes(txn.get(key.as_slice()).unwrap_or(vec![0; 8]).try_into().unwrap());
+        if latest > current {
+          None?;
+        }
+        if current > latest {
+          txn.put(&key, current.to_le_bytes());
+          return Some(true);
+        }
+        Some(false)
+      };
+      let new_block = last_block_or_round(&mut txn, LATEST_BLOCK_KEY, self.number.0)?;
+      if new_block {
+        // Delete the latest round key
+        txn.del(&key(LATEST_ROUND_KEY));
+      }
+      let new_round = last_block_or_round(&mut txn, LATEST_ROUND_KEY, round_number.0.into())?;
+      if new_block || new_round {
+        // Delete the messages for the old round
+        txn.del(&key(PROPOSE_KEY));
+        txn.del(&key(PEVOTE_KEY));
+        txn.del(&key(PRECOMMIT_KEY));
+      }
+
+      // Check we haven't sent this message within this round
+      let msg_key = key(match res.data.step() {
+        Step::Propose => PROPOSE_KEY,
+        Step::Prevote => PEVOTE_KEY,
+        Step::Precommit => PRECOMMIT_KEY,
+      });
+      if txn.get(&msg_key).is_some() {
+        assert!(!new_block);
+        assert!(!new_round);
         None?;
       }
-      txn.put(&key, []);
+      // Put this message to the DB
+      txn.put(&msg_key, res.encode());
+
       txn.commit();
     }