diff --git a/allways/constants.py b/allways/constants.py
index 88fa760..3a1e460 100644
--- a/allways/constants.py
+++ b/allways/constants.py
@@ -137,6 +137,7 @@
 DEFAULT_MAX_SWAP_AMOUNT_RAO = 500_000_000  # 0.5 TAO
 RESERVATION_TTL_BLOCKS = 50  # ~10 min
 
-# Blocks past a retained send-cache entry's last-known timeout_block before the miner discards it. Above
-# MAX_EXTENSION_BLOCKS so a still-active (even fully-extended) swap is never dropped early. ~300 blocks ≈ 1h.
-SENT_CACHE_DISCARD_MARGIN_BLOCKS = MAX_EXTENSION_BLOCKS + DEFAULT_FULFILLMENT_TIMEOUT_BLOCKS
+# Blocks past a retained entry's last-known timeout_block before discard. Sized for the contract's worst case:
+# MAX_EXTENSIONS_PER_SWAP extensions each push the deadline up to MAX_EXTENSION_BLOCKS further (not cumulative).
+# A smaller margin can discard a still-active twice-extended swap and re-send on rediscovery (#461). ~550 ≈ 1.8h.
+SENT_CACHE_DISCARD_MARGIN_BLOCKS = MAX_EXTENSIONS_PER_SWAP * MAX_EXTENSION_BLOCKS + DEFAULT_FULFILLMENT_TIMEOUT_BLOCKS
diff --git a/allways/miner/fulfillment.py b/allways/miner/fulfillment.py
index 459bc9b..bde1af7 100644
--- a/allways/miner/fulfillment.py
+++ b/allways/miner/fulfillment.py
@@ -297,21 +297,19 @@ def process_swap(self, swap: Swap) -> bool:
 
         bt.logging.info(f'Processing swap {swap.id}: {swap.from_chain} -> {swap.to_chain}')
 
-        # Step 1: Verify swap safety (timeout, rate, collateral)
-        safety_result = self.verify_swap_safety(swap)
-        if safety_result is None:
-            bt.logging.warning(f'Swap {swap.id}: failed safety checks, skipping')
-            return False
-
-        user_receives_amount, my_source_address = safety_result
+        if sent is None:
+            # First pass — gate the send on safety (timeout cushion, rate,
+            # source funds), then send. The cushion blocks STARTING a fulfill
+            # with too little runway left for a rescue extension.
+            safety_result = self.verify_swap_safety(swap)
+            if safety_result is None:
+                bt.logging.warning(f'Swap {swap.id}: failed safety checks, skipping')
+                return False
+            user_receives_amount, my_source_address = safety_result
 
-        # Step 2: Verify user sent source funds
-        if not self.verify_user_sent_funds(swap, my_source_address):
-            return False
+            if not self.verify_user_sent_funds(swap, my_source_address):
+                return False
 
-        # Step 3: Send destination funds — unless we already did on a previous
-        # pass, in which case we skip straight to the mark_fulfilled retry.
-        if sent is None:
             send_result = self.send_dest_funds(swap, user_receives_amount)
             if not send_result:
                 bt.logging.error(f'Swap {swap.id}: failed to send dest funds')
@@ -326,6 +324,11 @@ def process_swap(self, swap: Swap) -> bool:
             self.sent[swap.id] = sent
             self.save_sent_cache()
         else:
+            # Funds are already out — skip the cushion/safety gate (scoped to
+            # STARTING a fulfill); retrying mark_fulfilled to the deadline only
+            # helps and avoids a timeout slash of a miner that paid (#462).
+            # Recompute the post-fee amount (rate is snapshotted on the swap).
+            _, user_receives_amount = expected_swap_amounts(swap, self.fee_divisor)
             # Keep the retained deadline current with any extension seen while
             # active, so cleanup never discards a still-extendable swap early.
             if swap.timeout_block > sent.timeout_block:
@@ -333,10 +336,9 @@ def process_swap(self, swap: Swap) -> bool:
                 self.save_sent_cache()
             bt.logging.info(f'Swap {swap.id}: retrying mark_fulfilled for cached send tx {sent.to_tx_hash[:16]}...')
 
-        # Step 4: Mark fulfilled on contract. We pass ``user_receives_amount``
-        # as ``to_amount`` because at mark_fulfilled time the contract stores
-        # the actual sent amount (post-fee), which is what ``swap.to_amount``
-        # becomes after the call.
+        # Mark fulfilled on contract. ``user_receives_amount`` is the post-fee
+        # amount the contract stores as ``to_amount`` (what ``swap.to_amount``
+        # becomes after the call).
         try:
             self.client.mark_fulfilled(
                 wallet=self.wallet,
diff --git a/tests/test_fulfillment.py b/tests/test_fulfillment.py
index e6c3d67..28ee884 100644
--- a/tests/test_fulfillment.py
+++ b/tests/test_fulfillment.py
@@ -12,7 +12,13 @@
 import pytest
 
 from allways.classes import Swap, SwapStatus
-from allways.constants import MINER_TIMEOUT_CUSHION_BLOCKS, SENT_CACHE_DISCARD_MARGIN_BLOCKS
+from allways.constants import (
+    DEFAULT_FULFILLMENT_TIMEOUT_BLOCKS,
+    MAX_EXTENSION_BLOCKS,
+    MAX_EXTENSIONS_PER_SWAP,
+    MINER_TIMEOUT_CUSHION_BLOCKS,
+    SENT_CACHE_DISCARD_MARGIN_BLOCKS,
+)
 from allways.miner.fulfillment import SentSwap, SwapFulfiller
 from allways.miner.swap_poller import MAX_REFRESH_MISSES, SwapPoller
 
@@ -120,6 +126,41 @@ def test_unmarked_stale_retained_marked_stale_removed_within_deadline(self):
         assert set(fulfiller.sent) == {1, 3}
         assert fulfiller.mark_fulfilled_attempts == {1: 2, 3: 1}
 
+    def test_mark_fulfilled_retry_not_gated_by_cushion_after_send(self):
+        # Regression for #462: once dest funds are out, the swap stays Active
+        # until mark_fulfilled lands, and an Active swap is slashed at timeout.
+        # The cushion is scoped to STARTING a fulfill, so it must NOT gate the
+        # post-send mark_fulfilled retry — otherwise a transient mark_fulfilled
+        # failure inside the final cushion window guarantees a slash of a miner
+        # that already paid. Uses the REAL verify_swap_safety (not stubbed) so
+        # the cushion actually runs on the retry path.
+        from allways.contract_client import ContractError
+
+        swap = make_swap(timeout_block=500)
+        fulfiller = make_fulfiller()
+        fulfiller.fee_divisor = 100
+        # Inside the cushion window: a first SEND would be gated off here.
+        fulfiller.subtensor.get_current_block.return_value = 500 - MINER_TIMEOUT_CUSHION_BLOCKS
+        # Dest funds already sent on a prior pass, mark_fulfilled not yet landed.
+        fulfiller.sent[swap.id] = SentSwap('already-sent-dest-tx', 777, marked_fulfilled=False, timeout_block=500)
+        fulfiller.send_dest_funds = MagicMock()
+        # Transient (non-rejection) failure — keeps the entry retryable.
+        fulfiller.client.mark_fulfilled.side_effect = ContractError('transient rpc failure')
+
+        result = fulfiller.process_swap(swap)
+
+        assert result is False  # mark_fulfilled didn't land this pass
+        fulfiller.send_dest_funds.assert_not_called()  # never re-send
+        # The retry was attempted despite being inside the cushion window.
+        fulfiller.client.mark_fulfilled.assert_called_once_with(
+            wallet=fulfiller.wallet,
+            swap_id=swap.id,
+            to_tx_hash='already-sent-dest-tx',
+            to_amount=3_415_500_000,
+            to_tx_block=777,
+        )
+        assert fulfiller.sent[swap.id].marked_fulfilled is False  # still retryable next pass
+
     def test_retained_send_blocks_resend_after_poller_misses_and_rediscovery(self):
         swap = make_swap(timeout_block=500)
         poll_client = MagicMock()
@@ -184,6 +225,32 @@ def test_unmarked_stale_retained_inside_deadline_margin(self):
         fulfiller.cleanup_stale_sends(active_swap_ids=set())
         assert set(fulfiller.sent) == {1, 2}
 
+    def test_unmarked_stale_retained_across_two_extensions(self):
+        # Regression for #461: the contract permits MAX_EXTENSIONS_PER_SWAP (2)
+        # timeout extensions, each pushing timeout_block forward by up to
+        # MAX_EXTENSION_BLOCKS relative to its own propose block (not cumulative),
+        # so a live deadline can reach D0 + 2 * MAX_EXTENSION_BLOCKS. If the cached
+        # snapshot predates both extensions (a get_swap gap drops the swap from the
+        # active set, so process_swap never refreshes it), the margin must still
+        # cover the fully-extended deadline. The old margin (1 * MAX_EXTENSION_BLOCKS
+        # + DEFAULT_FULFILLMENT_TIMEOUT_BLOCKS) would discard here and re-send on
+        # rediscovery.
+        d0 = 100
+        old_single_extension_margin = MAX_EXTENSION_BLOCKS + DEFAULT_FULFILLMENT_TIMEOUT_BLOCKS
+        live_deadline = d0 + MAX_EXTENSIONS_PER_SWAP * MAX_EXTENSION_BLOCKS
+        # Sanity-check this case actually exercises the gap the fix closes: the
+        # current block is past the old margin but the swap is still live on-chain.
+        current = d0 + old_single_extension_margin + 1
+        assert current > d0 + old_single_extension_margin  # would have been discarded pre-fix
+        assert current <= live_deadline  # but the swap is still active on-chain
+
+        fulfiller = make_fulfiller()
+        fulfiller.sent = {1: SentSwap('twice-extended-tx', 50, marked_fulfilled=False, timeout_block=d0)}
+        fulfiller.subtensor.get_current_block.return_value = current
+
+        fulfiller.cleanup_stale_sends(active_swap_ids=set())
+        assert set(fulfiller.sent) == {1}
+
     def test_legacy_entry_without_deadline_never_discarded(self):
         fulfiller = make_fulfiller()
         fulfiller.sent = {1: SentSwap('legacy-tx', 5, marked_fulfilled=False)}  # timeout_block defaults to 0