diff --git a/tests/tools/test_bot_relay.py b/tests/tools/test_bot_relay.py
index 4758defd63..0c584d0803 100644
--- a/tests/tools/test_bot_relay.py
+++ b/tests/tools/test_bot_relay.py
@@ -528,6 +528,33 @@ def test_drain_expires_old_envelope_with_queued_expired_reply(root):
     assert not reply["reply"]
 
 
+def test_the_outbox_is_claimed_oldest_first(root):
+    """Two DMs from one sender to one agent must arrive in the order they were sent. The Desktop
+    delivers each target's claimed envelopes in the order this list gives them, one turn at a
+    time, so the claim IS the delivery order — and sorting by filename ordered them by
+    ``uuid4().hex``. The names here are forced into the reverse of the send order to pin that
+    deterministically, which random ids reproduce half the time."""
+    first = bot_relay.enqueue_envelope(
+        root, target=_target(), message="do this first",
+        sender_profile="default", sender_handle="hermes",
+    )
+    second = bot_relay.enqueue_envelope(
+        root, target=_target(), message="then this",
+        sender_profile="default", sender_handle="hermes",
+    )
+    outbox = bot_relay.relay_root(root) / bot_relay.OUTBOX_DIR
+    now = _time2.time()
+    for env, name, sent_at in ((first, "f" * 32, now - 2), (second, "0" * 32, now - 1)):
+        path = outbox / f"{name}.json"
+        (outbox / f"{env['id']}.json").rename(path)
+        _os2.utime(path, (sent_at, sent_at))
+
+    claimed = bot_relay.claim_pending_envelopes(root)
+
+    assert [e["id"] for e in claimed] == [first["id"], second["id"]]
+    assert [e["message"] for e in claimed] == ["do this first", "then this"]
+
+
 def test_drain_delivers_fresh_envelope_under_ttl(root):
     env = bot_relay.enqueue_envelope(
         root, target=_target(), message="on time",
diff --git a/tools/bot_relay.py b/tools/bot_relay.py
index e65cdcdb5b..f0a2f343c1 100644
--- a/tools/bot_relay.py
+++ b/tools/bot_relay.py
@@ -242,6 +242,15 @@ def _expire_if_stale(root: Path | str, path: Path, ttl: float, now: float) -> bo
     return True
 
 
+def _queued_at(path: Path) -> tuple[float, str]:
+    """Claim order for one outbox entry: oldest first. ``mtime`` is what ``_sweep_stale`` already
+    treats as an envelope's age, and unlike the whole-second ``created_at`` field it separates two
+    DMs sent in the same second. The name only breaks ties."""
+    with contextlib.suppress(OSError):
+        return (path.stat().st_mtime, path.name)
+    return (0.0, path.name)
+
+
 def claim_pending_envelopes(root: Path | str) -> list[dict]:
     """Drain the outbox (rename → claimed/ so a second drain can't double-deliver).
     TTL-expired envelopes get a 'queued_expired' reply and are removed instead.
@@ -255,7 +264,10 @@ def claim_pending_envelopes(root: Path | str) -> list[dict]:
     ttl = _envelope_ttl_seconds()
     now = time.time()
     out: list[dict] = []
-    for path in sorted((base / OUTBOX_DIR).glob("*.json")):
+    # Oldest first: the Desktop delivers each target's claimed envelopes in the order this list
+    # gives them, so a sender's two DMs to one agent arrive in the order they were sent. Sorting
+    # by filename ordered them by ``uuid4().hex`` — at random.
+    for path in sorted((base / OUTBOX_DIR).glob("*.json"), key=_queued_at):
         if ttl > 0 and _expire_if_stale(root, path, ttl, now):
             with contextlib.suppress(OSError):
                 path.unlink()