diff --git a/tests/test_memory_log.py b/tests/test_memory_log.py
index b47a8bab2..d446fd8a9 100644
--- a/tests/test_memory_log.py
+++ b/tests/test_memory_log.py
@@ -300,6 +300,16 @@ class TestTradingMemoryLogCore:
         assert "Buy entry 0" not in ctx
         assert "Buy entry 5" in ctx
 
+    def test_the_most_recent_decisions_are_the_latest_dated_not_the_latest_written(self, tmp_path):
+        """A backfill writes January after June; June is still the most recent lesson."""
+        log = make_log(tmp_path)
+        _seed_completed(tmp_path, "NVDA", "2026-06-01", "Buy entry June.", "Correct.")
+        for i in range(5):
+            _seed_completed(tmp_path, "NVDA", f"2026-01-{i+1:02d}", f"Buy entry {i}.", "Correct.")
+        ctx = log.get_past_context("NVDA", n_same=5)
+        assert "Buy entry June" in ctx and "Buy entry 0" not in ctx
+        assert ctx.index("Buy entry June") < ctx.index("Buy entry 4")
+
     def test_n_cross_limit_respected(self, tmp_path):
         """Only the n_cross most recent cross-ticker entries are included."""
         log = make_log(tmp_path)
@@ -341,6 +351,16 @@ class TestTradingMemoryLogCore:
         dates = [e["date"] for e in entries]
         assert dates == ["2026-01-03", "2026-01-04", "2026-01-05"]
 
+    def test_rotation_prunes_the_oldest_dated_not_the_first_written(self, tmp_path):
+        """A backfill writes older dates last; rotation still keeps the newest decisions."""
+        log = TradingMemoryLog({
+            "memory_log_path": str(tmp_path / "trading_memory.md"),
+            "memory_log_max_entries": 3,
+        })
+        for date in ("2026-06-01", "2026-06-02", "2026-01-01", "2026-01-02", "2026-01-03"):
+            _resolve_entry(log, "NVDA", date, DECISION_BUY, f"Lesson {date}.")
+        assert sorted(e["date"] for e in log.load_entries()) == ["2026-01-03", "2026-06-01", "2026-06-02"]
+
     def test_rotation_never_prunes_pending(self, tmp_path):
         """Pending entries (unresolved) are kept regardless of the cap."""
         log = TradingMemoryLog({
diff --git a/tradingagents/memory/log.py b/tradingagents/memory/log.py
index a8ce85a8a..fd6aa0d30 100644
--- a/tradingagents/memory/log.py
+++ b/tradingagents/memory/log.py
@@ -109,7 +109,10 @@ class TradingMemoryLog:
             return ""
 
         same, cross = [], []
-        for e in reversed(entries):
+        # Most recent by decision date, then by the later write: a backfill writes
+        # older decisions last.
+        newest = sorted(range(len(entries)), key=lambda i: (entries[i]["date"], i), reverse=True)
+        for e in (entries[i] for i in newest):
             if len(same) >= n_same and len(cross) >= n_cross:
                 break
             if e["ticker"] == ticker and len(same) < n_same:
@@ -271,7 +274,7 @@ class TradingMemoryLog:
         return tag + "]"
 
     def _apply_rotation(self, blocks: list[str]) -> list[str]:
-        """Drop oldest resolved blocks when their count exceeds max_entries.
+        """Drop the oldest-dated resolved blocks when their count exceeds max_entries.
 
         Pending blocks are always kept (they represent unprocessed work).
         Returns ``blocks`` unchanged when rotation is disabled or under cap.
@@ -279,12 +282,12 @@ class TradingMemoryLog:
         if not self._max_entries or self._max_entries <= 0:
             return blocks
 
-        # Tag each block with (kept, is_resolved) by parsing tag-line markers.
+        # Tag each block with (block, is_resolved, decision date) from its tag line.
         decisions = []
         for block in blocks:
             stripped = block.strip()
             if not stripped:
-                decisions.append((block, False))
+                decisions.append((block, False, ""))
                 continue
             tag_line = stripped.splitlines()[0].strip()
             is_resolved = (
@@ -292,20 +295,18 @@ class TradingMemoryLog:
                 and tag_line.endswith("]")
                 and not tag_line.endswith("| pending]")
             )
-            decisions.append((block, is_resolved))
+            decisions.append((block, is_resolved, tag_line[1:].split("|")[0].strip()))
 
-        resolved_count = sum(1 for _, r in decisions if r)
+        resolved_count = sum(1 for _, r, _ in decisions if r)
         if resolved_count <= self._max_entries:
             return blocks
 
-        to_drop = resolved_count - self._max_entries
-        kept: list[str] = []
-        for block, is_resolved in decisions:
-            if is_resolved and to_drop > 0:
-                to_drop -= 1
-                continue
-            kept.append(block)
-        return kept
+        # The oldest by decision date, then by position: a backfill writes older
+        # decisions last.
+        resolved = [i for i, (_, is_resolved, _) in enumerate(decisions) if is_resolved]
+        dated = sorted(resolved, key=lambda i: (decisions[i][2], i))
+        dropped = set(dated[:resolved_count - self._max_entries])
+        return [block for i, (block, _, _) in enumerate(decisions) if i not in dropped]
 
     def _parse_entry(self, raw: str) -> dict | None:
         lines = raw.strip().splitlines()