diff --git a/skillopt/optimizer/slow_update.py b/skillopt/optimizer/slow_update.py
index a2264ec0..d51af3d9 100644
--- a/skillopt/optimizer/slow_update.py
+++ b/skillopt/optimizer/slow_update.py
@@ -21,6 +21,7 @@
 import json
 import os
 import traceback
+from typing import Any
 
 from skillopt.model import chat_optimizer
 from skillopt.prompts import load_prompt
@@ -156,6 +157,37 @@ def _read_trajectory(rollout_dir: str, task_id: str) -> str:
 # ── Structured comparison pairs ─────────────────────────────────────────────
 
 
+def _is_result_success(res: dict | Any) -> bool:
+    """Determine whether a rollout result indicates success across metrics.
+
+    Handles explicit 'hard' flags, general 'score' metrics, 'exact_match',
+    and soft threshold metrics to prevent miscategorizing benchmark outcomes.
+    """
+    if not res or not isinstance(res, dict):
+        return False
+    if "hard" in res:
+        try:
+            return float(res["hard"]) >= 0.5
+        except (ValueError, TypeError):
+            return bool(res["hard"])
+    if "score" in res:
+        try:
+            return float(res["score"]) >= 0.5
+        except (ValueError, TypeError):
+            return bool(res["score"])
+    if "exact_match" in res:
+        try:
+            return float(res["exact_match"]) >= 0.5
+        except (ValueError, TypeError):
+            return bool(res["exact_match"])
+    if "soft" in res:
+        try:
+            return float(res["soft"]) >= 1.0 - 1e-6
+        except (ValueError, TypeError):
+            return bool(res["soft"])
+    return False
+
+
 def build_comparison_pairs(
     results_prev: list[dict],
     results_curr: list[dict],
@@ -183,8 +215,8 @@ def build_comparison_pairs(
         tid = str(item.get("id", ""))
         prev = prev_by_id.get(tid, {})
         curr = curr_by_id.get(tid, {})
-        prev_ok = bool(prev.get("hard", 0))
-        curr_ok = bool(curr.get("hard", 0))
+        prev_ok = _is_result_success(prev)
+        curr_ok = _is_result_success(curr)
 
         if not prev_ok and curr_ok:
             category = "improved"
@@ -201,13 +233,13 @@ def build_comparison_pairs(
             "category": category,
             "prev": {
                 "hard": int(prev_ok),
-                "soft": float(prev.get("soft", 0.0)),
+                "soft": float(prev.get("soft", 1.0 if prev_ok else 0.0)),
                 "predicted_answer": prev.get("predicted_answer", prev.get("answer", "N/A")),
                 "fail_reason": prev.get("fail_reason", ""),
             },
             "curr": {
                 "hard": int(curr_ok),
-                "soft": float(curr.get("soft", 0.0)),
+                "soft": float(curr.get("soft", 1.0 if curr_ok else 0.0)),
                 "predicted_answer": curr.get("predicted_answer", curr.get("answer", "N/A")),
                 "fail_reason": curr.get("fail_reason", ""),
             },
diff --git a/tests/test_slow_update_robustness.py b/tests/test_slow_update_robustness.py
new file mode 100644
index 00000000..22fd4f63
--- /dev/null
+++ b/tests/test_slow_update_robustness.py
@@ -0,0 +1,133 @@
+"""Tests for slow update field manipulation and longitudinal comparison robustness."""
+
+from __future__ import annotations
+
+import json
+import os
+import tempfile
+
+from skillopt.optimizer.slow_update import (
+    _is_result_success,
+    _strip_all_slow_update_fields,
+    build_comparison_pairs,
+    extract_slow_update_field,
+    has_slow_update_field,
+    inject_empty_slow_update_field,
+    replace_slow_update_field,
+    save_comparison_pairs,
+)
+
+
+def test_is_result_success_handles_diverse_metrics() -> None:
+    # Explicit hard boolean / float
+    assert _is_result_success({"hard": 1}) is True
+    assert _is_result_success({"hard": 0}) is False
+    assert _is_result_success({"hard": 1.0}) is True
+    assert _is_result_success({"hard": "true"}) is True
+
+    # General score metric
+    assert _is_result_success({"score": 1.0}) is True
+    assert _is_result_success({"score": 0.0}) is False
+    assert _is_result_success({"score": 0.8}) is True
+    assert _is_result_success({"score": 0.2}) is False
+
+    # Exact match metric
+    assert _is_result_success({"exact_match": 1}) is True
+    assert _is_result_success({"exact_match": 0}) is False
+
+    # Soft metric threshold
+    assert _is_result_success({"soft": 1.0}) is True
+    assert _is_result_success({"soft": 0.5}) is False
+
+    # Empty or invalid inputs
+    assert _is_result_success({}) is False
+    assert _is_result_success(None) is False
+    assert _is_result_success("not-a-dict") is False
+
+
+def test_build_comparison_pairs_categorization() -> None:
+    items = [
+        {"id": "task-1", "question": "Task 1 description"},
+        {"id": "task-2", "question": "Task 2 description"},
+        {"id": "task-3", "question": "Task 3 description"},
+        {"id": "task-4", "question": "Task 4 description"},
+    ]
+
+    # task-1: improved (fail -> pass)
+    # task-2: regressed (pass -> fail)
+    # task-3: persistent_fail (fail -> fail)
+    # task-4: stable_success (pass -> pass)
+    results_prev = [
+        {"id": "task-1", "score": 0.0, "predicted_answer": "wrong1"},
+        {"id": "task-2", "exact_match": 1.0, "predicted_answer": "correct2"},
+        {"id": "task-3", "hard": 0, "fail_reason": "timeout"},
+        {"id": "task-4", "hard": 1, "predicted_answer": "correct4"},
+    ]
+    results_curr = [
+        {"id": "task-1", "score": 1.0, "predicted_answer": "correct1"},
+        {"id": "task-2", "exact_match": 0.0, "predicted_answer": "wrong2"},
+        {"id": "task-3", "hard": 0, "fail_reason": "wrong_syntax"},
+        {"id": "task-4", "hard": 1, "predicted_answer": "correct4"},
+    ]
+
+    pairs = build_comparison_pairs(results_prev, results_curr, items)
+    assert len(pairs) == 4
+
+    by_id = {p["id"]: p for p in pairs}
+    assert by_id["task-1"]["category"] == "improved"
+    assert by_id["task-1"]["prev"]["hard"] == 0
+    assert by_id["task-1"]["curr"]["hard"] == 1
+
+    assert by_id["task-2"]["category"] == "regressed"
+    assert by_id["task-2"]["prev"]["hard"] == 1
+    assert by_id["task-2"]["curr"]["hard"] == 0
+
+    assert by_id["task-3"]["category"] == "persistent_fail"
+    assert by_id["task-3"]["prev"]["hard"] == 0
+    assert by_id["task-3"]["curr"]["hard"] == 0
+
+    assert by_id["task-4"]["category"] == "stable_success"
+    assert by_id["task-4"]["prev"]["hard"] == 1
+    assert by_id["task-4"]["curr"]["hard"] == 1
+
+
+def test_slow_update_field_lifecycle() -> None:
+    skill = "# Main Skill\n\nRule 1: Always verify assumptions."
+
+    assert not has_slow_update_field(skill)
+    injected = inject_empty_slow_update_field(skill)
+    assert has_slow_update_field(injected)
+    assert extract_slow_update_field(injected) == ""
+
+    # Idempotent inject
+    assert inject_empty_slow_update_field(injected) == injected
+
+    # Replace field with guidance
+    guidance = "Avoid premature tool exit on partial output."
+    updated = replace_slow_update_field(injected, guidance)
+    assert has_slow_update_field(updated)
+    assert extract_slow_update_field(updated) == guidance
+
+    # Stripping all fields
+    stripped = _strip_all_slow_update_fields(updated)
+    assert not has_slow_update_field(stripped)
+    assert stripped == skill.rstrip()
+
+
+def test_save_comparison_pairs_writes_valid_json() -> None:
+    pairs = [
+        {
+            "id": "item-1",
+            "task": "Test task",
+            "category": "improved",
+            "prev": {"hard": 0},
+            "curr": {"hard": 1},
+        }
+    ]
+    with tempfile.TemporaryDirectory() as tmpdir:
+        out_file = os.path.join(tmpdir, "comparison.json")
+        save_comparison_pairs(pairs, out_file)
+        assert os.path.exists(out_file)
+        with open(out_file, encoding="utf-8") as f:
+            loaded = json.load(f)
+        assert loaded == pairs