diff --git a/skills/skill-creator/scripts/run_loop.py b/skills/skill-creator/scripts/run_loop.py
index 30a263d6..56e68769 100755
--- a/skills/skill-creator/scripts/run_loop.py
+++ b/skills/skill-creator/scripts/run_loop.py
@@ -41,6 +41,25 @@ def split_eval_set(eval_set: list[dict], holdout: float, seed: int = 42) -> tupl
     test_set = trigger[:n_trigger_test] + no_trigger[:n_no_trigger_test]
     train_set = trigger[n_trigger_test:] + no_trigger[n_no_trigger_test:]
 
+    # A single-member class always lands entirely in the test split, and an
+    # empty train split would make the loop report "all passed" on iteration 1
+    # without testing anything. Fail loudly rather than silently producing a
+    # degenerate run.
+    if not eval_set:
+        raise ValueError("Eval set is empty; nothing to split.")
+    if len(trigger) > 0 and not trigger[n_trigger_test:]:
+        raise ValueError(
+            f"Cannot split eval set with holdout={holdout}: only {len(trigger)} "
+            "trigger query(ies), leaving none for the train split. Add at least "
+            "2 queries per polarity class or run with --holdout 0."
+        )
+    if len(no_trigger) > 0 and not no_trigger[n_no_trigger_test:]:
+        raise ValueError(
+            f"Cannot split eval set with holdout={holdout}: only {len(no_trigger)} "
+            "non-trigger query(ies), leaving none for the train split. Add at "
+            "least 2 queries per polarity class or run with --holdout 0."
+        )
+
     return train_set, test_set
 
 
diff --git a/skills/skill-creator/tests/test_run_loop.py b/skills/skill-creator/tests/test_run_loop.py
new file mode 100644
index 00000000..7c1cd79a
--- /dev/null
+++ b/skills/skill-creator/tests/test_run_loop.py
@@ -0,0 +1,56 @@
+"""Regression tests for run_loop.split_eval_set.
+
+Covers the degenerate-split bug: with a small eval set and holdout > 0, the
+train split could come back empty (or missing a polarity class), which made
+the optimization loop exit with "all_passed" on iteration 1 without testing
+anything.
+"""
+
+import sys
+from pathlib import Path
+
+import pytest
+
+SKILL_CREATOR = Path(__file__).resolve().parents[1]
+sys.path.insert(0, str(SKILL_CREATOR))
+
+from scripts.run_loop import split_eval_set  # noqa: E402
+
+
+def _eval_set(n_trigger: int, n_no_trigger: int) -> list[dict]:
+    return [
+        {"query": f"trigger-{i}", "should_trigger": True} for i in range(n_trigger)
+    ] + [
+        {"query": f"no-trigger-{i}", "should_trigger": False}
+        for i in range(n_no_trigger)
+    ]
+
+
+def test_balanced_set_splits_both_classes() -> None:
+    train, test = split_eval_set(_eval_set(3, 3), holdout=0.4)
+    assert train and test
+    assert any(e["should_trigger"] for e in train)
+    assert any(not e["should_trigger"] for e in train)
+    assert len(train) + len(test) == 6
+
+
+def test_single_trigger_query_fails_loudly() -> None:
+    with pytest.raises(ValueError, match="train split"):
+        split_eval_set(_eval_set(1, 3), holdout=0.4)
+
+
+def test_single_no_trigger_query_fails_loudly() -> None:
+    with pytest.raises(ValueError, match="train split"):
+        split_eval_set(_eval_set(3, 1), holdout=0.4)
+
+
+def test_two_query_eval_set_fails_loudly() -> None:
+    # 1 trigger + 1 no-trigger with the default holdout leaves an empty train
+    # split — the loop used to report "all_passed" instead of failing.
+    with pytest.raises(ValueError, match="train split"):
+        split_eval_set(_eval_set(1, 1), holdout=0.4)
+
+
+def test_empty_eval_set_fails_loudly() -> None:
+    with pytest.raises(ValueError, match="empty"):
+        split_eval_set([], holdout=0.4)