diff --git a/AGRARIAN_DEVELOPMENT_ROADMAP.md b/AGRARIAN_DEVELOPMENT_ROADMAP.md
index 255bbc1..5fa1060 100644
--- a/AGRARIAN_DEVELOPMENT_ROADMAP.md
+++ b/AGRARIAN_DEVELOPMENT_ROADMAP.md
@@ -887,7 +887,7 @@ Target deliverable: A small group can join a server, spawn into one biome, gathe
 - [x] Define accessibility rules for the learning system: hints, retries, readable wording, no hard lockout from basic survival, and non-punitive practice paths. Added learning accessibility rules to `Docs/KnowledgeAndSkillFoundation.md`, covering reusable hints, retries, readable wording, non-color-only warnings, no lockout from basic survival, safer practice paths, and diminishing returns to prevent exploit loops.
 - [x] Define the first subject content format: topic, concepts, difficulty tier, prerequisite concepts, in-game effect, practice action, and source note. Added a compact subject content schema to `Docs/KnowledgeAndSkillFoundation.md` with `topic`, `concepts`, `difficulty_tier`, `prerequisite_concepts`, `in_game_effect`, `practice_action`, and `source_note`, plus a fire-clearance example suitable for later data assets.
 - [x] Add a small MVP question bank for elementary survival knowledge. Added six elementary survival question records to `Docs/KnowledgeAndSkillFoundation.md` for fire clearance, potable water, cold exposure, shelter drainage, bleeding care, and fiber identification, each with answer options, correct answer, and practical feedback.
-- [ ] Define when deeper questions should matter: quality improvements, safer work, complex crafting, teaching others, and advanced branches.
+- [x] Define when deeper questions should matter: quality improvements, safer work, complex crafting, teaching others, and advanced branches. Added deeper-question timing rules to `Docs/KnowledgeAndSkillFoundation.md`, keeping advanced checks out of the first survival loop while tying them to quality improvements, safer work, complex crafting, teaching others, and advanced branches.
 - [ ] Add design notes for avoiding exploit farming and rote memorization.
 - [ ] Add persistence requirements for knowledge, skill experience, learned concepts, failed attempts, and tutorial state.
 - [ ] Add multiplayer rules for teaching, observation, shared work, and group skill benefits.
diff --git a/Docs/KnowledgeAndSkillFoundation.md b/Docs/KnowledgeAndSkillFoundation.md
index bc7e2fb..c8f48ee 100644
--- a/Docs/KnowledgeAndSkillFoundation.md
+++ b/Docs/KnowledgeAndSkillFoundation.md
@@ -473,3 +473,39 @@ feedback: Fiber is a basic binding material for primitive crafting and shelter.
 
 Question-bank rule: elementary questions should be short, practical, and tied to
 actions the player can immediately recognize in the MVP.
+
+## When Deeper Questions Matter
+
+Deeper questions should not decide whether a new player can survive the first
+night. They should matter when the player is trying to do better, teach others,
+or enter more complex branches.
+
+Quality improvements:
+
+- Use deeper checks when the player wants better yield, stronger construction,
+  more durable tools, safer food, better medicine, or more efficient work.
+
+Safer work:
+
+- Use deeper checks when incorrect assumptions could create fire spread, injury,
+  sickness, structural failure, bad weather exposure, or wasted scarce supplies.
+
+Complex crafting:
+
+- Use deeper checks for multi-stage recipes, material substitutions, tool
+  maintenance, preserved food, medicines, buildings, and later machinery.
+
+Teaching others:
+
+- Use deeper checks when a player or NPC attempts to teach a concept, create a
+  lesson note, train family/community members, or evaluate whether someone
+  understood a dangerous task.
+
+Advanced branches:
+
+- Use deeper checks for farming, animal care, medicine, engineering, trade,
+  navigation, governance, science, and future advanced technology.
+
+Depth rule: deeper questions should improve mastery and responsibility. They
+should not be busywork for actions the character has already demonstrated
+through repeated safe practice.
diff --git a/Scripts/verify_deeper_question_timing.py b/Scripts/verify_deeper_question_timing.py
new file mode 100644
index 0000000..a27849a
--- /dev/null
+++ b/Scripts/verify_deeper_question_timing.py
@@ -0,0 +1,40 @@
+#!/usr/bin/env python3
+"""Verify deeper-question timing rules are documented."""
+
+from pathlib import Path
+
+
+ROOT = Path(__file__).resolve().parents[1]
+DOC = ROOT / "Docs" / "KnowledgeAndSkillFoundation.md"
+ROADMAP = ROOT / "AGRARIAN_DEVELOPMENT_ROADMAP.md"
+
+REQUIRED = {
+    DOC: [
+        "## When Deeper Questions Matter",
+        "Quality improvements:",
+        "Safer work:",
+        "Complex crafting:",
+        "Teaching others:",
+        "Advanced branches:",
+        "Depth rule:",
+    ],
+    ROADMAP: [
+        "[x] Define when deeper questions should matter: quality improvements, safer work, complex crafting, teaching others, and advanced branches.",
+    ],
+}
+
+
+def main() -> None:
+    missing: list[str] = []
+    for path, snippets in REQUIRED.items():
+        text = path.read_text(encoding="utf-8")
+        for snippet in snippets:
+            if snippet not in text:
+                missing.append(f"{path.relative_to(ROOT)} missing {snippet!r}")
+    if missing:
+        raise SystemExit("FAILED: " + "; ".join(missing))
+    print("OK: deeper-question timing rules are documented.")
+
+
+if __name__ == "__main__":
+    main()