diff --git a/plugins/claude-code-best-practice/hooks/fewer-prompts-nudge-check.sh b/plugins/claude-code-best-practice/hooks/fewer-prompts-nudge-check.sh
new file mode 100755
index 0000000..26176f6
--- /dev/null
+++ b/plugins/claude-code-best-practice/hooks/fewer-prompts-nudge-check.sh
@@ -0,0 +1,12 @@
+#!/usr/bin/env bash
+set -eu
+
+COUNT_FILE="$HOME/.claude/perm_count.txt"
+count=$(cat "$COUNT_FILE" 2>/dev/null || echo 0)
+
+if [ "$count" -ge 5 ]; then
+  echo 0 > "$COUNT_FILE"
+  echo "{\"systemMessage\": \"このセッションで $count 回パーミッションの要求がありました。/fewer-permission-prompts を実行すると、よく使う操作を settings.json に自動追加してプロンプトを減らせます。\"}"
+else
+  echo 0 > "$COUNT_FILE"
+fi
diff --git a/plugins/claude-code-best-practice/hooks/fewer-prompts-nudge-increment.sh b/plugins/claude-code-best-practice/hooks/fewer-prompts-nudge-increment.sh
new file mode 100755
index 0000000..b382da4
--- /dev/null
+++ b/plugins/claude-code-best-practice/hooks/fewer-prompts-nudge-increment.sh
@@ -0,0 +1,6 @@
+#!/usr/bin/env bash
+set -eu
+
+COUNT_FILE="$HOME/.claude/perm_count.txt"
+count=$(cat "$COUNT_FILE" 2>/dev/null || echo 0)
+echo $((count + 1)) > "$COUNT_FILE"
diff --git a/plugins/claude-code-best-practice/hooks/hooks.json b/plugins/claude-code-best-practice/hooks/hooks.json
index 7d85719..cc54485 100644
--- a/plugins/claude-code-best-practice/hooks/hooks.json
+++ b/plugins/claude-code-best-practice/hooks/hooks.json
@@ -1,13 +1,24 @@
 {
-  "description": "Suggests running /fewer-permission-prompts each time the user invokes /clear.",
+  "description": "Counts permission requests per session and suggests /fewer-permission-prompts at Stop when the count reaches the threshold.",
   "hooks": {
-    "SessionStart": [
+    "PermissionRequest": [
       {
-        "matcher": "clear",
         "hooks": [
           {
             "type": "command",
-            "command": "${CLAUDE_PLUGIN_ROOT}/hooks/suggest-permissions-cleanup.sh"
+            "command": "${CLAUDE_PLUGIN_ROOT}/hooks/fewer-prompts-nudge-increment.sh",
+            "async": true
+          }
+        ]
+      }
+    ],
+    "Stop": [
+      {
+        "hooks": [
+          {
+            "type": "command",
+            "command": "${CLAUDE_PLUGIN_ROOT}/hooks/fewer-prompts-nudge-check.sh",
+            "timeout": 5
           }
         ]
       }
diff --git a/plugins/claude-code-best-practice/hooks/suggest-permissions-cleanup.sh b/plugins/claude-code-best-practice/hooks/suggest-permissions-cleanup.sh
deleted file mode 100755
index 26291bf..0000000
--- a/plugins/claude-code-best-practice/hooks/suggest-permissions-cleanup.sh
+++ /dev/null
@@ -1,8 +0,0 @@
-#!/usr/bin/env bash
-set -eu
-
-cat <<'EOF'
-{
-  "systemMessage": "💡 Tip: /clear したタイミングで許可設定の見直しをおすすめします。`/less-permission-prompts` を実行すると、繰り返し許可プロンプトが出るコマンドを検出し、allowlist に追加する候補を提案します。"
-}
-EOF