From 2a1e6155657213761520e6e081c09cb8e082d9bf Mon Sep 17 00:00:00 2001
From: Teknium <127238744+teknium1@users.noreply.github.com>
Date: Thu, 25 Jun 2026 12:54:19 -0700
Subject: [PATCH] fix: persist non-NULL system prompt on fresh turn setup
 (#45499) (#52616)

build_turn_context() created the DB session row via _ensure_db_session()
before the system prompt was restored/built, so a fresh API/gateway agent
carrying client-managed history inserted a row with system_prompt=NULL. That
tripped the misleading 'stored system prompt is null; rebuilding from scratch
... investigate the previous turn's write path' warning and a guaranteed
first-turn prefix cache miss. Move row creation to after _cached_system_prompt
is populated.

Verified live (OpenRouter + claude-sonnet-4.5): persistent-agent turns show
cache_read jumping to the full prefix on turn 2+ (write 24411 -> read 24411),
and the persisted system_prompt is non-NULL so fresh-agent restore keeps the
prefix cache warm.

Tests: turn-context ordering regression asserting _ensure_db_session runs
after _cached_system_prompt is populated.
---
 agent/turn_context.py            | 13 ++++++++++++-
 tests/agent/test_turn_context.py | 28 +++++++++++++++++++++++++++-
 2 files changed, 39 insertions(+), 2 deletions(-)

diff --git a/agent/turn_context.py b/agent/turn_context.py
index d7f376d1c4a..6efa22a68ca 100644
--- a/agent/turn_context.py
+++ b/agent/turn_context.py
@@ -142,7 +142,13 @@ def build_turn_context(
     # Guard stdio against OSError from broken pipes (systemd/headless/daemon).
     install_safe_stdio()
 
-    agent._ensure_db_session()
+    # NOTE: the DB session row is created later, AFTER the system prompt is
+    # restored/built (see _ensure_db_session() below the system-prompt block).
+    # Creating it here — before _cached_system_prompt is populated — inserts a
+    # row with system_prompt=NULL on a fresh API/gateway agent that carries
+    # client-managed history, which then trips the "stored system prompt is
+    # null; rebuilding from scratch" warning and a needless first-turn prefix
+    # cache miss. (Issue #45499.)
 
     # Tell auxiliary_client what the live main provider/model are for this turn.
     try:
@@ -309,6 +315,11 @@ def build_turn_context(
 
     active_system_prompt = agent._cached_system_prompt
 
+    # Create the DB session row now that _cached_system_prompt is populated, so
+    # the persisted snapshot is written non-NULL on the first turn (Issue
+    # #45499). Idempotent: _ensure_db_session() no-ops once the row exists.
+    agent._ensure_db_session()
+
     # Crash-resilience: persist the inbound user turn as soon as the session row exists.
     try:
         agent._persist_session(messages, conversation_history)
diff --git a/tests/agent/test_turn_context.py b/tests/agent/test_turn_context.py
index 05bea3d9e51..ae602723160 100644
--- a/tests/agent/test_turn_context.py
+++ b/tests/agent/test_turn_context.py
@@ -71,10 +71,13 @@ class _FakeAgent:
         self._invalid_tool_retries = -1
         self._vision_supported = None
         self._persist_calls = 0
+        # Records _cached_system_prompt at the moment _ensure_db_session()
+        # is called (regression guard for #45499 turn-setup ordering).
+        self._ensure_db_prompt_at_call = "<unset>"
 
     # --- methods the prologue calls ---
     def _ensure_db_session(self):
-        pass
+        self._ensure_db_prompt_at_call = self._cached_system_prompt
 
     def _restore_primary_runtime(self):
         pass
@@ -190,6 +193,29 @@ def test_no_review_when_memory_disabled():
     assert ctx.should_review_memory is False
 
 
+def test_ensure_db_session_runs_after_system_prompt_restore():
+    """Regression for #45499.
+
+    On a fresh API/gateway agent (``_cached_system_prompt is None``) the DB
+    session row must be created AFTER the system prompt is restored/built, so
+    the persisted snapshot is written non-NULL. If ``_ensure_db_session()``
+    ran first it would insert ``system_prompt=NULL`` and trip the misleading
+    "stored system prompt is null; rebuilding" warning plus a first-turn
+    prefix cache miss.
+    """
+    agent = _FakeAgent()
+    agent._cached_system_prompt = None  # fresh agent, no cached prompt yet
+
+    def _restore(_agent, _system_message, _history):
+        _agent._cached_system_prompt = "REBUILT-SYSTEM"
+
+    _build(agent, restore_or_build_system_prompt=_restore)
+
+    # The prompt was populated before the DB row was created.
+    assert agent._ensure_db_prompt_at_call == "REBUILT-SYSTEM"
+    assert agent._cached_system_prompt == "REBUILT-SYSTEM"
+
+
 # ── Between-turns MCP refresh (cache-safe late-binding) ──────────────────────
 #
 # A slow MCP server that connects after the agent's build-time tool snapshot