diff --git a/cortex/context_loader.py b/cortex/context_loader.py
index f1a1a7f..bf7974e 100644
--- a/cortex/context_loader.py
+++ b/cortex/context_loader.py
@@ -21,6 +21,7 @@ def load_context(
     include_short: bool = True,
     role_append: str = "",
     inject_datetime: bool = True,
+    mode: str = "chat",
 ) -> str:
     """
     Build the system-prompt context block for a given tier and memory toggles.
@@ -39,10 +40,18 @@ def load_context(
     inara_dir = persona_path()
     parts = []
 
-    # ── 0. Current date and time (per-role toggle — injected first so it's prominent) ──
+    # ── 0. System block — date/time and session mode (injected first so it's prominent) ──
+    system_lines = []
     if inject_datetime:
         now = datetime.now().astimezone()
-        parts.append(f"--- System ---\nCurrent date and time: {now.strftime('%A, %Y-%m-%d at %I:%M %p %Z')}")
+        system_lines.append(f"Current date and time: {now.strftime('%A, %Y-%m-%d at %I:%M %p %Z')}")
+    if mode == "otr":
+        system_lines.append(
+            "Current mode: Off The Record — "
+            "this conversation is private and will not be logged or included in memory distillation"
+        )
+    if system_lines:
+        parts.append("--- System ---\n" + "\n".join(system_lines))
 
     # ── 1. Core identity (always) ──────────────────────────────────
     for filename in _CORE:
diff --git a/cortex/routers/chat.py b/cortex/routers/chat.py
index bec1b48..39ef95e 100644
--- a/cortex/routers/chat.py
+++ b/cortex/routers/chat.py
@@ -95,6 +95,7 @@ async def _stream_chat(req: ChatRequest):
         include_long=req.include_long,
         include_mid=req.include_mid,
         include_short=req.include_short,
+        mode="otr" if req.off_record else "chat",
     )
     history = load_session(session_id)
     history.append({"role": "user", "content": req.message})