diff --git a/cli.py b/cli.py
index 57ec69e6..54013b0e 100755
--- a/cli.py
+++ b/cli.py
@@ -1099,6 +1099,7 @@ class HermesCLI:
         compact: bool = False,
         resume: str = None,
         checkpoints: bool = False,
+        pass_session_id: bool = False,
     ):
         """
         Initialize the Hermes CLI.
@@ -1113,6 +1114,7 @@ class HermesCLI:
             verbose: Enable verbose logging
             compact: Use compact display mode
             resume: Session ID to resume (restores conversation history from SQLite)
+            pass_session_id: Include the session ID in the agent's system prompt
         """
         # Initialize Rich console
         self.console = Console()
@@ -1194,6 +1196,7 @@ class HermesCLI:
             cp_cfg = {"enabled": cp_cfg}
         self.checkpoints_enabled = checkpoints or cp_cfg.get("enabled", False)
         self.checkpoint_max_snapshots = cp_cfg.get("max_snapshots", 50)
+        self.pass_session_id = pass_session_id
         
         # Ephemeral system prompt: env var takes precedence, then config
         self.system_prompt = (
@@ -1511,6 +1514,7 @@ class HermesCLI:
                 thinking_callback=self._on_thinking,
                 checkpoints_enabled=self.checkpoints_enabled,
                 checkpoint_max_snapshots=self.checkpoint_max_snapshots,
+                pass_session_id=self.pass_session_id,
             )
             # Apply any pending title now that the session exists in the DB
             if self._pending_title and self._session_db:
@@ -4654,6 +4658,7 @@ def main(
     worktree: bool = False,
     w: bool = False,
     checkpoints: bool = False,
+    pass_session_id: bool = False,
 ):
     """
     Hermes Agent CLI - Interactive AI Assistant
@@ -4759,6 +4764,7 @@ def main(
         compact=compact,
         resume=resume,
         checkpoints=checkpoints,
+        pass_session_id=pass_session_id,
     )
 
     # Inject worktree context into agent's system prompt
diff --git a/hermes_cli/main.py b/hermes_cli/main.py
index fe591212..78153535 100644
--- a/hermes_cli/main.py
+++ b/hermes_cli/main.py
@@ -495,6 +495,7 @@ def cmd_chat(args):
         "resume": getattr(args, "resume", None),
         "worktree": getattr(args, "worktree", False),
         "checkpoints": getattr(args, "checkpoints", False),
+        "pass_session_id": getattr(args, "pass_session_id", False),
     }
     # Filter out None values
     kwargs = {k: v for k, v in kwargs.items() if v is not None}
@@ -1895,6 +1896,12 @@ For more help on a command:
         default=False,
         help="Bypass all dangerous command approval prompts (use at your own risk)"
     )
+    parser.add_argument(
+        "--pass-session-id",
+        action="store_true",
+        default=False,
+        help="Include the session ID in the agent's system prompt"
+    )
     
     subparsers = parser.add_subparsers(dest="command", help="Command to run")
     
@@ -1966,6 +1973,12 @@ For more help on a command:
         default=False,
         help="Bypass all dangerous command approval prompts (use at your own risk)"
     )
+    chat_parser.add_argument(
+        "--pass-session-id",
+        action="store_true",
+        default=False,
+        help="Include the session ID in the agent's system prompt"
+    )
     chat_parser.set_defaults(func=cmd_chat)
 
     # =========================================================================
diff --git a/run_agent.py b/run_agent.py
index 608dde94..0d6fe545 100644
--- a/run_agent.py
+++ b/run_agent.py
@@ -233,6 +233,7 @@ class AIAgent:
         fallback_model: Dict[str, Any] = None,
         checkpoints_enabled: bool = False,
         checkpoint_max_snapshots: int = 50,
+        pass_session_id: bool = False,
     ):
         """
         Initialize the AI Agent.
@@ -287,6 +288,7 @@ class AIAgent:
         self.ephemeral_system_prompt = ephemeral_system_prompt
         self.platform = platform  # "cli", "telegram", "discord", "whatsapp", etc.
         self.skip_context_files = skip_context_files
+        self.pass_session_id = pass_session_id
         self.log_prefix_chars = log_prefix_chars
         self.log_prefix = f"{log_prefix} " if log_prefix else ""
         # Store effective base URL for feature detection (prompt caching, reasoning, etc.)
@@ -1483,9 +1485,10 @@ class AIAgent:
 
         from hermes_time import now as _hermes_now
         now = _hermes_now()
-        prompt_parts.append(
-            f"Conversation started: {now.strftime('%A, %B %d, %Y %I:%M %p')}"
-        )
+        timestamp_line = f"Conversation started: {now.strftime('%A, %B %d, %Y %I:%M %p')}"
+        if self.pass_session_id and self.session_id:
+            timestamp_line += f"\nSession ID: {self.session_id}"
+        prompt_parts.append(timestamp_line)
 
         platform_key = (self.platform or "").lower().strip()
         if platform_key in PLATFORM_HINTS: