diff --git a/code_puppy/cli_runner.py b/code_puppy/cli_runner.py
index 3f8d2c028..117f85f22 100644
--- a/code_puppy/cli_runner.py
+++ b/code_puppy/cli_runner.py
@@ -625,8 +625,8 @@ async def interactive_mode(message_renderer, initial_command: str = None) -> Non
             # The renderer is stopped in the finally block of main().
             break
 
-        # Check for clear command (supports both `clear` and `/clear`)
-        if task.strip().lower() in ("clear", "/clear"):
+        # Check for clear command (supports only `clear`)
+        if task.strip().lower() == "clear":
             from code_puppy.command_line.clipboard import get_clipboard_manager
             from code_puppy.messaging import (
                 emit_info,
diff --git a/code_puppy/command_line/core_commands.py b/code_puppy/command_line/core_commands.py
index afd7bdfbc..395d17713 100644
--- a/code_puppy/command_line/core_commands.py
+++ b/code_puppy/command_line/core_commands.py
@@ -167,6 +167,41 @@ def handle_paste_command(command: str) -> bool:
     return True
 
 
+@register_command(
+    name="clear",
+    description="Clear conversation history and rotate autosave session",
+    usage="/clear",
+    aliases=[],
+    category="core",
+)
+def handle_clear_command(command: str) -> bool:
+    """Clear conversation history, rotate autosave session, and clear pending clipboard images.
+
+    Resets the agent's context so it starts fresh, persists the current session
+    to autosave, and notifies the user of the cleanup.
+    """
+
+    from code_puppy.command_line.clipboard import get_clipboard_manager
+    from code_puppy.messaging import emit_warning, emit_system_message, emit_info
+    from code_puppy.agents import get_current_agent
+    from code_puppy.config import finalize_autosave_session
+
+    agent = get_current_agent()
+    new_session_id = finalize_autosave_session()
+    agent.clear_message_history()
+    emit_warning("Conversation history cleared!")
+    emit_system_message("The agent will not remember previous interactions.")
+    emit_info(f"Auto-save session rotated to: {new_session_id}")
+
+    # Also clear pending clipboard images
+    clipboard_manager = get_clipboard_manager()
+    clipboard_count = clipboard_manager.get_pending_count()
+    clipboard_manager.clear_pending()
+    if clipboard_count > 0:
+        emit_info(f"Cleared {clipboard_count} pending clipboard image(s)")
+    return True
+
+
 @register_command(
     name="tutorial",
     description="Run the interactive tutorial wizard",