diff --git a/cli.py b/cli.py
index fbc8f85250..f47427ff4f 100644
--- a/cli.py
+++ b/cli.py
@@ -5277,10 +5277,16 @@ class HermesCLI:
 
         # Resolve aliases via central registry so adding an alias is a one-line
         # change in hermes_cli/commands.py instead of touching every dispatch site.
-        from hermes_cli.commands import resolve_command as _resolve_cmd
+        from hermes_cli.commands import (
+            destructive_command_confirmation_message as _destructive_command_msg,
+            destructive_command_is_confirmed as _destructive_command_is_confirmed,
+            resolve_command as _resolve_cmd,
+        )
         _base_word = cmd_lower.split()[0].lstrip("/")
         _cmd_def = _resolve_cmd(_base_word)
         canonical = _cmd_def.name if _cmd_def else _base_word
+        _typed_command = cmd_original.split()[0].lstrip("/").lower()
+        _args = cmd_original.split(maxsplit=1)[1] if " " in cmd_original else ""
         
         if canonical in ("quit", "exit", "q"):
             return False
@@ -5295,6 +5301,9 @@ class HermesCLI:
         elif canonical == "config":
             self.show_config()
         elif canonical == "clear":
+            if not _destructive_command_is_confirmed(_args):
+                _cprint(_destructive_command_msg("clear", _typed_command))
+                return True
             self.new_session(silent=True)
             # Clear terminal screen.  Inside the TUI, Rich's console.clear()
             # goes through patch_stdout's StdoutProxy which swallows the
@@ -5412,6 +5421,9 @@ class HermesCLI:
                 else:
                     _cprint("  Session database not available.")
         elif canonical == "new":
+            if not _destructive_command_is_confirmed(_args):
+                _cprint(_destructive_command_msg("new", _typed_command))
+                return True
             self.new_session()
         elif canonical == "resume":
             self._handle_resume_command(cmd_original)
@@ -5431,6 +5443,9 @@ class HermesCLI:
                 # Re-queue the message so process_loop sends it to the agent
                 self._pending_input.put(retry_msg)
         elif canonical == "undo":
+            if not _destructive_command_is_confirmed(_args):
+                _cprint(_destructive_command_msg("undo", _typed_command))
+                return True
             self.undo_last()
         elif canonical == "branch":
             self._handle_branch_command(cmd_original)
diff --git a/gateway/run.py b/gateway/run.py
index 327f8ae32a..fe67fd523f 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -4259,6 +4259,15 @@ class GatewayRunner:
 
     async def _handle_reset_command(self, event: MessageEvent) -> str:
         """Handle /new or /reset command."""
+        from hermes_cli.commands import (
+            destructive_command_confirmation_message,
+            destructive_command_is_confirmed,
+        )
+
+        typed_command = event.get_command() or "new"
+        if not destructive_command_is_confirmed(event.get_command_args()):
+            return destructive_command_confirmation_message("new", typed_command)
+
         source = event.source
         
         # Get existing session key
@@ -5079,6 +5088,11 @@ class GatewayRunner:
     
     async def _handle_undo_command(self, event: MessageEvent) -> str:
         """Handle /undo command - remove the last user/assistant exchange."""
+        from hermes_cli.commands import (
+            destructive_command_confirmation_message,
+            destructive_command_is_confirmed,
+        )
+
         source = event.source
         session_entry = self.session_store.get_or_create_session(source)
         history = self.session_store.load_transcript(session_entry.session_id)
@@ -5092,7 +5106,11 @@ class GatewayRunner:
         
         if last_user_idx is None:
             return "Nothing to undo."
-        
+
+        if not destructive_command_is_confirmed(event.get_command_args()):
+            typed_command = event.get_command() or "undo"
+            return destructive_command_confirmation_message("undo", typed_command)
+
         removed_msg = history[last_user_idx].get("content", "")
         removed_count = len(history) - last_user_idx
         self.session_store.rewrite_transcript(session_entry.session_id, history[:last_user_idx])
diff --git a/hermes_cli/commands.py b/hermes_cli/commands.py
index 516392bd1d..90ffdb4609 100644
--- a/hermes_cli/commands.py
+++ b/hermes_cli/commands.py
@@ -59,15 +59,16 @@ class CommandDef:
 COMMAND_REGISTRY: list[CommandDef] = [
     # Session
     CommandDef("new", "Start a new session (fresh session ID + history)", "Session",
-               aliases=("reset",)),
+               aliases=("reset",), args_hint="[--yes]"),
     CommandDef("clear", "Clear screen and start a new session", "Session",
-               cli_only=True),
+               cli_only=True, args_hint="[--yes]"),
     CommandDef("history", "Show conversation history", "Session",
                cli_only=True),
     CommandDef("save", "Save the current conversation", "Session",
                cli_only=True),
     CommandDef("retry", "Retry the last message (resend to agent)", "Session"),
-    CommandDef("undo", "Remove the last user/assistant exchange", "Session"),
+    CommandDef("undo", "Remove the last user/assistant exchange", "Session",
+               args_hint="[--yes]"),
     CommandDef("title", "Set a title for the current session", "Session",
                args_hint="[name]"),
     CommandDef("branch", "Branch the current session (explore a different path)", "Session",
@@ -184,6 +185,18 @@ def _build_command_lookup() -> dict[str, CommandDef]:
 
 _COMMAND_LOOKUP: dict[str, CommandDef] = _build_command_lookup()
 
+_DESTRUCTIVE_COMMAND_ACTIONS: dict[str, str] = {
+    "new": "discard the current conversation history and start a fresh session",
+    "clear": "clear the screen and discard the current conversation history",
+    "undo": "remove the last user/assistant exchange from this session",
+}
+_DESTRUCTIVE_CONFIRM_TOKENS: frozenset[str] = frozenset({
+    "--yes",
+    "--confirm",
+    "yes",
+    "confirm",
+})
+
 
 def resolve_command(name: str) -> CommandDef | None:
     """Resolve a command name or alias to its CommandDef.
@@ -193,6 +206,26 @@ def resolve_command(name: str) -> CommandDef | None:
     return _COMMAND_LOOKUP.get(name.lower().lstrip("/"))
 
 
+def destructive_command_is_confirmed(args: str) -> bool:
+    """Return True when the command args include an explicit confirmation token."""
+    return any(token.lower() in _DESTRUCTIVE_CONFIRM_TOKENS for token in args.split())
+
+
+def destructive_command_confirmation_message(
+    canonical_name: str,
+    typed_name: str | None = None,
+) -> str:
+    """Build a consistent warning for destructive session commands."""
+    action = _DESTRUCTIVE_COMMAND_ACTIONS.get(canonical_name)
+    if not action:
+        raise KeyError(f"Unknown destructive command: {canonical_name}")
+    command_name = (typed_name or canonical_name).lstrip("/").lower()
+    return (
+        f"Confirmation required: this will {action}. "
+        f"Re-run `/{command_name} --yes` to continue."
+    )
+
+
 def _build_description(cmd: CommandDef) -> str:
     """Build a CLI-facing description string including usage hint."""
     if cmd.args_hint:
diff --git a/tests/cli/test_cli_new_session.py b/tests/cli/test_cli_new_session.py
index 0490aad9ce..0948004bc5 100644
--- a/tests/cli/test_cli_new_session.py
+++ b/tests/cli/test_cli_new_session.py
@@ -34,6 +34,7 @@ class _FakeAgent:
             [{"id": "t1", "content": "unfinished task", "status": "in_progress"}]
         )
         self.flush_memories = MagicMock()
+        self.commit_memory_session = MagicMock()
         self._invalidate_system_prompt = MagicMock()
 
         # Token counters (non-zero to verify reset)
@@ -116,6 +117,7 @@ def _make_cli(env_overrides=None, config_overrides=None, **kwargs):
         with patch.object(_cli_mod, "get_tool_definitions", return_value=[]), patch.dict(
             _cli_mod.__dict__, {"CLI_CONFIG": _clean_config}
         ):
+            _cli_mod._cprint = MagicMock()
             return _cli_mod.HermesCLI(**kwargs)
 
 
@@ -138,7 +140,7 @@ def test_new_command_creates_real_fresh_session_and_resets_agent_state(tmp_path)
     old_session_id = cli.session_id
     old_session_start = cli.session_start
 
-    cli.process_command("/new")
+    cli.process_command("/new --yes")
 
     assert cli.session_id != old_session_id
 
@@ -164,7 +166,7 @@ def test_reset_command_is_alias_for_new_session(tmp_path):
     cli = _prepare_cli_with_active_session(tmp_path)
     old_session_id = cli.session_id
 
-    cli.process_command("/reset")
+    cli.process_command("/reset --yes")
 
     assert cli.session_id != old_session_id
     assert cli._session_db.get_session(old_session_id)["end_reason"] == "new_session"
@@ -177,7 +179,7 @@ def test_clear_command_starts_new_session_before_redrawing(tmp_path):
     cli.show_banner = MagicMock()
 
     old_session_id = cli.session_id
-    cli.process_command("/clear")
+    cli.process_command("/clear --yes")
 
     assert cli.session_id != old_session_id
     assert cli._session_db.get_session(old_session_id)["end_reason"] == "new_session"
@@ -197,7 +199,7 @@ def test_new_session_resets_token_counters(tmp_path):
     assert agent.session_api_calls > 0
     assert agent.context_compressor.compression_count > 0
 
-    cli.process_command("/new")
+    cli.process_command("/new --yes")
 
     # All agent token counters must be zero
     assert agent.session_total_tokens == 0
@@ -220,3 +222,79 @@ def test_new_session_resets_token_counters(tmp_path):
     assert comp.last_total_tokens == 0
     assert comp.compression_count == 0
     assert comp._context_probed is False
+
+
+def test_new_command_requires_confirmation_before_resetting(tmp_path):
+    cli = _prepare_cli_with_active_session(tmp_path)
+    old_session_id = cli.session_id
+
+    cli.process_command("/new")
+
+    assert cli.session_id == old_session_id
+    assert cli._session_db.get_session(old_session_id) is not None
+    assert cli.conversation_history == [{"role": "user", "content": "hello"}]
+
+
+def test_reset_without_confirmation_does_not_reset_session(tmp_path):
+    cli = _prepare_cli_with_active_session(tmp_path)
+    old_session_id = cli.session_id
+
+    cli.process_command("/reset")
+
+    assert cli.session_id == old_session_id
+
+
+def test_reset_alias_warning_uses_typed_command():
+    from hermes_cli.commands import destructive_command_confirmation_message
+
+    assert "/reset --yes" in destructive_command_confirmation_message("new", "reset")
+
+
+def test_clear_requires_confirmation_before_redrawing(tmp_path):
+    cli = _prepare_cli_with_active_session(tmp_path)
+    cli.console = MagicMock()
+    cli.show_banner = MagicMock()
+    old_session_id = cli.session_id
+
+    cli.process_command("/clear")
+
+    assert cli.session_id == old_session_id
+    assert cli.conversation_history == [{"role": "user", "content": "hello"}]
+    cli.console.clear.assert_not_called()
+    cli.show_banner.assert_not_called()
+
+
+def test_undo_requires_confirmation_before_mutating_history():
+    cli = _make_cli()
+    cli.conversation_history = [
+        {"role": "user", "content": "first prompt"},
+        {"role": "assistant", "content": "first reply"},
+        {"role": "user", "content": "second prompt"},
+        {"role": "assistant", "content": "second reply"},
+    ]
+
+    cli.process_command("/undo")
+
+    assert [msg["content"] for msg in cli.conversation_history] == [
+        "first prompt",
+        "first reply",
+        "second prompt",
+        "second reply",
+    ]
+
+
+def test_undo_with_confirmation_removes_last_exchange():
+    cli = _make_cli()
+    cli.conversation_history = [
+        {"role": "user", "content": "first prompt"},
+        {"role": "assistant", "content": "first reply"},
+        {"role": "user", "content": "second prompt"},
+        {"role": "assistant", "content": "second reply"},
+    ]
+
+    cli.process_command("/undo --yes")
+
+    assert [msg["content"] for msg in cli.conversation_history] == [
+        "first prompt",
+        "first reply",
+    ]
diff --git a/tests/gateway/test_destructive_command_confirmation.py b/tests/gateway/test_destructive_command_confirmation.py
new file mode 100644
index 0000000000..01803f362a
--- /dev/null
+++ b/tests/gateway/test_destructive_command_confirmation.py
@@ -0,0 +1,129 @@
+"""Tests confirmation guards for destructive gateway session commands."""
+
+from datetime import datetime
+from types import SimpleNamespace
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+
+from gateway.config import GatewayConfig, Platform, PlatformConfig
+from gateway.platforms.base import MessageEvent
+from gateway.session import SessionEntry, SessionSource, build_session_key
+
+
+def _make_source() -> SessionSource:
+    return SessionSource(
+        platform=Platform.TELEGRAM,
+        user_id="u1",
+        chat_id="c1",
+        user_name="tester",
+        chat_type="dm",
+    )
+
+
+def _make_event(text: str) -> MessageEvent:
+    return MessageEvent(text=text, source=_make_source(), message_id="m1")
+
+
+def _make_runner():
+    from gateway.run import GatewayRunner
+
+    runner = object.__new__(GatewayRunner)
+    runner.config = GatewayConfig(
+        platforms={Platform.TELEGRAM: PlatformConfig(enabled=True, token="***")}
+    )
+    adapter = MagicMock()
+    adapter.send = AsyncMock()
+    runner.adapters = {Platform.TELEGRAM: adapter}
+    runner._voice_mode = {}
+    runner.hooks = SimpleNamespace(emit=AsyncMock(), loaded_hooks=False)
+    runner._session_model_overrides = {}
+    runner._pending_model_notes = {}
+    runner._background_tasks = set()
+
+    session_key = build_session_key(_make_source())
+    session_entry = SessionEntry(
+        session_key=session_key,
+        session_id="sess-old",
+        created_at=datetime.now(),
+        updated_at=datetime.now(),
+        platform=Platform.TELEGRAM,
+        chat_type="dm",
+    )
+    new_session_entry = SessionEntry(
+        session_key=session_key,
+        session_id="sess-new",
+        created_at=datetime.now(),
+        updated_at=datetime.now(),
+        platform=Platform.TELEGRAM,
+        chat_type="dm",
+    )
+    runner.session_store = MagicMock()
+    runner.session_store.get_or_create_session.return_value = session_entry
+    runner.session_store.reset_session.return_value = new_session_entry
+    runner.session_store._entries = {session_key: session_entry}
+    runner._running_agents = {}
+    runner._pending_messages = {}
+    runner._pending_approvals = {}
+    runner._session_db = None
+    runner._agent_cache_lock = None
+    runner._is_user_authorized = lambda _source: True
+    runner._format_session_info = lambda: ""
+
+    return runner
+
+
+@pytest.mark.asyncio
+async def test_new_requires_confirmation_before_reset():
+    runner = _make_runner()
+
+    result = await runner._handle_reset_command(_make_event("/new"))
+
+    assert "/new --yes" in result
+    runner.session_store.reset_session.assert_not_called()
+
+
+@pytest.mark.asyncio
+async def test_reset_alias_confirmation_mentions_reset():
+    runner = _make_runner()
+
+    result = await runner._handle_reset_command(_make_event("/reset"))
+
+    assert "/reset --yes" in result
+    runner.session_store.reset_session.assert_not_called()
+
+
+@pytest.mark.asyncio
+async def test_undo_requires_confirmation_before_rewriting_transcript():
+    runner = _make_runner()
+    runner.session_store.load_transcript.return_value = [
+        {"role": "user", "content": "hello"},
+        {"role": "assistant", "content": "hi"},
+    ]
+
+    result = await runner._handle_undo_command(_make_event("/undo"))
+
+    assert "/undo --yes" in result
+    runner.session_store.rewrite_transcript.assert_not_called()
+
+
+@pytest.mark.asyncio
+async def test_undo_with_confirmation_rewrites_transcript():
+    runner = _make_runner()
+    runner.session_store.load_transcript.return_value = [
+        {"role": "user", "content": "hello"},
+        {"role": "assistant", "content": "hi"},
+        {"role": "user", "content": "undo this"},
+        {"role": "assistant", "content": "ok"},
+    ]
+
+    result = await runner._handle_undo_command(_make_event("/undo --yes"))
+
+    runner.session_store.rewrite_transcript.assert_called_once_with(
+        "sess-old",
+        [
+            {"role": "user", "content": "hello"},
+            {"role": "assistant", "content": "hi"},
+        ],
+    )
+    assert "Undid 2 message(s)." in result
diff --git a/tests/gateway/test_session_boundary_hooks.py b/tests/gateway/test_session_boundary_hooks.py
index a556624363..76328265aa 100644
--- a/tests/gateway/test_session_boundary_hooks.py
+++ b/tests/gateway/test_session_boundary_hooks.py
@@ -79,7 +79,7 @@ async def test_reset_fires_finalize_hook(mock_invoke_hook):
     """/new must fire on_session_finalize with the OLD session id."""
     runner = _make_runner()
 
-    await runner._handle_reset_command(_make_event("/new"))
+    await runner._handle_reset_command(_make_event("/new --yes"))
 
     mock_invoke_hook.assert_any_call(
         "on_session_finalize", session_id="sess-old", platform="telegram"
@@ -92,7 +92,7 @@ async def test_reset_fires_reset_hook(mock_invoke_hook):
     """/new must fire on_session_reset with the NEW session id."""
     runner = _make_runner()
 
-    await runner._handle_reset_command(_make_event("/new"))
+    await runner._handle_reset_command(_make_event("/new --yes"))
 
     mock_invoke_hook.assert_any_call(
         "on_session_reset", session_id="sess-new", platform="telegram"
@@ -105,7 +105,7 @@ async def test_finalize_before_reset(mock_invoke_hook):
     """on_session_finalize must fire before on_session_reset."""
     runner = _make_runner()
 
-    await runner._handle_reset_command(_make_event("/new"))
+    await runner._handle_reset_command(_make_event("/new --yes"))
 
     calls = [c for c in mock_invoke_hook.call_args_list
              if c[0][0] in ("on_session_finalize", "on_session_reset")]
@@ -162,7 +162,7 @@ async def test_hook_error_does_not_break_reset(mock_invoke_hook):
     """Plugin hook errors must not prevent /new from completing."""
     runner = _make_runner()
 
-    result = await runner._handle_reset_command(_make_event("/new"))
+    result = await runner._handle_reset_command(_make_event("/new --yes"))
 
     # Should still return a success message despite hook errors
     assert "Session reset" in result or "New session" in result
diff --git a/tests/gateway/test_session_model_reset.py b/tests/gateway/test_session_model_reset.py
index 6529f3a11d..9be813a296 100644
--- a/tests/gateway/test_session_model_reset.py
+++ b/tests/gateway/test_session_model_reset.py
@@ -80,7 +80,7 @@ async def test_new_command_clears_session_model_override():
         "api_mode": "openai",
     }
 
-    await runner._handle_reset_command(_make_event("/new"))
+    await runner._handle_reset_command(_make_event("/new --yes"))
 
     assert session_key not in runner._session_model_overrides
 
@@ -93,7 +93,7 @@ async def test_new_command_no_override_is_noop():
 
     assert session_key not in runner._session_model_overrides
 
-    await runner._handle_reset_command(_make_event("/new"))
+    await runner._handle_reset_command(_make_event("/new --yes"))
 
     assert session_key not in runner._session_model_overrides
 
@@ -120,7 +120,7 @@ async def test_new_command_only_clears_own_session():
         "api_mode": "anthropic",
     }
 
-    await runner._handle_reset_command(_make_event("/new"))
+    await runner._handle_reset_command(_make_event("/new --yes"))
 
     assert session_key not in runner._session_model_overrides
     assert other_key in runner._session_model_overrides