diff --git a/duck_core/api.py b/duck_core/api.py
index 41dac97..baa3eb7 100644
--- a/duck_core/api.py
+++ b/duck_core/api.py
@@ -13,6 +13,7 @@ from pydantic import BaseModel
 
 from duck_core.approvals.service import ApprovalService
 from duck_core.config import get_settings
+from duck_core.conversations.store import ConversationStore
 from duck_core.events.store import EventStore
 from duck_core.experience.recorder import ExperienceRecorder
 from duck_core.memory.vector_memory import EmbeddingsUnavailableError, VectorMemory
@@ -26,15 +27,22 @@ logger = logging.getLogger(__name__)
 
 class ChatRequest(BaseModel):
     message: str
+    conversation_id: str | None = None
     workspace: str | None = None
     debug: bool = False
 
 
+class ConversationRequest(BaseModel):
+    title: str | None = None
+    workspace: str | None = None
+
+
 class ContinueRequest(BaseModel):
     approval_id: str
 
 
 def create_app() -> FastAPI:
+    get_settings.cache_clear()
     settings = get_settings()
     if settings.api_host == "0.0.0.0":
         logger.warning(
@@ -49,6 +57,7 @@ def create_app() -> FastAPI:
 
     task_store = TaskStore(settings.db_path)
     event_store = EventStore(settings.db_path)
+    conversations = ConversationStore(settings.db_path)
     model_client = ModelClient()
     approvals = ApprovalService(settings.db_path)
     runtime = RuntimeLoop(task_store, event_store, model_client, approval_service=approvals)
@@ -60,6 +69,7 @@ def create_app() -> FastAPI:
     async def startup() -> None:
         await task_store.init()
         await event_store.init()
+        await conversations.init()
         await approvals.init()
         await experience.init()
 
@@ -108,8 +118,69 @@ def create_app() -> FastAPI:
 
     @app.post("/v1/chat")
     async def chat(body: ChatRequest) -> dict[str, Any]:
-        result = await runtime.run_chat(body.message, body.workspace or settings.workspace, body.debug)
-        return result.__dict__
+        conversation = await conversations.ensure(
+            body.conversation_id,
+            title_from_message(body.message),
+            body.workspace or settings.workspace,
+        )
+        history = await conversation_history(conversation.conversation_id)
+        result = await runtime.run_chat(
+            body.message,
+            conversation.workspace,
+            body.debug,
+            history_messages=history,
+        )
+        await conversations.add_message(
+            conversation.conversation_id,
+            "user",
+            body.message,
+            task_id=result.task_id,
+            status=result.status,
+        )
+        await conversations.add_message(
+            conversation.conversation_id,
+            "assistant",
+            result.final_response,
+            reasoning_content=result.reasoning_content,
+            task_id=result.task_id,
+            status=result.status,
+        )
+        return {**result.__dict__, "conversation_id": conversation.conversation_id}
+
+    async def conversation_history(conversation_id: str) -> list[dict[str, str]]:
+        messages = await conversations.list_messages(conversation_id, limit=20)
+        return [
+            {"role": message.role, "content": message.content}
+            for message in messages
+            if message.role in {"user", "assistant"} and message.content
+        ]
+
+    def title_from_message(message: str) -> str:
+        title = " ".join(message.strip().split())
+        return title[:60] or "New chat"
+
+    @app.get("/v1/conversations")
+    async def list_conversations() -> list[dict[str, Any]]:
+        return [conversation.model_dump() for conversation in await conversations.list()]
+
+    @app.post("/v1/conversations")
+    async def create_conversation(body: ConversationRequest) -> dict[str, Any]:
+        conversation = await conversations.create(
+            body.title or "New chat",
+            body.workspace or settings.workspace,
+        )
+        return conversation.model_dump()
+
+    @app.get("/v1/conversations/{conversation_id}")
+    async def get_conversation(conversation_id: str) -> dict[str, Any]:
+        conversation = await conversations.get(conversation_id)
+        if conversation is None:
+            raise HTTPException(status_code=404, detail="Conversation not found")
+        messages = await conversations.list_messages(conversation_id)
+        return {
+            **conversation.model_dump(),
+            "messages": [message.model_dump() for message in messages],
+        }
 
     def sse(event: str, payload: dict[str, Any]) -> str:
         return f"event: {event}\ndata: {json.dumps(payload, ensure_ascii=False)}\n\n"
@@ -128,16 +199,23 @@ def create_app() -> FastAPI:
     @app.post("/v1/chat/stream")
     async def chat_stream(body: ChatRequest) -> StreamingResponse:
         async def generator():
+            conversation = await conversations.ensure(
+                body.conversation_id,
+                title_from_message(body.message),
+                body.workspace or settings.workspace,
+            )
+            history = await conversation_history(conversation.conversation_id)
             task = await task_store.create_task(
-                body.message, body.workspace or settings.workspace, body.debug
+                body.message, conversation.workspace, body.debug
             )
             task_event = await event_store.append(
                 task.task_id,
                 "task_created",
                 {
                     "message": body.message,
-                    "workspace": body.workspace or settings.workspace,
+                    "workspace": conversation.workspace,
                     "debug": body.debug,
+                    "conversation_id": conversation.conversation_id,
                 },
             )
             yield sse("task_created", task_event.model_dump())
@@ -145,9 +223,9 @@ def create_app() -> FastAPI:
             reasoning_parts: list[str] = []
             content_parts: list[str] = []
             try:
-                messages = runtime.context_builder.build_basic_messages(task)
+                messages = runtime.context_builder.build_basic_messages(task, history)
                 tool_observations = await runtime._run_action_loop(
-                    task.task_id, messages, body.workspace or settings.workspace
+                    task.task_id, messages, conversation.workspace
                 )
                 async for tool_event in emit_tool_events(task.task_id, task_event.sequence):
                     yield tool_event
@@ -158,10 +236,25 @@ def create_app() -> FastAPI:
                         "task_waiting_for_approval",
                         {"observations": tool_observations},
                     )
+                    await conversations.add_message(
+                        conversation.conversation_id,
+                        "user",
+                        body.message,
+                        task_id=task.task_id,
+                        status="waiting_for_approval",
+                    )
+                    await conversations.add_message(
+                        conversation.conversation_id,
+                        "assistant",
+                        "Waiting for approval.",
+                        task_id=task.task_id,
+                        status="waiting_for_approval",
+                    )
                     yield sse(
                         "done",
                         {
                             "task_id": task.task_id,
+                            "conversation_id": conversation.conversation_id,
                             "status": "waiting_for_approval",
                             "final_response": "Waiting for approval.",
                             "reasoning_content": None,
@@ -213,6 +306,21 @@ def create_app() -> FastAPI:
                     },
                 )
                 await task_store.complete_task(task.task_id, content)
+                await conversations.add_message(
+                    conversation.conversation_id,
+                    "user",
+                    body.message,
+                    task_id=task.task_id,
+                    status="completed",
+                )
+                await conversations.add_message(
+                    conversation.conversation_id,
+                    "assistant",
+                    content,
+                    reasoning_content=reasoning_content,
+                    task_id=task.task_id,
+                    status="completed",
+                )
                 await event_store.append(
                     task.task_id,
                     "task_completed",
@@ -225,6 +333,7 @@ def create_app() -> FastAPI:
                     "done",
                     {
                         "task_id": task.task_id,
+                        "conversation_id": conversation.conversation_id,
                         "status": "completed",
                         "final_response": content,
                         "reasoning_content": reasoning_content,
@@ -297,6 +406,7 @@ def create_app() -> FastAPI:
             raise HTTPException(status_code=404, detail="Approval not found for task")
         if approval.decision is None:
             raise HTTPException(status_code=409, detail="Approval is still pending")
+        conversation_id = await conversations.get_conversation_id_for_task(task_id)
 
         async def generator():
             reasoning_parts: list[str] = []
@@ -329,10 +439,19 @@ def create_app() -> FastAPI:
                         "task_waiting_for_approval",
                         {"observations": tool_observations},
                     )
+                    if conversation_id:
+                        await conversations.add_message(
+                            conversation_id,
+                            "assistant",
+                            "Waiting for approval.",
+                            task_id=task_id,
+                            status="waiting_for_approval",
+                        )
                     yield sse(
                         "done",
                         {
                             "task_id": task_id,
+                            "conversation_id": conversation_id,
                             "status": "waiting_for_approval",
                             "final_response": "Waiting for approval.",
                             "reasoning_content": None,
@@ -378,6 +497,15 @@ def create_app() -> FastAPI:
                     },
                 )
                 await task_store.complete_task(task_id, content)
+                if conversation_id:
+                    await conversations.add_message(
+                        conversation_id,
+                        "assistant",
+                        content,
+                        reasoning_content=reasoning_content,
+                        task_id=task_id,
+                        status="completed",
+                    )
                 await event_store.append(
                     task_id,
                     "task_completed",
@@ -390,6 +518,7 @@ def create_app() -> FastAPI:
                     "done",
                     {
                         "task_id": task_id,
+                        "conversation_id": conversation_id,
                         "status": "completed",
                         "final_response": content,
                         "reasoning_content": reasoning_content,
diff --git a/duck_core/context_builder.py b/duck_core/context_builder.py
index 7f14ea7..961745a 100644
--- a/duck_core/context_builder.py
+++ b/duck_core/context_builder.py
@@ -2,10 +2,15 @@ from duck_core.tasks.state import TaskState
 
 
 class ContextBuilder:
-    def build_basic_messages(self, task: TaskState) -> list[dict[str, str]]:
+    def build_basic_messages(
+        self,
+        task: TaskState,
+        history_messages: list[dict[str, str]] | None = None,
+    ) -> list[dict[str, str]]:
         return [
+            *(history_messages or []),
             {
                 "role": "user",
                 "content": task.user_message,
-            }
+            },
         ]
diff --git a/duck_core/conversations/__init__.py b/duck_core/conversations/__init__.py
new file mode 100644
index 0000000..32cad08
--- /dev/null
+++ b/duck_core/conversations/__init__.py
@@ -0,0 +1,3 @@
+__all__ = ["ConversationStore"]
+
+from duck_core.conversations.store import ConversationStore
diff --git a/duck_core/conversations/store.py b/duck_core/conversations/store.py
new file mode 100644
index 0000000..7b9b499
--- /dev/null
+++ b/duck_core/conversations/store.py
@@ -0,0 +1,210 @@
+from __future__ import annotations
+
+from pathlib import Path
+from typing import Any
+from uuid import uuid4
+
+import aiosqlite
+from pydantic import BaseModel
+
+from duck_core.tasks.store import utc_now
+
+
+class Conversation(BaseModel):
+    id: int | None = None
+    conversation_id: str
+    title: str
+    workspace: str
+    created_at: str
+    updated_at: str
+
+
+class ConversationMessage(BaseModel):
+    id: int | None = None
+    conversation_id: str
+    role: str
+    content: str
+    reasoning_content: str | None = None
+    task_id: str | None = None
+    status: str | None = None
+    created_at: str
+
+
+class ConversationStore:
+    def __init__(self, db_path: str):
+        self.db_path = Path(db_path)
+
+    async def init(self) -> None:
+        self.db_path.parent.mkdir(parents=True, exist_ok=True)
+        async with aiosqlite.connect(self.db_path) as db:
+            await db.execute(
+                """
+                create table if not exists conversations (
+                  id integer primary key autoincrement,
+                  conversation_id text not null unique,
+                  title text not null,
+                  workspace text not null,
+                  created_at text not null,
+                  updated_at text not null
+                )
+                """
+            )
+            await db.execute(
+                """
+                create table if not exists conversation_messages (
+                  id integer primary key autoincrement,
+                  conversation_id text not null,
+                  role text not null,
+                  content text not null,
+                  reasoning_content text,
+                  task_id text,
+                  status text,
+                  created_at text not null
+                )
+                """
+            )
+            await db.commit()
+
+    async def create(self, title: str, workspace: str) -> Conversation:
+        await self.init()
+        now = utc_now()
+        conversation_id = f"chat_{uuid4().hex[:12]}"
+        async with aiosqlite.connect(self.db_path) as db:
+            cursor = await db.execute(
+                """
+                insert into conversations(conversation_id, title, workspace, created_at, updated_at)
+                values (?, ?, ?, ?, ?)
+                """,
+                (conversation_id, title, workspace, now, now),
+            )
+            await db.commit()
+            row_id = cursor.lastrowid
+        return Conversation(
+            id=row_id,
+            conversation_id=conversation_id,
+            title=title,
+            workspace=workspace,
+            created_at=now,
+            updated_at=now,
+        )
+
+    async def ensure(
+        self, conversation_id: str | None, title: str, workspace: str
+    ) -> Conversation:
+        if conversation_id:
+            existing = await self.get(conversation_id)
+            if existing is not None:
+                return existing
+        return await self.create(title, workspace)
+
+    async def get(self, conversation_id: str) -> Conversation | None:
+        await self.init()
+        async with aiosqlite.connect(self.db_path) as db:
+            db.row_factory = aiosqlite.Row
+            cursor = await db.execute(
+                "select * from conversations where conversation_id = ?", (conversation_id,)
+            )
+            row = await cursor.fetchone()
+        return self._row_to_conversation(row) if row else None
+
+    async def list(self, limit: int = 50) -> list[Conversation]:
+        await self.init()
+        async with aiosqlite.connect(self.db_path) as db:
+            db.row_factory = aiosqlite.Row
+            cursor = await db.execute(
+                "select * from conversations order by updated_at desc limit ?", (limit,)
+            )
+            rows = await cursor.fetchall()
+        return [self._row_to_conversation(row) for row in rows]
+
+    async def add_message(
+        self,
+        conversation_id: str,
+        role: str,
+        content: str,
+        reasoning_content: str | None = None,
+        task_id: str | None = None,
+        status: str | None = None,
+    ) -> ConversationMessage:
+        await self.init()
+        now = utc_now()
+        async with aiosqlite.connect(self.db_path) as db:
+            cursor = await db.execute(
+                """
+                insert into conversation_messages(
+                  conversation_id, role, content, reasoning_content, task_id, status, created_at
+                ) values (?, ?, ?, ?, ?, ?, ?)
+                """,
+                (conversation_id, role, content, reasoning_content, task_id, status, now),
+            )
+            await db.execute(
+                "update conversations set updated_at = ? where conversation_id = ?",
+                (now, conversation_id),
+            )
+            await db.commit()
+            row_id = cursor.lastrowid
+        return ConversationMessage(
+            id=row_id,
+            conversation_id=conversation_id,
+            role=role,
+            content=content,
+            reasoning_content=reasoning_content,
+            task_id=task_id,
+            status=status,
+            created_at=now,
+        )
+
+    async def list_messages(
+        self, conversation_id: str, limit: int | None = None
+    ) -> list[ConversationMessage]:
+        await self.init()
+        sql = "select * from conversation_messages where conversation_id = ? order by id"
+        params: tuple[Any, ...] = (conversation_id,)
+        if limit is not None:
+            sql = (
+                "select * from (select * from conversation_messages where conversation_id = ? "
+                "order by id desc limit ?) order by id"
+            )
+            params = (conversation_id, limit)
+        async with aiosqlite.connect(self.db_path) as db:
+            db.row_factory = aiosqlite.Row
+            cursor = await db.execute(sql, params)
+            rows = await cursor.fetchall()
+        return [self._row_to_message(row) for row in rows]
+
+    async def get_conversation_id_for_task(self, task_id: str) -> str | None:
+        await self.init()
+        async with aiosqlite.connect(self.db_path) as db:
+            cursor = await db.execute(
+                """
+                select conversation_id from conversation_messages
+                where task_id = ?
+                order by id
+                limit 1
+                """,
+                (task_id,),
+            )
+            row = await cursor.fetchone()
+        return row[0] if row else None
+
+    def _row_to_conversation(self, row: aiosqlite.Row) -> Conversation:
+        return Conversation(
+            id=row["id"],
+            conversation_id=row["conversation_id"],
+            title=row["title"],
+            workspace=row["workspace"],
+            created_at=row["created_at"],
+            updated_at=row["updated_at"],
+        )
+
+    def _row_to_message(self, row: aiosqlite.Row) -> ConversationMessage:
+        return ConversationMessage(
+            id=row["id"],
+            conversation_id=row["conversation_id"],
+            role=row["role"],
+            content=row["content"],
+            reasoning_content=row["reasoning_content"],
+            task_id=row["task_id"],
+            status=row["status"],
+            created_at=row["created_at"],
+        )
diff --git a/duck_core/runtime_loop.py b/duck_core/runtime_loop.py
index 072910a..552ffe7 100644
--- a/duck_core/runtime_loop.py
+++ b/duck_core/runtime_loop.py
@@ -37,7 +37,11 @@ class RuntimeLoop:
         self.max_tool_iterations = max_tool_iterations
 
     async def run_chat(
-        self, message: str, workspace: str | None = None, debug: bool = False
+        self,
+        message: str,
+        workspace: str | None = None,
+        debug: bool = False,
+        history_messages: list[dict[str, str]] | None = None,
     ) -> ChatResult:
         task = await self.task_store.create_task(message, workspace, debug)
         await self.event_store.append(
@@ -46,7 +50,7 @@ class RuntimeLoop:
             {"message": message, "workspace": workspace, "debug": debug},
         )
         try:
-            messages = self.context_builder.build_basic_messages(task)
+            messages = self.context_builder.build_basic_messages(task, history_messages)
             tool_observations = await self._run_action_loop(task.task_id, messages, workspace)
             if any(observation.get("requires_approval") for observation in tool_observations):
                 await self.task_store.waiting_for_approval(task.task_id)
diff --git a/duck_core/tools/gateway.py b/duck_core/tools/gateway.py
index b4d0a09..28df56b 100644
--- a/duck_core/tools/gateway.py
+++ b/duck_core/tools/gateway.py
@@ -4,6 +4,7 @@ from duck_core.tools.base import Tool, ToolResult
 from duck_core.tools.file_read import FileReadTool
 from duck_core.tools.file_write import FileWriteTool
 from duck_core.tools.list_dir import ListDirTool
+from duck_core.tools.os_update_check import OsUpdateCheckTool
 from duck_core.tools.search_files import SearchFilesTool
 from duck_core.tools.shell_exec_safe import ShellExecSafeTool
 
@@ -20,6 +21,7 @@ class ToolGateway:
                 FileWriteTool(workspace),
                 ListDirTool(workspace),
                 SearchFilesTool(workspace),
+                OsUpdateCheckTool(workspace),
                 ShellExecSafeTool(workspace),
             ]
         )
diff --git a/duck_core/tools/os_update_check.py b/duck_core/tools/os_update_check.py
new file mode 100644
index 0000000..2555733
--- /dev/null
+++ b/duck_core/tools/os_update_check.py
@@ -0,0 +1,58 @@
+import shutil
+import subprocess
+from typing import Any
+
+from duck_core.tools.base import ToolResult
+
+
+class OsUpdateCheckTool:
+    name = "os_update_check"
+    risk_level = "low"
+
+    def __init__(self, workspace: str, timeout_seconds: int = 60, max_lines: int = 300):
+        self.workspace = workspace
+        self.timeout_seconds = timeout_seconds
+        self.max_lines = max_lines
+
+    async def run(self, args: dict[str, Any]) -> ToolResult:
+        if shutil.which("apt"):
+            return self._run_apt()
+        return ToolResult(
+            ok=False,
+            error="No supported package manager found for update checks.",
+            metadata={"supported_package_managers": ["apt"]},
+        )
+
+    def _run_apt(self) -> ToolResult:
+        try:
+            completed = subprocess.run(
+                ["apt", "list", "--upgradable"],
+                cwd=self.workspace,
+                text=True,
+                capture_output=True,
+                timeout=self.timeout_seconds,
+                check=False,
+            )
+        except subprocess.SubprocessError as exc:
+            return ToolResult(ok=False, error=str(exc), metadata={"package_manager": "apt"})
+
+        lines = completed.stdout.splitlines()
+        package_lines = [line for line in lines if "/" in line and "upgradable from:" in line]
+        output_lines = lines[: self.max_lines]
+        truncated = len(lines) > self.max_lines
+        if truncated:
+            output_lines.append(f"... truncated after {self.max_lines} lines")
+
+        return ToolResult(
+            ok=completed.returncode == 0,
+            output="\n".join(output_lines),
+            error=completed.stderr or None,
+            metadata={
+                "package_manager": "apt",
+                "command": "apt list --upgradable",
+                "returncode": completed.returncode,
+                "upgradable_count": len(package_lines),
+                "refreshed_cache": False,
+                "truncated": truncated,
+            },
+        )
diff --git a/duck_core/tools/shell_exec_safe.py b/duck_core/tools/shell_exec_safe.py
index daeb9d4..d06836d 100644
--- a/duck_core/tools/shell_exec_safe.py
+++ b/duck_core/tools/shell_exec_safe.py
@@ -58,9 +58,10 @@ class ShellExecSafeTool:
     async def run(self, args: dict[str, Any]) -> ToolResult:
         command = str(args.get("command", "")).strip()
         approved = bool(args.get("_approved"))
-        allowed, reason = self._is_allowed(command, approved=approved)
+        allowed, reason, blocked = self._is_allowed(command, approved=approved)
         if not allowed:
-            return ToolResult(ok=False, error=reason, metadata={"requires_approval": True})
+            metadata = {"blocked": True} if blocked else {"requires_approval": True}
+            return ToolResult(ok=False, error=reason, metadata=metadata)
         try:
             completed = subprocess.run(
                 command,
@@ -80,19 +81,29 @@ class ShellExecSafeTool:
             metadata={"returncode": completed.returncode, "command": command},
         )
 
-    def _is_allowed(self, command: str, approved: bool = False) -> tuple[bool, str | None]:
+    def _is_allowed(
+        self, command: str, approved: bool = False
+    ) -> tuple[bool, str | None, bool]:
         if not command:
-            return False, "Empty command"
+            return False, "Empty command", False
         lowered = command.lower()
-        for blocked in BLOCKLIST:
-            if lowered.startswith(blocked.lower()) or blocked.lower() in lowered:
-                return False, f"Command is blocked: {blocked}"
-        if approved:
-            return True, None
         parts = shlex.split(command)
+        for blocked in BLOCKLIST:
+            if self._matches_blocked_command(lowered, parts, blocked):
+                return False, f"Command is blocked: {blocked}", True
+        if approved:
+            return True, None, False
         prefix1 = parts[0] if parts else ""
         prefix2 = " ".join(parts[:2])
         prefix3 = " ".join(parts[:3])
         if prefix1 in ALLOWLIST or prefix2 in ALLOWLIST or prefix3 in ALLOWLIST:
-            return True, None
-        return False, "Command is outside allowlist and requires approval"
+            return True, None, False
+        return False, "Command is outside allowlist and requires approval", False
+
+    def _matches_blocked_command(
+        self, lowered_command: str, parts: list[str], blocked: str
+    ) -> bool:
+        lowered_blocked = blocked.lower()
+        if " " in lowered_blocked or "|" in lowered_blocked:
+            return lowered_command.startswith(lowered_blocked) or lowered_blocked in lowered_command
+        return bool(parts) and parts[0].lower() == lowered_blocked
diff --git a/duck_core/web/static/app.js b/duck_core/web/static/app.js
index 7535f5a..2481901 100644
--- a/duck_core/web/static/app.js
+++ b/duck_core/web/static/app.js
@@ -1,6 +1,8 @@
 const state = {
   running: false,
   messages: [],
+  currentConversationId: "",
+  conversations: [],
 };
 
 async function jsonFetch(url, options) {
@@ -52,6 +54,35 @@ function addMessage(role, content, meta = "", options = {}) {
   return article;
 }
 
+function clearMessages() {
+  const messages = document.querySelector("#messages");
+  if (messages) messages.innerHTML = "";
+  const events = document.querySelector("#events");
+  if (events) events.innerHTML = "";
+}
+
+function setConversationHeader(conversation) {
+  const title = document.querySelector("#chat-title");
+  const subtitle = document.querySelector("#chat-subtitle");
+  if (title) title.textContent = conversation?.title || "Chat";
+  if (subtitle) {
+    subtitle.textContent = conversation?.workspace
+      ? `Workspace: ${conversation.workspace}`
+      : "Messages are processed by the local Qwen role mapping through Duck Core.";
+  }
+}
+
+function addStoredMessage(message) {
+  const article = addMessage(
+    message.role,
+    message.content,
+    message.status || "saved",
+    {reasoning: message.role === "assistant" && Boolean(message.reasoning_content)},
+  );
+  if (message.reasoning_content) finishInlineReasoning(article, message.reasoning_content);
+  return article;
+}
+
 function createInlineReasoning() {
   const section = document.createElement("section");
   section.className = "message-reasoning is-collapsed";
@@ -112,6 +143,9 @@ function formatToolCommand(tool, args) {
   if (tool === "shell_exec_safe") return `$ ${args.command || tool}`;
   if (tool === "file_read") return `$ file_read ${args.path || ""}`.trim();
   if (tool === "file_write") return `$ file_write ${args.path || ""}`.trim();
+  if (tool === "list_dir") return `$ list_dir ${args.path || "."}`.trim();
+  if (tool === "search_files") return `$ search_files ${args.query || ""}`.trim();
+  if (tool === "os_update_check") return "$ os_update_check";
   return `$ ${tool || "tool"}`;
 }
 
@@ -363,6 +397,9 @@ async function handleAssistantStreamEvent(pending, name, data, context) {
   if (data.task_id) context.taskId = data.task_id;
   if (name === "task_created") {
     context.taskId = data.task_id;
+    if (data.payload?.conversation_id) {
+      state.currentConversationId = data.payload.conversation_id;
+    }
     setStatus("#task-status", data.task_id, "warn");
     return;
   }
@@ -396,6 +433,7 @@ async function handleAssistantStreamEvent(pending, name, data, context) {
     return;
   }
   if (name === "done") {
+    if (data.conversation_id) state.currentConversationId = data.conversation_id;
     if (!context.contentStarted) {
       setMessagePending(pending, data.final_response || "No final content returned.");
     }
@@ -403,6 +441,7 @@ async function handleAssistantStreamEvent(pending, name, data, context) {
     setStatus("#task-status", data.task_id, data.status === "completed" ? "ok" : "warn");
     finishInlineReasoning(pending, data.reasoning_content);
     await refreshEvents(data.task_id);
+    await refreshConversations();
     return;
   }
   if (name === "error") {
@@ -434,6 +473,59 @@ async function continueAfterInlineApproval(article, taskId, approvalId) {
   }
 }
 
+async function refreshConversations() {
+  const list = document.querySelector("#conversation-list");
+  if (!list) return;
+  state.conversations = await jsonFetch("/v1/conversations");
+  list.innerHTML = "";
+  if (!state.conversations.length) {
+    const empty = document.createElement("p");
+    empty.className = "conversation-empty";
+    empty.textContent = "No saved chats.";
+    list.append(empty);
+    return;
+  }
+  for (const conversation of state.conversations) {
+    const button = document.createElement("button");
+    button.type = "button";
+    button.className = "conversation-item";
+    button.dataset.conversationId = conversation.conversation_id;
+    button.classList.toggle("active", conversation.conversation_id === state.currentConversationId);
+
+    const title = document.createElement("strong");
+    title.textContent = conversation.title;
+    const workspace = document.createElement("span");
+    workspace.textContent = conversation.workspace;
+    button.append(title, workspace);
+    list.append(button);
+  }
+}
+
+async function selectConversation(conversationId) {
+  const conversation = await jsonFetch(`/v1/conversations/${conversationId}`);
+  state.currentConversationId = conversation.conversation_id;
+  document.querySelector("#workspace").value = conversation.workspace;
+  setConversationHeader(conversation);
+  clearMessages();
+  if (!conversation.messages.length) {
+    addMessage("assistant", "Новый чат готов.", "ready");
+  } else {
+    for (const message of conversation.messages) addStoredMessage(message);
+  }
+  await refreshConversations();
+}
+
+async function createNewConversation() {
+  const workspace = document.querySelector("#workspace").value || "./workspace";
+  const conversation = await jsonFetch("/v1/conversations", {
+    method: "POST",
+    headers: {"Content-Type": "application/json"},
+    body: JSON.stringify({title: "New chat", workspace}),
+  });
+  await selectConversation(conversation.conversation_id);
+  setStatus("#task-status", "none");
+}
+
 async function sendMessage() {
   if (state.running) return;
   const input = document.querySelector("#message");
@@ -451,6 +543,7 @@ async function sendMessage() {
   try {
     await streamChat({
       message,
+      conversation_id: state.currentConversationId || null,
       workspace: document.querySelector("#workspace").value,
       debug: document.querySelector("#debug").checked,
     }, async ({name, data}) => {
@@ -500,11 +593,14 @@ function bindChat() {
     }
   });
   document.querySelector("#new-chat")?.addEventListener("click", () => {
-    const messages = document.querySelector("#messages");
-    messages.innerHTML = "";
-    addMessage("assistant", "Новая сессия готова.", "ready");
-    document.querySelector("#events").innerHTML = "";
-    setStatus("#task-status", "none");
+    createNewConversation().catch(console.error);
+  });
+  document.querySelector("#reload-chat")?.addEventListener("click", () => {
+    if (state.currentConversationId) selectConversation(state.currentConversationId).catch(console.error);
+  });
+  document.querySelector("#conversation-list")?.addEventListener("click", (event) => {
+    const item = event.target.closest("[data-conversation-id]");
+    if (item) selectConversation(item.dataset.conversationId).catch(console.error);
   });
   document.querySelector("#messages")?.addEventListener("click", (event) => {
     const approvalButton = event.target.closest("[data-inline-approval-action]");
@@ -617,3 +713,8 @@ document.querySelector("#memory-search")?.addEventListener("click", async () =>
 bindChat();
 checkRuntime();
 loadSimplePages().catch(console.error);
+refreshConversations().then(() => {
+  if (state.conversations[0]) {
+    return selectConversation(state.conversations[0].conversation_id);
+  }
+}).catch(console.error);
diff --git a/duck_core/web/static/style.css b/duck_core/web/static/style.css
index def1cc7..a972cbe 100644
--- a/duck_core/web/static/style.css
+++ b/duck_core/web/static/style.css
@@ -233,7 +233,8 @@ button {
 }
 
 .settings-panel,
-.status-panel {
+.status-panel,
+.conversation-panel {
   display: grid;
   gap: 12px;
   padding: 14px;
@@ -243,11 +244,79 @@ button {
 }
 
 .settings-panel h2,
-.status-panel h2 {
+.status-panel h2,
+.conversation-panel h2 {
   font-size: 13px;
   color: #f8fafc;
 }
 
+.panel-heading {
+  display: flex;
+  align-items: center;
+  justify-content: space-between;
+  gap: 10px;
+}
+
+.panel-heading button {
+  display: grid;
+  place-items: center;
+  width: 28px;
+  height: 28px;
+  border: 0;
+  border-radius: 7px;
+  background: #f8fafc;
+  color: #111827;
+  font-size: 18px;
+  font-weight: 800;
+}
+
+.conversation-list {
+  display: grid;
+  gap: 6px;
+  max-height: 260px;
+  overflow: auto;
+}
+
+.conversation-item {
+  display: grid;
+  gap: 3px;
+  width: 100%;
+  border: 1px solid transparent;
+  border-radius: 7px;
+  padding: 9px 10px;
+  background: transparent;
+  color: #e5edf7;
+  text-align: left;
+}
+
+.conversation-item:hover,
+.conversation-item.active {
+  background: var(--sidebar-soft);
+  border-color: rgba(255,255,255,0.12);
+}
+
+.conversation-item strong,
+.conversation-item span {
+  min-width: 0;
+  overflow: hidden;
+  text-overflow: ellipsis;
+  white-space: nowrap;
+}
+
+.conversation-item strong {
+  font-size: 13px;
+}
+
+.conversation-item span,
+.conversation-empty {
+  color: #9ca3af;
+  font-size: 11px;
+}
+
+.conversation-empty {
+  margin: 0;
+}
+
 label {
   display: grid;
   gap: 7px;
diff --git a/duck_core/web/templates/index.html b/duck_core/web/templates/index.html
index 8ffdd9b..0529cad 100644
--- a/duck_core/web/templates/index.html
+++ b/duck_core/web/templates/index.html
@@ -25,6 +25,14 @@
           <a href="/experience">Experience</a>
         </nav>
 
+        <section class="conversation-panel" aria-labelledby="conversations-title">
+          <div class="panel-heading">
+            <h2 id="conversations-title">Chats</h2>
+            <button id="new-chat" type="button" title="New chat">+</button>
+          </div>
+          <div id="conversation-list" class="conversation-list"></div>
+        </section>
+
         <section class="settings-panel" aria-labelledby="settings-title">
           <h2 id="settings-title">Session</h2>
           <label>
@@ -59,10 +67,10 @@
       <main class="chat-shell">
         <header class="chat-header">
           <div>
-            <h2>Chat</h2>
-            <p>Messages are processed by the local Qwen role mapping through Duck Core.</p>
+            <h2 id="chat-title">Chat</h2>
+            <p id="chat-subtitle">Messages are processed by the local Qwen role mapping through Duck Core.</p>
           </div>
-          <button id="new-chat" class="secondary-button" type="button">New Chat</button>
+          <button id="reload-chat" class="secondary-button" type="button">Reload</button>
         </header>
 
         <section id="messages" class="messages" aria-live="polite">
diff --git a/prompts/roles/action.md b/prompts/roles/action.md
index 33df5ac..f3daed5 100644
--- a/prompts/roles/action.md
+++ b/prompts/roles/action.md
@@ -12,6 +12,9 @@ Available tools:
   Args: {"path": "."}
 - search_files: search text inside files in the current workspace.
   Args: {"query": "text to find", "path": ".", "glob": "*.py"}
+- os_update_check: check available operating system package updates without
+  refreshing package manager caches and without sudo.
+  Args: {}
 - shell_exec_safe: run a safe allowlisted shell command in the current workspace.
   Args: {"command": "pwd"}
 
@@ -21,3 +24,6 @@ follow-up information. Return actions=[] when the observations are sufficient
 for the thinker to answer.
 Use only the listed tools. Keep actions minimal and directly tied to the user's
 request. Do not invent tool names.
+For user requests like "check updates in the system", use os_update_check.
+Do not use apt update, apt-get update, sudo, su, or package installation commands
+for update checks.
diff --git a/tests/smoke/test_api_stream_chat.py b/tests/smoke/test_api_stream_chat.py
index fb0ae95..e18e78f 100644
--- a/tests/smoke/test_api_stream_chat.py
+++ b/tests/smoke/test_api_stream_chat.py
@@ -173,3 +173,7 @@ def test_continue_stream_executes_approved_tool_and_streams_answer(tmp_path, mon
     assert "event: content_delta" in body
     assert "continued after approval" in body
     assert "event: done" in body
+    conversation_id = re.search(r'"conversation_id"\s*:\s*"([^"]+)"', initial_body).group(1)
+    conversation = client.get(f"/v1/conversations/{conversation_id}").json()
+    assert conversation["messages"][-1]["content"] == "continued after approval"
+    assert conversation["messages"][-1]["status"] == "completed"
diff --git a/tests/smoke/test_conversations.py b/tests/smoke/test_conversations.py
new file mode 100644
index 0000000..43180d1
--- /dev/null
+++ b/tests/smoke/test_conversations.py
@@ -0,0 +1,129 @@
+import json
+
+from fastapi.testclient import TestClient
+
+from duck_core.api import create_app
+from duck_core.model_client import ModelResponse
+
+
+def test_conversations_api_stores_different_workspaces(tmp_path, monkeypatch):
+    monkeypatch.setenv("DUCK_DB_PATH", str(tmp_path / "duck.sqlite3"))
+    client = TestClient(create_app())
+
+    first = client.post(
+        "/v1/conversations",
+        json={"title": "Project A", "workspace": "/tmp/project-a"},
+    ).json()
+    second = client.post(
+        "/v1/conversations",
+        json={"title": "Project B", "workspace": "/tmp/project-b"},
+    ).json()
+    listed = client.get("/v1/conversations").json()
+
+    assert first["conversation_id"] != second["conversation_id"]
+    assert {item["workspace"] for item in listed} >= {"/tmp/project-a", "/tmp/project-b"}
+
+
+def test_chat_api_persists_messages_in_conversation(tmp_path, monkeypatch):
+    monkeypatch.setenv("DUCK_DB_PATH", str(tmp_path / "duck.sqlite3"))
+
+    async def fake_chat(self, role, messages, temperature=None, max_output_tokens=None, response_format=None):
+        if role == "action":
+            return ModelResponse(
+                role=role,
+                model="local-main",
+                content=json.dumps(
+                    {
+                        "kind": "action_directive",
+                        "intent": "answer directly",
+                        "risk_level": "none",
+                        "actions": [],
+                    }
+                ),
+                reasoning_content=None,
+                raw={},
+                latency_ms=1.0,
+            )
+        return ModelResponse(
+            role=role,
+            model="local-main",
+            content="Первый ответ сохранен.",
+            reasoning_content="short reasoning",
+            raw={},
+            latency_ms=1.0,
+        )
+
+    monkeypatch.setattr("duck_core.model_client.ModelClient.chat", fake_chat)
+    client = TestClient(create_app())
+    conversation = client.post(
+        "/v1/conversations",
+        json={"title": "Saved chat", "workspace": str(tmp_path)},
+    ).json()
+
+    response = client.post(
+        "/v1/chat",
+        json={
+            "conversation_id": conversation["conversation_id"],
+            "message": "Запомни это сообщение",
+            "debug": True,
+        },
+    ).json()
+    loaded = client.get(f"/v1/conversations/{conversation['conversation_id']}").json()
+
+    assert response["conversation_id"] == conversation["conversation_id"]
+    assert loaded["workspace"] == str(tmp_path)
+    assert [message["role"] for message in loaded["messages"]] == ["user", "assistant"]
+    assert loaded["messages"][0]["content"] == "Запомни это сообщение"
+    assert loaded["messages"][1]["content"] == "Первый ответ сохранен."
+    assert loaded["messages"][1]["reasoning_content"] == "short reasoning"
+
+
+def test_conversation_history_is_sent_to_model(tmp_path, monkeypatch):
+    monkeypatch.setenv("DUCK_DB_PATH", str(tmp_path / "duck.sqlite3"))
+    seen_thinker_messages = []
+
+    async def fake_chat(self, role, messages, temperature=None, max_output_tokens=None, response_format=None):
+        if role == "action":
+            return ModelResponse(
+                role=role,
+                model="local-main",
+                content=json.dumps(
+                    {
+                        "kind": "action_directive",
+                        "intent": "answer directly",
+                        "risk_level": "none",
+                        "actions": [],
+                    }
+                ),
+                reasoning_content=None,
+                raw={},
+                latency_ms=1.0,
+            )
+        seen_thinker_messages.append(messages)
+        return ModelResponse(
+            role=role,
+            model="local-main",
+            content=f"answer {len(seen_thinker_messages)}",
+            reasoning_content=None,
+            raw={},
+            latency_ms=1.0,
+        )
+
+    monkeypatch.setattr("duck_core.model_client.ModelClient.chat", fake_chat)
+    client = TestClient(create_app())
+    conversation = client.post(
+        "/v1/conversations",
+        json={"title": "History", "workspace": str(tmp_path)},
+    ).json()
+
+    client.post(
+        "/v1/chat",
+        json={"conversation_id": conversation["conversation_id"], "message": "first"},
+    )
+    client.post(
+        "/v1/chat",
+        json={"conversation_id": conversation["conversation_id"], "message": "second"},
+    )
+
+    second_call_content = [message["content"] for message in seen_thinker_messages[-1]]
+    assert second_call_content == ["first", "answer 1", "second"]
diff --git a/tests/smoke/test_runtime_tools.py b/tests/smoke/test_runtime_tools.py
index bd5b7d7..52f50dd 100644
--- a/tests/smoke/test_runtime_tools.py
+++ b/tests/smoke/test_runtime_tools.py
@@ -101,6 +101,41 @@ class FakeMultiStepToolModelClient:
         )
 
 
+class FakeUpdateCheckModelClient:
+    async def chat(self, role, messages):
+        if role == "action":
+            actions = []
+            if not any("tool_observations" in message["content"] for message in messages):
+                actions = [{"tool": "os_update_check", "args": {}, "reason": "Check OS updates"}]
+            return ModelResponse(
+                role=role,
+                model="local-main",
+                content=json.dumps(
+                    {
+                        "kind": "action_directive",
+                        "intent": "check system updates",
+                        "risk_level": "low",
+                        "actions": actions,
+                    }
+                ),
+                reasoning_content=None,
+                raw={},
+                latency_ms=5.0,
+            )
+        assert role == "thinker"
+        observation_text = "\n".join(message["content"] for message in messages)
+        assert "os_update_check" in observation_text
+        assert "requires_approval" not in observation_text
+        return ModelResponse(
+            role=role,
+            model="local-main",
+            content="Updates checked without approval loop.",
+            reasoning_content=None,
+            raw={},
+            latency_ms=12.0,
+        )
+
+
 @pytest.mark.asyncio
 async def test_runtime_executes_action_directive_tool_and_finishes_with_observation(tmp_path):
     (tmp_path / "note.txt").write_text("hello from tool")
@@ -142,6 +177,25 @@ async def test_runtime_runs_multiple_tool_steps_before_final_answer(tmp_path):
     assert finished_tools == ["list_dir", "file_read"]
 
 
+@pytest.mark.asyncio
+async def test_runtime_checks_system_updates_without_approval_loop(tmp_path):
+    db_path = str(tmp_path / "duck.sqlite3")
+    task_store = TaskStore(db_path)
+    event_store = EventStore(db_path)
+    loop = RuntimeLoop(task_store, event_store, FakeUpdateCheckModelClient())
+
+    result = await loop.run_chat("Привет. Проверь обновления в системе", str(tmp_path), debug=True)
+    events = await event_store.list_events(result.task_id)
+
+    assert result.status == "completed"
+    assert not any(event.event_type == "tool_approval_requested" for event in events)
+    assert any(
+        event.event_type == "tool_call_finished"
+        and event.payload["tool"] == "os_update_check"
+        for event in events
+    )
+
+
 class FakeApprovalModelClient:
     async def chat(self, role, messages):
         if role == "action":
diff --git a/tests/smoke/test_tool_gateway.py b/tests/smoke/test_tool_gateway.py
index b277a9d..3027e34 100644
--- a/tests/smoke/test_tool_gateway.py
+++ b/tests/smoke/test_tool_gateway.py
@@ -3,6 +3,7 @@ import pytest
 from duck_core.tools.file_read import FileReadTool
 from duck_core.tools.file_write import FileWriteTool
 from duck_core.tools.gateway import ToolGateway
+from duck_core.tools.os_update_check import OsUpdateCheckTool
 from duck_core.tools.shell_exec_safe import ShellExecSafeTool
 
 
@@ -26,9 +27,15 @@ async def test_shell_tool_blocks_dangerous_commands(tmp_path):
 
     allowed = await shell.run({"command": "pwd"})
     blocked = await shell.run({"command": "rm -rf ."})
+    sudo = await shell.run({"command": "sudo apt update"})
 
     assert allowed.ok is True
     assert blocked.ok is False
+    assert blocked.metadata.get("requires_approval") is not True
+    assert blocked.metadata["blocked"] is True
+    assert sudo.ok is False
+    assert sudo.metadata.get("requires_approval") is not True
+    assert sudo.metadata["blocked"] is True
 
 
 @pytest.mark.asyncio
@@ -76,3 +83,26 @@ async def test_tool_gateway_searches_file_contents(tmp_path):
     assert "src/app.py:1:duck tool gateway" in result.output
     assert result.metadata["matches"] == 1
     assert escaped.ok is False
+
+
+@pytest.mark.asyncio
+async def test_os_update_check_reports_apt_upgradable_packages(monkeypatch, tmp_path):
+    class Completed:
+        returncode = 0
+        stdout = "Listing...\\nbootlogd/stable 3.14-4 amd64 [upgradable from: 3.06-4]\\n"
+        stderr = "WARNING: apt does not have a stable CLI interface.\\n"
+
+    monkeypatch.setattr("duck_core.tools.os_update_check.shutil.which", lambda name: "/usr/bin/apt")
+    monkeypatch.setattr(
+        "duck_core.tools.os_update_check.subprocess.run",
+        lambda *args, **kwargs: Completed(),
+    )
+    tool = OsUpdateCheckTool(str(tmp_path))
+
+    result = await tool.run({})
+
+    assert result.ok is True
+    assert "bootlogd" in result.output
+    assert result.metadata["package_manager"] == "apt"
+    assert result.metadata["upgradable_count"] == 1
+    assert result.metadata["refreshed_cache"] is False