core/cli+agent: /compact and resume latest by workspace recency

Soft-compact history, model-summarize without tools, seed a new session;
/resume with no id loads the lately-used session for this workspace.

CLAUDE.md

@@ -56,6 +56,7 @@ Async SQLAlchemy + aiosqlite. `MemoryStore`: schema init (+ lightweight SQLite `
 - **`@tool` / `ToolRegistry`**: decorator infers JSON Schema from type hints; execute tools by name.
 - **`run_chat_loop`**: multi-round tool loop; default **streaming** text deltas + stream tool-call merge; parallel tools; tool-result char budget; soft context compact on request; cooperative cancel points; optional `on_limit`.
 - **`ChatAgent`**: optional `MemoryStore` (persist on success only); `stream`; system prompt; `pending_retry_text` + `retry()`.
+- **`/compact`**: soft-compact tool dumps → model summary (no tools) → **new** session seeded with summary message.
 - Events: text_delta, assistant_message, tool_call/result, max_rounds, **error** (`retryable`/`source`), **cancelled** (`reason`).
 - Config ``[agent]``: `system_prompt`, `max_tool_result_chars`, `parallel_tools`, `confirm_destructive`, `path_denylist`, `max_context_chars`.
 
@@ -75,8 +76,8 @@ Module-level `@tool` handlers. Call `set_workspace_root()` before use.
 
 Click app + readline REPL. Entry: `plyngent` / `python -m plyngent`.
 
-- **`plyngent chat`**: provider/model selection (flags or interactive), SQLite sessions via config `[database]` (file DB under user data if unset/`:memory:`), sessions bound to workspace dir; resumes latest **for cwd/`--workspace`** by default (`--new` / `--session`).
-- Slash: `/history`, `/sessions`, `/resume`, `/rounds`, `/retry`, …
+- **`plyngent chat`**: provider/model selection (flags or interactive), SQLite sessions via config `[database]` (file DB under user data if unset/`:memory:`), sessions bound to workspace dir; resumes **most recently updated** session for cwd/`--workspace` by default (`--new` / `--session`).
+- Slash: `/history`, `/sessions` (newest first), `/resume [id]`, `/compact`, `/rounds`, `/retry`, …
 - Explicit `/resume` or `--session` from another workspace prompts: **keep** session path, **update** binding to current, or **abort**.
 - Failed/cancelled turns: not written to DB; Ctrl+C cancels the in-flight turn task; **TTY confirms** (max-rounds / destructive tools) run off-loop via `asyncio.to_thread` + pause cancel so prompts do not abort the turn; auto-retry 10s/20s/30s; `/retry` manual.
 - **`plyngent providers`**: list config providers.

src/plyngent/agent/__init__.py

@@ -1,5 +1,7 @@
 from .chat import ChatAgent as ChatAgent
 from .client import ChatClient as ChatClient
+from .compact import build_compacted_seed_messages as build_compacted_seed_messages
+from .compact import summarize_messages as summarize_messages
 from .events import AgentEvent as AgentEvent
 from .events import AssistantMessageEvent as AssistantMessageEvent
 from .events import CancelledEvent as CancelledEvent

src/plyngent/agent/compact.py

@@ -0,0 +1,129 @@
+from __future__ import annotations
+
+from typing import TYPE_CHECKING
+
+from msgspec import UNSET
+
+from plyngent.lmproto.openai_compatible.model import (
+    AssistantChatMessage,
+    AssistantFunctionToolCall,
+    ChatCompletionsParam,
+    SystemChatMessage,
+    ToolChatMessage,
+    UserChatMessage,
+)
+
+from .budget import DEFAULT_CONTEXT_MAX_CHARS, compact_messages_for_request
+
+if TYPE_CHECKING:
+    from collections.abc import Sequence
+
+    from plyngent.lmproto.openai_compatible.model import AnyChatMessage
+
+    from .client import ChatClient
+
+_SUMMARY_SYSTEM = (
+    "You compress chat histories for a coding agent. "
+    "Write a dense, factual summary that preserves: goals, decisions, "
+    "file paths touched, commands run, open tasks, and constraints. "
+    "Omit chit-chat and redundant tool dumps. Use short bullet sections. "
+    "Do not invent facts not present in the transcript."
+)
+
+_SUMMARY_USER_PREFIX = (
+    "Summarize the following conversation for continued agent work. "
+    "Output only the summary (no preamble).\n\n--- transcript ---\n"
+)
+
+
+def format_transcript(messages: Sequence[AnyChatMessage]) -> str:
+    """Render messages as plain text for a summarization prompt."""
+    lines: list[str] = []
+    for msg in messages:
+        if isinstance(msg, SystemChatMessage):
+            lines.append(f"[system] {msg.content}")
+        elif isinstance(msg, UserChatMessage):
+            lines.append(f"[user] {msg.content}")
+        elif isinstance(msg, AssistantChatMessage):
+            content = msg.content if isinstance(msg.content, str) else ""
+            if content:
+                lines.append(f"[assistant] {content}")
+            tool_calls = msg.tool_calls
+            if tool_calls is not UNSET and tool_calls:
+                for call in tool_calls:
+                    if isinstance(call, AssistantFunctionToolCall):
+                        lines.append(
+                            f"[assistant tool_call] {call.function.name}({call.function.arguments})"
+                        )
+                    else:
+                        lines.append(f"[assistant tool_call] custom id={call.id}")
+        elif isinstance(msg, ToolChatMessage):
+            lines.append(f"[tool {msg.tool_call_id}] {msg.content}")
+        else:
+            lines.append(f"[message] {msg!r}")
+    return "\n".join(lines)
+
+
+def soft_compact_transcript(
+    messages: Sequence[AnyChatMessage],
+    *,
+    max_chars: int = DEFAULT_CONTEXT_MAX_CHARS,
+) -> str:
+    """Soft-compact tool dumps then format as transcript text."""
+    compacted = compact_messages_for_request(messages, max_chars=max_chars)
+    return format_transcript(compacted)
+
+
+async def summarize_messages(
+    client: ChatClient,
+    messages: Sequence[AnyChatMessage],
+    *,
+    model: str,
+    max_context_chars: int = DEFAULT_CONTEXT_MAX_CHARS,
+    temperature: float | None = 0.2,
+) -> str:
+    """Soft-compact history and ask the model for a dense summary (no tools)."""
+    if not messages:
+        msg = "nothing to compact"
+        raise ValueError(msg)
+    transcript = soft_compact_transcript(messages, max_chars=max_context_chars)
+    if not transcript.strip():
+        msg = "nothing to compact"
+        raise ValueError(msg)
+    param = ChatCompletionsParam(
+        messages=[
+            SystemChatMessage(content=_SUMMARY_SYSTEM),
+            UserChatMessage(content=_SUMMARY_USER_PREFIX + transcript),
+        ],
+        model=model,
+        temperature=temperature if temperature is not None else UNSET,
+    )
+    response = await client.chat_completions(param, stream=False)
+    if not response.choices:
+        msg = "summarization response contained no choices"
+        raise RuntimeError(msg)
+    content = response.choices[0].message.content
+    if not isinstance(content, str) or not content.strip():
+        msg = "summarization returned empty content"
+        raise RuntimeError(msg)
+    return content.strip()
+
+
+def build_compacted_seed_messages(
+    summary: str,
+    *,
+    system_prompt: str | None = None,
+    source_session_id: int | None = None,
+) -> list[AnyChatMessage]:
+    """Messages to seed a new session after compact."""
+    out: list[AnyChatMessage] = []
+    if system_prompt:
+        out.append(SystemChatMessage(content=system_prompt))
+    src = f"session {source_session_id}" if source_session_id is not None else "prior session"
+    body = (
+        f"Conversation summary (compacted from {src}):\n\n"
+        f"{summary}\n\n"
+        "Continue from this summary. Prefer not to re-ask for information already covered."
+    )
+    out.append(UserChatMessage(content=body))
+    return out

src/plyngent/cli/readline_setup.py

@@ -24,6 +24,7 @@ SLASH_COMMANDS: tuple[str, ...] = (
     "/sessions",
     "/new",
     "/resume",
+    "/compact",
     "/provider",
     "/model",
     "/tools",

src/plyngent/cli/repl.py

@@ -28,9 +28,10 @@ Commands:
   /quit, /exit       Leave the REPL
   /clear             Clear in-memory conversation (keeps session id)
   /history [n]       Show last n messages in this session (default 20)
-  /sessions          List sessions for this workspace
+  /sessions          List sessions for this workspace (newest first)
   /new [name]        Start a new session (bound to workspace)
-  /resume <id>       Resume a session by id (prompts if workspace differs)
+  /resume [id]       Resume session id, or latest for this workspace if omitted
+  /compact [name]    Soft-compact + model-summarize into a new session
   /provider [name]   Show or switch provider
   /model [id]        Show or switch model
   /tools [on|off]    Show or toggle tools
@@ -86,12 +87,19 @@ async def _cmd_new(state: ReplState, arg: str) -> None:
 
 async def _cmd_resume(state: ReplState, arg: str) -> None:
     if not arg.strip():
-        click.echo("usage: /resume <session_id>")
+        mode = await state.resume_latest_or_new()
+        if mode == "new":
+            click.echo(f"no prior session; created new session {state.session_id}")
+        else:
+            click.echo(
+                f"resumed latest session {state.session_id} "
+                f"({len(state.agent.messages)} messages) workspace={state.workspace}"
+            )
         return
     try:
         session_id = int(arg.strip())
     except ValueError:
-        click.echo("session id must be an integer")
+        click.echo("session id must be an integer (or omit for latest)")
         return
     try:
         await state.resume_session(session_id)
@@ -104,6 +112,22 @@ async def _cmd_resume(state: ReplState, arg: str) -> None:
     )
 
 
+async def _cmd_compact(state: ReplState, arg: str) -> None:
+    name = arg.strip() or None
+    click.secho("compacting (soft-compact + model summary)…", fg="yellow")
+    try:
+        old_id, new_id, summary = await state.compact_to_new_session(name=name)
+    except ValueError as exc:
+        click.echo(f"error: {exc}")
+        return
+    except Exception as exc:  # noqa: BLE001 — surface model/API failures
+        click.secho(f"error: compact failed: {exc}", fg="red")
+        return
+    preview = summary if len(summary) <= 400 else summary[:400] + "…"  # noqa: PLR2004
+    click.echo(f"compacted session {old_id} -> new session {new_id}")
+    click.secho(preview, fg="bright_black")
+
+
 def _cmd_provider(state: ReplState, arg: str) -> None:
     if not arg.strip():
         click.echo(f"provider={state.provider_name}")
@@ -245,6 +269,7 @@ async def _dispatch_slash(state: ReplState, command: str, arg: str) -> bool:
         "sessions": lambda: _cmd_sessions(state),
         "new": lambda: _cmd_new(state, arg),
         "resume": lambda: _cmd_resume(state, arg),
+        "compact": lambda: _cmd_compact(state, arg),
         "provider": lambda: _cmd_provider(state, arg),
         "model": lambda: _cmd_model(state, arg),
         "tools": lambda: _cmd_tools(state, arg),

src/plyngent/cli/state.py

@@ -142,14 +142,54 @@ class ReplState:
         await self.agent.load_history()
 
     async def resume_latest_or_new(self, name: str = "chat") -> str:
-        """Resume latest session for this workspace, or create one if none exist."""
-        sessions = await self.memory.list_sessions(workspace=self.workspace)
-        if not sessions:
+        """Resume most recently updated session for this workspace, or create one."""
+        latest = await self.memory.get_latest_session(workspace=self.workspace)
+        if latest is None:
             await self.new_session(name=name)
             return "new"
-        latest = max(sessions, key=lambda s: (s.updated_at, s.sid))
         # Same-workspace list: no mismatch prompt expected.
         self.session_id = latest.sid
         self.agent = self._make_agent()
         await self.agent.load_history()
+        _ = await self.memory.touch_session(latest.sid)
         return "resume"
+
+    async def compact_to_new_session(self, *, name: str | None = None) -> tuple[int, int, str]:
+        """Soft-compact + model-summarize current history into a new workspace session.
+
+        Returns ``(old_session_id, new_session_id, summary)``.
+        """
+        from plyngent.agent.compact import build_compacted_seed_messages, summarize_messages
+
+        old_id = self.session_id
+        if old_id is None:
+            msg = "no active session to compact"
+            raise ValueError(msg)
+        messages = list(self.agent.messages)
+        if len(messages) < 1:
+            msg = "nothing to compact (empty history)"
+            raise ValueError(msg)
+
+        summary = await summarize_messages(
+            self.client,
+            messages,
+            model=self.model,
+            max_context_chars=self.agent.max_context_chars,
+        )
+        session_name = name or f"compact-from-{old_id}"
+        await self.new_session(name=session_name)
+        new_id = self.session_id
+        if new_id is None:
+            msg = "failed to create compact session"
+            raise RuntimeError(msg)
+
+        seed = build_compacted_seed_messages(
+            summary,
+            system_prompt=self.agent.system_prompt,
+            source_session_id=old_id,
+        )
+        self.agent.messages = list(seed)
+        for message in seed:
+            _ = await self.memory.append_message(new_id, message)
+        self.agent.pending_retry_text = None
+        return old_id, new_id, summary

tests/test_agent/test_compact_summarize.py

@@ -0,0 +1,111 @@
+from __future__ import annotations
+
+from typing import TYPE_CHECKING, Literal, overload
+
+from plyngent.agent.compact import (
+    build_compacted_seed_messages,
+    format_transcript,
+    soft_compact_transcript,
+    summarize_messages,
+)
+from plyngent.lmproto.openai_compatible.model import (
+    AssistantChatMessage,
+    ChatCompletionChoice,
+    ChatCompletionChunk,
+    ChatCompletionResponse,
+    ChatCompletionsParam,
+    SystemChatMessage,
+    ToolChatMessage,
+    UserChatMessage,
+)
+
+if TYPE_CHECKING:
+    from collections.abc import AsyncIterator
+
+
+def test_format_transcript() -> None:
+    text = format_transcript(
+        [
+            UserChatMessage(content="hi"),
+            AssistantChatMessage(content="yo"),
+            ToolChatMessage(content="out", tool_call_id="1"),
+        ]
+    )
+    assert "[user] hi" in text
+    assert "[assistant] yo" in text
+    assert "[tool 1] out" in text
+
+
+def test_soft_compact_transcript_shrinks_tools() -> None:
+    big = "Z" * 2000
+    messages = [
+        UserChatMessage(content="u"),
+        ToolChatMessage(content=big, tool_call_id="1"),
+        ToolChatMessage(content="recent", tool_call_id="2"),
+    ]
+    out = soft_compact_transcript(messages, max_chars=500)
+    assert "truncated" in out or len(out) < len(big) + 50
+    assert "recent" in out
+
+
+def test_build_compacted_seed_messages() -> None:
+    seed = build_compacted_seed_messages("summary text", system_prompt="sys", source_session_id=3)
+    assert isinstance(seed[0], SystemChatMessage)
+    assert seed[0].content == "sys"
+    assert isinstance(seed[1], UserChatMessage)
+    assert "summary text" in seed[1].content
+    assert "session 3" in seed[1].content
+
+
+class SummaryClient:
+    last: ChatCompletionsParam | None
+
+    def __init__(self) -> None:
+        self.last = None
+
+    @overload
+    async def chat_completions(
+        self, param: ChatCompletionsParam, *, stream: Literal[False] = False
+    ) -> ChatCompletionResponse: ...
+
+    @overload
+    async def chat_completions(
+        self, param: ChatCompletionsParam, *, stream: Literal[True]
+    ) -> AsyncIterator[ChatCompletionChunk]: ...
+
+    async def chat_completions(
+        self, param: ChatCompletionsParam, *, stream: bool = False
+    ) -> ChatCompletionResponse | AsyncIterator[ChatCompletionChunk]:
+        del stream
+        self.last = param
+        return ChatCompletionResponse(
+            id="1",
+            object="chat.completion",
+            created=0,
+            model="t",
+            choices=[
+                ChatCompletionChoice(
+                    index=0,
+                    message=AssistantChatMessage(content="  done summary  "),
+                    logprobs={},
+                    finish_reason="stop",
+                )
+            ],
+            system_fingerprint="",
+            usage={},
+        )
+
+
+async def test_summarize_messages() -> None:
+    client = SummaryClient()
+    summary = await summarize_messages(
+        client,
+        [UserChatMessage(content="hello"), AssistantChatMessage(content="world")],
+        model="m",
+    )
+    assert summary == "done summary"
+    assert client.last is not None
+    assert client.last.model == "m"
+    from msgspec import UNSET
+
+    assert client.last.tools is UNSET

tests/test_cli/test_compact_cmd.py

@@ -0,0 +1,133 @@
+from __future__ import annotations
+
+from typing import TYPE_CHECKING, Literal, overload
+
+import pytest
+import tomlkit
+
+from plyngent.agent import ChatAgent
+from plyngent.cli.state import ReplState
+from plyngent.config.models import DatabaseConfig, OpenAIProvider
+from plyngent.config.store import ConfigStore
+from plyngent.lmproto.openai_compatible.model import (
+    AssistantChatMessage,
+    ChatCompletionChoice,
+    ChatCompletionChunk,
+    ChatCompletionResponse,
+    ChatCompletionsParam,
+    UserChatMessage,
+)
+from plyngent.memory import MemoryStore
+from plyngent.tools import set_workspace_root
+
+if TYPE_CHECKING:
+    from collections.abc import AsyncIterator
+    from pathlib import Path
+
+
+class SummaryClient:
+    @overload
+    async def chat_completions(
+        self, param: ChatCompletionsParam, *, stream: Literal[False] = False
+    ) -> ChatCompletionResponse: ...
+
+    @overload
+    async def chat_completions(
+        self, param: ChatCompletionsParam, *, stream: Literal[True]
+    ) -> AsyncIterator[ChatCompletionChunk]: ...
+
+    async def chat_completions(
+        self, param: ChatCompletionsParam, *, stream: bool = False
+    ) -> ChatCompletionResponse | AsyncIterator[ChatCompletionChunk]:
+        del param, stream
+        return ChatCompletionResponse(
+            id="1",
+            object="chat.completion",
+            created=0,
+            model="m",
+            choices=[
+                ChatCompletionChoice(
+                    index=0,
+                    message=AssistantChatMessage(content="compacted goals: ship feature"),
+                    logprobs={},
+                    finish_reason="stop",
+                )
+            ],
+            system_fingerprint="",
+            usage={},
+        )
+
+
+async def test_compact_to_new_session(tmp_path: Path) -> None:
+    _ = set_workspace_root(tmp_path)
+    memory = await MemoryStore.open(DatabaseConfig())
+    try:
+        provider = OpenAIProvider(access_key_or_token="sk-test")
+        config = ConfigStore(path=tmp_path / "plyngent.toml", document=tomlkit.document())
+        config.providers = {"local": provider}
+        state = ReplState(
+            config=config,
+            memory=memory,
+            workspace=tmp_path,
+            provider_name="local",
+            provider=provider,
+            model="gpt-test",
+            tools_enabled=False,
+        )
+        state.client = SummaryClient()
+        await state.new_session("orig")
+        old_id = state.session_id
+        assert old_id is not None
+        state.agent = ChatAgent(
+            state.client,
+            model=state.model,
+            memory=state.memory,
+            session_id=old_id,
+            system_prompt="Be brief.",
+        )
+        state.agent.messages = [
+            UserChatMessage(content="do work"),
+            AssistantChatMessage(content="done lots of stuff"),
+        ]
+        for msg in state.agent.messages:
+            _ = await memory.append_message(old_id, msg)
+
+        new_old, new_id, summary = await state.compact_to_new_session()
+        assert new_old == old_id
+        assert new_id != old_id
+        assert state.session_id == new_id
+        assert "compacted goals" in summary
+        loaded = await memory.list_messages(new_id)
+        assert any("compacted goals" in getattr(m, "content", "") for m in loaded)
+        # Old session still exists and is listable
+        sessions = await memory.list_sessions(workspace=tmp_path)
+        ids = {s.sid for s in sessions}
+        assert old_id in ids
+        assert new_id in ids
+    finally:
+        await memory.close()
+
+
+async def test_compact_empty_fails(tmp_path: Path) -> None:
+    _ = set_workspace_root(tmp_path)
+    memory = await MemoryStore.open(DatabaseConfig())
+    try:
+        provider = OpenAIProvider(access_key_or_token="sk-test")
+        config = ConfigStore(path=tmp_path / "plyngent.toml", document=tomlkit.document())
+        config.providers = {"local": provider}
+        state = ReplState(
+            config=config,
+            memory=memory,
+            workspace=tmp_path,
+            provider_name="local",
+            provider=provider,
+            model="gpt-test",
+            tools_enabled=False,
+        )
+        state.client = SummaryClient()
+        await state.new_session("empty")
+        state.agent.messages = []
+        with pytest.raises(ValueError, match="nothing to compact"):
+            _ = await state.compact_to_new_session()
+    finally:
+        await memory.close()