diff --git a/surfsense_backend/app/agents/new_chat/chat_deepagent.py b/surfsense_backend/app/agents/new_chat/chat_deepagent.py
index e2df5dff5..ccc06f272 100644
--- a/surfsense_backend/app/agents/new_chat/chat_deepagent.py
+++ b/surfsense_backend/app/agents/new_chat/chat_deepagent.py
@@ -447,6 +447,7 @@ async def create_surfsense_deep_agent(
     deepagent_middleware = [
         TodoListMiddleware(),
         KnowledgeBaseSearchMiddleware(
+            llm=llm,
             search_space_id=search_space_id,
             available_connectors=available_connectors,
             available_document_types=available_document_types,
diff --git a/surfsense_backend/app/agents/new_chat/middleware/knowledge_search.py b/surfsense_backend/app/agents/new_chat/middleware/knowledge_search.py
index 474d3f858..3728f229c 100644
--- a/surfsense_backend/app/agents/new_chat/middleware/knowledge_search.py
+++ b/surfsense_backend/app/agents/new_chat/middleware/knowledge_search.py
@@ -15,14 +15,19 @@ import logging
 import re
 import uuid
 from collections.abc import Sequence
+from datetime import UTC, datetime
 from typing import Any
 
 from langchain.agents.middleware import AgentMiddleware, AgentState
+from langchain_core.language_models import BaseChatModel
 from langchain_core.messages import AIMessage, BaseMessage, HumanMessage, ToolMessage
 from langgraph.runtime import Runtime
+from litellm import token_counter
+from pydantic import BaseModel, Field, ValidationError
 from sqlalchemy import select
 from sqlalchemy.ext.asyncio import AsyncSession
 
+from app.agents.new_chat.utils import parse_date_or_datetime, resolve_date_range
 from app.db import NATIVE_TO_LEGACY_DOCTYPE, Document, Folder, shielded_async_session
 from app.retriever.chunks_hybrid_search import ChucksHybridSearchRetriever
 from app.utils.document_converters import embed_texts
@@ -32,6 +37,23 @@ logger = logging.getLogger(__name__)
 _perf_log = get_perf_logger()
 
 
+class KBSearchPlan(BaseModel):
+    """Structured internal plan for KB retrieval."""
+
+    optimized_query: str = Field(
+        min_length=1,
+        description="Optimized retrieval query preserving the user's intent.",
+    )
+    start_date: str | None = Field(
+        default=None,
+        description="Optional ISO start date or datetime for KB search filtering.",
+    )
+    end_date: str | None = Field(
+        default=None,
+        description="Optional ISO end date or datetime for KB search filtering.",
+    )
+
+
 def _extract_text_from_message(message: BaseMessage) -> str:
     """Extract plain text from a message content."""
     content = getattr(message, "content", "")
@@ -61,6 +83,212 @@ def _safe_filename(value: str, *, fallback: str = "untitled.xml") -> str:
     return name
 
 
+def _render_recent_conversation(
+    messages: Sequence[BaseMessage],
+    *,
+    llm: BaseChatModel | None = None,
+    user_text: str = "",
+    max_messages: int = 6,
+) -> str:
+    """Render recent dialogue for internal planning under a token budget.
+
+    Prefers the latest messages and uses the project's existing model-aware
+    token budgeting hooks when available on the LLM (`_count_tokens`,
+    `_get_max_input_tokens`). Falls back to the prior fixed-message heuristic
+    if token counting is unavailable.
+    """
+    rendered: list[tuple[str, str]] = []
+    for message in messages:
+        role: str | None = None
+        if isinstance(message, HumanMessage):
+            role = "user"
+        elif isinstance(message, AIMessage):
+            if getattr(message, "tool_calls", None):
+                continue
+            role = "assistant"
+        else:
+            continue
+
+        text = _extract_text_from_message(message).strip()
+        if not text:
+            continue
+        text = re.sub(r"\s+", " ", text)
+        rendered.append((role, text))
+
+    if not rendered:
+        return ""
+
+    # Exclude the latest user message from "recent conversation" because it is
+    # already passed separately as "Latest user message" in the planner prompt.
+    if rendered and rendered[-1][0] == "user" and rendered[-1][1] == user_text.strip():
+        rendered = rendered[:-1]
+
+    if not rendered:
+        return ""
+
+    def _legacy_render() -> str:
+        legacy_lines: list[str] = []
+        for role, text in rendered[-max_messages:]:
+            clipped = text[:400].rstrip() + "..." if len(text) > 400 else text
+            legacy_lines.append(f"{role}: {clipped}")
+        return "\n".join(legacy_lines)
+
+    def _count_prompt_tokens(conversation_text: str) -> int | None:
+        prompt = _build_kb_planner_prompt(
+            recent_conversation=conversation_text or "(none)",
+            user_text=user_text,
+        )
+        message_payload = [{"role": "user", "content": prompt}]
+
+        count_fn = getattr(llm, "_count_tokens", None) if llm is not None else None
+        if callable(count_fn):
+            try:
+                return count_fn(message_payload)
+            except Exception:
+                pass
+
+        profile = getattr(llm, "profile", None) if llm is not None else None
+        model_names: list[str] = []
+        if isinstance(profile, dict):
+            tcms = profile.get("token_count_models")
+            if isinstance(tcms, list):
+                model_names.extend(
+                    name for name in tcms if isinstance(name, str) and name
+                )
+            tcm = profile.get("token_count_model")
+            if isinstance(tcm, str) and tcm and tcm not in model_names:
+                model_names.append(tcm)
+        model_name = model_names[0] if model_names else getattr(llm, "model", None)
+        if not isinstance(model_name, str) or not model_name:
+            return None
+        try:
+            return token_counter(messages=message_payload, model=model_name)
+        except Exception:
+            return None
+
+    get_max_input_tokens = getattr(llm, "_get_max_input_tokens", None) if llm else None
+    if callable(get_max_input_tokens):
+        try:
+            max_input_tokens = int(get_max_input_tokens())
+        except Exception:
+            max_input_tokens = None
+    else:
+        profile = getattr(llm, "profile", None) if llm is not None else None
+        max_input_tokens = (
+            profile.get("max_input_tokens")
+            if isinstance(profile, dict)
+            and isinstance(profile.get("max_input_tokens"), int)
+            else None
+        )
+
+    if not isinstance(max_input_tokens, int) or max_input_tokens <= 0:
+        return _legacy_render()
+
+    output_reserve = min(max(int(max_input_tokens * 0.02), 256), 1024)
+    budget = max_input_tokens - output_reserve
+    if budget <= 0:
+        return _legacy_render()
+
+    selected_lines: list[str] = []
+    for role, text in reversed(rendered):
+        candidate_line = f"{role}: {text}"
+        candidate_lines = [candidate_line, *selected_lines]
+        candidate_conversation = "\n".join(candidate_lines)
+        token_count = _count_prompt_tokens(candidate_conversation)
+        if token_count is None:
+            return _legacy_render()
+        if token_count <= budget:
+            selected_lines = candidate_lines
+            continue
+
+        # If the full message does not fit, keep as much of this most-recent
+        # older message as possible via binary search.
+        lo, hi = 1, len(text)
+        best_line: str | None = None
+        while lo <= hi:
+            mid = (lo + hi) // 2
+            clipped_text = text[:mid].rstrip() + "..."
+            clipped_line = f"{role}: {clipped_text}"
+            clipped_conversation = "\n".join([clipped_line, *selected_lines])
+            clipped_tokens = _count_prompt_tokens(clipped_conversation)
+            if clipped_tokens is None:
+                break
+            if clipped_tokens <= budget:
+                best_line = clipped_line
+                lo = mid + 1
+            else:
+                hi = mid - 1
+
+        if best_line is not None:
+            selected_lines = [best_line, *selected_lines]
+        break
+
+    if not selected_lines:
+        return _legacy_render()
+
+    return "\n".join(selected_lines)
+
+
+def _build_kb_planner_prompt(
+    *,
+    recent_conversation: str,
+    user_text: str,
+) -> str:
+    """Build a compact internal prompt for KB query rewriting and date scoping."""
+    today = datetime.now(UTC).date().isoformat()
+    return (
+        "You optimize internal knowledge-base search inputs for document retrieval.\n"
+        "Return JSON only with this exact shape:\n"
+        '{"optimized_query":"string","start_date":"ISO string or null","end_date":"ISO string or null"}\n\n'
+        "Rules:\n"
+        "- Preserve the user's intent.\n"
+        "- Rewrite the query to improve retrieval using concrete entities, acronyms, projects, tools, people, and document-specific terms when helpful.\n"
+        "- Keep the query concise and retrieval-focused.\n"
+        "- Only use date filters when the latest user request or recent dialogue clearly implies a time range.\n"
+        "- If you use date filters, prefer returning both bounds.\n"
+        "- If no date filter is useful, return null for both dates.\n"
+        "- Do not include markdown, prose, or explanations.\n\n"
+        f"Today's UTC date: {today}\n\n"
+        f"Recent conversation:\n{recent_conversation or '(none)'}\n\n"
+        f"Latest user message:\n{user_text}"
+    )
+
+
+def _extract_json_payload(text: str) -> str:
+    """Extract a JSON object from a raw LLM response."""
+    stripped = text.strip()
+    fenced = re.search(r"```(?:json)?\s*(\{.*?\})\s*```", stripped, re.DOTALL)
+    if fenced:
+        return fenced.group(1)
+
+    start = stripped.find("{")
+    end = stripped.rfind("}")
+    if start != -1 and end != -1 and end > start:
+        return stripped[start : end + 1]
+    return stripped
+
+
+def _parse_kb_search_plan_response(response_text: str) -> KBSearchPlan:
+    """Parse and validate the planner's JSON response."""
+    payload = json.loads(_extract_json_payload(response_text))
+    return KBSearchPlan.model_validate(payload)
+
+
+def _normalize_optional_date_range(
+    start_date: str | None,
+    end_date: str | None,
+) -> tuple[datetime | None, datetime | None]:
+    """Normalize optional planner dates into a UTC datetime range."""
+    parsed_start = parse_date_or_datetime(start_date) if start_date else None
+    parsed_end = parse_date_or_datetime(end_date) if end_date else None
+
+    if parsed_start is None and parsed_end is None:
+        return None, None
+
+    resolved_start, resolved_end = resolve_date_range(parsed_start, parsed_end)
+    return resolved_start, resolved_end
+
+
 def _build_document_xml(
     document: dict[str, Any],
     matched_chunk_ids: set[int] | None = None,
@@ -264,6 +492,8 @@ async def search_knowledge_base(
     available_connectors: list[str] | None = None,
     available_document_types: list[str] | None = None,
     top_k: int = 10,
+    start_date: datetime | None = None,
+    end_date: datetime | None = None,
 ) -> list[dict[str, Any]]:
     """Run a single unified hybrid search against the knowledge base.
 
@@ -286,6 +516,8 @@ async def search_knowledge_base(
             top_k=retriever_top_k,
             search_space_id=search_space_id,
             document_type=doc_types,
+            start_date=start_date,
+            end_date=end_date,
             query_embedding=embedding.tolist(),
         )
 
@@ -346,16 +578,71 @@ class KnowledgeBaseSearchMiddleware(AgentMiddleware):  # type: ignore[type-arg]
     def __init__(
         self,
         *,
+        llm: BaseChatModel | None = None,
         search_space_id: int,
         available_connectors: list[str] | None = None,
         available_document_types: list[str] | None = None,
         top_k: int = 10,
     ) -> None:
+        self.llm = llm
         self.search_space_id = search_space_id
         self.available_connectors = available_connectors
         self.available_document_types = available_document_types
         self.top_k = top_k
 
+    async def _plan_search_inputs(
+        self,
+        *,
+        messages: Sequence[BaseMessage],
+        user_text: str,
+    ) -> tuple[str, datetime | None, datetime | None]:
+        """Rewrite the KB query and infer optional date filters with the LLM."""
+        if self.llm is None:
+            return user_text, None, None
+
+        recent_conversation = _render_recent_conversation(
+            messages,
+            llm=self.llm,
+            user_text=user_text,
+        )
+        prompt = _build_kb_planner_prompt(
+            recent_conversation=recent_conversation,
+            user_text=user_text,
+        )
+        loop = asyncio.get_running_loop()
+        t0 = loop.time()
+
+        try:
+            response = await self.llm.ainvoke(
+                [HumanMessage(content=prompt)],
+                config={"tags": ["surfsense:internal"]},
+            )
+            plan = _parse_kb_search_plan_response(_extract_text_from_message(response))
+            optimized_query = (
+                re.sub(r"\s+", " ", plan.optimized_query).strip() or user_text
+            )
+            start_date, end_date = _normalize_optional_date_range(
+                plan.start_date,
+                plan.end_date,
+            )
+            _perf_log.info(
+                "[kb_fs_middleware] planner in %.3fs query=%r optimized=%r start=%s end=%s",
+                loop.time() - t0,
+                user_text[:80],
+                optimized_query[:120],
+                start_date.isoformat() if start_date else None,
+                end_date.isoformat() if end_date else None,
+            )
+            return optimized_query, start_date, end_date
+        except (json.JSONDecodeError, ValidationError, ValueError) as exc:
+            logger.warning(
+                "KB planner returned invalid output, using raw query: %s", exc
+            )
+        except Exception as exc:  # pragma: no cover - defensive fallback
+            logger.warning("KB planner failed, using raw query: %s", exc)
+
+        return user_text, None, None
+
     def before_agent(  # type: ignore[override]
         self,
         state: AgentState,
@@ -388,13 +675,19 @@ class KnowledgeBaseSearchMiddleware(AgentMiddleware):  # type: ignore[type-arg]
 
         t0 = _perf_log and asyncio.get_event_loop().time()
         existing_files = state.get("files")
+        planned_query, start_date, end_date = await self._plan_search_inputs(
+            messages=messages,
+            user_text=user_text,
+        )
 
         search_results = await search_knowledge_base(
-            query=user_text,
+            query=planned_query,
             search_space_id=self.search_space_id,
             available_connectors=self.available_connectors,
             available_document_types=self.available_document_types,
             top_k=self.top_k,
+            start_date=start_date,
+            end_date=end_date,
         )
         new_files = await build_scoped_filesystem(
             documents=search_results,
@@ -405,9 +698,10 @@ class KnowledgeBaseSearchMiddleware(AgentMiddleware):  # type: ignore[type-arg]
 
         if t0 is not None:
             _perf_log.info(
-                "[kb_fs_middleware] completed in %.3fs query=%r new_files=%d total=%d",
+                "[kb_fs_middleware] completed in %.3fs query=%r optimized=%r new_files=%d total=%d",
                 asyncio.get_event_loop().time() - t0,
                 user_text[:80],
+                planned_query[:120],
                 len(new_files),
                 len(new_files) + len(existing_files or {}),
             )
diff --git a/surfsense_backend/app/connectors/google_gmail_connector.py b/surfsense_backend/app/connectors/google_gmail_connector.py
index bd4f78bc2..dd81973c6 100644
--- a/surfsense_backend/app/connectors/google_gmail_connector.py
+++ b/surfsense_backend/app/connectors/google_gmail_connector.py
@@ -310,7 +310,7 @@ class GoogleGmailConnector:
         Fetch recent messages from Gmail within specified date range.
         Args:
             max_results: Maximum number of messages to fetch (default: 50)
-            start_date: Start date in YYYY-MM-DD format (default: 30 days ago)
+            start_date: Start date in YYYY-MM-DD format (default: 3 days ago)
             end_date: End date in YYYY-MM-DD format (default: today)
         Returns:
             Tuple containing (messages list with details, error message or None)
@@ -334,8 +334,8 @@ class GoogleGmailConnector:
                 start_query = start_dt.strftime("%Y/%m/%d")
                 query_parts.append(f"after:{start_query}")
             else:
-                # Default to 30 days ago
-                cutoff_date = datetime.now() - timedelta(days=30)
+                # Default to 3 days ago
+                cutoff_date = datetime.now() - timedelta(days=3)
                 date_query = cutoff_date.strftime("%Y/%m/%d")
                 query_parts.append(f"after:{date_query}")
 
diff --git a/surfsense_backend/tests/integration/document_upload/test_stripe_page_purchases.py b/surfsense_backend/tests/integration/document_upload/test_stripe_page_purchases.py
index af1e8c728..1c8f7f990 100644
--- a/surfsense_backend/tests/integration/document_upload/test_stripe_page_purchases.py
+++ b/surfsense_backend/tests/integration/document_upload/test_stripe_page_purchases.py
@@ -152,7 +152,9 @@ class _FakeReconciliationStripeClient:
 
 
 class TestStripeCheckoutSessionCreation:
-    async def test_get_status_reflects_backend_toggle(self, client, headers, monkeypatch):
+    async def test_get_status_reflects_backend_toggle(
+        self, client, headers, monkeypatch
+    ):
         monkeypatch.setattr(stripe_routes.config, "STRIPE_PAGE_BUYING_ENABLED", False)
         disabled_response = await client.get("/api/v1/stripe/status", headers=headers)
         assert disabled_response.status_code == 200, disabled_response.text
@@ -237,7 +239,9 @@ class TestStripeCheckoutSessionCreation:
         )
 
         assert response.status_code == 503, response.text
-        assert response.json()["detail"] == "Page purchases are temporarily unavailable."
+        assert (
+            response.json()["detail"] == "Page purchases are temporarily unavailable."
+        )
 
         purchase_count = await _fetchrow("SELECT COUNT(*) AS count FROM page_purchases")
         assert purchase_count is not None
diff --git a/surfsense_backend/tests/integration/retriever/conftest.py b/surfsense_backend/tests/integration/retriever/conftest.py
index 2e0c166e5..d2443723c 100644
--- a/surfsense_backend/tests/integration/retriever/conftest.py
+++ b/surfsense_backend/tests/integration/retriever/conftest.py
@@ -3,7 +3,7 @@
 from __future__ import annotations
 
 import uuid
-from datetime import UTC, datetime
+from datetime import UTC, datetime, timedelta
 
 import pytest_asyncio
 from sqlalchemy.ext.asyncio import AsyncSession
@@ -22,6 +22,7 @@ def _make_document(
     content: str,
     search_space_id: int,
     created_by_id: str,
+    updated_at: datetime | None = None,
 ) -> Document:
     uid = uuid.uuid4().hex[:12]
     return Document(
@@ -34,7 +35,7 @@ def _make_document(
         search_space_id=search_space_id,
         created_by_id=created_by_id,
         embedding=DUMMY_EMBEDDING,
-        updated_at=datetime.now(UTC),
+        updated_at=updated_at or datetime.now(UTC),
         status={"state": "ready"},
     )
 
@@ -104,3 +105,54 @@ async def seed_large_doc(
         "search_space": db_search_space,
         "user": db_user,
     }
+
+
+@pytest_asyncio.fixture
+async def seed_date_filtered_docs(
+    db_session: AsyncSession, db_user: User, db_search_space: SearchSpace
+):
+    """Insert matching docs with different timestamps for date-filter tests."""
+    user_id = str(db_user.id)
+    space_id = db_search_space.id
+    now = datetime.now(UTC)
+
+    recent_doc = _make_document(
+        title="Recent OCV Notes",
+        document_type=DocumentType.FILE,
+        content="ocv meeting decisions and action items",
+        search_space_id=space_id,
+        created_by_id=user_id,
+        updated_at=now,
+    )
+    old_doc = _make_document(
+        title="Old OCV Notes",
+        document_type=DocumentType.FILE,
+        content="ocv meeting decisions and action items",
+        search_space_id=space_id,
+        created_by_id=user_id,
+        updated_at=now - timedelta(days=730),
+    )
+
+    db_session.add_all([recent_doc, old_doc])
+    await db_session.flush()
+
+    db_session.add_all(
+        [
+            _make_chunk(
+                content="ocv meeting decisions and action items recent",
+                document_id=recent_doc.id,
+            ),
+            _make_chunk(
+                content="ocv meeting decisions and action items old",
+                document_id=old_doc.id,
+            ),
+        ]
+    )
+    await db_session.flush()
+
+    return {
+        "recent_doc": recent_doc,
+        "old_doc": old_doc,
+        "search_space": db_search_space,
+        "user": db_user,
+    }
diff --git a/surfsense_backend/tests/integration/retriever/test_knowledge_search_date_filters.py b/surfsense_backend/tests/integration/retriever/test_knowledge_search_date_filters.py
new file mode 100644
index 000000000..910d882a7
--- /dev/null
+++ b/surfsense_backend/tests/integration/retriever/test_knowledge_search_date_filters.py
@@ -0,0 +1,62 @@
+"""Integration smoke tests for KB search query/date scoping."""
+
+from __future__ import annotations
+
+from contextlib import asynccontextmanager
+from datetime import UTC, datetime, timedelta
+
+import numpy as np
+import pytest
+
+from app.agents.new_chat.middleware.knowledge_search import search_knowledge_base
+
+from .conftest import DUMMY_EMBEDDING
+
+pytestmark = pytest.mark.integration
+
+
+async def test_search_knowledge_base_applies_date_filters(
+    db_session,
+    seed_date_filtered_docs,
+    monkeypatch,
+):
+    """Date filters should remove older matching documents from scoped KB results."""
+
+    @asynccontextmanager
+    async def fake_shielded_async_session():
+        yield db_session
+
+    monkeypatch.setattr(
+        "app.agents.new_chat.middleware.knowledge_search.shielded_async_session",
+        fake_shielded_async_session,
+    )
+    monkeypatch.setattr(
+        "app.agents.new_chat.middleware.knowledge_search.embed_texts",
+        lambda texts: [np.array(DUMMY_EMBEDDING) for _ in texts],
+    )
+
+    space_id = seed_date_filtered_docs["search_space"].id
+    recent_cutoff = datetime.now(UTC) - timedelta(days=30)
+
+    unfiltered_results = await search_knowledge_base(
+        query="ocv meeting decisions",
+        search_space_id=space_id,
+        available_document_types=["FILE"],
+        top_k=10,
+    )
+    filtered_results = await search_knowledge_base(
+        query="ocv meeting decisions",
+        search_space_id=space_id,
+        available_document_types=["FILE"],
+        top_k=10,
+        start_date=recent_cutoff,
+        end_date=datetime.now(UTC),
+    )
+
+    unfiltered_ids = {result["document"]["id"] for result in unfiltered_results}
+    filtered_ids = {result["document"]["id"] for result in filtered_results}
+
+    assert seed_date_filtered_docs["recent_doc"].id in unfiltered_ids
+    assert seed_date_filtered_docs["old_doc"].id in unfiltered_ids
+    assert seed_date_filtered_docs["recent_doc"].id in filtered_ids
+    assert seed_date_filtered_docs["old_doc"].id not in filtered_ids
diff --git a/surfsense_backend/tests/unit/middleware/test_knowledge_search.py b/surfsense_backend/tests/unit/middleware/test_knowledge_search.py
index 5c22371a4..163dd0d1d 100644
--- a/surfsense_backend/tests/unit/middleware/test_knowledge_search.py
+++ b/surfsense_backend/tests/unit/middleware/test_knowledge_search.py
@@ -1,12 +1,16 @@
-"""Unit tests for knowledge_search middleware helpers.
+"""Unit tests for knowledge_search middleware helpers."""
 
-These test pure functions that don't require a database.
-"""
+import json
 
 import pytest
+from langchain_core.messages import AIMessage, HumanMessage
 
 from app.agents.new_chat.middleware.knowledge_search import (
+    KnowledgeBaseSearchMiddleware,
     _build_document_xml,
+    _normalize_optional_date_range,
+    _parse_kb_search_plan_response,
+    _render_recent_conversation,
     _resolve_search_types,
 )
 
@@ -131,3 +135,234 @@ class TestBuildDocumentXml:
             line for line in lines if "<![CDATA[" in line and "<chunk" in line
         ]
         assert len(chunk_lines) == 3
+
+
+# ── planner parsing / date normalization ───────────────────────────────
+
+
+class TestPlannerHelpers:
+    def test_parse_kb_search_plan_response_accepts_plain_json(self):
+        plan = _parse_kb_search_plan_response(
+            json.dumps(
+                {
+                    "optimized_query": "ocv meeting decisions summary",
+                    "start_date": "2026-03-01",
+                    "end_date": "2026-03-31",
+                }
+            )
+        )
+        assert plan.optimized_query == "ocv meeting decisions summary"
+        assert plan.start_date == "2026-03-01"
+        assert plan.end_date == "2026-03-31"
+
+    def test_parse_kb_search_plan_response_accepts_fenced_json(self):
+        plan = _parse_kb_search_plan_response(
+            """```json
+            {"optimized_query":"deel founders guide","start_date":null,"end_date":null}
+            ```"""
+        )
+        assert plan.optimized_query == "deel founders guide"
+        assert plan.start_date is None
+        assert plan.end_date is None
+
+    def test_normalize_optional_date_range_returns_none_when_absent(self):
+        start_date, end_date = _normalize_optional_date_range(None, None)
+        assert start_date is None
+        assert end_date is None
+
+    def test_normalize_optional_date_range_resolves_single_bound(self):
+        start_date, end_date = _normalize_optional_date_range("2026-03-01", None)
+        assert start_date is not None
+        assert end_date is not None
+        assert start_date.date().isoformat() == "2026-03-01"
+        assert end_date >= start_date
+
+
+class FakeLLM:
+    def __init__(self, response_text: str):
+        self.response_text = response_text
+        self.calls: list[dict] = []
+
+    async def ainvoke(self, messages, config=None):
+        self.calls.append({"messages": messages, "config": config})
+        return AIMessage(content=self.response_text)
+
+
+class FakeBudgetLLM:
+    def __init__(self, *, max_input_tokens: int):
+        self._max_input_tokens_value = max_input_tokens
+
+    def _get_max_input_tokens(self) -> int:
+        return self._max_input_tokens_value
+
+    def _count_tokens(self, messages) -> int:
+        # Deterministic, simple proxy for tests: count characters as tokens.
+        return sum(len(msg.get("content", "")) for msg in messages)
+
+
+class TestKnowledgeBaseSearchMiddlewarePlanner:
+    def test_render_recent_conversation_prefers_latest_messages_under_budget(self):
+        messages = [
+            HumanMessage(content="old user context " * 40),
+            AIMessage(content="old assistant answer " * 35),
+            HumanMessage(content="recent user context " * 20),
+            AIMessage(content="recent assistant answer " * 18),
+            HumanMessage(content="latest question"),
+        ]
+
+        rendered = _render_recent_conversation(
+            messages,
+            llm=FakeBudgetLLM(max_input_tokens=900),
+            user_text="latest question",
+        )
+
+        assert "recent user context" in rendered
+        assert "recent assistant answer" in rendered
+        assert "latest question" not in rendered
+        assert rendered.index("recent user context") < rendered.index(
+            "recent assistant answer"
+        )
+
+    def test_render_recent_conversation_falls_back_to_legacy_without_budgeting(self):
+        messages = [
+            HumanMessage(content="message one"),
+            AIMessage(content="message two"),
+            HumanMessage(content="latest question"),
+        ]
+
+        rendered = _render_recent_conversation(
+            messages,
+            llm=None,
+            user_text="latest question",
+        )
+
+        assert "user: message one" in rendered
+        assert "assistant: message two" in rendered
+        assert "latest question" not in rendered
+
+    async def test_middleware_uses_optimized_query_and_dates(self, monkeypatch):
+        captured: dict = {}
+
+        async def fake_search_knowledge_base(**kwargs):
+            captured.update(kwargs)
+            return []
+
+        async def fake_build_scoped_filesystem(**kwargs):
+            return {}
+
+        monkeypatch.setattr(
+            "app.agents.new_chat.middleware.knowledge_search.search_knowledge_base",
+            fake_search_knowledge_base,
+        )
+        monkeypatch.setattr(
+            "app.agents.new_chat.middleware.knowledge_search.build_scoped_filesystem",
+            fake_build_scoped_filesystem,
+        )
+
+        llm = FakeLLM(
+            json.dumps(
+                {
+                    "optimized_query": "ocv meeting decisions action items",
+                    "start_date": "2026-03-01",
+                    "end_date": "2026-03-31",
+                }
+            )
+        )
+        middleware = KnowledgeBaseSearchMiddleware(llm=llm, search_space_id=37)
+
+        result = await middleware.abefore_agent(
+            {
+                "messages": [
+                    HumanMessage(content="what happened in our OCV meeting last month?")
+                ]
+            },
+            runtime=None,
+        )
+
+        assert result is not None
+        assert captured["query"] == "ocv meeting decisions action items"
+        assert captured["start_date"] is not None
+        assert captured["end_date"] is not None
+        assert captured["start_date"].date().isoformat() == "2026-03-01"
+        assert captured["end_date"].date().isoformat() == "2026-03-31"
+        assert llm.calls[0]["config"] == {"tags": ["surfsense:internal"]}
+
+    async def test_middleware_falls_back_when_planner_returns_invalid_json(
+        self,
+        monkeypatch,
+    ):
+        captured: dict = {}
+
+        async def fake_search_knowledge_base(**kwargs):
+            captured.update(kwargs)
+            return []
+
+        async def fake_build_scoped_filesystem(**kwargs):
+            return {}
+
+        monkeypatch.setattr(
+            "app.agents.new_chat.middleware.knowledge_search.search_knowledge_base",
+            fake_search_knowledge_base,
+        )
+        monkeypatch.setattr(
+            "app.agents.new_chat.middleware.knowledge_search.build_scoped_filesystem",
+            fake_build_scoped_filesystem,
+        )
+
+        middleware = KnowledgeBaseSearchMiddleware(
+            llm=FakeLLM("not json"),
+            search_space_id=37,
+        )
+
+        await middleware.abefore_agent(
+            {"messages": [HumanMessage(content="summarize founders guide by deel")]},
+            runtime=None,
+        )
+
+        assert captured["query"] == "summarize founders guide by deel"
+        assert captured["start_date"] is None
+        assert captured["end_date"] is None
+
+    async def test_middleware_passes_none_dates_when_planner_returns_nulls(
+        self,
+        monkeypatch,
+    ):
+        captured: dict = {}
+
+        async def fake_search_knowledge_base(**kwargs):
+            captured.update(kwargs)
+            return []
+
+        async def fake_build_scoped_filesystem(**kwargs):
+            return {}
+
+        monkeypatch.setattr(
+            "app.agents.new_chat.middleware.knowledge_search.search_knowledge_base",
+            fake_search_knowledge_base,
+        )
+        monkeypatch.setattr(
+            "app.agents.new_chat.middleware.knowledge_search.build_scoped_filesystem",
+            fake_build_scoped_filesystem,
+        )
+
+        middleware = KnowledgeBaseSearchMiddleware(
+            llm=FakeLLM(
+                json.dumps(
+                    {
+                        "optimized_query": "deel founders guide summary",
+                        "start_date": None,
+                        "end_date": None,
+                    }
+                )
+            ),
+            search_space_id=37,
+        )
+
+        await middleware.abefore_agent(
+            {"messages": [HumanMessage(content="summarize founders guide by deel")]},
+            runtime=None,
+        )
+
+        assert captured["query"] == "deel founders guide summary"
+        assert captured["start_date"] is None
+        assert captured["end_date"] is None