diff --git a/.env.example b/.env.example
index 7d5265b..6e6affc 100644
--- a/.env.example
+++ b/.env.example
@@ -30,11 +30,11 @@ GEMINI_MODEL=gemini-2.5-flash
 # LITELLM_MODEL=gemini/gemini-2.5-flash
 # ANTHROPIC_API_KEY=sk-ant-...
 
-# ── Langfuse observability ────────────────────────────────────────────────────
-# Get keys from http://localhost:3000 after running docker compose up
+# ── Langfuse observability (v3) ───────────────────────────────────────────────
+# Get keys from http://localhost:3010 after running docker compose up
 LANGFUSE_PUBLIC_KEY=pk-lf-your-public-key
 LANGFUSE_SECRET_KEY=sk-lf-your-secret-key
-LANGFUSE_HOST=http://localhost:3000
+LANGFUSE_HOST=http://localhost:3010
 
 # ── Infrastructure ────────────────────────────────────────────────────────────
 REDIS_URL=redis://localhost:6379/0
diff --git a/README.md b/README.md
index 2d7abcb..4c6e0fe 100644
--- a/README.md
+++ b/README.md
@@ -17,15 +17,18 @@
 ## Features
 
 - **Multi-provider LLM support** via LiteLLM — swap between Gemini, DeepSeek, Claude, GPT-4o, Groq, Ollama, and 100+ more with a single env var change, zero code changes
+- **Split planner model** — route the one-token routing decision to a cheap/fast model (`PLANNER_MODEL`) while keeping a capable model for synthesis; falls back to the same model if unset
+- **LLM retry with jitter** — all LLM calls automatically retry up to 3× with exponential backoff and random jitter, handling transient rate-limit and network errors
 - **FastAPI** production API with structured JSON logging and request-ID tracing
 - **LangGraph** workflow: `planner → tool → synthesizer` state machine with persistent memory across turns
+- **History truncation** — only the most recent 10 turns are sent to the LLM; full history is preserved in the Postgres checkpoint
 - **DuckDuckGo search** — real web search with no API key required
-- **Redis** session memory — conversation context survives API restarts
-- **Postgres** run history — every agent run persisted for audit and replay
-- **Langfuse** LLM tracing — full trace context, per-request handlers, generation-level spans
-- **Prometheus + Grafana** — request rate, latency histograms (p50/p95/p99), agent run duration, error rate
-- **Nuxt 3 frontend** — dark-mode chat UI + live status dashboard
-- **Docker Compose** 8-container stack — API, frontend, Redis, Postgres, Langfuse, Prometheus, Grafana
+- **Postgres** run history and LangGraph checkpoints — every agent run persisted for audit and replay; persistent multi-turn memory per session
+- **Alembic** database migrations — schema changes are versioned and applied automatically at startup
+- **Langfuse** LLM tracing — full trace context, node-level spans nested under a root trace per request
+- **Prometheus + Grafana** — request rate, latency histograms (p50/p95/p99), agent run duration, tool execution counts
+- **Nuxt 3 frontend** — dark-mode chat UI + live status dashboard with 120s request timeout and clear error messages
+- **Docker Compose** 11-container stack — API, frontend, Redis, Postgres, Langfuse (web + worker + ClickHouse + MinIO), Prometheus, Grafana
 - **uv** — fast, reproducible Python dependency management
 - **Ruff + Pyright** — lint, format, and strict type checking
 - **pytest** — unit, integration, and eval suites with automatic LLM mocking
@@ -243,8 +246,12 @@ agent-platform/
 │       ├── tools/             # DuckDuckGo search tool
 │       └── llm.py             # Unified LLM factory (all providers)
 ├── infra/
-│   └── docker/
-│       └── Dockerfile         # Multistage Python build
+│   ├── docker/
+│   │   └── Dockerfile         # Multistage Python build
+│   ├── migrations/            # Alembic migration scripts
+│   │   ├── env.py             # Migration env (excludes LangGraph tables)
+│   │   └── versions/          # Versioned schema migrations
+│   └── clickhouse/            # ClickHouse config (used by Langfuse)
 ├── monitoring/
 │   ├── prometheus/            # prometheus.yml scrape config
 │   └── grafana/               # Provisioned datasources + dashboards
@@ -291,6 +298,7 @@ just ci            # full local CI gate
 | `OLLAMA_BASE_URL`  | `http://localhost:11434` | Ollama server URL                        |
 | `OLLAMA_MODEL`     | `llama3.2`         | Ollama model name                              |
 | `LITELLM_MODEL`    | `gemini/gemini-2.5-flash` | Any LiteLLM model string              |
+| `PLANNER_MODEL`    | *(same as LITELLM_MODEL)* | Cheaper model for the one-token routing step; falls back to `LITELLM_MODEL` if blank |
 
 Any API key supported by LiteLLM (`ANTHROPIC_API_KEY`, `DEEPSEEK_API_KEY`, etc.) is passed through automatically.
 
@@ -344,8 +352,8 @@ Full LLM traces with per-request handlers. Open http://localhost:3010. Create a
 | Orchestration | LangGraph, LangChain                                |
 | LLM           | LiteLLM (100+ providers) · Gemini 2.5 Flash default |
 | Search        | DuckDuckGo (no API key)                             |
-| Memory        | Redis + LangGraph MemorySaver                       |
-| History       | Postgres + SQLAlchemy async + asyncpg               |
+| Memory        | LangGraph AsyncPostgresSaver (falls back to MemorySaver) |
+| History       | Postgres + SQLAlchemy async + asyncpg + Alembic     |
 | Tracing       | Langfuse                                            |
 | Metrics       | Prometheus, Grafana                                 |
 | Logging       | structlog (JSON in production)                      |
diff --git a/alembic.ini b/alembic.ini
new file mode 100644
index 0000000..15d5479
--- /dev/null
+++ b/alembic.ini
@@ -0,0 +1,149 @@
+# A generic, single database configuration.
+
+[alembic]
+# path to migration scripts.
+# this is typically a path given in POSIX (e.g. forward slashes)
+# format, relative to the token %(here)s which refers to the location of this
+# ini file
+script_location = %(here)s/infra/migrations
+
+# template used to generate migration file names; The default value is %%(rev)s_%%(slug)s
+# Uncomment the line below if you want the files to be prepended with date and time
+# see https://alembic.sqlalchemy.org/en/latest/tutorial.html#editing-the-ini-file
+# for all available tokens
+# file_template = %%(year)d_%%(month).2d_%%(day).2d_%%(hour).2d%%(minute).2d-%%(rev)s_%%(slug)s
+# Or organize into date-based subdirectories (requires recursive_version_locations = true)
+# file_template = %%(year)d/%%(month).2d/%%(day).2d_%%(hour).2d%%(minute).2d_%%(second).2d_%%(rev)s_%%(slug)s
+
+# sys.path path, will be prepended to sys.path if present.
+# defaults to the current working directory.  for multiple paths, the path separator
+# is defined by "path_separator" below.
+prepend_sys_path = .
+
+
+# timezone to use when rendering the date within the migration file
+# as well as the filename.
+# If specified, requires the tzdata library which can be installed by adding
+# `alembic[tz]` to the pip requirements.
+# string value is passed to ZoneInfo()
+# leave blank for localtime
+# timezone =
+
+# max length of characters to apply to the "slug" field
+# truncate_slug_length = 40
+
+# set to 'true' to run the environment during
+# the 'revision' command, regardless of autogenerate
+# revision_environment = false
+
+# set to 'true' to allow .pyc and .pyo files without
+# a source .py file to be detected as revisions in the
+# versions/ directory
+# sourceless = false
+
+# version location specification; This defaults
+# to <script_location>/versions.  When using multiple version
+# directories, initial revisions must be specified with --version-path.
+# The path separator used here should be the separator specified by "path_separator"
+# below.
+# version_locations = %(here)s/bar:%(here)s/bat:%(here)s/alembic/versions
+
+# path_separator; This indicates what character is used to split lists of file
+# paths, including version_locations and prepend_sys_path within configparser
+# files such as alembic.ini.
+# The default rendered in new alembic.ini files is "os", which uses os.pathsep
+# to provide os-dependent path splitting.
+#
+# Note that in order to support legacy alembic.ini files, this default does NOT
+# take place if path_separator is not present in alembic.ini.  If this
+# option is omitted entirely, fallback logic is as follows:
+#
+# 1. Parsing of the version_locations option falls back to using the legacy
+#    "version_path_separator" key, which if absent then falls back to the legacy
+#    behavior of splitting on spaces and/or commas.
+# 2. Parsing of the prepend_sys_path option falls back to the legacy
+#    behavior of splitting on spaces, commas, or colons.
+#
+# Valid values for path_separator are:
+#
+# path_separator = :
+# path_separator = ;
+# path_separator = space
+# path_separator = newline
+#
+# Use os.pathsep. Default configuration used for new projects.
+path_separator = os
+
+# set to 'true' to search source files recursively
+# in each "version_locations" directory
+# new in Alembic version 1.10
+# recursive_version_locations = false
+
+# the output encoding used when revision files
+# are written from script.py.mako
+# output_encoding = utf-8
+
+# database URL.  This is consumed by the user-maintained env.py script only.
+# other means of configuring database URLs may be customized within the env.py
+# file.
+sqlalchemy.url = driver://user:pass@localhost/dbname
+
+
+[post_write_hooks]
+# post_write_hooks defines scripts or Python functions that are run
+# on newly generated revision scripts.  See the documentation for further
+# detail and examples
+
+# format using "black" - use the console_scripts runner, against the "black" entrypoint
+# hooks = black
+# black.type = console_scripts
+# black.entrypoint = black
+# black.options = -l 79 REVISION_SCRIPT_FILENAME
+
+# lint with attempts to fix using "ruff" - use the module runner, against the "ruff" module
+# hooks = ruff
+# ruff.type = module
+# ruff.module = ruff
+# ruff.options = check --fix REVISION_SCRIPT_FILENAME
+
+# Alternatively, use the exec runner to execute a binary found on your PATH
+# hooks = ruff
+# ruff.type = exec
+# ruff.executable = ruff
+# ruff.options = check --fix REVISION_SCRIPT_FILENAME
+
+# Logging configuration.  This is also consumed by the user-maintained
+# env.py script only.
+[loggers]
+keys = root,sqlalchemy,alembic
+
+[handlers]
+keys = console
+
+[formatters]
+keys = generic
+
+[logger_root]
+level = WARNING
+handlers = console
+qualname =
+
+[logger_sqlalchemy]
+level = WARNING
+handlers =
+qualname = sqlalchemy.engine
+
+[logger_alembic]
+level = INFO
+handlers =
+qualname = alembic
+
+[handler_console]
+class = StreamHandler
+args = (sys.stderr,)
+level = NOTSET
+formatter = generic
+
+[formatter_generic]
+format = %(levelname)-5.5s [%(name)s] %(message)s
+datefmt = %H:%M:%S
diff --git a/apps/api/agent.py b/apps/api/agent.py
index 65a518a..34d7a4b 100644
--- a/apps/api/agent.py
+++ b/apps/api/agent.py
@@ -1,6 +1,7 @@
+import contextlib
 import time
 import uuid
-from typing import cast
+from typing import Any, cast
 
 import structlog
 from fastapi import APIRouter, BackgroundTasks, Request
@@ -66,29 +67,48 @@ async def run_agent(
 
     invoke_config: RunnableConfig = {"configurable": {"thread_id": thread_id}}
 
-    langfuse_handler = None
-    if settings.langfuse_public_key and settings.langfuse_secret_key:
-        try:
-            from langfuse.callback import CallbackHandler  # type: ignore[import-untyped]
-
-            lf_kwargs: dict[str, object] = {
-                "public_key": settings.langfuse_public_key,
-                "secret_key": settings.langfuse_secret_key,
-                "host": settings.langfuse_host,
-                "user_id": body.user_id,
-                "session_id": thread_id,
-                "trace_name": _LANGFUSE_TRACE_NAME,
-                "tags": [settings.environment, settings.llm_provider],
-            }
-            langfuse_handler = CallbackHandler(**lf_kwargs)  # type: ignore[arg-type]
-            invoke_config["callbacks"] = [langfuse_handler]
-        except Exception as exc:
-            log.warning("langfuse.callback.unavailable", error=str(exc))
+    # ── Run agent ────────────────────────────────────────────────────────────
+    # Use the single Langfuse client initialised at startup (app.state.langfuse).
+    # CallbackHandler is created INSIDE start_as_current_observation so that the
+    # active OTel span is already set when the handler builds its child spans —
+    # this is what makes node/LLM observations appear nested under the root trace.
+    lf_client: Any = getattr(request.app.state, "langfuse", None)
 
     start = time.perf_counter()
-    result = await request.app.state.agent.ainvoke(cast(AgentState, state), config=invoke_config)
-    duration = time.perf_counter() - start
+    result: dict[str, Any] = {}
+
+    if lf_client is not None:
+        with lf_client.start_as_current_observation(
+            name=_LANGFUSE_TRACE_NAME,
+            as_type="span",
+            input={"user_message": body.input},
+        ) as root_obs:
+            with contextlib.suppress(Exception):
+                lf_client.update_current_trace(
+                    name=_LANGFUSE_TRACE_NAME,
+                    user_id=body.user_id,
+                    session_id=thread_id,
+                    tags=[settings.environment, settings.llm_provider],
+                    metadata={"thread_id": thread_id, "llm_provider": settings.llm_provider},
+                )
+            # Create CallbackHandler here, after the parent span is active,
+            # so LangGraph node spans are captured as children of root_obs.
+            with contextlib.suppress(Exception):
+                from langfuse.langchain import CallbackHandler  # type: ignore[import-untyped]
+
+                invoke_config["callbacks"] = [CallbackHandler()]
+
+            result = await request.app.state.agent.ainvoke(
+                cast(AgentState, state), config=invoke_config
+            )
+            with contextlib.suppress(Exception):
+                root_obs.update(output=result.get("final_output"))
+    else:
+        result = await request.app.state.agent.ainvoke(
+            cast(AgentState, state), config=invoke_config
+        )
 
+    duration = time.perf_counter() - start
     agent_run_duration_seconds.observe(duration)
     duration_ms = round(duration * 1000, 2)
 
@@ -101,8 +121,8 @@ async def run_agent(
         thread_id=thread_id,
     )
 
-    if langfuse_handler is not None:
-        background_tasks.add_task(langfuse_handler.langfuse.flush)
+    if lf_client is not None:
+        background_tasks.add_task(lf_client.flush)
 
     background_tasks.add_task(
         _persist_run,
diff --git a/apps/api/config.py b/apps/api/config.py
index 4609566..7f5c109 100644
--- a/apps/api/config.py
+++ b/apps/api/config.py
@@ -2,7 +2,7 @@
 
 
 class Settings(BaseSettings):
-    model_config = SettingsConfigDict(env_file=".env", env_file_encoding="utf-8")
+    model_config = SettingsConfigDict(env_file=".env", env_file_encoding="utf-8", extra="ignore")
 
     app_name: str = "Agent Platform"
     environment: str = "development"
@@ -31,6 +31,13 @@ class Settings(BaseSettings):
     #   gemini/gemini-2.5-flash, anthropic/claude-opus-4-7, openai/gpt-4o
     #   groq/llama-3.1-8b-instant, bedrock/anthropic.claude-3-5-sonnet-20241022-v2:0
     litellm_model: str = "gemini/gemini-2.5-flash"
+    # Cheap fast model used only for planner routing (outputs one token).
+    # Defaults to same as litellm_model so it works out-of-the-box without config.
+    planner_model: str = ""
+
+    @property
+    def resolved_planner_model(self) -> str:
+        return self.planner_model or self.litellm_model
 
     # ── Langfuse observability ────────────────────────────────────────────────
     langfuse_public_key: str | None = None
diff --git a/apps/api/main.py b/apps/api/main.py
index 83692ba..6fb6c0b 100644
--- a/apps/api/main.py
+++ b/apps/api/main.py
@@ -1,3 +1,4 @@
+import contextlib
 from contextlib import asynccontextmanager
 
 import structlog
@@ -26,11 +27,31 @@ async def lifespan(app: FastAPI):
     log.info("startup", app=settings.app_name, env=settings.environment, llm=settings.llm_provider)
 
     try:
-        from apps.api.db.session import create_tables
+        import asyncio
 
-        await create_tables()
+        from alembic import command as alembic_command
+        from alembic.config import Config as AlembicConfig
+
+        alembic_cfg = AlembicConfig("alembic.ini")
+        await asyncio.to_thread(alembic_command.upgrade, alembic_cfg, "head")
+        log.info("db.migrations.applied")
     except Exception as exc:
-        log.warning("db.init.skipped", reason=str(exc))
+        log.warning("db.migrations.skipped", reason=str(exc))
+
+    # Initialize Langfuse once at startup so the OTel tracer provider is set up
+    # exactly once. Re-creating Langfuse() per request resets the OTel context
+    # and breaks parent-span propagation for child observations.
+    app.state.langfuse = None
+    if settings.langfuse_public_key and settings.langfuse_secret_key:
+        with contextlib.suppress(Exception):
+            from langfuse import Langfuse  # type: ignore[import-untyped]
+
+            app.state.langfuse = Langfuse(
+                public_key=settings.langfuse_public_key,
+                secret_key=settings.langfuse_secret_key,
+                host=settings.langfuse_host,
+            )
+            log.info("tracing.backend", backend="langfuse", host=settings.langfuse_host)
 
     # Build agent graph with Postgres checkpointer for persistent memory.
     # Uses the same agentdb already running; falls back to MemorySaver if unavailable.
@@ -54,6 +75,11 @@ async def lifespan(app: FastAPI):
 
     yield
 
+    lf = getattr(app.state, "langfuse", None)
+    if lf is not None:
+        with contextlib.suppress(Exception):
+            lf.flush()
+
     ctx = getattr(app.state, "checkpointer_ctx", None)
     if ctx is not None:
         try:  # noqa: SIM105
diff --git a/apps/web/app/composables/useAgent.ts b/apps/web/app/composables/useAgent.ts
index 8fdfb67..7443480 100644
--- a/apps/web/app/composables/useAgent.ts
+++ b/apps/web/app/composables/useAgent.ts
@@ -16,15 +16,27 @@ export function useAgent() {
   const apiUrl = config.public.apiUrl
 
   async function runAgent(payload: AgentRequest): Promise<AgentResponse> {
-    const response = await fetch(`${apiUrl}/agent/run`, {
-      method: 'POST',
-      headers: { 'Content-Type': 'application/json' },
-      body: JSON.stringify(payload),
-    })
+    const url = `${apiUrl}/agent/run`
+    let response: Response
+
+    try {
+      response = await fetch(url, {
+        method: 'POST',
+        headers: { 'Content-Type': 'application/json' },
+        body: JSON.stringify(payload),
+        signal: AbortSignal.timeout(120_000), // 2-min hard timeout
+      })
+    } catch (e: unknown) {
+      // Network-level failure (no response received)
+      const reason = e instanceof Error ? e.message : String(e)
+      const label = reason === 'The operation was aborted.' ? 'Request timed out (>2 min)' : reason
+      throw new Error(`Cannot reach API at ${url} — ${label}`)
+    }
 
     if (!response.ok) {
-      const error = await response.text()
-      throw new Error(`Agent error (${response.status}): ${error}`)
+      let body = ''
+      try { body = await response.text() } catch { /* ignore */ }
+      throw new Error(`API error ${response.status} — ${body || response.statusText}`)
     }
 
     return response.json() as Promise<AgentResponse>
diff --git a/apps/web/app/composables/useHealth.ts b/apps/web/app/composables/useHealth.ts
index f3b17eb..5533774 100644
--- a/apps/web/app/composables/useHealth.ts
+++ b/apps/web/app/composables/useHealth.ts
@@ -13,21 +13,23 @@ export function useHealth() {
 
   async function checkHealth(): Promise<void> {
     const start = Date.now()
+    const url = `${apiUrl}/health`
     try {
-      const response = await fetch(`${apiUrl}/health`)
+      const response = await fetch(url, { signal: AbortSignal.timeout(10_000) })
       const latency_ms = Date.now() - start
 
       if (!response.ok) {
-        health.value = { status: 'error', error: `HTTP ${response.status}`, latency_ms }
+        health.value = { status: 'error', error: `HTTP ${response.status} from ${url}`, latency_ms }
         return
       }
 
       const data = await response.json()
       health.value = { status: 'ok', ...data, latency_ms }
     } catch (e: unknown) {
+      const reason = e instanceof Error ? e.message : 'Connection failed'
       health.value = {
         status: 'error',
-        error: e instanceof Error ? e.message : 'Connection failed',
+        error: `${url} — ${reason}`,
         latency_ms: Date.now() - start,
       }
     }
diff --git a/apps/web/app/pages/index.vue b/apps/web/app/pages/index.vue
index 375bcf4..54d0818 100644
--- a/apps/web/app/pages/index.vue
+++ b/apps/web/app/pages/index.vue
@@ -1,5 +1,18 @@
 <template>
   <div class="flex flex-col h-[calc(100vh-57px)]">
+    <!-- Session header -->
+    <div class="flex items-center justify-between px-4 py-2 border-b border-gray-800/60 bg-gray-950">
+      <span class="text-[11px] text-gray-500 font-mono">
+        Session: <span class="text-gray-400">{{ sessionId }}</span>
+      </span>
+      <button
+        @click="newSession"
+        class="text-[11px] text-gray-500 hover:text-gray-300 transition-colors px-2 py-1 rounded-lg hover:bg-gray-800"
+      >
+        + New chat
+      </button>
+    </div>
+
     <div class="flex-1 overflow-y-auto px-4 py-6 space-y-4 custom-scrollbar" ref="chatContainer">
       <!-- Empty state -->
       <div v-if="messages.length === 0" class="flex flex-col items-center justify-center h-full gap-4 text-center">
@@ -41,7 +54,7 @@
             <div class="text-[11px] font-semibold uppercase tracking-wider mb-1.5 opacity-60">
               {{ msg.role === 'user' ? 'You' : 'Agent' }}
             </div>
-            <div class="leading-relaxed text-sm whitespace-pre-wrap">{{ msg.content }}</div>
+            <div class="leading-relaxed text-sm md-content" v-html="renderMarkdown(msg.content)" />
             <!-- Tool result badge -->
             <div v-if="msg.tool_result" class="mt-2">
               <details class="text-xs">
@@ -115,7 +128,16 @@
 </template>
 
 <script setup lang="ts">
-import { nextTick, ref } from 'vue'
+import { nextTick, ref, watch } from 'vue'
+import { marked } from 'marked'
+
+marked.setOptions({ breaks: true })
+
+function renderMarkdown(text: string): string {
+  return marked.parse(text) as string
+}
+
+const SESSION_KEY = 'agent-session-id'
 
 const { runAgent } = useAgent()
 const chatContainer = ref<HTMLElement | null>(null)
@@ -131,7 +153,12 @@ const messages = ref<Message[]>([])
 const inputText = ref('')
 const loading = ref(false)
 const error = ref<string | null>(null)
-const sessionId = ref(`session-${Date.now()}`)
+
+const storedId = import.meta.client ? localStorage.getItem(SESSION_KEY) : null
+const sessionId = ref(storedId || `session-${Date.now()}`)
+if (import.meta.client) {
+  watch(sessionId, (id) => localStorage.setItem(SESSION_KEY, id), { immediate: true })
+}
 
 const suggestedPrompts = [
   'Search for the latest AI news',
@@ -178,6 +205,12 @@ function scrollToBottom(): void {
     chatContainer.value.scrollTop = chatContainer.value.scrollHeight
   }
 }
+
+function newSession(): void {
+  messages.value = []
+  error.value = null
+  sessionId.value = `session-${Date.now()}`
+}
 </script>
 
 <style scoped>
@@ -185,4 +218,24 @@ function scrollToBottom(): void {
 .custom-scrollbar::-webkit-scrollbar-track { background: transparent; }
 .custom-scrollbar::-webkit-scrollbar-thumb { background: #374151; border-radius: 4px; }
 .custom-scrollbar::-webkit-scrollbar-thumb:hover { background: #4b5563; }
+
+/* Markdown content styling */
+.md-content :deep(p) { margin: 0.35em 0; }
+.md-content :deep(p:first-child) { margin-top: 0; }
+.md-content :deep(p:last-child) { margin-bottom: 0; }
+.md-content :deep(strong) { font-weight: 600; color: #f9fafb; }
+.md-content :deep(em) { font-style: italic; }
+.md-content :deep(code) { background: #111827; border-radius: 4px; padding: 1px 5px; font-size: 0.8em; font-family: ui-monospace, monospace; color: #a5b4fc; }
+.md-content :deep(pre) { background: #111827; border-radius: 8px; padding: 10px 14px; overflow-x: auto; margin: 0.5em 0; }
+.md-content :deep(pre code) { background: transparent; padding: 0; font-size: 0.78em; color: #d1d5db; }
+.md-content :deep(ul) { list-style: disc; padding-left: 1.4em; margin: 0.4em 0; }
+.md-content :deep(ol) { list-style: decimal; padding-left: 1.4em; margin: 0.4em 0; }
+.md-content :deep(li) { margin: 0.15em 0; }
+.md-content :deep(h1), .md-content :deep(h2), .md-content :deep(h3) { font-weight: 600; color: #f9fafb; margin: 0.6em 0 0.3em; }
+.md-content :deep(h1) { font-size: 1.15em; }
+.md-content :deep(h2) { font-size: 1.05em; }
+.md-content :deep(h3) { font-size: 0.95em; }
+.md-content :deep(blockquote) { border-left: 3px solid #4b5563; padding-left: 0.75em; color: #9ca3af; margin: 0.4em 0; }
+.md-content :deep(a) { color: #60a5fa; text-decoration: underline; }
+.md-content :deep(hr) { border-color: #374151; margin: 0.5em 0; }
 </style>
diff --git a/apps/web/package-lock.json b/apps/web/package-lock.json
index 2a634a3..0cb5170 100644
--- a/apps/web/package-lock.json
+++ b/apps/web/package-lock.json
@@ -7,6 +7,7 @@
       "name": "web",
       "hasInstallScript": true,
       "dependencies": {
+        "marked": "^15.0.12",
         "nuxt": "^4.4.2",
         "vue": "^3.5.32",
         "vue-router": "^5.0.4"
@@ -7200,6 +7201,18 @@
         "source-map-js": "^1.2.1"
       }
     },
+    "node_modules/marked": {
+      "version": "15.0.12",
+      "resolved": "https://registry.npmjs.org/marked/-/marked-15.0.12.tgz",
+      "integrity": "sha512-8dD6FusOQSrpv9Z1rdNMdlSgQOIP880DHqnohobOmYLElGEqAL/JvxvuxZO16r4HtjTlfPRDC1hbvxC9dPN2nA==",
+      "license": "MIT",
+      "bin": {
+        "marked": "bin/marked.js"
+      },
+      "engines": {
+        "node": ">= 18"
+      }
+    },
     "node_modules/math-intrinsics": {
       "version": "1.1.0",
       "resolved": "https://registry.npmjs.org/math-intrinsics/-/math-intrinsics-1.1.0.tgz",
diff --git a/apps/web/package.json b/apps/web/package.json
index 997ca22..92e70e8 100644
--- a/apps/web/package.json
+++ b/apps/web/package.json
@@ -10,6 +10,7 @@
     "postinstall": "nuxt prepare"
   },
   "dependencies": {
+    "marked": "^15.0.12",
     "nuxt": "^4.4.2",
     "vue": "^3.5.32",
     "vue-router": "^5.0.4"
diff --git a/docker-compose.yml b/docker-compose.yml
index c7ddb58..dc0229a 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -11,7 +11,7 @@ services:
       - "8000:8000"
     env_file: .env
     environment:
-      LANGFUSE_HOST: http://langfuse:3000
+      LANGFUSE_HOST: http://langfuse-web:3000
       ENVIRONMENT: production
       REDIS_URL: redis://redis:6379/0
       DATABASE_URL: postgresql+asyncpg://agent:agent@agentdb:5432/agent
@@ -20,7 +20,7 @@ services:
         condition: service_healthy
       redis:
         condition: service_healthy
-      langfuse:
+      langfuse-web:
         condition: service_started
     restart: unless-stopped
     networks:
@@ -49,7 +49,7 @@ services:
     networks:
       - agent-net
 
-  # ── Redis (session memory + caching) ─────────────────────────────────────────
+  # ── Redis (shared — used by agent platform AND Langfuse worker queue) ────────
   redis:
     image: redis:7-alpine
     command: redis-server --maxmemory 256mb --maxmemory-policy allkeys-lru
@@ -66,13 +66,15 @@ services:
       timeout: 5s
       retries: 5
 
-  # ── Agent Postgres (run history) ─────────────────────────────────────────────
+  # ── Agent Postgres (run history + LangGraph checkpoints) ─────────────────────
   agentdb:
     image: postgres:16-alpine
     environment:
       POSTGRES_USER: agent
       POSTGRES_PASSWORD: agent
       POSTGRES_DB: agent
+    ports:
+      - "5433:5432"
     volumes:
       - agentdb_data:/var/lib/postgresql/data
     restart: unless-stopped
@@ -84,41 +86,160 @@ services:
       timeout: 5s
       retries: 5
 
-  # ── Langfuse LLM observability ───────────────────────────────────────────────
-  langfuse:
-    image: langfuse/langfuse:2
+  # ── Langfuse Postgres (user accounts, API keys, project config) ──────────────
+  langfusedb:
+    image: postgres:16-alpine
+    environment:
+      POSTGRES_USER: langfuse
+      POSTGRES_PASSWORD: langfuse
+      POSTGRES_DB: langfuse
+    volumes:
+      - langfusedb_data:/var/lib/postgresql/data
+    restart: unless-stopped
+    networks:
+      - agent-net
+    healthcheck:
+      test: ["CMD-SHELL", "pg_isready -U langfuse"]
+      interval: 10s
+      timeout: 5s
+      retries: 5
+
+  # ── ClickHouse (Langfuse v3 — stores traces, spans, generations) ─────────────
+  clickhouse:
+    image: clickhouse/clickhouse-server:24.12-alpine
+    environment:
+      CLICKHOUSE_USER: clickhouse
+      CLICKHOUSE_PASSWORD: clickhouse
+      CLICKHOUSE_DEFAULT_ACCESS_MANAGEMENT: "1"
+    volumes:
+      - clickhouse_data:/var/lib/clickhouse
+      - ./infra/clickhouse/config.d:/etc/clickhouse-server/config.d:ro
+    restart: unless-stopped
+    networks:
+      - agent-net
+    healthcheck:
+      test: ["CMD-SHELL", "wget --no-verbose --tries=1 --spider http://127.0.0.1:8123/ping || exit 1"]
+      interval: 10s
+      timeout: 5s
+      retries: 5
+
+  # ── MinIO (Langfuse v3 — S3-compatible blob storage for media/exports) ────────
+  minio:
+    image: minio/minio
+    command: server /data --console-address ":9001"
+    ports:
+      - "9092:9000"
+      - "9093:9001"
+    environment:
+      MINIO_ROOT_USER: minio
+      MINIO_ROOT_PASSWORD: miniosecret
+    volumes:
+      - minio_data:/data
+    restart: unless-stopped
+    networks:
+      - agent-net
+    healthcheck:
+      test: ["CMD-SHELL", "curl -f http://localhost:9000/minio/health/live || exit 1"]
+      interval: 10s
+      timeout: 5s
+      retries: 5
+
+  # ── MinIO bucket init (creates the 'langfuse' bucket on first run) ────────────
+  minio-init:
+    image: minio/mc
+    depends_on:
+      minio:
+        condition: service_healthy
+    entrypoint: >
+      /bin/sh -c "
+      mc alias set local http://minio:9000 minio miniosecret &&
+      mc mb local/langfuse --ignore-existing
+      "
+    networks:
+      - agent-net
+    restart: on-failure
+
+  # ── Langfuse Web (v3) ────────────────────────────────────────────────────────
+  langfuse-web:
+    image: langfuse/langfuse:3
     ports:
       - "3010:3000"
     environment:
       DATABASE_URL: postgresql://langfuse:langfuse@langfusedb:5432/langfuse
+      CLICKHOUSE_MIGRATION_URL: clickhouse://clickhouse:clickhouse@clickhouse:9000/default
+      CLICKHOUSE_URL: http://clickhouse:8123
+      CLICKHOUSE_USER: clickhouse
+      CLICKHOUSE_PASSWORD: clickhouse
+      LANGFUSE_S3_MEDIA_UPLOAD_ENABLED: "true"
+      LANGFUSE_S3_MEDIA_UPLOAD_BUCKET: langfuse
+      LANGFUSE_S3_MEDIA_UPLOAD_ENDPOINT: http://minio:9000
+      LANGFUSE_S3_MEDIA_UPLOAD_REGION: auto
+      LANGFUSE_S3_MEDIA_UPLOAD_ACCESS_KEY_ID: minio
+      LANGFUSE_S3_MEDIA_UPLOAD_SECRET_ACCESS_KEY: miniosecret
+      LANGFUSE_S3_MEDIA_UPLOAD_FORCE_PATH_STYLE: "true"
+      LANGFUSE_S3_EVENT_UPLOAD_BUCKET: langfuse
+      LANGFUSE_S3_EVENT_UPLOAD_ENDPOINT: http://minio:9000
+      LANGFUSE_S3_EVENT_UPLOAD_REGION: auto
+      LANGFUSE_S3_EVENT_UPLOAD_ACCESS_KEY_ID: minio
+      LANGFUSE_S3_EVENT_UPLOAD_SECRET_ACCESS_KEY: miniosecret
+      LANGFUSE_S3_EVENT_UPLOAD_FORCE_PATH_STYLE: "true"
+      REDIS_HOST: redis
+      REDIS_PORT: "6379"
       NEXTAUTH_SECRET: changethis_dev_secret_32chars_min
       SALT: changethis_dev_salt
       NEXTAUTH_URL: http://localhost:3010
+      # Generate with: openssl rand -hex 32
+      ENCRYPTION_KEY: bc7e26109507c8497949ad8762321373f38ea92cd64c0703ee6e1b4ccf6f4c44
       TELEMETRY_ENABLED: "false"
     depends_on:
       langfusedb:
         condition: service_healthy
+      clickhouse:
+        condition: service_healthy
+      redis:
+        condition: service_healthy
+      minio-init:
+        condition: service_completed_successfully
     restart: unless-stopped
     networks:
       - agent-net
 
-  # ── Langfuse Postgres ────────────────────────────────────────────────────────
-  langfusedb:
-    image: postgres:16-alpine
+  # ── Langfuse Worker (v3) — processes async jobs (scoring, exports, evals) ────
+  langfuse-worker:
+    image: langfuse/langfuse-worker:3
     environment:
-      POSTGRES_USER: langfuse
-      POSTGRES_PASSWORD: langfuse
-      POSTGRES_DB: langfuse
-    volumes:
-      - langfusedb_data:/var/lib/postgresql/data
+      DATABASE_URL: postgresql://langfuse:langfuse@langfusedb:5432/langfuse
+      CLICKHOUSE_MIGRATION_URL: clickhouse://clickhouse:clickhouse@clickhouse:9000/default
+      CLICKHOUSE_URL: http://clickhouse:8123
+      CLICKHOUSE_USER: clickhouse
+      CLICKHOUSE_PASSWORD: clickhouse
+      LANGFUSE_S3_MEDIA_UPLOAD_ENABLED: "true"
+      LANGFUSE_S3_MEDIA_UPLOAD_BUCKET: langfuse
+      LANGFUSE_S3_MEDIA_UPLOAD_ENDPOINT: http://minio:9000
+      LANGFUSE_S3_MEDIA_UPLOAD_REGION: auto
+      LANGFUSE_S3_MEDIA_UPLOAD_ACCESS_KEY_ID: minio
+      LANGFUSE_S3_MEDIA_UPLOAD_SECRET_ACCESS_KEY: miniosecret
+      LANGFUSE_S3_MEDIA_UPLOAD_FORCE_PATH_STYLE: "true"
+      LANGFUSE_S3_EVENT_UPLOAD_BUCKET: langfuse
+      LANGFUSE_S3_EVENT_UPLOAD_ENDPOINT: http://minio:9000
+      LANGFUSE_S3_EVENT_UPLOAD_REGION: auto
+      LANGFUSE_S3_EVENT_UPLOAD_ACCESS_KEY_ID: minio
+      LANGFUSE_S3_EVENT_UPLOAD_SECRET_ACCESS_KEY: miniosecret
+      LANGFUSE_S3_EVENT_UPLOAD_FORCE_PATH_STYLE: "true"
+      REDIS_HOST: redis
+      REDIS_PORT: "6379"
+      ENCRYPTION_KEY: bc7e26109507c8497949ad8762321373f38ea92cd64c0703ee6e1b4ccf6f4c44
+      TELEMETRY_ENABLED: "false"
+    depends_on:
+      langfusedb:
+        condition: service_healthy
+      clickhouse:
+        condition: service_healthy
+      redis:
+        condition: service_healthy
     restart: unless-stopped
     networks:
       - agent-net
-    healthcheck:
-      test: ["CMD-SHELL", "pg_isready -U langfuse"]
-      interval: 10s
-      timeout: 5s
-      retries: 5
 
   # ── Prometheus metrics ───────────────────────────────────────────────────────
   prometheus:
@@ -163,4 +284,6 @@ volumes:
   redis_data:
   agentdb_data:
   langfusedb_data:
+  clickhouse_data:
+  minio_data:
   grafana_data:
diff --git a/infra/clickhouse/config.d/cluster.xml b/infra/clickhouse/config.d/cluster.xml
new file mode 100644
index 0000000..ed386e3
--- /dev/null
+++ b/infra/clickhouse/config.d/cluster.xml
@@ -0,0 +1,51 @@
+<clickhouse>
+    <!-- Bind to all interfaces so other containers can connect -->
+    <listen_host>0.0.0.0</listen_host>
+
+    <!-- Built-in Keeper — single node, no external ZooKeeper needed -->
+    <keeper_server>
+        <tcp_port>9181</tcp_port>
+        <server_id>1</server_id>
+        <log_storage_path>/var/lib/clickhouse/coordination/log</log_storage_path>
+        <snapshot_storage_path>/var/lib/clickhouse/coordination/snapshots</snapshot_storage_path>
+        <coordination_settings>
+            <operation_timeout_ms>10000</operation_timeout_ms>
+            <session_timeout_ms>30000</session_timeout_ms>
+            <raft_logs_level>warning</raft_logs_level>
+        </coordination_settings>
+        <raft_configuration>
+            <server>
+                <id>1</id>
+                <hostname>127.0.0.1</hostname>
+                <port>9444</port>
+            </server>
+        </raft_configuration>
+    </keeper_server>
+
+    <!-- Point ZooKeeper client to local Keeper -->
+    <zookeeper>
+        <node>
+            <host>127.0.0.1</host>
+            <port>9181</port>
+        </node>
+    </zookeeper>
+
+    <!-- Single-shard cluster named 'default' — satisfies ON CLUSTER default queries -->
+    <remote_servers>
+        <default>
+            <shard>
+                <replica>
+                    <host>127.0.0.1</host>
+                    <port>9000</port>
+                </replica>
+            </shard>
+        </default>
+    </remote_servers>
+
+    <!-- Replica identity macros -->
+    <macros>
+        <cluster>default</cluster>
+        <shard>1</shard>
+        <replica>clickhouse-01</replica>
+    </macros>
+</clickhouse>
diff --git a/infra/migrations/README b/infra/migrations/README
new file mode 100644
index 0000000..98e4f9c
--- /dev/null
+++ b/infra/migrations/README
@@ -0,0 +1 @@
+Generic single-database configuration.
\ No newline at end of file
diff --git a/infra/migrations/env.py b/infra/migrations/env.py
new file mode 100644
index 0000000..dec3bab
--- /dev/null
+++ b/infra/migrations/env.py
@@ -0,0 +1,68 @@
+from logging.config import fileConfig
+
+from alembic import context
+from sqlalchemy import engine_from_config, pool
+
+config = context.config
+
+if config.config_file_name is not None:
+    fileConfig(config.config_file_name)
+
+# Wire to the app's ORM models so autogenerate can diff against them.
+from apps.api.config import settings  # noqa: E402
+from apps.api.db.models import Base  # noqa: E402
+
+target_metadata = Base.metadata
+
+# Override the URL from settings so we never need it hardcoded in alembic.ini.
+# Strip +asyncpg — Alembic uses the sync psycopg driver.
+_sync_url = settings.database_url.replace("postgresql+asyncpg://", "postgresql://")
+config.set_main_option("sqlalchemy.url", _sync_url)
+
+# LangGraph manages its own tables (checkpoints, checkpoint_blobs, etc.).
+# Exclude them from autogenerate so Alembic never generates drop/create for them.
+_LANGGRAPH_TABLES = {
+    "checkpoints",
+    "checkpoint_blobs",
+    "checkpoint_writes",
+    "checkpoint_migrations",
+}
+
+
+def include_object(object, name, type_, reflected, compare_to) -> bool:  # noqa: A002
+    return not (type_ == "table" and name in _LANGGRAPH_TABLES)
+
+
+def run_migrations_offline() -> None:
+    url = config.get_main_option("sqlalchemy.url")
+    context.configure(
+        url=url,
+        target_metadata=target_metadata,
+        literal_binds=True,
+        dialect_opts={"paramstyle": "named"},
+        include_object=include_object,
+    )
+    with context.begin_transaction():
+        context.run_migrations()
+
+
+def run_migrations_online() -> None:
+    connectable = engine_from_config(
+        config.get_section(config.config_ini_section, {}),
+        prefix="sqlalchemy.",
+        poolclass=pool.NullPool,
+    )
+    with connectable.connect() as connection:
+        context.configure(
+            connection=connection,
+            target_metadata=target_metadata,
+            include_object=include_object,
+        )
+        with context.begin_transaction():
+            context.run_migrations()
+
+
+if context.is_offline_mode():
+    run_migrations_offline()
+else:
+    run_migrations_online()
diff --git a/infra/migrations/script.py.mako b/infra/migrations/script.py.mako
new file mode 100644
index 0000000..1101630
--- /dev/null
+++ b/infra/migrations/script.py.mako
@@ -0,0 +1,28 @@
+"""${message}
+
+Revision ID: ${up_revision}
+Revises: ${down_revision | comma,n}
+Create Date: ${create_date}
+
+"""
+from typing import Sequence, Union
+
+from alembic import op
+import sqlalchemy as sa
+${imports if imports else ""}
+
+# revision identifiers, used by Alembic.
+revision: str = ${repr(up_revision)}
+down_revision: Union[str, Sequence[str], None] = ${repr(down_revision)}
+branch_labels: Union[str, Sequence[str], None] = ${repr(branch_labels)}
+depends_on: Union[str, Sequence[str], None] = ${repr(depends_on)}
+
+
+def upgrade() -> None:
+    """Upgrade schema."""
+    ${upgrades if upgrades else "pass"}
+
+
+def downgrade() -> None:
+    """Downgrade schema."""
+    ${downgrades if downgrades else "pass"}
diff --git a/infra/migrations/versions/4cbb88e1252b_initial_agent_runs.py b/infra/migrations/versions/4cbb88e1252b_initial_agent_runs.py
new file mode 100644
index 0000000..b6fafa3
--- /dev/null
+++ b/infra/migrations/versions/4cbb88e1252b_initial_agent_runs.py
@@ -0,0 +1,48 @@
+"""initial_agent_runs
+
+Revision ID: 4cbb88e1252b
+Revises:
+Create Date: 2026-04-18 16:43:40.358527
+
+"""
+
+from collections.abc import Sequence
+
+import sqlalchemy as sa
+from alembic import op
+from sqlalchemy.dialects import postgresql
+
+revision: str = "4cbb88e1252b"
+down_revision: str | Sequence[str] | None = None
+branch_labels: str | Sequence[str] | None = None
+depends_on: str | Sequence[str] | None = None
+
+
+def upgrade() -> None:
+    op.create_table(
+        "agent_runs",
+        sa.Column("id", postgresql.UUID(as_uuid=True), nullable=False),
+        sa.Column("session_id", sa.String(length=64), nullable=False),
+        sa.Column("user_id", sa.String(length=64), nullable=False),
+        sa.Column("input", sa.Text(), nullable=False),
+        sa.Column("output", sa.Text(), nullable=True),
+        sa.Column("tool_result", sa.Text(), nullable=True),
+        sa.Column("tool_used", sa.Boolean(), nullable=False),
+        sa.Column("duration_ms", sa.Float(), nullable=False),
+        sa.Column("llm_provider", sa.String(length=32), nullable=False),
+        sa.Column(
+            "created_at",
+            sa.DateTime(timezone=True),
+            server_default=sa.text("now()"),
+            nullable=False,
+        ),
+        sa.PrimaryKeyConstraint("id"),
+    )
+    op.create_index("ix_agent_runs_session_id", "agent_runs", ["session_id"])
+    op.create_index("ix_agent_runs_user_id", "agent_runs", ["user_id"])
+
+
+def downgrade() -> None:
+    op.drop_index("ix_agent_runs_user_id", table_name="agent_runs")
+    op.drop_index("ix_agent_runs_session_id", table_name="agent_runs")
+    op.drop_table("agent_runs")
diff --git a/pyproject.toml b/pyproject.toml
index 76a129e..da2e840 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -11,7 +11,7 @@ dependencies = [
     "httpx>=0.28.0",
     "langchain>=0.3.0",
     "langchain-google-genai>=2.0.0",
-    "langfuse>=2.0.0,<3.0.0",
+    "langfuse>=3.14.6,<4.0.0",
     "langgraph>=0.2.0",
     "prometheus-client>=0.21.0",
     "pydantic-settings>=2.6.0",
@@ -26,6 +26,7 @@ dependencies = [
     "langchain-community>=0.3.0",
     "litellm>=1.83.7",
     "langgraph-checkpoint-postgres>=3.0.5",
+    "ddgs>=9.14.0",
 ]
 
 [project.scripts]
@@ -38,6 +39,7 @@ build-backend = "uv_build"
 [dependency-groups]
 dev = [
     "pre-commit>=4.0.0",
+    "psycopg2-binary>=2.9.11",
     "pyright>=1.1.390",
     "pytest>=8.3.0",
     "pytest-asyncio>=0.24.0",
diff --git a/services/agent/graph/state.py b/services/agent/graph/state.py
index e253857..794641d 100644
--- a/services/agent/graph/state.py
+++ b/services/agent/graph/state.py
@@ -1,6 +1,12 @@
 import operator
 from typing import Annotated, TypedDict
 
+# Each turn appends 2 strings ("User: ..." + "Assistant: ...").
+# Sending the full history to every LLM call grows the prompt unboundedly.
+# We keep only the most recent N turns in the prompt while the full history
+# stays safely stored in the Postgres checkpoint.
+_MAX_HISTORY_TURNS = 10
+
 
 class AgentState(TypedDict):
     input: str
@@ -11,4 +17,8 @@ class AgentState(TypedDict):
 
 
 def format_history(state: AgentState) -> str:
-    return "\n".join(state["messages"]) if state["messages"] else "(no prior messages)"
+    msgs = state["messages"]
+    if not msgs:
+        return "(no prior messages)"
+    recent = msgs[-(_MAX_HISTORY_TURNS * 2) :]
+    return "\n".join(recent)
diff --git a/services/agent/graph/workflow.py b/services/agent/graph/workflow.py
index 29178ae..524745c 100644
--- a/services/agent/graph/workflow.py
+++ b/services/agent/graph/workflow.py
@@ -10,8 +10,8 @@
 
 
 def _route(state: AgentState) -> str:
-    next_step = state.get("next_step") or ""
-    return "tool" if "tool" in next_step else "synth"
+    next_step = (state.get("next_step") or "").strip().lower()
+    return "tool" if next_step.startswith("tool:") else "synth"
 
 
 def build_graph(checkpointer: Any = None) -> Any:
diff --git a/services/agent/llm.py b/services/agent/llm.py
index 4a04723..3368c68 100644
--- a/services/agent/llm.py
+++ b/services/agent/llm.py
@@ -15,9 +15,29 @@ def _setenv(key: str, value: str | None) -> None:
         os.environ[key] = value
 
 
-@lru_cache(maxsize=4)
-def get_llm(temperature: float = 0.0):  # noqa: ANN201
-    """Return a configured LangChain chat model based on LLM_PROVIDER. Cached per temperature."""
+def _with_retry(llm):  # noqa: ANN001, ANN201
+    """Wrap a LangChain chat model with 3-attempt exponential-backoff retry.
+
+    Handles transient provider errors (5xx, network timeouts, brief rate limits)
+    without surfacing them to the user. If all 3 attempts fail, the exception
+    propagates normally.
+    """
+    return llm.with_retry(
+        retry_if_exception_type=(Exception,),
+        wait_exponential_jitter=True,
+        stop_after_attempt=3,
+    )
+
+
+@lru_cache(maxsize=8)
+def get_llm(temperature: float = 0.0, task: str = "default"):  # noqa: ANN201
+    """Return a configured LangChain chat model based on LLM_PROVIDER.
+
+    Args:
+        temperature: Sampling temperature. 0 = deterministic (used by planner).
+        task: "planner" uses a cheap fast model; "default" uses the main model.
+              Cached per (temperature, task) pair.
+    """
     from apps.api.config import settings
 
     provider = settings.llm_provider.lower()
@@ -26,21 +46,24 @@ def get_llm(temperature: float = 0.0):  # noqa: ANN201
         from langchain_google_genai import ChatGoogleGenerativeAI
 
         _setenv("GOOGLE_API_KEY", settings.google_api_key)
-        return ChatGoogleGenerativeAI(model=settings.gemini_model, temperature=temperature)
+        model = settings.gemini_model
+        return _with_retry(ChatGoogleGenerativeAI(model=model, temperature=temperature))
 
     if provider == "openai":
         from langchain_openai import ChatOpenAI
 
         _setenv("OPENAI_API_KEY", settings.openai_api_key)
-        return ChatOpenAI(model=settings.openai_model, temperature=temperature)
+        return _with_retry(ChatOpenAI(model=settings.openai_model, temperature=temperature))
 
     if provider == "ollama":
         from langchain_community.chat_models import ChatOllama  # type: ignore[import-untyped]
 
-        return ChatOllama(
-            base_url=settings.ollama_base_url,
-            model=settings.ollama_model,
-            temperature=temperature,
+        return _with_retry(
+            ChatOllama(
+                base_url=settings.ollama_base_url,
+                model=settings.ollama_model,
+                temperature=temperature,
+            )
         )
 
     if provider == "groq":
@@ -51,12 +74,13 @@ def get_llm(temperature: float = 0.0):  # noqa: ANN201
                 "langchain-groq is not installed. Run: uv add langchain-groq"
             ) from err
         _setenv("GROQ_API_KEY", settings.groq_api_key)
-        return ChatGroq(model=settings.groq_model, temperature=temperature)
+        return _with_retry(ChatGroq(model=settings.groq_model, temperature=temperature))
 
     if provider == "litellm":
         from langchain_community.chat_models import ChatLiteLLM  # type: ignore[import-untyped]
 
-        return ChatLiteLLM(model=settings.litellm_model, temperature=temperature)
+        model = settings.resolved_planner_model if task == "planner" else settings.litellm_model
+        return _with_retry(ChatLiteLLM(model=model, temperature=temperature))
 
     raise ValueError(
         f"Unknown LLM_PROVIDER '{provider}'. Choose one of: gemini, openai, ollama, groq, litellm"
diff --git a/services/agent/nodes/planner.py b/services/agent/nodes/planner.py
index 7b2a7bd..66342be 100644
--- a/services/agent/nodes/planner.py
+++ b/services/agent/nodes/planner.py
@@ -1,6 +1,7 @@
 from __future__ import annotations
 
 import structlog
+from langchain_core.runnables import RunnableConfig
 
 from services.agent.graph.state import AgentState, format_history
 from services.agent.llm import get_llm
@@ -8,30 +9,38 @@
 log = structlog.get_logger(__name__)
 
 _SYSTEM_PROMPT = """\
-You are a planner agent. You have a conversation history and a new user message.
+You are a routing agent. Read the user message and decide how to answer.
 
 Conversation history:
 {history}
 
-New user message: {input}
+User message: {input}
 
-Decide whether the user's request requires an external search or can be answered directly.
-Respond with EXACTLY one of:
-- "tool:search"   — if the user needs up-to-date or external information
-- "final"         — if you can answer from knowledge or conversation history
-"""
+Output rules — one line only, no explanation:
+- When the user asks about current events, live data, news, prices, sports scores, or any fact that may have changed recently: output  tool:search <concise search query>  (e.g. "tool:search bitcoin price today")
+- When you can answer from training knowledge or the conversation history: output  final
 
+Your output:"""
 
-def planner_node(state: AgentState) -> dict[str, str | list[str] | None]:
+
+def planner_node(state: AgentState, config: RunnableConfig) -> dict[str, str | None]:
     history = format_history(state)
     log.debug(
         "planner.start", input_length=len(state["input"]), history_turns=len(state["messages"])
     )
 
-    llm = get_llm(temperature=0)
+    llm = get_llm(temperature=0, task="planner")
     prompt = _SYSTEM_PROMPT.format(history=history, input=state["input"])
-    raw = llm.invoke(prompt).content
-    response = (raw if isinstance(raw, str) else str(raw)).strip().lower()
-
-    log.debug("planner.decision", next_step=response)
-    return {"next_step": response, "messages": [f"User: {state['input']}"]}
+    raw = llm.invoke(prompt, config=config).content
+    # Take only the first non-empty line to avoid verbose LLM output
+    first_line = next(
+        (
+            ln.strip()
+            for ln in (raw if isinstance(raw, str) else str(raw)).splitlines()
+            if ln.strip()
+        ),
+        "final",
+    ).lower()
+
+    log.debug("planner.decision", next_step=first_line)
+    return {"next_step": first_line}
diff --git a/services/agent/nodes/synthesizer.py b/services/agent/nodes/synthesizer.py
index e1c6b41..ced69dd 100644
--- a/services/agent/nodes/synthesizer.py
+++ b/services/agent/nodes/synthesizer.py
@@ -1,6 +1,7 @@
 from __future__ import annotations
 
 import structlog
+from langchain_core.runnables import RunnableConfig
 
 from services.agent.graph.state import AgentState, format_history
 from services.agent.llm import get_llm
@@ -21,7 +22,7 @@
 """
 
 
-def synth_node(state: AgentState) -> dict[str, str | list[str] | None]:
+def synth_node(state: AgentState, config: RunnableConfig) -> dict[str, str | list[str] | None]:
     history = format_history(state)
     log.debug("synth.start", has_tool_result=state.get("tool_result") is not None)
 
@@ -31,8 +32,11 @@ def synth_node(state: AgentState) -> dict[str, str | list[str] | None]:
         tool_result=state.get("tool_result") or "N/A",
         input=state["input"],
     )
-    raw = llm.invoke(prompt).content
+    raw = llm.invoke(prompt, config=config).content
     response = raw if isinstance(raw, str) else str(raw)
 
     log.debug("synth.complete", output_length=len(response))
-    return {"final_output": response, "messages": [f"Assistant: {response}"]}
+    return {
+        "final_output": response,
+        "messages": [f"User: {state['input']}", f"Assistant: {response}"],
+    }
diff --git a/services/agent/nodes/tools.py b/services/agent/nodes/tools.py
index 02d0a5d..4226108 100644
--- a/services/agent/nodes/tools.py
+++ b/services/agent/nodes/tools.py
@@ -1,6 +1,7 @@
 from __future__ import annotations
 
 import structlog
+from langchain_core.runnables import RunnableConfig
 
 from apps.api.metrics import TOOL_EXECUTIONS
 from services.agent.graph.state import AgentState
@@ -9,10 +10,18 @@
 log = structlog.get_logger(__name__)
 
 
-def tool_node(state: AgentState) -> dict[str, str | None]:
-    query = state["input"]
+def tool_node(state: AgentState, config: RunnableConfig) -> dict[str, str | None]:
+    # Planner may embed a refined query after the colon: "tool:search bitcoin price"
+    # Fall back to the raw user input when no query is specified.
+    next_step = state.get("next_step") or ""
+    suffix = (
+        next_step[len("tool:search") :].strip()
+        if next_step.lower().startswith("tool:search")
+        else ""
+    )
+    query = suffix if suffix else state["input"]
     log.info("tool.execute", tool="search", query=query)
     TOOL_EXECUTIONS.labels(tool_name="search").inc()
-    result = search_tool.invoke({"query": query})
+    result = search_tool.invoke({"query": query}, config=config)
     log.debug("tool.result", tool="search", result_length=len(result))
     return {"tool_result": result}
diff --git a/services/agent/tools/search.py b/services/agent/tools/search.py
index 0b7aec9..244f746 100644
--- a/services/agent/tools/search.py
+++ b/services/agent/tools/search.py
@@ -1,7 +1,7 @@
 from __future__ import annotations
 
 import structlog
-from duckduckgo_search import DDGS
+from ddgs import DDGS
 from langchain_core.tools import tool
 
 log = structlog.get_logger(__name__)
diff --git a/tests/conftest.py b/tests/conftest.py
index 862e32b..c240115 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -17,7 +17,7 @@
 class _MockLLM:
     """Deterministic LLM stub — returns predictable content based on prompt context."""
 
-    def invoke(self, prompt: str) -> MagicMock:
+    def invoke(self, prompt: str, **_kwargs) -> MagicMock:
         resp = MagicMock()
         # Planner prompts contain "tool:search" or "final" decision cues
         if (
diff --git a/tests/integration/test_agent_run.py b/tests/integration/test_agent_run.py
index c6929f6..e2ab891 100644
--- a/tests/integration/test_agent_run.py
+++ b/tests/integration/test_agent_run.py
@@ -14,8 +14,6 @@
 from apps.api.db.session import get_db
 from apps.api.main import app
 
-client = TestClient(app)
-
 
 async def _fake_db():
     """Fake DB session — no real Postgres needed."""
@@ -33,7 +31,14 @@ def override_db():
     app.dependency_overrides.pop(get_db, None)
 
 
-def test_agent_run_basic() -> None:
+@pytest.fixture()
+def client():
+    """TestClient used as context manager so the FastAPI lifespan runs."""
+    with TestClient(app, raise_server_exceptions=True) as c:
+        yield c
+
+
+def test_agent_run_basic(client: TestClient) -> None:
     response = client.post("/agent/run", json={"input": "Hello, what is 2+2?"})
     assert response.status_code == 200
     data = response.json()
@@ -42,7 +47,7 @@ def test_agent_run_basic() -> None:
     assert "session_id" in data
 
 
-def test_agent_run_with_user_id() -> None:
+def test_agent_run_with_user_id(client: TestClient) -> None:
     response = client.post(
         "/agent/run",
         json={"input": "test query", "user_id": "user-123"},
@@ -50,7 +55,7 @@ def test_agent_run_with_user_id() -> None:
     assert response.status_code == 200
 
 
-def test_agent_run_with_session_id() -> None:
+def test_agent_run_with_session_id(client: TestClient) -> None:
     """Session ID enables thread-based memory via LangGraph checkpointer."""
     response = client.post(
         "/agent/run",
@@ -62,12 +67,12 @@ def test_agent_run_with_session_id() -> None:
     assert data["duration_ms"] >= 0
 
 
-def test_agent_run_missing_input_returns_422() -> None:
+def test_agent_run_missing_input_returns_422(client: TestClient) -> None:
     response = client.post("/agent/run", json={})
     assert response.status_code == 422
 
 
-def test_agent_run_increments_metrics() -> None:
+def test_agent_run_increments_metrics(client: TestClient) -> None:
     """Verify that calling /agent/run updates the agent_runs_total counter."""
     client.post("/agent/run", json={"input": "metrics test"})
     metrics_after = client.get("/metrics").text
diff --git a/tests/unit/test_fixes.py b/tests/unit/test_fixes.py
new file mode 100644
index 0000000..b9ed007
--- /dev/null
+++ b/tests/unit/test_fixes.py
@@ -0,0 +1,242 @@
+"""Tests for the four production fixes:
+1. Unbounded messages truncation
+2. LLM retry wrapping
+3. Planner model splitting
+4. Alembic migration is at head
+"""
+
+from __future__ import annotations
+
+import contextlib
+from unittest.mock import MagicMock
+
+import pytest
+
+# ── Fix 1: Unbounded messages ────────────────────────────────────────────────
+
+
+class TestHistoryTruncation:
+    def _make_state(self, n_turns: int):
+        from services.agent.graph.state import AgentState
+
+        msgs = []
+        for i in range(n_turns):
+            msgs.append(f"User: question {i}")
+            msgs.append(f"Assistant: answer {i}")
+        return AgentState(
+            input="latest question",
+            messages=msgs,
+            next_step=None,
+            tool_result=None,
+            final_output=None,
+        )
+
+    def test_short_history_returned_in_full(self):
+        from services.agent.graph.state import format_history  # noqa: PLC0415
+
+        state = self._make_state(3)
+        result = format_history(state)
+        assert "question 0" in result
+        assert "question 2" in result
+
+    def test_long_history_is_truncated(self):
+        from services.agent.graph.state import _MAX_HISTORY_TURNS, format_history
+
+        n_turns = _MAX_HISTORY_TURNS + 5
+        state = self._make_state(n_turns)
+        result = format_history(state)
+        # Oldest turns must be gone
+        assert "question 0" not in result
+        # Most recent turns must be present
+        assert f"question {n_turns - 1}" in result
+
+    def test_truncation_keeps_exactly_max_turns(self):
+        from services.agent.graph.state import _MAX_HISTORY_TURNS, format_history
+
+        n_turns = _MAX_HISTORY_TURNS + 3
+        state = self._make_state(n_turns)
+        result = format_history(state)
+        lines = [ln for ln in result.splitlines() if ln.strip()]
+        assert len(lines) == _MAX_HISTORY_TURNS * 2
+
+    def test_empty_history_returns_placeholder(self):
+        from services.agent.graph.state import AgentState, format_history
+
+        state = AgentState(
+            input="hi", messages=[], next_step=None, tool_result=None, final_output=None
+        )
+        assert format_history(state) == "(no prior messages)"
+
+    def test_stored_messages_unaffected(self):
+        """format_history truncates the view; it must NOT mutate state['messages']."""
+        from services.agent.graph.state import _MAX_HISTORY_TURNS, format_history
+
+        n_turns = _MAX_HISTORY_TURNS + 5
+        state = self._make_state(n_turns)
+        format_history(state)
+        assert len(state["messages"]) == n_turns * 2
+
+
+# ── Fix 2: LLM retry ────────────────────────────────────────────────────────
+
+
+class TestLLMRetry:
+    def test_get_llm_returns_runnable_with_retry(self):
+        """get_llm() result must expose .invoke() (i.e. it's a valid Runnable)."""
+        from services.agent.llm import get_llm
+
+        llm = get_llm(temperature=0, task="default")
+        assert hasattr(llm, "invoke")
+
+    def test_llm_retries_on_transient_error(self):
+        """A model that fails twice then succeeds should return the success result."""
+        call_count = 0
+
+        class FlakyLLM:
+            def invoke(self, prompt, **kwargs):
+                nonlocal call_count
+                call_count += 1
+                if call_count < 3:
+                    raise ConnectionError("transient")
+                resp = MagicMock()
+                resp.content = "success"
+                return resp
+
+            def with_retry(self, **kwargs):
+                # Return a wrapper that calls invoke up to stop_after_attempt times
+                stop = kwargs.get("stop_after_attempt", 3)
+
+                class Retried:
+                    def invoke(self, prompt, **kw):  # noqa: N805
+                        last_exc: Exception = RuntimeError("no attempts")
+                        for _ in range(stop):
+                            try:
+                                return FlakyLLM().invoke(prompt)
+                            except Exception as e:
+                                last_exc = e
+                        raise last_exc
+
+                return Retried()
+
+        flaky = FlakyLLM()
+        wrapped = flaky.with_retry(stop_after_attempt=3)
+        result = wrapped.invoke("test")
+        assert result.content == "success"
+
+    def test_llm_raises_after_all_retries_exhausted(self):
+        """If every attempt fails, the final exception must propagate."""
+
+        class AlwaysFailLLM:
+            def invoke(self, prompt, **kwargs):
+                raise RuntimeError("always fails")
+
+            def with_retry(self, stop_after_attempt=3, **kwargs):
+                stop = stop_after_attempt
+
+                class Retried:
+                    def invoke(self, prompt, **kw):  # noqa: N805
+                        for _ in range(stop):
+                            with contextlib.suppress(RuntimeError):
+                                AlwaysFailLLM().invoke(prompt)
+                        raise RuntimeError("always fails")
+
+                return Retried()
+
+        wrapped = AlwaysFailLLM().with_retry(stop_after_attempt=3)
+        with pytest.raises(RuntimeError, match="always fails"):
+            wrapped.invoke("test")
+
+
+# ── Fix 3: Planner model split ───────────────────────────────────────────────
+
+
+class TestPlannerModelSplit:
+    def test_resolved_planner_model_uses_custom_when_set(self, monkeypatch):
+        from apps.api.config import Settings
+
+        monkeypatch.setenv("LLM_PROVIDER", "litellm")
+        monkeypatch.setenv("LITELLM_MODEL", "deepseek/deepseek-chat")
+        monkeypatch.setenv("PLANNER_MODEL", "gemini/gemini-2.0-flash-lite")
+        s = Settings()
+        assert s.resolved_planner_model == "gemini/gemini-2.0-flash-lite"
+
+    def test_resolved_planner_model_falls_back_to_litellm(self, monkeypatch):
+        from apps.api.config import Settings
+
+        monkeypatch.setenv("LLM_PROVIDER", "litellm")
+        monkeypatch.setenv("LITELLM_MODEL", "deepseek/deepseek-chat")
+        monkeypatch.setenv("PLANNER_MODEL", "")
+        s = Settings()
+        assert s.resolved_planner_model == "deepseek/deepseek-chat"
+
+    def test_planner_node_calls_get_llm_with_planner_task(self, monkeypatch):
+        """Planner node must request task='planner' from the factory."""
+        captured = {}
+
+        def mock_get_llm(temperature=0.0, task="default"):
+            captured["task"] = task
+            captured["temperature"] = temperature
+            m = MagicMock()
+            m.invoke.return_value = MagicMock(content="final")
+            return m
+
+        monkeypatch.setattr("services.agent.nodes.planner.get_llm", mock_get_llm)
+
+        from langchain_core.runnables import RunnableConfig
+
+        from services.agent.graph.state import AgentState
+        from services.agent.nodes.planner import planner_node
+
+        state = AgentState(
+            input="What is LangGraph?",
+            messages=[],
+            next_step=None,
+            tool_result=None,
+            final_output=None,
+        )
+        planner_node(state, RunnableConfig())
+
+        assert captured["task"] == "planner"
+        assert captured["temperature"] == 0
+
+
+# ── Fix 4: Alembic at head ───────────────────────────────────────────────────
+
+
+class TestAlembicMigration:
+    def test_migration_script_exists(self):
+        from pathlib import Path
+
+        versions = list(Path("infra/migrations/versions").glob("*.py"))
+        assert len(versions) >= 1, "No migration scripts found"
+
+    def test_alembic_is_at_head(self):
+        """The live database must be at the latest migration revision.
+        Skipped automatically when no Postgres is available (e.g. in unit CI)."""
+        import pytest
+        from alembic.config import Config as AlembicConfig
+        from alembic.runtime.migration import MigrationContext
+        from alembic.script import ScriptDirectory
+        from sqlalchemy import create_engine
+        from sqlalchemy.exc import OperationalError
+
+        from apps.api.config import settings
+
+        sync_url = settings.database_url.replace("postgresql+asyncpg://", "postgresql://")
+        engine = create_engine(
+            sync_url, poolclass=__import__("sqlalchemy.pool", fromlist=["NullPool"]).NullPool
+        )
+        try:
+            engine.connect().close()
+        except OperationalError:
+            pytest.skip("Postgres not available — skipping DB migration check")
+
+        alembic_cfg = AlembicConfig("alembic.ini")
+        script = ScriptDirectory.from_config(alembic_cfg)
+
+        with engine.connect() as conn:
+            ctx = MigrationContext.configure(conn)
+            current = ctx.get_current_revision()
+
+        head = script.get_current_head()
+        assert current == head, f"DB is at {current!r}, expected head {head!r}"
diff --git a/uv.lock b/uv.lock
index 25e8e0e..321e0b4 100644
--- a/uv.lock
+++ b/uv.lock
@@ -13,6 +13,7 @@ source = { editable = "." }
 dependencies = [
     { name = "alembic" },
     { name = "asyncpg" },
+    { name = "ddgs" },
     { name = "duckduckgo-search" },
     { name = "fastapi" },
     { name = "httpx" },
@@ -36,6 +37,7 @@ dependencies = [
 [package.dev-dependencies]
 dev = [
     { name = "pre-commit" },
+    { name = "psycopg2-binary" },
     { name = "pyright" },
     { name = "pytest" },
     { name = "pytest-asyncio" },
@@ -47,6 +49,7 @@ dev = [
 requires-dist = [
     { name = "alembic", specifier = ">=1.14.0" },
     { name = "asyncpg", specifier = ">=0.30.0" },
+    { name = "ddgs", specifier = ">=9.14.0" },
     { name = "duckduckgo-search", specifier = ">=7.0.0" },
     { name = "fastapi", specifier = ">=0.115.0" },
     { name = "httpx", specifier = ">=0.28.0" },
@@ -54,7 +57,7 @@ requires-dist = [
     { name = "langchain-community", specifier = ">=0.3.0" },
     { name = "langchain-google-genai", specifier = ">=2.0.0" },
     { name = "langchain-openai", specifier = ">=0.3.0" },
-    { name = "langfuse", specifier = ">=2.0.0,<3.0.0" },
+    { name = "langfuse", specifier = ">=3.14.6,<4.0.0" },
     { name = "langgraph", specifier = ">=0.2.0" },
     { name = "langgraph-checkpoint-postgres", specifier = ">=3.0.5" },
     { name = "litellm", specifier = ">=1.83.7" },
@@ -70,6 +73,7 @@ requires-dist = [
 [package.metadata.requires-dev]
 dev = [
     { name = "pre-commit", specifier = ">=4.0.0" },
+    { name = "psycopg2-binary", specifier = ">=2.9.11" },
     { name = "pyright", specifier = ">=1.1.390" },
     { name = "pytest", specifier = ">=8.3.0" },
     { name = "pytest-asyncio", specifier = ">=0.24.0" },
@@ -606,6 +610,20 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/c3/be/d0d44e092656fe7a06b55e6103cbce807cdbdee17884a5367c68c9860853/dataclasses_json-0.6.7-py3-none-any.whl", hash = "sha256:0dbf33f26c8d5305befd61b39d2b3414e8a407bedc2834dea9b8d642666fb40a", size = 28686, upload-time = "2024-06-09T16:20:16.715Z" },
 ]
 
+[[package]]
+name = "ddgs"
+version = "9.14.0"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
+    { name = "click" },
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