diff --git a/surfsense_backend/app/agents/new_chat/anonymous_agent.py b/surfsense_backend/app/agents/new_chat/anonymous_agent.py
new file mode 100644
index 000000000..c783d9a45
--- /dev/null
+++ b/surfsense_backend/app/agents/new_chat/anonymous_agent.py
@@ -0,0 +1,168 @@
+"""Minimal anonymous / free-chat agent.
+
+The no-login chat experience must stay dead simple: the user asks a question
+and the model answers, optionally using ``web_search`` and an optionally
+uploaded **read-only** document. We deliberately bypass the full SurfSense deep
+agent stack (filesystem, file-intent, knowledge-base persistence, subagents,
+skills, memory) because those middlewares stage or persist "documents" that an
+anonymous session can never see again -- which produced phantom
+"I saved it to a file" answers for free users.
+
+For any other SurfSense capability the model is instructed (via the system
+prompt built here) to tell the user to create a free account instead of
+pretending to perform the action.
+"""
+
+from __future__ import annotations
+
+from datetime import UTC, datetime
+from typing import Any
+
+from deepagents.backends import StateBackend
+from langchain.agents import create_agent
+from langchain.agents.middleware import (
+    ModelCallLimitMiddleware,
+    ToolCallLimitMiddleware,
+)
+from langchain_core.language_models import BaseChatModel
+from langgraph.types import Checkpointer
+
+from app.agents.new_chat.context import SurfSenseContextSchema
+from app.agents.new_chat.middleware import (
+    RetryAfterMiddleware,
+    create_surfsense_compaction_middleware,
+)
+from app.agents.new_chat.tools.web_search import create_web_search_tool
+
+# Cap how much of an uploaded document we inline into the system prompt. The
+# upload endpoint allows files up to several MB, but the doc is re-sent on
+# every turn and counts against the anonymous token quota, so we bound it.
+_MAX_DOC_CHARS = 50_000
+
+
+def build_anonymous_system_prompt(anon_doc: dict[str, Any] | None = None) -> str:
+    """Build the system prompt for the minimal anonymous chat agent.
+
+    The prompt keeps the assistant focused on plain Q/A + web search, inlines
+    any uploaded document as read-only context, and redirects every other
+    SurfSense feature to account registration.
+    """
+    today = datetime.now(UTC).strftime("%A, %B %d, %Y")
+
+    doc_section = ""
+    if anon_doc:
+        title = str(anon_doc.get("title") or "uploaded_document")
+        content = str(anon_doc.get("content") or "")
+        truncated = content[:_MAX_DOC_CHARS]
+        truncation_note = ""
+        if len(content) > _MAX_DOC_CHARS:
+            truncation_note = (
+                "\n\n[Note: the document was truncated because it is large; "
+                "only the beginning is shown.]"
+            )
+        doc_section = (
+            "\n\n## Uploaded document (read-only)\n"
+            f'The user uploaded a document named "{title}". Its contents are '
+            "provided below for reference only. You may read it and answer "
+            "questions about it, but you cannot modify, save, or store it.\n\n"
+            f'<uploaded_document title="{title}">\n'
+            f"{truncated}{truncation_note}\n"
+            "</uploaded_document>"
+        )
+
+    return (
+        "You are SurfSense's free AI assistant, available to everyone without "
+        "login.\n\n"
+        f"Today's date is {today}.\n\n"
+        "## How to help\n"
+        "- Answer the user's questions directly and conversationally. You are "
+        "a straightforward question-and-answer assistant.\n"
+        "- When a question needs current, real-time, or factual information "
+        "from the internet (news, prices, weather, recent events, live data), "
+        "use the `web_search` tool. Otherwise, answer directly from your own "
+        "knowledge.\n"
+        "- Be concise, accurate, and helpful. Use Markdown formatting when it "
+        "improves readability."
+        f"{doc_section}\n\n"
+        "## What is not available here\n"
+        "This is the free, no-login experience. You CANNOT save files or "
+        "notes, generate reports, podcasts, resumes, presentations, or images, "
+        "search or build a knowledge base, connect to apps (Gmail, Google "
+        "Drive, Notion, Slack, Calendar, Discord, and similar), set up "
+        "automations, or remember anything across sessions.\n\n"
+        "If the user asks for any of these, do NOT pretend to do them and "
+        "never claim you saved, created, or stored anything. Instead, briefly "
+        "let them know the feature requires a free SurfSense account and "
+        "invite them to create one at https://www.surfsense.com. Then offer to "
+        "help with what you can do here (answering questions and searching the "
+        "web)."
+    )
+
+
+async def create_anonymous_chat_agent(
+    *,
+    llm: BaseChatModel,
+    checkpointer: Checkpointer,
+    anon_session_id: str | None = None,
+    anon_doc: dict[str, Any] | None = None,
+    enable_web_search: bool = True,
+):
+    """Create a minimal Q/A agent for anonymous / free chat.
+
+    Unlike :func:`create_surfsense_deep_agent`, this agent has no filesystem,
+    file-intent, knowledge-base persistence, subagent, skills, or memory
+    middleware. Its only tool is ``web_search`` (when ``enable_web_search`` is
+    True), and any uploaded document is injected into the system prompt as
+    read-only context.
+
+    Args:
+        llm: The chat model to use (already built by the caller).
+        checkpointer: LangGraph checkpointer for the ephemeral anon thread.
+        anon_session_id: Anonymous session id (used only for telemetry/metadata).
+        anon_doc: Optional ``{"title", "content"}`` for an uploaded document.
+        enable_web_search: When False, the agent runs as a pure LLM with no
+            tools (used when the user toggles web search off).
+    """
+    tools = (
+        [create_web_search_tool(search_space_id=None, available_connectors=None)]
+        if enable_web_search
+        else []
+    )
+
+    # Reliability-only middleware. Nothing here touches the database or
+    # filesystem: call limits guard against loops, compaction summarises long
+    # histories into in-graph state, and retry handles provider rate limits.
+    middleware: list[Any] = [
+        ModelCallLimitMiddleware(thread_limit=120, run_limit=80, exit_behavior="end"),
+    ]
+    if tools:
+        middleware.append(
+            ToolCallLimitMiddleware(
+                thread_limit=300, run_limit=80, exit_behavior="continue"
+            )
+        )
+    middleware.append(create_surfsense_compaction_middleware(llm, StateBackend))
+    middleware.append(RetryAfterMiddleware(max_retries=3))
+
+    system_prompt = build_anonymous_system_prompt(anon_doc)
+
+    agent = create_agent(
+        llm,
+        system_prompt=system_prompt,
+        tools=tools,
+        middleware=middleware,
+        context_schema=SurfSenseContextSchema,
+        checkpointer=checkpointer,
+    )
+    return agent.with_config(
+        {
+            "recursion_limit": 40,
+            "metadata": {
+                "ls_integration": "surfsense_anonymous_chat",
+                "anon_session_id": anon_session_id,
+            },
+        }
+    )
+
+
+__all__ = ["build_anonymous_system_prompt", "create_anonymous_chat_agent"]
diff --git a/surfsense_backend/app/automations/triggers/builtin/event/filter.py b/surfsense_backend/app/automations/triggers/builtin/event/filter.py
index 9f13cd51e..742281fc6 100644
--- a/surfsense_backend/app/automations/triggers/builtin/event/filter.py
+++ b/surfsense_backend/app/automations/triggers/builtin/event/filter.py
@@ -65,8 +65,7 @@ def _match_condition(condition: Any, actual: Any) -> bool:
         return False
     if isinstance(condition, dict):
         return all(
-            _apply_operator(op, operand, actual)
-            for op, operand in condition.items()
+            _apply_operator(op, operand, actual) for op, operand in condition.items()
         )
     return actual == condition
 
diff --git a/surfsense_backend/app/automations/triggers/builtin/event/selector.py b/surfsense_backend/app/automations/triggers/builtin/event/selector.py
index 9c000e716..ee00a6094 100644
--- a/surfsense_backend/app/automations/triggers/builtin/event/selector.py
+++ b/surfsense_backend/app/automations/triggers/builtin/event/selector.py
@@ -41,9 +41,7 @@ async def _select_and_start(event_dict: dict[str, Any]) -> None:
             await _start_one(session, trigger=trigger, event=event)
 
 
-async def _eligible(
-    session: AsyncSession, *, event: Event
-) -> list[AutomationTrigger]:
+async def _eligible(session: AsyncSession, *, event: Event) -> list[AutomationTrigger]:
     """Enabled ``event`` triggers for this event type whose filter matches."""
     stmt = select(AutomationTrigger).where(
         AutomationTrigger.type == TriggerType.EVENT,
diff --git a/surfsense_backend/app/routes/anonymous_chat_routes.py b/surfsense_backend/app/routes/anonymous_chat_routes.py
index f9d694e5a..eb952e684 100644
--- a/surfsense_backend/app/routes/anonymous_chat_routes.py
+++ b/surfsense_backend/app/routes/anonymous_chat_routes.py
@@ -351,10 +351,9 @@ async def stream_anonymous_chat(
     async def _generate():
         from langchain_core.messages import AIMessage, HumanMessage
 
-        from app.agents.new_chat.chat_deepagent import create_surfsense_deep_agent
+        from app.agents.new_chat.anonymous_agent import create_anonymous_chat_agent
         from app.agents.new_chat.checkpointer import get_checkpointer
         from app.db import shielded_async_session
-        from app.services.connector_service import ConnectorService
         from app.services.new_streaming_service import VercelStreamingService
         from app.services.token_tracking_service import start_turn
         from app.tasks.chat.stream_new_chat import StreamResult, _stream_agent_events
@@ -363,24 +362,23 @@ async def stream_anonymous_chat(
         streaming_service = VercelStreamingService()
 
         try:
-            async with shielded_async_session() as session:
-                connector_service = ConnectorService(session, search_space_id=None)
+            async with shielded_async_session():
                 checkpointer = await get_checkpointer()
 
                 anon_thread_id = f"anon-{session_id}-{request_id}"
 
-                agent = await create_surfsense_deep_agent(
+                # Load the optional uploaded document as read-only context.
+                anon_doc = await _load_anon_document(session_id)
+
+                # Minimal Q/A agent: web_search only (when enabled), no
+                # filesystem / persistence / subagents. The uploaded document
+                # is injected into the system prompt as read-only context.
+                agent = await create_anonymous_chat_agent(
                     llm=llm,
-                    search_space_id=0,
-                    db_session=session,
-                    connector_service=connector_service,
                     checkpointer=checkpointer,
-                    user_id=None,
-                    thread_id=None,
-                    agent_config=agent_config,
-                    enabled_tools=list(enabled_for_agent),
-                    disabled_tools=None,
                     anon_session_id=session_id,
+                    anon_doc=anon_doc,
+                    enable_web_search="web_search" in enabled_for_agent,
                 )
 
                 langchain_messages = []
@@ -396,7 +394,6 @@ async def stream_anonymous_chat(
 
                 input_state = {
                     "messages": langchain_messages,
-                    "search_space_id": 0,
                 }
 
                 langgraph_config = {
@@ -500,6 +497,38 @@ ANON_ALLOWED_EXTENSIONS = PLAINTEXT_EXTENSIONS | DIRECT_CONVERT_EXTENSIONS
 ANON_DOC_REDIS_PREFIX = "anon:doc:"
 
 
+async def _load_anon_document(session_id: str) -> dict[str, Any] | None:
+    """Read the anonymous session's uploaded document from Redis.
+
+    Returns ``{"title", "content"}`` for read-only injection into the agent's
+    system prompt, or ``None`` when nothing was uploaded for this session.
+    """
+    import json as _json
+
+    import redis.asyncio as aioredis
+
+    redis_client = aioredis.from_url(config.REDIS_APP_URL, decode_responses=True)
+    redis_key = f"{ANON_DOC_REDIS_PREFIX}{session_id}"
+    try:
+        data = await redis_client.get(redis_key)
+        if not data:
+            return None
+        payload = _json.loads(data)
+    except Exception as exc:  # pragma: no cover - defensive
+        logger.warning("Failed to load anonymous document from Redis: %s", exc)
+        return None
+    finally:
+        await redis_client.aclose()
+
+    content = str(payload.get("content") or "")
+    if not content:
+        return None
+    return {
+        "title": str(payload.get("filename") or "uploaded_document"),
+        "content": content,
+    }
+
+
 class AnonDocResponse(BaseModel):
     filename: str
     size_bytes: int
diff --git a/surfsense_backend/app/session_events.py b/surfsense_backend/app/session_events.py
index b2ec57fcc..048df2b46 100644
--- a/surfsense_backend/app/session_events.py
+++ b/surfsense_backend/app/session_events.py
@@ -79,9 +79,11 @@ def _after_commit(session: Session) -> None:
     ]
     for task in tasks:
         task.add_done_callback(
-            lambda t: logger.error("event publish failed: %s", t.exception())
-            if not t.cancelled() and t.exception()
-            else None
+            lambda t: (
+                logger.error("event publish failed: %s", t.exception())
+                if not t.cancelled() and t.exception()
+                else None
+            )
         )
 
 
diff --git a/surfsense_backend/tests/unit/event_bus/test_catalog.py b/surfsense_backend/tests/unit/event_bus/test_catalog.py
index cbd377b02..b09482bea 100644
--- a/surfsense_backend/tests/unit/event_bus/test_catalog.py
+++ b/surfsense_backend/tests/unit/event_bus/test_catalog.py
@@ -24,6 +24,7 @@ def _event_type(type_: str = "test.thing") -> EventType:
 
 def test_register_then_get_returns_the_event_type(isolated_event_catalog: None) -> None:
     from app.event_bus.catalog import catalog
+
     catalog.register(_event_type())
 
     assert catalog.get("test.thing") is not None
@@ -32,12 +33,14 @@ def test_register_then_get_returns_the_event_type(isolated_event_catalog: None)
 
 def test_get_unknown_type_returns_none(isolated_event_catalog: None) -> None:
     from app.event_bus.catalog import catalog
+
     assert catalog.get("does.not.exist") is None
 
 
 def test_register_duplicate_type_raises(isolated_event_catalog: None) -> None:
     """A type is a contract; registering it twice is a bug, not an override."""
     from app.event_bus.catalog import catalog
+
     catalog.register(_event_type())
 
     with pytest.raises(ValueError, match="already registered"):
@@ -47,6 +50,7 @@ def test_register_duplicate_type_raises(isolated_event_catalog: None) -> None:
 def test_all_is_a_defensive_snapshot(isolated_event_catalog: None) -> None:
     """Mutating the returned dict must not corrupt the registry."""
     from app.event_bus.catalog import catalog
+
     catalog.register(_event_type())
 
     snapshot = catalog.all()
diff --git a/surfsense_web/components/assistant-ui/inline-citation.tsx b/surfsense_web/components/assistant-ui/inline-citation.tsx
index cbf3c82d6..6a8f2e035 100644
--- a/surfsense_web/components/assistant-ui/inline-citation.tsx
+++ b/surfsense_web/components/assistant-ui/inline-citation.tsx
@@ -51,7 +51,9 @@ export const InlineCitation: FC<InlineCitationProps> = ({ chunkId, isDocsChunk =
 						doc
 					</span>
 				</TooltipTrigger>
-				<TooltipContent>{isDocsChunk ? "Documentation reference" : "Uploaded document"}</TooltipContent>
+				<TooltipContent>
+					{isDocsChunk ? "Documentation reference" : "Uploaded document"}
+				</TooltipContent>
 			</Tooltip>
 		);
 	}
diff --git a/surfsense_web/components/free-chat/free-chat-page.tsx b/surfsense_web/components/free-chat/free-chat-page.tsx
index 927eaef87..2ee026cc3 100644
--- a/surfsense_web/components/free-chat/free-chat-page.tsx
+++ b/surfsense_web/components/free-chat/free-chat-page.tsx
@@ -15,6 +15,7 @@ import {
 	type TokenUsageData,
 	TokenUsageProvider,
 } from "@/components/assistant-ui/token-usage-context";
+import { Alert, AlertDescription, AlertTitle } from "@/components/ui/alert";
 import { useAnonymousMode } from "@/contexts/anonymous-mode";
 import { TimelineDataUI } from "@/features/chat-messages/timeline";
 import {
@@ -101,11 +102,16 @@ export function FreeChatPage() {
 	const anonMode = useAnonymousMode();
 	const modelSlug = anonMode.isAnonymous ? anonMode.modelSlug : "";
 	const resetKey = anonMode.isAnonymous ? anonMode.resetKey : 0;
+	const webSearchEnabled = anonMode.isAnonymous ? anonMode.webSearchEnabled : true;
 
 	const [messages, setMessages] = useState<ThreadMessageLike[]>([]);
 	const [isRunning, setIsRunning] = useState(false);
 	const [tokenUsageStore] = useState(() => createTokenUsageStore());
 	const abortControllerRef = useRef<AbortController | null>(null);
+	// Mirror the latest messages into a ref so onNew stays a stable callback
+	// (it reads history on demand instead of depending on the array).
+	const messagesRef = useRef<ThreadMessageLike[]>([]);
+	messagesRef.current = messages;
 
 	// Turnstile CAPTCHA state
 	const [captchaRequired, setCaptchaRequired] = useState(false);
@@ -152,6 +158,7 @@ export function FreeChatPage() {
 				model_slug: modelSlug,
 				messages: messageHistory,
 			};
+			if (!webSearchEnabled) reqBody.disabled_tools = ["web_search"];
 			if (turnstileToken) reqBody.turnstile_token = turnstileToken;
 
 			const response = await fetch(`${BACKEND_URL}/api/v1/public/anon-chat/stream`, {
@@ -301,7 +308,7 @@ export function FreeChatPage() {
 				throw err;
 			}
 		},
-		[modelSlug, tokenUsageStore]
+		[modelSlug, tokenUsageStore, webSearchEnabled]
 	);
 
 	const onNew = useCallback(
@@ -345,7 +352,7 @@ export function FreeChatPage() {
 				},
 			]);
 
-			const messageHistory = messages
+			const messageHistory = messagesRef.current
 				.filter((m) => m.role === "user" || m.role === "assistant")
 				.map((m) => {
 					let text = "";
@@ -395,7 +402,7 @@ export function FreeChatPage() {
 				abortControllerRef.current = null;
 			}
 		},
-		[messages, doStream]
+		[modelSlug, anonMode, doStream]
 	);
 
 	/** Called when Turnstile resolves successfully. Stores the token and auto-retries. */
@@ -481,19 +488,21 @@ export function FreeChatPage() {
 					</div>
 
 					{captchaRequired && TURNSTILE_SITE_KEY && (
-						<div className="flex flex-col items-center gap-3 border-b border-border/40 bg-muted/30 py-4">
-							<div className="flex items-center gap-2 text-sm text-muted-foreground">
-								<ShieldCheck className="h-4 w-4" />
-								<span>Quick verification to continue chatting</span>
-							</div>
-							<Turnstile
-								ref={turnstileRef}
-								siteKey={TURNSTILE_SITE_KEY}
-								onSuccess={handleTurnstileSuccess}
-								onError={() => turnstileRef.current?.reset()}
-								onExpire={() => turnstileRef.current?.reset()}
-								options={{ theme: "auto", size: "normal" }}
-							/>
+						<div className="flex justify-center border-b bg-muted/30 px-4 py-4">
+							<Alert className="w-auto max-w-md">
+								<ShieldCheck />
+								<AlertTitle>Quick verification to continue chatting</AlertTitle>
+								<AlertDescription>
+									<Turnstile
+										ref={turnstileRef}
+										siteKey={TURNSTILE_SITE_KEY}
+										onSuccess={handleTurnstileSuccess}
+										onError={() => turnstileRef.current?.reset()}
+										onExpire={() => turnstileRef.current?.reset()}
+										options={{ theme: "auto", size: "normal" }}
+									/>
+								</AlertDescription>
+							</Alert>
 						</div>
 					)}
 
diff --git a/surfsense_web/components/free-chat/free-composer.tsx b/surfsense_web/components/free-chat/free-composer.tsx
index 943ace9aa..46d9e0259 100644
--- a/surfsense_web/components/free-chat/free-composer.tsx
+++ b/surfsense_web/components/free-chat/free-composer.tsx
@@ -6,6 +6,7 @@ import { type FC, useCallback, useRef, useState } from "react";
 import { toast } from "sonner";
 import { TooltipIconButton } from "@/components/assistant-ui/tooltip-icon-button";
 import { Button } from "@/components/ui/button";
+import { Separator } from "@/components/ui/separator";
 import { Switch } from "@/components/ui/switch";
 import { Tooltip, TooltipContent, TooltipTrigger } from "@/components/ui/tooltip";
 import { useAnonymousMode } from "@/contexts/anonymous-mode";
@@ -71,10 +72,11 @@ export const FreeComposer: FC = () => {
 	const { gate } = useLoginGate();
 	const anonMode = useAnonymousMode();
 	const [text, setText] = useState("");
-	const [webSearchEnabled, setWebSearchEnabled] = useState(true);
 	const fileInputRef = useRef<HTMLInputElement>(null);
 
 	const hasUploadedDoc = anonMode.isAnonymous && anonMode.uploadedDoc !== null;
+	const webSearchEnabled = anonMode.isAnonymous ? anonMode.webSearchEnabled : true;
+	const setWebSearchEnabled = anonMode.isAnonymous ? anonMode.setWebSearchEnabled : () => {};
 
 	const handleTextChange = useCallback(
 		(e: React.ChangeEvent<HTMLTextAreaElement>) => {
@@ -189,14 +191,11 @@ export const FreeComposer: FC = () => {
 							<Button
 								type="button"
 								variant="ghost"
+								size="sm"
 								onClick={handleUploadClick}
-								className={cn(
-									"h-auto gap-1.5 rounded-md px-2 py-1 text-xs transition-colors",
-									"text-muted-foreground hover:text-accent-foreground hover:bg-accent",
-									hasUploadedDoc && "text-primary"
-								)}
+								className={cn(hasUploadedDoc && "text-primary")}
 							>
-								<Paperclip className="size-3.5" />
+								<Paperclip data-icon="inline-start" />
 								{hasUploadedDoc ? "1/1" : "Upload"}
 							</Button>
 						</TooltipTrigger>
@@ -207,13 +206,13 @@ export const FreeComposer: FC = () => {
 						</TooltipContent>
 					</Tooltip>
 
-					<div className="h-4 w-px bg-border/60" />
+					<Separator orientation="vertical" className="h-4" />
 
 					<Tooltip>
 						<TooltipTrigger asChild>
 							<label
 								htmlFor="free-web-search-toggle"
-								className="flex items-center gap-1.5 cursor-pointer select-none rounded-md px-2 py-1 text-xs text-muted-foreground hover:text-accent-foreground hover:bg-accent transition-colors"
+								className="flex cursor-pointer select-none items-center gap-1.5 rounded-md px-2 py-1 text-xs text-muted-foreground transition-colors hover:bg-accent hover:text-accent-foreground"
 							>
 								<Globe className="size-3.5" />
 								<span className="hidden sm:inline">Web</span>
@@ -221,7 +220,6 @@ export const FreeComposer: FC = () => {
 									id="free-web-search-toggle"
 									checked={webSearchEnabled}
 									onCheckedChange={setWebSearchEnabled}
-									className="scale-75"
 								/>
 							</label>
 						</TooltipTrigger>
diff --git a/surfsense_web/components/free-chat/free-model-selector.tsx b/surfsense_web/components/free-chat/free-model-selector.tsx
index b7ae60bd3..9bf4ecee5 100644
--- a/surfsense_web/components/free-chat/free-model-selector.tsx
+++ b/surfsense_web/components/free-chat/free-model-selector.tsx
@@ -1,10 +1,18 @@
 "use client";
 
-import { Bot, Check, ChevronDown, Search } from "lucide-react";
+import { Bot, Check, ChevronDown } from "lucide-react";
 import { useRouter } from "next/navigation";
-import { useCallback, useEffect, useMemo, useRef, useState } from "react";
+import { useCallback, useEffect, useMemo, useState } from "react";
 import { Badge } from "@/components/ui/badge";
 import { Button } from "@/components/ui/button";
+import {
+	Command,
+	CommandEmpty,
+	CommandGroup,
+	CommandInput,
+	CommandItem,
+	CommandList,
+} from "@/components/ui/command";
 import { Popover, PopoverContent, PopoverTrigger } from "@/components/ui/popover";
 import { useAnonymousMode } from "@/contexts/anonymous-mode";
 import type { AnonModel } from "@/contracts/types/anonymous-chat.types";
@@ -19,21 +27,18 @@ export function FreeModelSelector({ className }: { className?: string }) {
 
 	const [open, setOpen] = useState(false);
 	const [models, setModels] = useState<AnonModel[]>([]);
-	const [searchQuery, setSearchQuery] = useState("");
-	const [focusedIndex, setFocusedIndex] = useState(-1);
-	const searchInputRef = useRef<HTMLInputElement>(null);
 
 	useEffect(() => {
-		anonymousChatApiService.getModels().then(setModels).catch(console.error);
-	}, []);
-
-	const handleOpenChange = useCallback((next: boolean) => {
-		if (next) {
-			setSearchQuery("");
-			setFocusedIndex(-1);
-			requestAnimationFrame(() => searchInputRef.current?.focus());
-		}
-		setOpen(next);
+		const controller = new AbortController();
+		anonymousChatApiService
+			.getModels()
+			.then((data) => {
+				if (!controller.signal.aborted) setModels(data);
+			})
+			.catch((err) => {
+				if (!controller.signal.aborted) console.error(err);
+			});
+		return () => controller.abort();
 	}, []);
 
 	const currentModel = useMemo(
@@ -41,22 +46,12 @@ export function FreeModelSelector({ className }: { className?: string }) {
 		[models, currentSlug]
 	);
 
+	// Free models first, premium last; immutable sort to avoid mutating state.
 	const sortedModels = useMemo(
-		() => [...models].sort((a, b) => Number(a.is_premium) - Number(b.is_premium)),
+		() => models.toSorted((a, b) => Number(a.is_premium) - Number(b.is_premium)),
 		[models]
 	);
 
-	const filteredModels = useMemo(() => {
-		if (!searchQuery.trim()) return sortedModels;
-		const q = searchQuery.toLowerCase();
-		return sortedModels.filter(
-			(m) =>
-				m.name.toLowerCase().includes(q) ||
-				m.model_name.toLowerCase().includes(q) ||
-				m.provider.toLowerCase().includes(q)
-		);
-	}, [sortedModels, searchQuery]);
-
 	const handleSelect = useCallback(
 		(model: AnonModel) => {
 			setOpen(false);
@@ -70,42 +65,15 @@ export function FreeModelSelector({ className }: { className?: string }) {
 		[currentSlug, anonMode, router]
 	);
 
-	const handleKeyDown = useCallback(
-		(e: React.KeyboardEvent<HTMLInputElement>) => {
-			const count = filteredModels.length;
-			if (count === 0) return;
-			switch (e.key) {
-				case "ArrowDown":
-					e.preventDefault();
-					setFocusedIndex((p) => (p < count - 1 ? p + 1 : 0));
-					break;
-				case "ArrowUp":
-					e.preventDefault();
-					setFocusedIndex((p) => (p > 0 ? p - 1 : count - 1));
-					break;
-				case "Enter":
-					e.preventDefault();
-					if (focusedIndex >= 0 && focusedIndex < count) {
-						handleSelect(filteredModels[focusedIndex]);
-					}
-					break;
-			}
-		},
-		[filteredModels, focusedIndex, handleSelect]
-	);
-
 	return (
-		<Popover open={open} onOpenChange={handleOpenChange}>
+		<Popover open={open} onOpenChange={setOpen}>
 			<PopoverTrigger asChild>
 				<Button
 					variant="ghost"
 					size="sm"
 					role="combobox"
 					aria-expanded={open}
-					className={cn(
-						"h-8 gap-2 px-3 text-sm bg-muted hover:bg-muted/80 border-0 select-none",
-						className
-					)}
+					className={cn("gap-2 bg-muted hover:bg-muted/80", className)}
 				>
 					{currentModel ? (
 						<>
@@ -118,90 +86,47 @@ export function FreeModelSelector({ className }: { className?: string }) {
 							<span className="text-muted-foreground">Select Model</span>
 						</>
 					)}
-					<ChevronDown className="h-3.5 w-3.5 text-muted-foreground ml-1 shrink-0" />
+					<ChevronDown className="ml-1 size-3.5 shrink-0 text-muted-foreground" />
 				</Button>
 			</PopoverTrigger>
-			<PopoverContent
-				className="w-[320px] p-0 rounded-lg shadow-lg overflow-hidden select-none"
-				align="start"
-				sideOffset={8}
-				onCloseAutoFocus={(e) => e.preventDefault()}
-			>
-				<div className="relative">
-					<Search className="absolute left-3 top-1/2 -translate-y-1/2 size-3.5 text-muted-foreground pointer-events-none" />
-					<input
-						ref={searchInputRef}
-						placeholder="Search models"
-						value={searchQuery}
-						onChange={(e) => setSearchQuery(e.target.value)}
-						onKeyDown={handleKeyDown}
-						className="w-full pl-8 pr-3 py-2.5 text-sm bg-transparent focus:outline-none placeholder:text-muted-foreground"
-					/>
-				</div>
-				<div className="overflow-y-auto max-h-[320px] py-1 space-y-0.5">
-					{filteredModels.length === 0 ? (
-						<div className="flex flex-col items-center justify-center gap-2 py-8 px-4">
-							<Search className="size-6 text-muted-foreground" />
-							<p className="text-sm text-muted-foreground">No models found</p>
-						</div>
-					) : (
-						filteredModels.map((model, index) => {
-							const isSelected = model.seo_slug === currentSlug;
-							const isFocused = focusedIndex === index;
-							return (
-								<div
-									key={model.id}
-									role="option"
-									tabIndex={0}
-									aria-selected={isSelected}
-									onClick={() => handleSelect(model)}
-									onKeyDown={(e) => {
-										if (e.key === "Enter" || e.key === " ") {
-											e.preventDefault();
-											handleSelect(model);
-										}
-									}}
-									onMouseEnter={() => setFocusedIndex(index)}
-									className={cn(
-										"group flex items-center gap-2.5 px-3 py-2 rounded-xl cursor-pointer",
-										"transition-colors duration-150 mx-2",
-										"hover:bg-accent hover:text-accent-foreground",
-										isFocused && "bg-accent text-accent-foreground",
-										isSelected && "bg-accent text-accent-foreground"
-									)}
-								>
-									<div className="shrink-0">
-										{getProviderIcon(model.provider, { className: "size-5" })}
-									</div>
-									<div className="flex-1 min-w-0">
-										<div className="flex items-center gap-1.5">
-											<span className="font-medium text-sm truncate">{model.name}</span>
-											{model.is_premium ? (
-												<Badge
-													variant="secondary"
-													className="text-[9px] px-1 py-0 h-3.5 bg-purple-100 text-purple-700 dark:bg-purple-900/50 dark:text-purple-300 border-0"
-												>
-													Premium
-												</Badge>
-											) : (
-												<Badge
-													variant="secondary"
-													className="text-[9px] px-1 py-0 h-3.5 bg-emerald-100 text-emerald-700 dark:bg-emerald-900/50 dark:text-emerald-300 border-0"
-												>
-													Free
-												</Badge>
-											)}
+			<PopoverContent className="w-[320px] p-0" align="start" sideOffset={8}>
+				<Command
+					filter={(value, search) => (value.toLowerCase().includes(search.toLowerCase()) ? 1 : 0)}
+				>
+					<CommandInput placeholder="Search models" />
+					<CommandList>
+						<CommandEmpty>No models found.</CommandEmpty>
+						<CommandGroup>
+							{sortedModels.map((model) => {
+								const isSelected = model.seo_slug === currentSlug;
+								return (
+									<CommandItem
+										key={model.id}
+										value={`${model.name} ${model.model_name} ${model.provider}`}
+										onSelect={() => handleSelect(model)}
+										className="gap-2.5"
+									>
+										<div className="shrink-0">
+											{getProviderIcon(model.provider, { className: "size-5" })}
 										</div>
-										<span className="text-xs text-muted-foreground truncate block">
-											{model.model_name}
-										</span>
-									</div>
-									{isSelected && <Check className="size-4 text-primary shrink-0" />}
-								</div>
-							);
-						})
-					)}
-				</div>
+										<div className="flex min-w-0 flex-1 flex-col">
+											<div className="flex items-center gap-1.5">
+												<span className="truncate text-sm font-medium">{model.name}</span>
+												<Badge variant={model.is_premium ? "default" : "secondary"}>
+													{model.is_premium ? "Premium" : "Free"}
+												</Badge>
+											</div>
+											<span className="block truncate text-xs text-muted-foreground">
+												{model.model_name}
+											</span>
+										</div>
+										{isSelected && <Check className="size-4 shrink-0 text-primary" />}
+									</CommandItem>
+								);
+							})}
+						</CommandGroup>
+					</CommandList>
+				</Command>
 			</PopoverContent>
 		</Popover>
 	);
diff --git a/surfsense_web/components/free-chat/free-right-panel.tsx b/surfsense_web/components/free-chat/free-right-panel.tsx
index f2b07815f..f37af6142 100644
--- a/surfsense_web/components/free-chat/free-right-panel.tsx
+++ b/surfsense_web/components/free-chat/free-right-panel.tsx
@@ -4,6 +4,14 @@ import { Lock } from "lucide-react";
 import Link from "next/link";
 import type { FC } from "react";
 import { Button } from "@/components/ui/button";
+import {
+	Empty,
+	EmptyContent,
+	EmptyDescription,
+	EmptyHeader,
+	EmptyMedia,
+	EmptyTitle,
+} from "@/components/ui/empty";
 
 interface GatedTabProps {
 	title: string;
@@ -11,16 +19,20 @@ interface GatedTabProps {
 }
 
 const GatedTab: FC<GatedTabProps> = ({ title, description }) => (
-	<div className="flex flex-col items-center justify-center gap-3 p-8 text-center">
-		<div className="rounded-full bg-muted p-3">
-			<Lock className="size-5 text-muted-foreground" />
-		</div>
-		<h3 className="text-sm font-medium">{title}</h3>
-		<p className="text-xs text-muted-foreground max-w-[200px]">{description}</p>
-		<Button size="sm" asChild>
-			<Link href="/register">Create Free Account</Link>
-		</Button>
-	</div>
+	<Empty>
+		<EmptyHeader>
+			<EmptyMedia variant="icon">
+				<Lock />
+			</EmptyMedia>
+			<EmptyTitle>{title}</EmptyTitle>
+			<EmptyDescription>{description}</EmptyDescription>
+		</EmptyHeader>
+		<EmptyContent>
+			<Button size="sm" asChild>
+				<Link href="/register">Create Free Account</Link>
+			</Button>
+		</EmptyContent>
+	</Empty>
 );
 
 export const ReportsGatedPlaceholder: FC = () => (
diff --git a/surfsense_web/components/free-chat/quota-bar.tsx b/surfsense_web/components/free-chat/quota-bar.tsx
index 0693ef539..6b2368218 100644
--- a/surfsense_web/components/free-chat/quota-bar.tsx
+++ b/surfsense_web/components/free-chat/quota-bar.tsx
@@ -2,6 +2,7 @@
 
 import { OctagonAlert, Orbit } from "lucide-react";
 import Link from "next/link";
+import { Button } from "@/components/ui/button";
 import { Progress } from "@/components/ui/progress";
 import { cn } from "@/lib/utils";
 
@@ -19,38 +20,30 @@ export function QuotaBar({ used, limit, warningThreshold, className }: QuotaBarP
 	const isExceeded = used >= limit;
 
 	return (
-		<div className={cn("space-y-1.5", className)}>
-			<div className="flex justify-between items-center text-xs">
+		<div className={cn("flex flex-col gap-1.5", className)}>
+			<div className="flex items-center justify-between text-xs">
 				<span className="text-muted-foreground">
 					{used.toLocaleString()} / {limit.toLocaleString()} tokens
 				</span>
 				{isExceeded ? (
-					<span className="font-medium text-red-500">Limit reached</span>
+					<span className="font-medium text-destructive">Limit reached</span>
 				) : isWarning ? (
-					<span className="font-medium text-amber-500 flex items-center gap-1">
-						<OctagonAlert className="h-3 w-3" />
+					<span className="flex items-center gap-1 font-medium text-highlight">
+						<OctagonAlert className="size-3" />
 						{remaining.toLocaleString()} remaining
 					</span>
 				) : (
 					<span className="font-medium">{percentage.toFixed(0)}%</span>
 				)}
 			</div>
-			<Progress
-				value={percentage}
-				className={cn(
-					"h-1.5",
-					isExceeded && "[&>div]:bg-red-500",
-					isWarning && !isExceeded && "[&>div]:bg-amber-500"
-				)}
-			/>
+			<Progress value={percentage} className="h-1.5" />
 			{isExceeded && (
-				<Link
-					href="/register"
-					className="flex items-center justify-center gap-1.5 rounded-md bg-linear-to-r from-purple-600 to-blue-600 px-3 py-1.5 text-xs font-medium text-white transition-opacity hover:opacity-90"
-				>
-					<Orbit className="h-3 w-3" />
-					Create free account for 5M more tokens
-				</Link>
+				<Button asChild size="sm" className="mt-0.5 w-full">
+					<Link href="/register">
+						<Orbit data-icon="inline-start" />
+						Create free account for 5M more tokens
+					</Link>
+				</Button>
 			)}
 		</div>
 	);
diff --git a/surfsense_web/components/free-chat/quota-warning-banner.tsx b/surfsense_web/components/free-chat/quota-warning-banner.tsx
index 828e8006e..e6aa89d42 100644
--- a/surfsense_web/components/free-chat/quota-warning-banner.tsx
+++ b/surfsense_web/components/free-chat/quota-warning-banner.tsx
@@ -3,6 +3,7 @@
 import { OctagonAlert, Orbit, X } from "lucide-react";
 import Link from "next/link";
 import { useState } from "react";
+import { Alert, AlertDescription, AlertTitle } from "@/components/ui/alert";
 import { Button } from "@/components/ui/button";
 import { cn } from "@/lib/utils";
 
@@ -27,61 +28,46 @@ export function QuotaWarningBanner({
 
 	if (isExceeded) {
 		return (
-			<div
-				className={cn(
-					"rounded-lg border border-red-200 bg-red-50 dark:border-red-800 dark:bg-red-950/50 p-4",
-					className
-				)}
-			>
-				<div className="flex items-start gap-3">
-					<OctagonAlert className="h-5 w-5 text-red-500 shrink-0 mt-0.5" />
-					<div className="flex-1 space-y-2">
-						<p className="text-sm font-medium text-red-800 dark:text-red-200">
-							Free token limit reached
-						</p>
-						<p className="text-xs text-red-600 dark:text-red-300">
-							You&apos;ve used all {limit.toLocaleString()} free tokens. Create a free account to
-							get $5 of premium credit and access to all models.
-						</p>
-						<Link
-							href="/register"
-							className="inline-flex items-center gap-1.5 rounded-md bg-linear-to-r from-purple-600 to-blue-600 px-4 py-2 text-sm font-medium text-white transition-opacity hover:opacity-90"
-						>
-							<Orbit className="h-4 w-4" />
+			<Alert variant="destructive" className={className}>
+				<OctagonAlert />
+				<AlertTitle>Free token limit reached</AlertTitle>
+				<AlertDescription>
+					<p>
+						You&apos;ve used all {limit.toLocaleString()} free tokens. Create a free account to get
+						$5 of premium credit and access to all models.
+					</p>
+					<Button asChild size="sm" className="mt-1">
+						<Link href="/register">
+							<Orbit data-icon="inline-start" />
 							Create Free Account
 						</Link>
-					</div>
-				</div>
-			</div>
+					</Button>
+				</AlertDescription>
+			</Alert>
 		);
 	}
 
 	return (
-		<div
-			className={cn(
-				"rounded-lg border border-amber-200 bg-amber-50 dark:border-amber-800 dark:bg-amber-950/50 p-3",
-				className
-			)}
-		>
-			<div className="flex items-center gap-3">
-				<OctagonAlert className="h-4 w-4 text-amber-500 shrink-0" />
-				<p className="flex-1 text-xs text-amber-700 dark:text-amber-300">
-					You&apos;ve used {used.toLocaleString()} of {limit.toLocaleString()} free tokens.{" "}
-					<Link href="/register" className="font-medium underline hover:no-underline">
-						Create an account
-					</Link>{" "}
-					for $5 of premium credit.
-				</p>
-				<Button
-					type="button"
-					variant="ghost"
-					size="icon"
-					onClick={() => setDismissed(true)}
-					className="size-6 text-amber-400 hover:bg-transparent hover:text-amber-600 dark:hover:text-amber-200"
-				>
-					<X className="h-4 w-4" />
-				</Button>
-			</div>
-		</div>
+		<Alert variant="warning" className={cn("pr-10", className)}>
+			<OctagonAlert />
+			<AlertTitle>Running low on free tokens</AlertTitle>
+			<AlertDescription>
+				You&apos;ve used {used.toLocaleString()} of {limit.toLocaleString()} free tokens.{" "}
+				<Link href="/register" className="font-medium underline hover:no-underline">
+					Create an account
+				</Link>{" "}
+				for $5 of premium credit.
+			</AlertDescription>
+			<Button
+				type="button"
+				variant="ghost"
+				size="icon"
+				onClick={() => setDismissed(true)}
+				aria-label="Dismiss"
+				className="absolute top-2 right-2 size-6"
+			>
+				<X />
+			</Button>
+		</Alert>
 	);
 }
diff --git a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
index 881fbe2b0..a90d6b32e 100644
--- a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
+++ b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
@@ -89,10 +89,7 @@ const DesktopLocalTabContent = dynamic(
 	{ ssr: false }
 );
 
-const NON_DELETABLE_DOCUMENT_TYPES: readonly string[] = [
-	"USER_MEMORY",
-	"TEAM_MEMORY",
-];
+const NON_DELETABLE_DOCUMENT_TYPES: readonly string[] = ["USER_MEMORY", "TEAM_MEMORY"];
 const MEMORY_DOCUMENTS: DocumentNodeDoc[] = [
 	{
 		id: -1001,
diff --git a/surfsense_web/components/new-chat/document-mention-picker.tsx b/surfsense_web/components/new-chat/document-mention-picker.tsx
index 769327e1e..43a5cad74 100644
--- a/surfsense_web/components/new-chat/document-mention-picker.tsx
+++ b/surfsense_web/components/new-chat/document-mention-picker.tsx
@@ -220,13 +220,7 @@ export const DocumentMentionPicker = forwardRef<
 	DocumentMentionPickerRef,
 	DocumentMentionPickerProps
 >(function DocumentMentionPicker(
-	{
-		searchSpaceId,
-		onSelectionChange,
-		onDone,
-		initialSelectedDocuments = [],
-		externalSearch = "",
-	},
+	{ searchSpaceId, onSelectionChange, onDone, initialSelectedDocuments = [], externalSearch = "" },
 	ref
 ) {
 	const search = externalSearch;
diff --git a/surfsense_web/components/ui/empty.tsx b/surfsense_web/components/ui/empty.tsx
new file mode 100644
index 000000000..79145502f
--- /dev/null
+++ b/surfsense_web/components/ui/empty.tsx
@@ -0,0 +1,94 @@
+import { cva, type VariantProps } from "class-variance-authority";
+
+import { cn } from "@/lib/utils";
+
+function Empty({ className, ...props }: React.ComponentProps<"div">) {
+	return (
+		<div
+			data-slot="empty"
+			className={cn(
+				"flex min-w-0 flex-1 flex-col items-center justify-center gap-6 rounded-lg border-dashed p-6 text-center text-balance md:p-12",
+				className
+			)}
+			{...props}
+		/>
+	);
+}
+
+function EmptyHeader({ className, ...props }: React.ComponentProps<"div">) {
+	return (
+		<div
+			data-slot="empty-header"
+			className={cn("flex max-w-sm flex-col items-center gap-2 text-center", className)}
+			{...props}
+		/>
+	);
+}
+
+const emptyMediaVariants = cva(
+	"mb-2 flex shrink-0 items-center justify-center [&_svg]:pointer-events-none [&_svg]:shrink-0",
+	{
+		variants: {
+			variant: {
+				default: "bg-transparent",
+				icon: "flex size-10 shrink-0 items-center justify-center rounded-lg bg-muted text-foreground [&_svg:not([class*='size-'])]:size-6",
+			},
+		},
+		defaultVariants: {
+			variant: "default",
+		},
+	}
+);
+
+function EmptyMedia({
+	className,
+	variant = "default",
+	...props
+}: React.ComponentProps<"div"> & VariantProps<typeof emptyMediaVariants>) {
+	return (
+		<div
+			data-slot="empty-icon"
+			data-variant={variant}
+			className={cn(emptyMediaVariants({ variant, className }))}
+			{...props}
+		/>
+	);
+}
+
+function EmptyTitle({ className, ...props }: React.ComponentProps<"div">) {
+	return (
+		<div
+			data-slot="empty-title"
+			className={cn("text-lg font-medium tracking-tight", className)}
+			{...props}
+		/>
+	);
+}
+
+function EmptyDescription({ className, ...props }: React.ComponentProps<"p">) {
+	return (
+		<div
+			data-slot="empty-description"
+			className={cn(
+				"text-sm/relaxed text-muted-foreground [&>a]:underline [&>a]:underline-offset-4 [&>a:hover]:text-primary",
+				className
+			)}
+			{...props}
+		/>
+	);
+}
+
+function EmptyContent({ className, ...props }: React.ComponentProps<"div">) {
+	return (
+		<div
+			data-slot="empty-content"
+			className={cn(
+				"flex w-full max-w-sm min-w-0 flex-col items-center gap-4 text-sm text-balance",
+				className
+			)}
+			{...props}
+		/>
+	);
+}
+
+export { Empty, EmptyHeader, EmptyTitle, EmptyDescription, EmptyContent, EmptyMedia };
diff --git a/surfsense_web/contexts/anonymous-mode.tsx b/surfsense_web/contexts/anonymous-mode.tsx
index eaf0996c3..c24a5cb1b 100644
--- a/surfsense_web/contexts/anonymous-mode.tsx
+++ b/surfsense_web/contexts/anonymous-mode.tsx
@@ -9,6 +9,8 @@ export interface AnonymousModeContextValue {
 	setModelSlug: (slug: string) => void;
 	uploadedDoc: { filename: string; sizeBytes: number } | null;
 	setUploadedDoc: (doc: { filename: string; sizeBytes: number } | null) => void;
+	webSearchEnabled: boolean;
+	setWebSearchEnabled: (enabled: boolean) => void;
 	resetKey: number;
 	resetChat: () => void;
 }
@@ -34,6 +36,7 @@ export function AnonymousModeProvider({
 	const [uploadedDoc, setUploadedDoc] = useState<{ filename: string; sizeBytes: number } | null>(
 		null
 	);
+	const [webSearchEnabled, setWebSearchEnabled] = useState(true);
 	const [resetKey, setResetKey] = useState(0);
 
 	const resetChat = () => setResetKey((k) => k + 1);
@@ -56,10 +59,12 @@ export function AnonymousModeProvider({
 			setModelSlug,
 			uploadedDoc,
 			setUploadedDoc,
+			webSearchEnabled,
+			setWebSearchEnabled,
 			resetKey,
 			resetChat,
 		}),
-		[modelSlug, uploadedDoc, resetKey]
+		[modelSlug, uploadedDoc, webSearchEnabled, resetKey]
 	);
 
 	return <AnonymousModeContext.Provider value={value}>{children}</AnonymousModeContext.Provider>;