improved chat ui

src/App.tsx

@@ -5,7 +5,8 @@ import { EmbedAuthWrapper } from './components/EmbedAuthWrapper';
 import { CriticalView } from './views/CriticalView';
 import { AuthCallback } from './components/Auth';
 import { pb } from './lib/pocketbase';
-import { initStore, setStore } from './store';
+import { initStore, setStore, store, appendAIHelpTipHistory } from './store';
+import { generateAIHelpTip, hasFireworksApiKey } from './lib/ai-help';
 
 // const CriticalView = lazy(() => import('./views/CriticalView').then(m => ({ default: m.CriticalView })));
 const UrgencyView = lazy(() => import('./views/UrgencyView').then(m => ({ default: m.UrgencyView })));
@@ -27,6 +28,8 @@ const App: Component = () => {
   const [isAuthenticated, setIsAuthenticated] = createSignal(pb.authStore.isValid);
   const [location, setLocation] = createSignal(window.location.href);
   const [isDesktop, setIsDesktop] = createSignal(window.matchMedia("(min-width: 768px)").matches);
+  const [aiHelpTip, setAiHelpTip] = createSignal<string | null>(null);
+  const [hasRequestedSessionTip, setHasRequestedSessionTip] = createSignal(false);
 
   createEffect(() => {
     const view = currentView();
@@ -39,6 +42,25 @@ const App: Component = () => {
     currentView() === "help_ai" && isDesktop() ? lastNonAIView() : currentView()
   );
 
+  createEffect(() => {
+    const ready = isAuthenticated() && isDesktop() && !store.isInitializing;
+    if (!ready) return;
+    if (!hasFireworksApiKey()) return;
+    if (hasRequestedSessionTip()) return;
+
+    setHasRequestedSessionTip(true);
+    void (async () => {
+      try {
+        const nextTip = await generateAIHelpTip(store.aiHelpTipHistory);
+        if (!nextTip) return;
+        setAiHelpTip(nextTip);
+        await appendAIHelpTipHistory(nextTip);
+      } catch (err) {
+        console.error("Failed to generate AI help tip", err);
+      }
+    })();
+  });
+
   onMount(() => {
     const mediaQuery = window.matchMedia("(min-width: 768px)");
     const openHelpGuide = (sectionId?: string) => {
@@ -81,6 +103,8 @@ const App: Component = () => {
     const removeListener = pb.authStore.onChange((token) => {
       const wasAuthenticated = isAuthenticated();
       setIsAuthenticated(!!token);
+      setHasRequestedSessionTip(false);
+      setAiHelpTip(null);
 
       if (token && (isFirstRun || !wasAuthenticated)) {
         initStore();
@@ -155,6 +179,7 @@ const App: Component = () => {
                         setView={setCurrentView}
                         isAIHelpOpen={currentView() === "help_ai" && isDesktop()}
                         onToggleAIHelp={() => setCurrentView(currentView() === "help_ai" ? lastNonAIView() : "help_ai")}
+                        aiHelpTip={aiHelpTip()}
                         hideQuickEntry={currentView() === "help_ai" && !isDesktop()}
                     >
                         <Suspense fallback={<div class="flex items-center justify-center h-full"><div class="animate-spin rounded-full h-8 w-8 border-b-2 border-primary"></div></div>}>

src/components/AIHelpPanel.tsx

@@ -1,30 +1,16 @@
 import { type Component, For, Show, createEffect, createMemo, createSignal } from "solid-js";
-import { Bot, LoaderCircle, RefreshCw, Send } from "lucide-solid";
+import { MessageCircle, LoaderCircle, RefreshCw, Send } from "lucide-solid";
 import { Button } from "@/components/ui/button";
 import { cn } from "@/lib/utils";
-import { FIREWORKS_API_KEY, FIREWORKS_API_URL, FIREWORKS_HELP_MODEL } from "@/lib/app-config";
+import { FIREWORKS_HELP_MODEL } from "@/lib/app-config";
-import helpGuide from "../../docs/HELP_GUIDE.md?raw";
+import { askAIHelp, hasFireworksApiKey } from "@/lib/ai-help";
+import { MarkdownMessage } from "./MarkdownMessage";
 
 type ChatMessage = {
     role: "user" | "assistant";
     content: string;
 };
 
-const SYSTEM_PROMPT = `You are the TasGrid AI Help assistant.
-
-You answer questions about TasGrid using the reference guide below.
-
-You must follow this instruction exactly: "use only this guide for all information and never assume you know something that isn't mentioned in the guide"
-
-If the guide does not contain the answer, say that the guide does not mention it.
-Do not use outside product knowledge.
-Do not invent buttons, workflows, settings, or behaviors.
-Prefer concise, practical answers.
-When helpful, mention the relevant section name from the guide.
-
-TASGRID REFERENCE GUIDE
-${helpGuide}`;
-
 const SUGGESTED_PROMPTS = [
     "How does sharing work in TasGrid?",
     "What is the difference between Handoff and Collaborative?",
@@ -33,7 +19,7 @@ const SUGGESTED_PROMPTS = [
     "How do recurrence and templates behave?"
 ];
 
-const INITIAL_MESSAGE = "Ask about TasGrid features, workflows, or edge cases. I only answer from the reference guide, so if the guide does not mention something, I will tell you.";
+const INITIAL_MESSAGE = "Ask a question about how TasGrid works.";
 
 export const AIHelpPanel: Component<{
     variant?: "page" | "sidebar";
@@ -48,7 +34,10 @@ export const AIHelpPanel: Component<{
     const [error, setError] = createSignal<string | null>(null);
     let messagesViewport: HTMLDivElement | undefined;
 
-    const hasApiKey = createMemo(() => FIREWORKS_API_KEY.trim().length > 0);
+    const hasApiKey = createMemo(() => hasFireworksApiKey());
+    const showSuggestions = createMemo(() =>
+        hasApiKey() && messages().length === 1 && messages()[0]?.role === "assistant"
+    );
 
     createEffect(() => {
         messages();
@@ -79,7 +68,7 @@ export const AIHelpPanel: Component<{
                 ...nextMessages,
                 {
                     role: "assistant",
-                    content: "AI Help is not configured yet. Add `VITE_FIREWORKS_API_KEY` to the app environment to enable Fireworks responses."
+                    content: "Questions are not configured yet. Add `VITE_FIREWORKS_API_KEY` to the app environment to enable responses."
                 }
             ]);
             setIsLoading(false);
@@ -87,39 +76,7 @@ export const AIHelpPanel: Component<{
         }
 
         try {
-            const response = await fetch(FIREWORKS_API_URL, {
+            const assistantText = await askAIHelp(nextMessages);
-                method: "POST",
-                headers: {
-                    "Content-Type": "application/json",
-                    "Authorization": `Bearer ${FIREWORKS_API_KEY}`
-                },
-                body: JSON.stringify({
-                    model: FIREWORKS_HELP_MODEL,
-                    reasoning_effort: "low",
-                    temperature: 0.2,
-                    max_tokens: 700,
-                    messages: [
-                        { role: "system", content: SYSTEM_PROMPT },
-                        ...nextMessages.map(message => ({
-                            role: message.role,
-                            content: message.content
-                        }))
-                    ]
-                })
-            });
-
-            if (!response.ok) {
-                const bodyText = await response.text();
-                throw new Error(bodyText || `Request failed with status ${response.status}`);
-            }
-
-            const data = await response.json();
-            const assistantText = data?.choices?.[0]?.message?.content?.trim();
-
-            if (!assistantText) {
-                throw new Error("The help assistant did not return any text.");
-            }
-
             setMessages(prev => [...prev, { role: "assistant", content: assistantText }]);
         } catch (err) {
             const message = err instanceof Error ? err.message : "Unknown error";
@@ -159,8 +116,8 @@ export const AIHelpPanel: Component<{
                 isSidebar() ? "px-3 py-3" : "px-4 py-4 sm:px-5"
             )}>
                 <div class="flex items-center gap-2 min-w-0">
-                    <Bot size={16} class="text-primary shrink-0" />
+                    <MessageCircle size={16} class="text-primary shrink-0" />
-                    <h1 class={cn("font-semibold tracking-tight", isSidebar() ? "text-sm" : "text-lg")}>AI Help</h1>
+                    <h1 class={cn("font-semibold tracking-tight", isSidebar() ? "text-sm" : "text-lg")}>Ask Questions</h1>
                 </div>
                 <Button
                     variant="ghost"
@@ -177,32 +134,12 @@ export const AIHelpPanel: Component<{
                 "flex min-h-0 flex-1 flex-col",
                 isSidebar() ? "p-3 gap-3" : "p-4 gap-3 sm:p-5"
             )}>
-                <Show
+                <Show when={!hasApiKey()}>
-                    when={hasApiKey()}
+                    <div class={cn(
-                    fallback={
+                        "rounded-2xl border border-amber-500/30 bg-amber-500/10",
-                        <div class={cn(
+                        isSidebar() ? "p-3 text-[0.75rem]" : "p-4 text-sm"
-                            "rounded-2xl border border-amber-500/30 bg-amber-500/10",
+                    )}>
-                            isSidebar() ? "p-3 text-[0.75rem]" : "p-4 text-sm"
+                        Add `VITE_FIREWORKS_API_KEY` to enable Ask Questions. The view is wired to Fireworks model `{FIREWORKS_HELP_MODEL}`.
-                        )}>
-                            Add `VITE_FIREWORKS_API_KEY` to enable AI Help. The view is wired to Fireworks model `{FIREWORKS_HELP_MODEL}`.
-                        </div>
-                    }
-                >
-                    <div class="flex flex-wrap gap-2">
-                        <For each={SUGGESTED_PROMPTS}>
-                            {(prompt) => (
-                                <button
-                                    class={cn(
-                                        "rounded-full border border-border bg-background text-left font-medium text-foreground transition-colors hover:bg-muted",
-                                        isSidebar() ? "px-2.5 py-1.5 text-[0.6875rem]" : "px-3 py-2 text-xs sm:text-sm"
-                                    )}
-                                    onClick={() => void submitQuestion(prompt)}
-                                    disabled={isLoading()}
-                                >
-                                    {prompt}
-                                </button>
-                            )}
-                        </For>
                     </div>
                 </Show>
 
@@ -215,24 +152,51 @@ export const AIHelpPanel: Component<{
                 >
                     <For each={messages()}>
                         {(message) => (
-                            <div class={cn("flex", message.role === "user" ? "justify-end" : "justify-start")}>
+                            <div class="space-y-2">
-                                <div
+                                <div class={cn("flex", message.role === "user" ? "justify-end" : "justify-start")}>
-                                    class={cn(
+                                    <div
-                                        "rounded-2xl px-4 py-3 leading-relaxed whitespace-pre-wrap shadow-sm",
+                                        class={cn(
-                                        isSidebar() ? "max-w-[92%] text-[0.75rem]" : "max-w-[90%] sm:max-w-[80%] text-sm",
+                                            "rounded-2xl px-4 py-3 leading-relaxed whitespace-pre-wrap shadow-sm",
-                                        message.role === "user"
+                                            isSidebar() ? "max-w-[92%]" : "max-w-[90%] sm:max-w-[80%]",
-                                            ? "bg-primary text-primary-foreground"
+                                            message.role === "user"
-                                            : "bg-card border border-border text-foreground"
+                                                ? "bg-primary text-primary-foreground"
-                                    )}
+                                                : "bg-card border border-border text-foreground"
-                                >
+                                        )}
-                                    <div class="mb-1 flex items-center gap-2 text-[0.625rem] font-black uppercase tracking-[0.18em] opacity-70">
+                                    >
-                                        <Show when={message.role === "assistant"} fallback={<span>You</span>}>
+                                        <div class="mb-1 flex items-center gap-2 text-[0.625rem] font-black uppercase tracking-[0.18em] opacity-70">
-                                            <Bot size={12} />
+                                            <Show when={message.role === "assistant"} fallback={<span>You</span>}>
-                                            <span>Guide Assistant</span>
+                                                <MessageCircle size={12} />
-                                        </Show>
+                                                <span>TasGrid Help</span>
+                                            </Show>
+                                        </div>
+                                        <MarkdownMessage
+                                            content={message.content}
+                                            class={cn(
+                                                message.role === "user"
+                                                    ? "prose-invert prose-headings:text-primary-foreground prose-p:text-primary-foreground prose-strong:text-primary-foreground prose-code:bg-primary-foreground/15 prose-code:text-primary-foreground prose-a:text-primary-foreground prose-blockquote:text-primary-foreground"
+                                                    : ""
+                                            )}
+                                        />
                                     </div>
-                                    <div>{message.content}</div>
                                 </div>
+                                <Show when={showSuggestions() && message.role === "assistant"}>
+                                    <div class={cn("flex flex-wrap gap-2", isSidebar() ? "pl-1" : "pl-1")}>
+                                        <For each={SUGGESTED_PROMPTS}>
+                                            {(prompt) => (
+                                                <button
+                                                    class={cn(
+                                                        "rounded-full border border-border bg-card text-left font-medium text-foreground transition-colors hover:bg-muted",
+                                                        isSidebar() ? "px-2.5 py-1.5 text-[0.6875rem]" : "px-3 py-2 text-xs sm:text-sm"
+                                                    )}
+                                                    onClick={() => void submitQuestion(prompt)}
+                                                    disabled={isLoading()}
+                                                >
+                                                    {prompt}
+                                                </button>
+                                            )}
+                                        </For>
+                                    </div>
+                                </Show>
                             </div>
                         )}
                     </For>
@@ -241,15 +205,15 @@ export const AIHelpPanel: Component<{
                         <div class="flex justify-start">
                             <div class={cn(
                                 "rounded-2xl px-4 py-3 leading-relaxed shadow-sm bg-card border border-border text-foreground",
-                                isSidebar() ? "max-w-[92%] text-[0.75rem]" : "max-w-[80%] text-sm"
+                                isSidebar() ? "max-w-[92%] text-sm" : "max-w-[80%] text-sm"
                             )}>
                                 <div class="mb-1 flex items-center gap-2 text-[0.625rem] font-black uppercase tracking-[0.18em] opacity-70">
-                                    <Bot size={12} />
+                                    <MessageCircle size={12} />
-                                    <span>Guide Assistant</span>
+                                    <span>TasGrid Help</span>
                                 </div>
                                 <div class="flex items-center gap-2 text-muted-foreground">
                                     <LoaderCircle size={14} class="animate-spin" />
-                                    Looking through the guide...
+                                    Finding an answer...
                                 </div>
                             </div>
                         </div>
@@ -282,7 +246,7 @@ export const AIHelpPanel: Component<{
                         placeholder="Ask how a TasGrid feature works, what a setting does, or why something may behave a certain way..."
                         class={cn(
                             "flex w-full rounded-xl border border-input bg-background transition-colors placeholder:text-muted-foreground/60 focus-visible:outline-none focus-visible:ring-1 focus-visible:ring-ring resize-none leading-relaxed",
-                            isSidebar() ? "min-h-[88px] px-3 py-2.5 text-[0.75rem]" : "min-h-[96px] px-3 py-2.5 text-sm"
+                            isSidebar() ? "min-h-[88px] px-3 py-2.5 text-sm" : "min-h-[96px] px-3 py-2.5 text-sm"
                         )}
                     />
                     <div class={cn(
@@ -295,7 +259,7 @@ export const AIHelpPanel: Component<{
                             disabled={isLoading() || !input().trim()}
                         >
                             <Send size={14} />
-                            Ask AI Help
+                            Ask Question
                         </Button>
                     </div>
                 </form>

src/components/Layout.tsx

@@ -17,6 +17,7 @@ interface LayoutProps {
     setView: (v: string) => void;
     isAIHelpOpen?: boolean;
     onToggleAIHelp?: () => void;
+    aiHelpTip?: string | null;
     hideQuickEntry?: boolean;
 }
 
@@ -116,6 +117,7 @@ export const Layout: Component<LayoutProps> = (props) => {
                             setView={props.setView}
                             isAIHelpOpen={!!props.isAIHelpOpen}
                             onToggleAIHelp={() => props.onToggleAIHelp?.()}
+                            aiHelpTip={props.aiHelpTip}
                             isLocked={isSidebarLocked()}
                             setIsLocked={setIsSidebarLocked}
                             isPeeking={isSidebarPeeking()}

src/components/MarkdownMessage.tsx

@@ -0,0 +1,111 @@
+import { type Component, createMemo } from "solid-js";
+import { cn } from "@/lib/utils";
+
+const escapeHtml = (value: string) =>
+    value
+        .replace(/&/g, "&")
+        .replace(/</g, "&lt;")
+        .replace(/>/g, "&gt;")
+        .replace(/"/g, "&quot;")
+        .replace(/'/g, "&#39;");
+
+const applyInlineMarkdown = (value: string) => {
+    let text = escapeHtml(value);
+
+    text = text.replace(/`([^`]+)`/g, "<code>$1</code>");
+    text = text.replace(/\[([^\]]+)\]\((https?:\/\/[^\s)]+)\)/g, '<a href="$2" target="_blank" rel="noreferrer">$1</a>');
+    text = text.replace(/\*\*([^*]+)\*\*/g, "<strong>$1</strong>");
+    text = text.replace(/(^|[\s(])\*([^*]+)\*(?=[\s).,!?:;]|$)/g, '$1<em>$2</em>');
+
+    return text;
+};
+
+const renderMarkdown = (markdown: string) => {
+    const lines = markdown.replace(/\r\n/g, "\n").split("\n");
+    const html: string[] = [];
+    let i = 0;
+
+    while (i < lines.length) {
+        const line = lines[i];
+        const trimmed = line.trim();
+
+        if (!trimmed) {
+            i += 1;
+            continue;
+        }
+
+        if (trimmed.startsWith("```")) {
+            const codeLines: string[] = [];
+            i += 1;
+            while (i < lines.length && !lines[i].trim().startsWith("```")) {
+                codeLines.push(lines[i]);
+                i += 1;
+            }
+            if (i < lines.length) i += 1;
+            html.push(`<pre><code>${escapeHtml(codeLines.join("\n"))}</code></pre>`);
+            continue;
+        }
+
+        if (/^[-*]\s+/.test(trimmed)) {
+            const items: string[] = [];
+            while (i < lines.length && /^[-*]\s+/.test(lines[i].trim())) {
+                items.push(`<li>${applyInlineMarkdown(lines[i].trim().replace(/^[-*]\s+/, ""))}</li>`);
+                i += 1;
+            }
+            html.push(`<ul>${items.join("")}</ul>`);
+            continue;
+        }
+
+        if (/^\d+\.\s+/.test(trimmed)) {
+            const items: string[] = [];
+            while (i < lines.length && /^\d+\.\s+/.test(lines[i].trim())) {
+                items.push(`<li>${applyInlineMarkdown(lines[i].trim().replace(/^\d+\.\s+/, ""))}</li>`);
+                i += 1;
+            }
+            html.push(`<ol>${items.join("")}</ol>`);
+            continue;
+        }
+
+        if (/^>\s?/.test(trimmed)) {
+            const quoteLines: string[] = [];
+            while (i < lines.length && /^>\s?/.test(lines[i].trim())) {
+                quoteLines.push(applyInlineMarkdown(lines[i].trim().replace(/^>\s?/, "")));
+                i += 1;
+            }
+            html.push(`<blockquote><p>${quoteLines.join("<br />")}</p></blockquote>`);
+            continue;
+        }
+
+        const paragraphLines: string[] = [];
+        while (i < lines.length && lines[i].trim() && !lines[i].trim().startsWith("```") && !/^[-*]\s+/.test(lines[i].trim()) && !/^\d+\.\s+/.test(lines[i].trim()) && !/^>\s?/.test(lines[i].trim())) {
+            paragraphLines.push(applyInlineMarkdown(lines[i].trim()));
+            i += 1;
+        }
+        html.push(`<p>${paragraphLines.join("<br />")}</p>`);
+    }
+
+    return html.join("");
+};
+
+export const MarkdownMessage: Component<{
+    content: string;
+    class?: string;
+}> = (props) => {
+    const html = createMemo(() => renderMarkdown(props.content));
+
+    return (
+        <div
+            class={cn(
+                "prose prose-sm dark:prose-invert max-w-none",
+                "prose-p:my-2 prose-ul:my-2 prose-ol:my-2 prose-li:my-0",
+                "prose-pre:my-3 prose-pre:rounded-lg prose-pre:bg-muted prose-pre:p-3",
+                "prose-code:rounded prose-code:bg-muted prose-code:px-1 prose-code:py-0.5 prose-code:text-[0.9em]",
+                "prose-code:before:content-none prose-code:after:content-none",
+                "prose-a:text-primary prose-a:underline prose-a:underline-offset-4",
+                "prose-blockquote:border-l-4 prose-blockquote:border-primary prose-blockquote:pl-4 prose-blockquote:italic",
+                props.class
+            )}
+            innerHTML={html()}
+        />
+    );
+};

src/components/Navigation.tsx

@@ -1,5 +1,5 @@
 import { type Component, For, Show } from "solid-js";
-import { LayoutDashboard, ListTodo, Settings, Clock, ArrowUpCircle, PanelLeftClose, Snowflake, Pickaxe, ChevronDown, Gauge, TrendingUp, Users, Box, BarChart3, HelpCircle, Bot } from "lucide-solid";
+import { LayoutDashboard, ListTodo, Settings, Clock, ArrowUpCircle, PanelLeftClose, Snowflake, Pickaxe, ChevronDown, Gauge, TrendingUp, Users, Box, BarChart3, HelpCircle, MessageCircle } from "lucide-solid";
 import { cn } from "@/lib/utils";
 import { Button } from "./ui/button";
 import { Popover, PopoverContent, PopoverTrigger } from "@/components/ui/popover";
@@ -42,7 +42,6 @@ const mobileNavGroups: MobileNavGroup[] = [
             { icon: LayoutDashboard, label: "Matrix", view: "matrix" },
         ]
     },
-    { icon: Bot, label: "AI Help", view: "help_ai" },
     {
         icon: Gauge, label: "Flow", items: [
             { icon: Snowflake, label: "Snowball", view: "snowball" },
@@ -50,6 +49,7 @@ const mobileNavGroups: MobileNavGroup[] = [
             { icon: BarChart3, label: "Progress", view: "progress" },
         ]
     },
+    { icon: MessageCircle, label: "Ask", view: "help_ai" },
     { icon: Settings, label: "Settings", view: "settings" },
 ];
 
@@ -306,6 +306,7 @@ export const Sidebar: Component<{
     setView: (v: string) => void;
     isAIHelpOpen: boolean;
     onToggleAIHelp: () => void;
+    aiHelpTip?: string | null;
     isLocked: boolean;
     setIsLocked: (v: boolean) => void;
     isPeeking: boolean;
@@ -356,7 +357,17 @@ export const Sidebar: Component<{
                 </Show>
             </div>
 
-
+            <div class="px-3 pb-2">
+                <ContextSwitcher
+                    isLocked={props.isLocked}
+                    isPeeking={props.isPeeking}
+                    setIsPeeking={props.setIsPeeking}
+                    onOpenChange={(open) => {
+                        setSwitcherOpen(open);
+                        props.onDropdownOpenChange?.(open);
+                    }}
+                />
+            </div>
 
             <nav class="flex-1 px-3 space-y-1 mt-2 min-h-0">
                 <For each={desktopNavItems}>
@@ -387,34 +398,28 @@ export const Sidebar: Component<{
                     <AIHelpPanel variant="sidebar" class="h-[32rem]" />
                 </div>
 
-                {/* Context Switcher - Only visible if there are oversight contexts */}
-                <div class={cn(
-                    "transition-all duration-200",
-                    (!props.isLocked && !props.isPeeking) ? "opacity-0 pointer-events-none" : "opacity-100 delay-100"
-                )}>
-                    <ContextSwitcher
-                        isLocked={props.isLocked}
-                        isPeeking={props.isPeeking}
-                        setIsPeeking={props.setIsPeeking}
-                        onOpenChange={(open) => {
-                            setSwitcherOpen(open);
-                            props.onDropdownOpenChange?.(open);
-                        }}
-                    />
-                </div>
-
                 <div class="border-t border-border pt-3 space-y-1">
                 <button
                     onClick={props.onToggleAIHelp}
                     class={cn(
-                        "flex items-center space-x-3 w-full px-3 py-2.5 rounded-lg transition-all duration-200 group text-sm",
+                        "flex w-full items-start gap-3 px-3 py-2.5 rounded-lg transition-all duration-200 group text-sm text-left",
                         props.isAIHelpOpen
                             ? "bg-primary text-primary-foreground shadow-sm"
                             : "text-muted-foreground hover:bg-muted hover:text-foreground"
                     )}
                 >
-                    <Bot size={16} class={cn("transition-transform group-hover:scale-110")} />
+                    <MessageCircle size={16} class={cn("transition-transform group-hover:scale-110 mt-0.5 shrink-0")} />
-                    <span class="font-medium">AI Help</span>
+                    <div class="min-w-0 flex-1">
+                        <div class="font-medium">Ask Questions</div>
+                        <div
+                            class={cn(
+                                "text-[0.625rem] leading-snug transition-opacity duration-700",
+                                props.aiHelpTip ? "opacity-50" : "opacity-0"
+                            )}
+                        >
+                            {props.aiHelpTip || " "}
+                        </div>
+                    </div>
                 </button>
                 <button
                     onClick={() => props.setView("help")}

src/lib/ai-help.ts

@@ -0,0 +1,112 @@
+import { FIREWORKS_API_KEY, FIREWORKS_API_URL, FIREWORKS_HELP_MODEL } from "@/lib/app-config";
+import helpGuide from "../../docs/HELP_GUIDE.md?raw";
+
+type ChatRequestMessage = {
+    role: "system" | "user" | "assistant";
+    content: string;
+};
+
+const HELP_SYSTEM_PROMPT = `You answer questions about TasGrid using the reference guide below.
+
+You must follow this instruction exactly: "use only this guide for all information and never assume you know something that isn't mentioned in the guide"
+
+If the guide does not contain the answer, say that the guide does not mention it.
+Do not use outside product knowledge.
+Do not invent buttons, workflows, settings, or behaviors.
+Prefer concise, practical answers.
+When helpful, mention the relevant section name from the guide.
+
+TASGRID REFERENCE GUIDE
+${helpGuide}`;
+
+const normalizeLine = (value: string) =>
+    value
+        .trim()
+        .replace(/^["'\s]+|["'\s]+$/g, "")
+        .replace(/\s+/g, " ")
+        .toLowerCase();
+
+export const hasFireworksApiKey = () => FIREWORKS_API_KEY.trim().length > 0;
+
+const requestFireworks = async (messages: ChatRequestMessage[], options?: { maxTokens?: number; temperature?: number }) => {
+    const response = await fetch(FIREWORKS_API_URL, {
+        method: "POST",
+        headers: {
+            "Content-Type": "application/json",
+            "Authorization": `Bearer ${FIREWORKS_API_KEY}`
+        },
+        body: JSON.stringify({
+            model: FIREWORKS_HELP_MODEL,
+            reasoning_effort: "low",
+            temperature: options?.temperature ?? 0.2,
+            max_tokens: options?.maxTokens ?? 700,
+            messages
+        })
+    });
+
+    if (!response.ok) {
+        const bodyText = await response.text();
+        throw new Error(bodyText || `Request failed with status ${response.status}`);
+    }
+
+    const data = await response.json();
+    const content = data?.choices?.[0]?.message?.content?.trim();
+
+    if (!content) {
+        throw new Error("The help assistant did not return any text.");
+    }
+
+    return content;
+};
+
+export const askAIHelp = async (messages: Array<{ role: "user" | "assistant"; content: string }>) =>
+    requestFireworks(
+        [
+            { role: "system", content: HELP_SYSTEM_PROMPT },
+            ...messages
+        ],
+        { maxTokens: 700, temperature: 0.2 }
+    );
+
+export const generateAIHelpTip = async (history: string[]) => {
+    const recentHistory = history.slice(-10);
+    const historyBlock = recentHistory.length > 0
+        ? recentHistory.map((tip, index) => `${index + 1}. ${tip}`).join("\n")
+        : "No previous tips.";
+
+    const tipPrompt = `Create one short TasGrid desktop tip based only on the guide.
+
+Rules:
+- Maximum one sentence.
+- Return plain text only.
+- No title, no bullet, no quotes.
+- Keep it subtle and practical.
+- Do not repeat or closely paraphrase any previous tip.
+- Use only this guide for all information and never assume you know something that isn't mentioned in the guide.
+
+Previous tips to avoid:
+${historyBlock}`;
+
+    const seen = new Set(recentHistory.map(normalizeLine));
+
+    for (let attempt = 0; attempt < 2; attempt += 1) {
+        const response = await requestFireworks(
+            [
+                { role: "system", content: HELP_SYSTEM_PROMPT },
+                { role: "user", content: tipPrompt }
+            ],
+            { maxTokens: 80, temperature: 0.5 }
+        );
+
+        const firstLine = response.split("\n")[0]?.trim() || "";
+        const cleaned = firstLine.replace(/^[-*•\d.\s]+/, "").trim();
+        const normalized = normalizeLine(cleaned);
+
+        if (!cleaned || !normalized) continue;
+        if (seen.has(normalized)) continue;
+
+        return cleaned;
+    }
+
+    return null;
+};

src/store/preferences.ts

@@ -28,6 +28,7 @@ export const syncPreferences = async () => {
             collapsedUntilUpdatedTasks: store.collapsedUntilUpdatedTasks,
             subscribedBuckets: store.subscribedBuckets,
             supervisorUserIds: store.personalContextSupervisorIds,
+            aiHelpTipHistory: store.aiHelpTipHistory,
             lastCompletedTaskCleanupDate: store.lastCompletedTaskCleanupDate
         };
 
@@ -174,3 +175,15 @@ export const removeNoteFilterTemplate = async (id: string) => {
 export const clearNoteFilter = () => {
     setStore("noteFilter", createDefaultFilter());
 };
+
+export const appendAIHelpTipHistory = async (tip: string) => {
+    const normalizedTip = tip.trim();
+    if (!normalizedTip) return;
+
+    setStore("aiHelpTipHistory", prev => {
+        const next = [...prev.filter(existing => existing !== normalizedTip), normalizedTip];
+        return next.slice(-10);
+    });
+
+    await syncPreferences();
+};

src/store/state.ts

@@ -183,6 +183,7 @@ export interface TaskStore {
     buckets: Bucket[];
     subscribedBuckets: string[];
     personalContextSupervisorIds: string[];
+    aiHelpTipHistory: string[];
     notes: Note[];
     isNotepadMode: boolean;
     quickloadTasks: string[];
@@ -202,6 +203,7 @@ export interface ScopedTaskgridPrefs {
     noteFilter?: Filter;
     subscribedBuckets?: string[];
     supervisorUserIds?: string[];
+    aiHelpTipHistory?: string[];
     dismissedTaskUpdateIndicators?: Record<string, string>;
     collapsedUntilUpdatedTasks?: Record<string, string>;
     migratedStructuredTagsV2?: boolean;
@@ -246,6 +248,7 @@ export const [store, setStore] = createStore<TaskStore>({
     buckets: [],
     subscribedBuckets: [],
     personalContextSupervisorIds: [],
+    aiHelpTipHistory: [],
     notes: [],
     isNotepadMode: false,
     quickloadTasks: [],
@@ -295,6 +298,7 @@ export const applyScopedPrefsToStore = (prefs: ScopedTaskgridPrefs) => {
         prefId: currentUserId,
         subscribedBuckets: prefs.subscribedBuckets || [],
         personalContextSupervisorIds: personalContext?.supervisorUserIds || prefs.supervisorUserIds || [],
+        aiHelpTipHistory: prefs.aiHelpTipHistory || [],
         tagDefinitions: (prefs.tagDefinitions || []).filter((def: TagDefinition) => !def.name.startsWith("@")),
         filterTemplates: prefs.filterTemplates || [],
         quickloadTasks: prefs.quickloadTasks || [],