ai fixes

apps/web/src/app/api/library/context/route.ts

@@ -0,0 +1,19 @@
+import { handleApi } from "@/lib/api";
+import {
+  formatLibraryContextForPrompt,
+  getLibraryContextForTopic,
+} from "@/lib/services/library-context";
+import { requireUser } from "@/lib/services/user";
+
+export async function GET(request: Request) {
+  return handleApi(async () => {
+    const { user } = await requireUser();
+    const { searchParams } = new URL(request.url);
+    const topic = searchParams.get("topic")?.trim() ?? "";
+    const payload = await getLibraryContextForTopic(user.id, topic);
+    return {
+      ...payload,
+      formatted: formatLibraryContextForPrompt(payload),
+    };
+  });
+}

apps/web/src/app/api/teacher/route.ts

@@ -1,5 +1,10 @@
 import { handleApi } from "@/lib/api";
-import { createTeacherLesson, getTeacherHistory } from "@/lib/services/teacher";
+import { ServiceUnavailableError } from "@/lib/errors";
+import {
+  createTeacherLesson,
+  getTeacherHistory,
+  TeacherAiUnavailableError,
+} from "@/lib/services/teacher";
 import { requireUser } from "@/lib/services/user";
 import { parseJsonBody } from "@/lib/validation";
 import {
@@ -9,20 +14,17 @@ import {
 
 export async function POST(request: Request) {
   return handleApi(async () => {
-    // #region agent log
-    fetch('http://127.0.0.1:7257/ingest/abfa22e4-3d86-4176-9679-7c59b1f0489f',{method:'POST',headers:{'Content-Type':'application/json','X-Debug-Session-Id':'04e12c'},body:JSON.stringify({sessionId:'04e12c',location:'api/teacher/route.ts:POST',message:'teacher POST start',data:{},timestamp:Date.now(),hypothesisId:'H1'})}).catch(()=>{});
-    // #endregion
     const parsed = await parseJsonBody(request, teacherCreateSchema);
     const body = normalizeTeacherCreateBody(parsed);
-    // #region agent log
-    fetch('http://127.0.0.1:7257/ingest/abfa22e4-3d86-4176-9679-7c59b1f0489f',{method:'POST',headers:{'Content-Type':'application/json','X-Debug-Session-Id':'04e12c'},body:JSON.stringify({sessionId:'04e12c',location:'api/teacher/route.ts:POST',message:'teacher body validated',data:{topicLen:body.topic.length,hasExplorationId:!!body.explorationId},timestamp:Date.now(),hypothesisId:'H1'})}).catch(()=>{});
-    // #endregion
     const { user } = await requireUser();
-    const result = await createTeacherLesson(user.id, body);
+    try {
-    // #region agent log
+      return await createTeacherLesson(user.id, body);
-    fetch('http://127.0.0.1:7257/ingest/abfa22e4-3d86-4176-9679-7c59b1f0489f',{method:'POST',headers:{'Content-Type':'application/json','X-Debug-Session-Id':'04e12c'},body:JSON.stringify({sessionId:'04e12c',location:'api/teacher/route.ts:POST',message:'teacher lesson created',data:{source:result.source,lessonId:result.id},timestamp:Date.now(),hypothesisId:'H2'})}).catch(()=>{});
+    } catch (e) {
-    // #endregion
+      if (e instanceof TeacherAiUnavailableError) {
-    return result;
+        throw new ServiceUnavailableError(e.message);
+      }
+      throw e;
+    }
   });
 }
 

apps/web/src/app/teacher/page.tsx

@@ -3,29 +3,19 @@
 import { useState, useEffect, Suspense } from "react";
 import { useMutation, useQuery, useQueryClient } from "@tanstack/react-query";
 import { useSearchParams } from "next/navigation";
+import type {
+  TeacherLessonContent,
+  TeacherLessonData,
+  TeacherDifficulty,
+  TeacherLength,
+} from "@adventureos/shared";
 import { AppShell } from "@/components/layout/app-shell";
+import {
+  resolveResearchAssignmentDisplay,
+  type ResearchAssignmentDisplay,
+} from "@/lib/teacher/teacher-render";
 
-type LessonContent = {
+type Lesson = TeacherLessonData;
-  title?: string;
-  introduction?: string;
-  objectives?: string[];
-  readingSteps?: string[];
-  reflectionPrompt?: string;
-  flashcards: { front: string; back: string }[];
-  quiz: { question: string; options: string[]; answer: number }[];
-  assignment: string;
-};
-
-type Lesson = {
-  id: string;
-  topic: string;
-  content: LessonContent;
-  status: string;
-  completedNote?: string | null;
-  createdAt: string;
-  source?: "ai" | "fallback";
-  fallbackReason?: "offline" | "model_unavailable" | "parse_failed" | "generation_failed" | "timeout";
-};
 
 export default function TeacherPage() {
   return (
@@ -39,12 +29,16 @@ function TeacherPageContent() {
   const searchParams = useSearchParams();
   const qc = useQueryClient();
   const [topic, setTopic] = useState("");
+  const [difficulty, setDifficulty] = useState<TeacherDifficulty>("beginner");
+  const [length, setLength] = useState<TeacherLength>("standard");
   const [explorationId, setExplorationId] = useState<string | null>(null);
   const [selectedId, setSelectedId] = useState<string | null>(null);
-  const [content, setContent] = useState<LessonContent | null>(null);
+  const [content, setContent] = useState<TeacherLessonContent | null>(null);
   const [contentSource, setContentSource] = useState<"ai" | "fallback" | null>(null);
   const [fallbackReason, setFallbackReason] = useState<string | null>(null);
   const [revealedQuiz, setRevealedQuiz] = useState<Record<number, number | null>>({});
+  const [revealedShortAnswers, setRevealedShortAnswers] = useState<Record<number, boolean>>({});
+  const [showAnswerKey, setShowAnswerKey] = useState(false);
   const [completionNote, setCompletionNote] = useState("");
 
   useEffect(() => {
@@ -63,6 +57,17 @@ function TeacherPageContent() {
     },
   });
 
+  const resetLessonView = () => {
+    setContent(null);
+    setContentSource(null);
+    setFallbackReason(null);
+    setSelectedId(null);
+    setRevealedQuiz({});
+    setRevealedShortAnswers({});
+    setShowAnswerKey(false);
+    setCompletionNote("");
+  };
+
   const loadLesson = useMutation({
     mutationFn: async (id: string) => {
       const res = await fetch(`/api/teacher/${id}`);
@@ -76,6 +81,8 @@ function TeacherPageContent() {
       setFallbackReason(data.fallbackReason ?? null);
       setTopic(data.topic);
       setRevealedQuiz({});
+      setRevealedShortAnswers({});
+      setShowAnswerKey(false);
       setCompletionNote(data.completedNote ?? "");
     },
   });
@@ -87,6 +94,9 @@ function TeacherPageContent() {
         headers: { "Content-Type": "application/json" },
         body: JSON.stringify({
           topic,
+          difficulty,
+          length,
+          includeLibraryContext: true,
           ...(explorationId ? { explorationId } : {}),
         }),
       });
@@ -102,6 +112,8 @@ function TeacherPageContent() {
       setFallbackReason(data.fallbackReason ?? null);
       setSelectedId(data.id);
       setRevealedQuiz({});
+      setRevealedShortAnswers({});
+      setShowAnswerKey(false);
       qc.invalidateQueries({ queryKey: ["teacher"] });
     },
   });
@@ -120,120 +132,271 @@ function TeacherPageContent() {
     onSuccess: () => qc.invalidateQueries({ queryKey: ["teacher"] }),
   });
 
+  const overview = content?.overview ?? content?.introduction;
+  const objectives = content?.learningObjectives ?? content?.objectives;
+  const researchDisplay = content ? resolveResearchAssignmentDisplay(content) : null;
+
   return (
     <AppShell>
-      <div className="p-4 pb-20 md:pb-4">
+      <div className="p-4 pb-20 md:pb-4 max-w-3xl">
         <h1 className="font-bold text-lg mb-2">The Teacher</h1>
         <p className="text-sm text-[var(--warm-grey)] mb-4">
-          Ask the Guide to create flashcards, quizzes, and research assignments on any topic.
+          A calm mini-lesson with explanation, research steps, library suggestions, homework, and a quiz.
         </p>
 
-        <div className="flex gap-2 mb-6">
+        <div className="retro-window p-4 mb-6 space-y-3">
           <input
-            className="retro-window-inset flex-1 p-2"
+            className="retro-window-inset w-full p-2"
-            placeholder="e.g. How Roman roads were built"
+            placeholder="e.g. DNS, Ottoman history, cryptography"
             value={topic}
             onChange={(e) => setTopic(e.target.value)}
+            disabled={generate.isPending}
           />
-          <button
+          <div className="flex flex-wrap gap-3 text-sm">
-            className="retro-btn retro-btn-primary"
+            <label className="flex items-center gap-2">
-            onClick={() => generate.mutate()}
+              <span className="text-[var(--warm-grey)]">Difficulty</span>
-            disabled={!topic || generate.isPending}
+              <select
-          >
+                className="retro-window-inset p-1"
-            {generate.isPending ? "Teaching..." : "Teach Me"}
+                value={difficulty}
-          </button>
+                onChange={(e) => setDifficulty(e.target.value as TeacherDifficulty)}
+                disabled={generate.isPending}
+              >
+                <option value="beginner">Beginner</option>
+                <option value="intermediate">Intermediate</option>
+                <option value="advanced">Advanced</option>
+              </select>
+            </label>
+            <label className="flex items-center gap-2">
+              <span className="text-[var(--warm-grey)]">Length</span>
+              <select
+                className="retro-window-inset p-1"
+                value={length}
+                onChange={(e) => setLength(e.target.value as TeacherLength)}
+                disabled={generate.isPending}
+              >
+                <option value="short">Short</option>
+                <option value="standard">Standard</option>
+                <option value="deep">Deep dive</option>
+              </select>
+            </label>
+          </div>
+          <div className="flex flex-wrap gap-2">
+            <button
+              className="retro-btn retro-btn-primary"
+              onClick={() => generate.mutate()}
+              disabled={!topic.trim() || generate.isPending}
+            >
+              {generate.isPending ? "Preparing lesson…" : "Generate Lesson"}
+            </button>
+            <button
+              className="retro-btn"
+              type="button"
+              onClick={resetLessonView}
+              disabled={generate.isPending}
+            >
+              Clear
+            </button>
+          </div>
         </div>
 
+        {generate.isPending && (
+          <p className="text-sm text-[var(--warm-grey)] mb-4 italic">
+            The Guide is preparing your lesson on “{topic}”…
+          </p>
+        )}
+
         {generate.isError && (
           <p className="text-sm text-[var(--muted-rose)] mb-4">
             {generate.error instanceof Error
               ? generate.error.message
-              : "Could not generate lesson. Check AI Health."}
+              : "Could not generate lesson. Check AI Health in Settings."}
           </p>
         )}
 
         {contentSource === "fallback" && (
           <p className="text-sm text-[var(--warm-grey)] mb-4 italic">
             {fallbackReason === "timeout"
-              ? "AI timed out — your model may be too large for this machine. Try a smaller model (e.g. llama3.2:1b) in Settings or .env."
+              ? "AI timed out — try a smaller model in Settings."
-              : fallbackReason === "generation_failed"
+              : fallbackReason === "parse_failed"
-                ? "AI could not generate a lesson (check that your Ollama model is installed) — showing a basic offline template."
+                ? "AI responded but the lesson could not be parsed — showing a basic template."
-                : "AI is offline or unavailable — showing a basic offline lesson template."}
+                : fallbackReason === "generation_failed"
+                  ? "AI could not generate a full lesson — showing a basic offline template."
+                  : "AI is offline or unavailable — showing a basic offline lesson template."}
           </p>
         )}
 
         {content && (
           <div className="space-y-4">
-            {content.title && (
+            {content.title && <h2 className="font-bold text-base">{content.title}</h2>}
-              <h2 className="font-bold text-base">{content.title}</h2>
+
-            )}
+            {overview && (
-            {content.introduction && (
+              <Section title="Overview">
-              <Section title="Introduction">
+                <p className="serif text-sm whitespace-pre-wrap">{overview}</p>
-                <p className="serif text-sm">{content.introduction}</p>
               </Section>
             )}
-            {content.objectives && content.objectives.length > 0 && (
+
+            {content.whyItMatters && (
+              <Section title="Why This Matters">
+                <p className="serif text-sm whitespace-pre-wrap">{content.whyItMatters}</p>
+              </Section>
+            )}
+
+            {objectives && objectives.length > 0 && (
               <Section title="Learning Objectives">
                 <ul className="text-sm list-disc pl-5 space-y-1">
-                  {content.objectives.map((o, i) => (
+                  {objectives.map((o, i) => (
                     <li key={i}>{o}</li>
                   ))}
                 </ul>
               </Section>
             )}
-            {content.readingSteps && content.readingSteps.length > 0 && (
+
-              <Section title="Reading & Research">
+            {content.explanation && (
-                <ol className="text-sm list-decimal pl-5 space-y-1">
+              <Section title="Explanation">
-                  {content.readingSteps.map((step, i) => (
+                <p className="serif text-sm whitespace-pre-wrap">{content.explanation}</p>
-                    <li key={i}>{step}</li>
-                  ))}
-                </ol>
               </Section>
             )}
-            <Section title="Flashcards">
+
-              <div className="grid gap-2">
+            {researchDisplay && (
-                {content.flashcards.map((c, i) => (
+              <Section title="Research Assignment">
-                  <Flashcard key={i} front={c.front} back={c.back} />
+                <ResearchAssignmentBlock display={researchDisplay} />
-                ))}
+              </Section>
-              </div>
+            )}
-            </Section>
+
-            <Section title="Quiz">
+            <Section title="Books From Your Library">
-              {content.quiz.map((q, i) => (
+              {content.calibreSuggestions && content.calibreSuggestions.length > 0 ? (
-                <QuizQuestion
+                <ul className="text-sm space-y-2">
-                  key={i}
+                  {content.calibreSuggestions.map((book, i) => (
-                  question={q.question}
+                    <li key={i}>
-                  options={q.options}
+                      <span className="font-bold">{book.title}</span>
-                  answer={q.answer}
+                      {book.authors.length > 0 && (
-                  selected={revealedQuiz[i] ?? null}
+                        <span className="text-[var(--warm-grey)]"> — {book.authors.join(", ")}</span>
-                  onSelect={(idx) => setRevealedQuiz({ ...revealedQuiz, [i]: idx })}
+                      )}
-                />
+                      <p className="text-sm mt-0.5">{book.reason}</p>
-              ))}
+                    </li>
-            </Section>
+                  ))}
-            <Section title="Research Assignment">
+                </ul>
-              <p className="serif">{content.assignment}</p>
+              ) : (
-              {content.reflectionPrompt && (
+                <p className="text-sm text-[var(--warm-grey)] italic">
-                <p className="text-sm italic mt-2 text-[var(--warm-grey)]">
+                  No matching library books were found for this topic.
-                  Reflection: {content.reflectionPrompt}
                 </p>
               )}
-              {selectedId && (
-                <div className="mt-4">
-                  <textarea
-                    className="retro-window-inset w-full p-2 text-sm min-h-[60px]"
-                    placeholder="What did you learn from this assignment?"
-                    value={completionNote}
-                    onChange={(e) => setCompletionNote(e.target.value)}
-                  />
-                  <button
-                    className="retro-btn retro-btn-primary mt-2 text-sm"
-                    onClick={() => complete.mutate()}
-                    disabled={complete.isPending}
-                  >
-                    Mark assignment complete
-                  </button>
-                </div>
-              )}
             </Section>
+
+            {content.externalReading && content.externalReading.length > 0 && (
+              <Section title="Further Reading">
+                <ul className="text-sm list-disc pl-5 space-y-1">
+                  {content.externalReading.map((item, i) => (
+                    <li key={i}>{item}</li>
+                  ))}
+                </ul>
+              </Section>
+            )}
+
+            {content.homework && (
+              <Section title="Homework">
+                <p className="serif text-sm font-bold">{content.homework.task}</p>
+                {content.homework.instructions.length > 0 && (
+                  <ol className="text-sm list-decimal pl-5 space-y-1 mt-2">
+                    {content.homework.instructions.map((step, i) => (
+                      <li key={i}>{step}</li>
+                    ))}
+                  </ol>
+                )}
+              </Section>
+            )}
+
+            {content.flashcards.length > 0 && (
+              <Section title="Flashcards">
+                <div className="grid gap-2">
+                  {content.flashcards.map((c, i) => (
+                    <Flashcard key={i} front={c.front} back={c.back} />
+                  ))}
+                </div>
+              </Section>
+            )}
+
+            {content.quiz.length > 0 && (
+              <Section title="Quiz">
+                {content.quiz.map((q, i) =>
+                  q.type === "short_answer" ? (
+                    <ShortAnswerQuestion
+                      key={i}
+                      question={q.question}
+                      answer={q.answerText ?? String(q.answer)}
+                      explanation={q.explanation}
+                      revealed={revealedShortAnswers[i] ?? false}
+                      onReveal={() =>
+                        setRevealedShortAnswers({ ...revealedShortAnswers, [i]: true })
+                      }
+                    />
+                  ) : (
+                    <QuizQuestion
+                      key={i}
+                      question={q.question}
+                      options={q.options ?? []}
+                      answer={q.answer}
+                      selected={revealedQuiz[i] ?? null}
+                      onSelect={(idx) => setRevealedQuiz({ ...revealedQuiz, [i]: idx })}
+                    />
+                  )
+                )}
+              </Section>
+            )}
+
+            {content.answerKey && content.answerKey.length > 0 && (
+              <Section title="Answer Key">
+                <button
+                  type="button"
+                  className="retro-btn text-sm mb-2"
+                  onClick={() => setShowAnswerKey(!showAnswerKey)}
+                >
+                  {showAnswerKey ? "Hide answers" : "Show answers"}
+                </button>
+                {showAnswerKey && (
+                  <ol className="text-sm list-decimal pl-5 space-y-2">
+                    {content.answerKey.map((entry, i) => (
+                      <li key={i}>
+                        <span className="font-bold">{entry.answer}</span>
+                        {entry.explanation && (
+                          <p className="text-[var(--warm-grey)] mt-0.5">{entry.explanation}</p>
+                        )}
+                      </li>
+                    ))}
+                  </ol>
+                )}
+              </Section>
+            )}
+
+            {content.reflectionPrompt && (
+              <Section title="Reflection">
+                <p className="serif text-sm italic">{content.reflectionPrompt}</p>
+              </Section>
+            )}
+
+            {content.nextLessonSuggestion && (
+              <Section title="Next Lesson">
+                <p className="text-sm">{content.nextLessonSuggestion}</p>
+              </Section>
+            )}
+
+            {selectedId && (
+              <Section title="Complete Assignment">
+                <textarea
+                  className="retro-window-inset w-full p-2 text-sm min-h-[60px]"
+                  placeholder="What did you learn from this assignment?"
+                  value={completionNote}
+                  onChange={(e) => setCompletionNote(e.target.value)}
+                />
+                <button
+                  className="retro-btn retro-btn-primary mt-2 text-sm"
+                  onClick={() => complete.mutate()}
+                  disabled={complete.isPending}
+                >
+                  Mark assignment complete
+                </button>
+              </Section>
+            )}
           </div>
         )}
 
@@ -267,6 +430,32 @@ function TeacherPageContent() {
   );
 }
 
+export function ResearchAssignmentBlock({ display }: { display: ResearchAssignmentDisplay }) {
+  if (display.kind === "string") {
+    return <p className="serif text-sm whitespace-pre-wrap">{display.text}</p>;
+  }
+
+  const { steps, expectedOutcome, estimatedTimeMinutes } = display.data;
+  return (
+    <div className="text-sm space-y-2">
+      {estimatedTimeMinutes != null && (
+        <p className="text-[var(--warm-grey)]">Estimated time: ~{estimatedTimeMinutes} minutes</p>
+      )}
+      <ol className="list-decimal pl-5 space-y-1">
+        {steps.map((step, i) => (
+          <li key={i}>{step}</li>
+        ))}
+      </ol>
+      {expectedOutcome && (
+        <p className="serif mt-2">
+          <span className="font-bold">Expected outcome: </span>
+          {expectedOutcome}
+        </p>
+      )}
+    </div>
+  );
+}
+
 function Flashcard({ front, back }: { front: string; back: string }) {
   const [flipped, setFlipped] = useState(false);
   return (
@@ -307,7 +496,7 @@ function QuizQuestion({
           if (showResult && !picked && isCorrect) cls = "text-[var(--bliss-green)]";
           return (
             <li key={j}>
-              <button className={`text-left ${cls}`} onClick={() => onSelect(j)}>
+              <button type="button" className={`text-left ${cls}`} onClick={() => onSelect(j)}>
                 {String.fromCharCode(65 + j)}. {o}
               </button>
             </li>
@@ -318,6 +507,39 @@ function QuizQuestion({
   );
 }
 
+function ShortAnswerQuestion({
+  question,
+  answer,
+  explanation,
+  revealed,
+  onReveal,
+}: {
+  question: string;
+  answer: string;
+  explanation?: string;
+  revealed: boolean;
+  onReveal: () => void;
+}) {
+  return (
+    <div className="retro-window-inset p-3 mb-2">
+      <p className="font-bold text-sm mb-2">{question}</p>
+      <p className="text-xs text-[var(--warm-grey)] mb-2">Short answer</p>
+      {!revealed ? (
+        <button type="button" className="retro-btn text-sm" onClick={onReveal}>
+          Reveal answer
+        </button>
+      ) : (
+        <div>
+          <p className="text-sm text-[var(--bliss-green)] font-bold">{answer}</p>
+          {explanation && (
+            <p className="text-sm text-[var(--warm-grey)] mt-1">{explanation}</p>
+          )}
+        </div>
+      )}
+    </div>
+  );
+}
+
 function Section({ title, children }: { title: string; children: React.ReactNode }) {
   return (
     <div className="retro-window p-4">

apps/web/src/lib/ai/ai-normalize.test.ts

@@ -3,6 +3,7 @@ import {
   normalizeExplorationPayload,
   normalizeTeacherPayload,
   safeParseAiJson,
+  isInvalidObjectString,
 } from "./ai-normalize";
 
 describe("safeParseAiJson", () => {
@@ -17,12 +18,63 @@ describe("normalizeTeacherPayload", () => {
       flashcards: [{ front: "Q", back: "A" }],
       quiz: [{ question: "Pick one", options: ["a", "b"], answer: "1" }],
       homework: "Read for 20 minutes",
+    }) as Record<string, unknown>;
+    expect(normalized.assignment).toBe("Read for 20 minutes");
+    expect((normalized.quiz as { answer: number }[])[0].answer).toBe(1);
+  });
+
+  it("flattens object assignment instead of [object Object]", () => {
+    const normalized = normalizeTeacherPayload({
+      flashcards: [],
+      quiz: [],
+      assignment: {
+        task: "Research Roman roads",
+        steps: ["Find a map", "Note three facts"],
+      },
+    }) as Record<string, unknown>;
+    expect(normalized.assignment).toContain("Research Roman roads");
+    expect(normalized.researchAssignment).toMatchObject({
+      steps: ["Find a map", "Note three facts"],
     });
-    expect(normalized).toMatchObject({
+    expect(isInvalidObjectString(normalized.assignment as string)).toBe(false);
-      assignment: "Read for 20 minutes",
+  });
-      quiz: [{ answer: 1 }],
+
+  it("handles structured researchAssignment from AI", () => {
+    const normalized = normalizeTeacherPayload({
+      flashcards: [{ front: "Q", back: "A" }],
+      quiz: [
+        {
+          question: "What is DNS?",
+          type: "short_answer",
+          answer: "Domain Name System",
+        },
+      ],
+      researchAssignment: {
+        steps: ["Look up DNS basics", "Draw a diagram"],
+        expectedOutcome: "A labeled diagram",
+        estimatedTimeMinutes: 25,
+      },
+    }) as Record<string, unknown>;
+    expect(normalized.researchAssignment).toEqual({
+      steps: ["Look up DNS basics", "Draw a diagram"],
+      expectedOutcome: "A labeled diagram",
+      estimatedTimeMinutes: 25,
     });
   });
+
+  it("maps letter quiz answers", () => {
+    const normalized = normalizeTeacherPayload({
+      flashcards: [],
+      quiz: [
+        {
+          question: "Pick B",
+          options: ["wrong", "right", "nope"],
+          answer: "B",
+        },
+      ],
+    }) as Record<string, unknown>;
+    expect((normalized.quiz as { answer: number }[])[0].answer).toBe(1);
+  });
 });
 
 describe("normalizeExplorationPayload", () => {

apps/web/src/lib/ai/ai-normalize.ts

@@ -1,4 +1,10 @@
 import { parseAiJson } from "./parse-json";
+import {
+  extractText,
+  extractStringList,
+  isObjectObject,
+  normalizeQuizAnswer,
+} from "../teacher/extract-text";
 
 export function safeParseAiJson(raw: string): unknown | null {
   try {
@@ -8,17 +14,155 @@ export function safeParseAiJson(raw: string): unknown | null {
   }
 }
 
+function normalizeResearchAssignment(
+  raw: unknown,
+  readingSteps: string[],
+  assignmentText: string
+): {
+  researchAssignment?: {
+    steps: string[];
+    expectedOutcome?: string;
+    estimatedTimeMinutes?: number;
+  };
+  readingSteps?: string[];
+} {
+  if (raw && typeof raw === "object" && !Array.isArray(raw)) {
+    const o = raw as Record<string, unknown>;
+    const steps = extractStringList(o.steps ?? o.readingSteps);
+    const expectedOutcome = extractText(o.expectedOutcome ?? o.outcome);
+    const timeRaw = o.estimatedTimeMinutes ?? o.timeMinutes ?? o.duration;
+    const estimatedTimeMinutes =
+      timeRaw != null && Number.isFinite(Number(timeRaw)) ? Number(timeRaw) : undefined;
+    if (steps.length || expectedOutcome) {
+      return {
+        researchAssignment: {
+          steps: steps.length ? steps : readingSteps,
+          expectedOutcome: expectedOutcome || undefined,
+          estimatedTimeMinutes,
+        },
+      };
+    }
+  }
+
+  if (readingSteps.length) {
+    return {
+      researchAssignment: {
+        steps: readingSteps,
+        expectedOutcome: assignmentText || undefined,
+      },
+      readingSteps,
+    };
+  }
+
+  if (assignmentText) {
+    return {
+      researchAssignment: { steps: [assignmentText] },
+    };
+  }
+
+  return {};
+}
+
+function normalizeHomework(raw: unknown): {
+  task: string;
+  instructions: string[];
+} | undefined {
+  if (raw == null) return undefined;
+  if (typeof raw === "string") {
+    const task = raw.trim();
+    return task ? { task, instructions: [] } : undefined;
+  }
+  if (typeof raw === "object" && !Array.isArray(raw)) {
+    const o = raw as Record<string, unknown>;
+    const task = extractText(o.task ?? o.assignment ?? o.description);
+    const instructions = extractStringList(o.instructions ?? o.steps);
+    if (task || instructions.length) {
+      return { task: task || instructions[0] || "", instructions };
+    }
+  }
+  return undefined;
+}
+
+function normalizeCalibreSuggestions(raw: unknown) {
+  if (!Array.isArray(raw)) return undefined;
+  const items = raw
+    .map((item) => {
+      if (!item || typeof item !== "object") return null;
+      const o = item as Record<string, unknown>;
+      const title = extractText(o.title);
+      if (!title) return null;
+      const authors = Array.isArray(o.authors)
+        ? o.authors.map((a) => extractText(a)).filter(Boolean)
+        : extractText(o.author)
+          ? [extractText(o.author)]
+          : [];
+      const reason = extractText(o.reason ?? o.why);
+      return { title, authors, reason: reason || "Relevant to this topic" };
+    })
+    .filter(Boolean);
+  return items.length ? items : undefined;
+}
+
 export function normalizeTeacherPayload(data: unknown): unknown {
   if (!data || typeof data !== "object") return data;
   const o = data as Record<string, unknown>;
 
+  const overview = extractText(o.overview ?? o.introduction);
+  const whyItMatters = extractText(o.whyItMatters ?? o.why_this_matters);
+  const explanation = extractText(o.explanation ?? o.body);
+  const objectives = extractStringList(
+    o.learningObjectives ?? o.objectives ?? o.learning_objectives
+  );
+  const readingSteps = extractStringList(o.readingSteps ?? o.reading_steps);
+  const externalReading = extractStringList(o.externalReading ?? o.external_reading);
+  const reflectionPrompt = extractText(o.reflectionPrompt ?? o.reflection);
+  const nextLessonSuggestion = extractText(
+    o.nextLessonSuggestion ?? o.next_lesson ?? o.nextTopic
+  );
+
+  const homeworkRaw = o.homework;
+  let assignmentText = "";
+  let assignmentObjectSteps: string[] = [];
+
+  if (o.assignment && typeof o.assignment === "object" && !Array.isArray(o.assignment)) {
+    const assignmentObj = o.researchAssignment ?? o.research_assignment ?? o.assignment;
+    if (assignmentObj && typeof assignmentObj === "object" && !Array.isArray(assignmentObj)) {
+      const a = assignmentObj as Record<string, unknown>;
+      assignmentText = extractText(a.task ?? a.assignment ?? a.description);
+      assignmentObjectSteps = extractStringList(a.steps ?? a.instructions);
+    }
+  } else {
+    assignmentText = extractText(o.assignment);
+  }
+
+  if (!assignmentText && homeworkRaw && typeof homeworkRaw === "object" && !Array.isArray(homeworkRaw)) {
+    assignmentText = extractText((homeworkRaw as Record<string, unknown>).task);
+  }
+  if (!assignmentText && typeof o.homework === "string") {
+    assignmentText = extractText(o.homework);
+  }
+
+  const researchFields = normalizeResearchAssignment(
+    o.researchAssignment ?? o.research_assignment ?? (assignmentObjectSteps.length ? {
+      steps: assignmentObjectSteps,
+      expectedOutcome: assignmentText,
+    } : undefined),
+    readingSteps.length ? readingSteps : assignmentObjectSteps,
+    assignmentText
+  );
+
+  const homework = normalizeHomework(homeworkRaw);
+  if (!assignmentText && homework?.task) {
+    assignmentText = homework.task;
+  }
+
   const flashcards = Array.isArray(o.flashcards)
     ? o.flashcards
         .map((c) => {
           if (!c || typeof c !== "object") return null;
           const card = c as Record<string, unknown>;
-          const front = String(card.front ?? "").trim();
+          const front = extractText(card.front);
-          const back = String(card.back ?? "").trim();
+          const back = extractText(card.back);
           if (!front && !back) return null;
           return { front, back };
         })
@@ -30,36 +174,90 @@ export function normalizeTeacherPayload(data: unknown): unknown {
         .map((q) => {
           if (!q || typeof q !== "object") return null;
           const item = q as Record<string, unknown>;
-          const options = Array.isArray(item.options)
+          const question = extractText(item.question);
-            ? item.options.map((opt) => String(opt))
+          if (!question) return null;
-            : [];
+
-          if (options.length === 0) return null;
+          const typeRaw = extractText(item.type).toLowerCase();
-          let answer = Number(item.answer ?? 0);
+          const type =
-          if (!Number.isFinite(answer)) answer = 0;
+            typeRaw === "short_answer" || typeRaw === "short answer"
-          if (answer < 0 || answer >= options.length) answer = 0;
+              ? ("short_answer" as const)
+              : ("multiple_choice" as const);
+
+          const options =
+            type === "multiple_choice"
+              ? extractStringList(item.options ?? item.choices)
+              : [];
+
+          if (type === "multiple_choice" && options.length === 0) return null;
+
+          const { answerIndex, answerText } =
+            type === "multiple_choice"
+              ? normalizeQuizAnswer(item.answer ?? item.correct, options)
+              : {
+                  answerIndex: 0,
+                  answerText: extractText(item.answer ?? item.correct) || "See explanation",
+                };
+
+          const explanation = extractText(item.explanation ?? item.rationale);
+
           return {
-            question: String(item.question ?? "Question"),
+            question,
-            options,
+            type,
-            answer,
+            options: type === "multiple_choice" ? options : undefined,
+            answer: answerIndex,
+            answerText,
+            explanation: explanation || undefined,
           };
         })
         .filter(Boolean)
     : [];
 
+  const answerKey = Array.isArray(o.answerKey ?? o.answer_key)
+    ? (o.answerKey ?? o.answer_key as unknown[])
+        .map((entry, idx) => {
+          if (!entry || typeof entry !== "object") return null;
+          const e = entry as Record<string, unknown>;
+          const answer = extractText(e.answer);
+          if (!answer) return null;
+          const questionIndex = Number(e.questionIndex ?? e.question ?? idx);
+          return {
+            questionIndex: Number.isFinite(questionIndex) ? questionIndex : idx,
+            answer,
+            explanation: extractText(e.explanation) || undefined,
+          };
+        })
+        .filter(Boolean)
+    : quiz.map((q, i) => ({
+        questionIndex: i,
+        answer: q.answerText ?? String(q.answer),
+        explanation: q.explanation,
+      }));
+
+  const calibreSuggestions = normalizeCalibreSuggestions(
+    o.calibreSuggestions ?? o.librarySuggestions ?? o.booksFromLibrary
+  );
+
+  const safeAssignment =
+    assignmentText && !isObjectObject(assignmentText) ? assignmentText : undefined;
+
   return {
-    title: o.title != null ? String(o.title) : undefined,
+    title: extractText(o.title) || undefined,
-    introduction: o.introduction != null ? String(o.introduction) : undefined,
+    overview: overview || undefined,
-    objectives: Array.isArray(o.objectives)
+    introduction: overview || undefined,
-      ? o.objectives.map(String).filter(Boolean)
+    whyItMatters: whyItMatters || undefined,
-      : undefined,
+    learningObjectives: objectives.length ? objectives : undefined,
-    readingSteps: Array.isArray(o.readingSteps)
+    objectives: objectives.length ? objectives : undefined,
-      ? o.readingSteps.map(String).filter(Boolean)
+    explanation: explanation || undefined,
-      : undefined,
+    ...researchFields,
-    reflectionPrompt:
+    calibreSuggestions,
-      o.reflectionPrompt != null ? String(o.reflectionPrompt) : undefined,
+    externalReading: externalReading.length ? externalReading : undefined,
+    homework,
+    reflectionPrompt: reflectionPrompt || undefined,
     flashcards,
     quiz,
-    assignment: String(o.assignment ?? o.homework ?? "").trim(),
+    answerKey,
+    nextLessonSuggestion: nextLessonSuggestion || undefined,
+    assignment: safeAssignment ?? homework?.task ?? researchFields.researchAssignment?.steps?.[0] ?? "",
   };
 }
 
@@ -78,13 +276,13 @@ export function normalizeExplorationPayload(data: unknown): unknown {
       .map((item) => {
         if (!item || typeof item !== "object") return null;
         const e = item as Record<string, unknown>;
-        const title = String(e.title ?? "").trim();
+        const title = extractText(e.title);
         if (!title) return null;
         const minutes = Number(e.minutes ?? e.duration ?? 20);
         return {
           title,
-          hook: String(e.hook ?? e.description ?? e.reason ?? title).trim(),
+          hook: extractText(e.hook ?? e.description ?? e.reason ?? title),
-          category: String(e.category ?? "general").trim(),
+          category: extractText(e.category) || "general",
           minutes: Number.isFinite(minutes) && minutes > 0 ? minutes : 20,
         };
       })
@@ -98,22 +296,6 @@ export function debugAiLog(
   data: Record<string, unknown>
 ) {
   console.error(`[adventureos-ai] ${location}: ${message}`, JSON.stringify(data));
-  // #region agent log
-  fetch("http://127.0.0.1:7257/ingest/abfa22e4-3d86-4176-9679-7c59b1f0489f", {
-    method: "POST",
-    headers: {
-      "Content-Type": "application/json",
-      "X-Debug-Session-Id": "04e12c",
-    },
-    body: JSON.stringify({
-      sessionId: "04e12c",
-      location,
-      message,
-      data,
-      timestamp: Date.now(),
-    }),
-  }).catch(() => {});
-  // #endregion
 }
 
 export function isAiTimeoutError(error: unknown): boolean {
@@ -122,3 +304,7 @@ export function isAiTimeoutError(error: unknown): boolean {
   if (error.message.toLowerCase().includes("timeout")) return true;
   return (error as Error & { code?: number }).code === 23;
 }
+
+export function isInvalidObjectString(value: string | undefined): boolean {
+  return !value || isObjectObject(value);
+}

apps/web/src/lib/ai/prompts/defaults.ts

@@ -32,20 +32,45 @@ Return JSON: { "patterns": ["..."], "encouragement": "...", "focus_suggestion":
     name: "Homework Generation",
     description: "Teacher homework assignments",
     category: "template",
-    body: `Create topic-specific learning materials about: {{topic}}
+    body: `Create a useful mini-lesson about: {{topic}}
-Include a short introduction, learning objectives, reading/research steps, homework, reflection prompt, flashcards, and a quiz.
+Difficulty: {{difficulty}}. Length: {{length}}.
-Return JSON only:
+Personal context: {{context}}
+Library context (ONLY cite these books if relevant; never invent owned books):
+{{library_context}}
+
+Return JSON only with ALL sections filled (not one-line answers):
 {
-  "title": "...",
+  "title": "clear lesson title",
-  "introduction": "...",
+  "overview": "2-4 sentences introducing the topic",
-  "objectives": ["..."],
+  "whyItMatters": "2-3 sentences on real-world relevance",
-  "readingSteps": ["..."],
+  "learningObjectives": ["3-5 specific objectives"],
-  "reflectionPrompt": "...",
+  "explanation": "beginner-friendly explanation (short=2 paragraphs, standard=3-4, deep=5+)",
+  "researchAssignment": {
+    "steps": ["3-5 concrete research steps"],
+    "expectedOutcome": "what the learner should produce",
+    "estimatedTimeMinutes": 20
+  },
+  "calibreSuggestions": [{ "title", "authors": ["..."], "reason": "why this book helps" }],
+  "externalReading": ["general topic directions without URLs"],
+  "homework": { "task": "...", "instructions": ["..."] },
+  "reflectionPrompt": "one thoughtful question",
   "flashcards": [{ "front", "back" }],
-  "quiz": [{ "question", "options": ["a","b","c","d"], "answer": 0 }],
+  "quiz": [{
-  "assignment": "..."
+    "question": "...",
+    "type": "multiple_choice",
+    "options": ["a","b","c","d"],
+    "answer": 0,
+    "explanation": "why this is correct"
+  }],
+  "answerKey": [{ "questionIndex": 0, "answer": "...", "explanation": "..." }],
+  "nextLessonSuggestion": "optional follow-up topic"
 }
-Use answer as a 0-based index number.`,
+Rules:
+- Include 3-5 quiz questions (mix multiple_choice and short_answer if possible).
+- For multiple_choice use answer as 0-based index.
+- For short_answer omit options; put the answer text in answer as a string.
+- If no library books match, set calibreSuggestions to [] and mention it in overview.
+- Be specific to {{topic}}. Tone: calm, curious, practical.`,
   },
   reflection_prompt: {
     name: "Reflection Prompt",
@@ -114,7 +139,9 @@ Be concise, encouraging, and practical. Output valid JSON only.`,
     name: "Teacher Instructions",
     description: "Teacher content persona",
     category: "system_prompt",
-    body: `Explain concepts simply. Use examples from everyday life. Encourage curiosity over perfection.`,
+    body: `You are a calm, wise tutor giving a structured mini-learning session — not a generic chat reply.
+Explain simply with everyday examples. Give practical homework and a fair quiz with an answer key.
+Encourage curiosity over perfection. Never overwhelm. Output valid JSON only.`,
   },
 };
 
@@ -126,7 +153,9 @@ export const PLACEHOLDER_DOCS = [
   { key: "reading_progress", description: "Reading stats" },
   { key: "exercise_summary", description: "Exercise activity" },
   { key: "prayer_summary", description: "Prayer/litany progress" },
-  { key: "learning_topics", description: "Current learning topics" },
+  { key: "library_context", description: "User Calibre library metadata for this topic" },
+  { key: "difficulty", description: "Lesson difficulty: beginner, intermediate, advanced" },
+  { key: "length", description: "Lesson length: short, standard, deep" },
   { key: "chronicle_context", description: "Long-term journey context" },
 ];
 

apps/web/src/lib/services/ai-chat.ts

@@ -2,6 +2,11 @@ import { and, eq, desc, isNull } from "drizzle-orm";
 import { db, aiChatSessions, aiChatMessages } from "../db";
 import { buildMentorContext, formatContextForPrompt } from "./ai-context";
 import { generateChatReply, getAiAvailability } from "./ai";
+import {
+  formatLibraryContextForPrompt,
+  getLibraryContextForTopic,
+  shouldIncludeLibraryContextInChat,
+} from "./library-context";
 import { listMemories, getProfileSummary } from "./ai-memory";
 import { MEMORY_CATEGORIES, type MemoryCategory } from "@adventureos/shared";
 
@@ -66,6 +71,16 @@ export async function sendChatMessage(userId: string, sessionId: string, content
     logContext: true,
   });
 
+  let contextBlock = formatContextForPrompt(ctx);
+  if (shouldIncludeLibraryContextInChat(content)) {
+    try {
+      const libraryPayload = await getLibraryContextForTopic(userId, content);
+      contextBlock = `${contextBlock}\n\n${formatLibraryContextForPrompt(libraryPayload)}`;
+    } catch {
+      /* library optional */
+    }
+  }
+
   let reply: string;
   let offline = false;
   let memoryIdsUsed = ctx.memoryIds;
@@ -81,7 +96,7 @@ export async function sendChatMessage(userId: string, sessionId: string, content
 
     const generated = await generateChatReply(userId, {
       userMessage: content,
-      contextBlock: formatContextForPrompt(ctx),
+      contextBlock,
       history,
     });
 

apps/web/src/lib/services/ai-teacher.test.ts

@@ -8,7 +8,7 @@ vi.mock("./ai-config", () => ({
 }));
 
 vi.mock("./ai-templates", () => ({
-  getTemplateBody: vi.fn(async () => "topic: {{topic}}"),
+  getTemplateBody: vi.fn(async () => "topic: {{topic}} difficulty: {{difficulty}}"),
 }));
 
 vi.mock("../ai/provider-registry", () => ({
@@ -16,12 +16,30 @@ vi.mock("../ai/provider-registry", () => ({
 }));
 
 vi.mock("./user", () => ({
-  requireUser: vi.fn(async () => ({ user: { id: "user-1" } })),
+  requireUser: vi.fn(async () => ({ user: { id: "user-1", displayName: "Traveler" } })),
 }));
 
 import { getAiBehaviorConfig, getAiProviderConfig } from "./ai-config";
 import { getProvider } from "../ai/provider-registry";
 
+const onlineAvailability = {
+  enabled: true,
+  creativity: 0.7,
+  personality: "supportive_mentor",
+  verbosity: "balanced",
+  strictMode: false,
+};
+
+const onlineProviderConfig = {
+  enabled: true,
+  type: "ollama" as const,
+  baseUrl: "http://localhost:11434",
+  model: "test",
+  maxTokens: 1000,
+  temperature: 0.7,
+  timeoutMs: 30000,
+};
+
 describe("teacherSchema", () => {
   it("coerces string quiz answers to numbers", () => {
     const parsed = teacherSchema.parse({
@@ -32,18 +50,34 @@ describe("teacherSchema", () => {
     expect(parsed.quiz[0].answer).toBe(0);
   });
 
-  it("accepts optional structured fields", () => {
+  it("accepts extended structured fields", () => {
     const parsed = teacherSchema.parse({
-      title: "Roman Roads",
+      title: "DNS Basics",
-      introduction: "A brief intro",
+      overview: "Intro to DNS",
-      objectives: ["Learn basics"],
+      whyItMatters: "Used everywhere",
-      readingSteps: ["Find a source"],
+      learningObjectives: ["Understand DNS"],
-      reflectionPrompt: "What surprised you?",
+      explanation: "DNS maps names to IPs",
+      researchAssignment: {
+        steps: ["Look up DNS"],
+        expectedOutcome: "Summary",
+        estimatedTimeMinutes: 20,
+      },
+      calibreSuggestions: [{ title: "Networking", authors: ["Author"], reason: "Relevant" }],
+      homework: { task: "Draw diagram", instructions: ["Use pen"] },
       flashcards: [{ front: "Q", back: "A" }],
-      quiz: [{ question: "Q?", options: ["a", "b"], answer: 0 }],
+      quiz: [
+        {
+          question: "Q?",
+          type: "multiple_choice",
+          options: ["a", "b"],
+          answer: 0,
+          answerText: "a",
+        },
+      ],
       assignment: "Research",
     });
-    expect(parsed.title).toBe("Roman Roads");
+    expect(parsed.title).toBe("DNS Basics");
+    expect(parsed.researchAssignment?.steps).toHaveLength(1);
   });
 });
 
@@ -61,28 +95,16 @@ describe("generateTeacherContent", () => {
   });
 
   it("returns AI content when provider succeeds", async () => {
-    vi.mocked(getAiBehaviorConfig).mockResolvedValue({
+    vi.mocked(getAiBehaviorConfig).mockResolvedValue(onlineAvailability);
-      enabled: true,
+    vi.mocked(getAiProviderConfig).mockResolvedValue(onlineProviderConfig);
-      creativity: 0.7,
-      personality: "supportive_mentor",
-      verbosity: "balanced",
-      strictMode: false,
-    });
-    vi.mocked(getAiProviderConfig).mockResolvedValue({
-      enabled: true,
-      type: "ollama",
-      baseUrl: "http://localhost:11434",
-      model: "test",
-      maxTokens: 1000,
-      temperature: 0.7,
-      timeoutMs: 30000,
-    });
     vi.mocked(getProvider).mockReturnValue({
       type: "ollama",
       healthCheck: vi.fn(async () => ({ status: "online" as const })),
       listModels: vi.fn(async () => []),
       generateText: vi.fn(async () => ({
         text: JSON.stringify({
+          overview: "Intro",
+          explanation: "Details here",
           flashcards: [{ front: "What is Rust?", back: "A systems language" }],
           quiz: [
             {
@@ -91,7 +113,7 @@ describe("generateTeacherContent", () => {
               answer: 0,
             },
           ],
-          assignment: "Read chapter 1",
+          researchAssignment: { steps: ["Read chapter 1"], expectedOutcome: "Notes" },
         }),
         model: "test",
         latencyMs: 10,
@@ -99,52 +121,30 @@ describe("generateTeacherContent", () => {
     });
 
     const { generateTeacherContent } = await import("./ai");
-    const result = await generateTeacherContent("Rust ownership", "user-1");
+    const result = await generateTeacherContent("Rust ownership", "user-1", {
+      difficulty: "beginner",
+      length: "standard",
+    });
     expect(result.source).toBe("ai");
     expect(result.content.flashcards[0].back).toContain("systems language");
   });
 
-  it("returns fallback when AI is disabled", async () => {
+  it("throws when AI is unavailable", async () => {
     vi.mocked(getAiBehaviorConfig).mockResolvedValue({
+      ...onlineAvailability,
       enabled: false,
-      creativity: 0.7,
-      personality: "supportive_mentor",
-      verbosity: "balanced",
-      strictMode: false,
-    });
-    vi.mocked(getAiProviderConfig).mockResolvedValue({
-      enabled: true,
-      type: "ollama",
-      baseUrl: "http://localhost:11434",
-      model: "test",
-      maxTokens: 1000,
-      temperature: 0.7,
-      timeoutMs: 30000,
     });
+    vi.mocked(getAiProviderConfig).mockResolvedValue(onlineProviderConfig);
 
     const { generateTeacherContent } = await import("./ai");
-    const result = await generateTeacherContent("Stoicism", "user-1");
+    await expect(generateTeacherContent("Stoicism", "user-1")).rejects.toThrow(
-    expect(result.source).toBe("fallback");
+      "AI is unavailable"
-    expect(result.content.assignment).toContain("Stoicism");
+    );
   });
 
   it("returns fallback when AI JSON is invalid and strictMode is off", async () => {
-    vi.mocked(getAiBehaviorConfig).mockResolvedValue({
+    vi.mocked(getAiBehaviorConfig).mockResolvedValue(onlineAvailability);
-      enabled: true,
+    vi.mocked(getAiProviderConfig).mockResolvedValue(onlineProviderConfig);
-      creativity: 0.7,
-      personality: "supportive_mentor",
-      verbosity: "balanced",
-      strictMode: false,
-    });
-    vi.mocked(getAiProviderConfig).mockResolvedValue({
-      enabled: true,
-      type: "ollama",
-      baseUrl: "http://localhost:11434",
-      model: "test",
-      maxTokens: 1000,
-      temperature: 0.7,
-      timeoutMs: 30000,
-    });
     vi.mocked(getProvider).mockReturnValue({
       type: "ollama",
       healthCheck: vi.fn(async () => ({ status: "online" as const })),
@@ -159,5 +159,6 @@ describe("generateTeacherContent", () => {
     const { generateTeacherContent } = await import("./ai");
     const result = await generateTeacherContent("Stoicism", "user-1");
     expect(result.source).toBe("fallback");
+    expect(result.fallbackReason).toBe("parse_failed");
   });
 });

apps/web/src/lib/services/ai.ts

@@ -4,9 +4,11 @@ import {
   pickRandomQuests,
 } from "@adventureos/shared";
 import { getProvider } from "../ai/provider-registry";
+import type { TeacherDifficulty, TeacherLength } from "@adventureos/shared";
 import {
   debugAiLog,
   isAiTimeoutError,
+  isInvalidObjectString,
   normalizeExplorationPayload,
   normalizeTeacherPayload,
   safeParseAiJson,
@@ -55,21 +57,59 @@ const mentorSchema = z.object({
   letter: z.string(),
 });
 
+const teacherResearchAssignmentSchema = z.object({
+  steps: z.array(z.string()),
+  expectedOutcome: z.string().optional(),
+  estimatedTimeMinutes: z.coerce.number().optional(),
+});
+
+const teacherHomeworkSchema = z.object({
+  task: z.string(),
+  instructions: z.array(z.string()),
+});
+
+const teacherCalibreSuggestionSchema = z.object({
+  title: z.string(),
+  authors: z.array(z.string()),
+  reason: z.string(),
+});
+
 export const teacherSchema = z.object({
   title: z.string().optional(),
   introduction: z.string().optional(),
+  overview: z.string().optional(),
+  whyItMatters: z.string().optional(),
   objectives: z.array(z.string()).optional(),
+  learningObjectives: z.array(z.string()).optional(),
+  explanation: z.string().optional(),
+  researchAssignment: teacherResearchAssignmentSchema.optional(),
   readingSteps: z.array(z.string()).optional(),
+  calibreSuggestions: z.array(teacherCalibreSuggestionSchema).optional(),
+  externalReading: z.array(z.string()).optional(),
+  homework: teacherHomeworkSchema.optional(),
   reflectionPrompt: z.string().optional(),
   flashcards: z.array(z.object({ front: z.string(), back: z.string() })),
   quiz: z.array(
     z.object({
       question: z.string(),
-      options: z.array(z.string()),
+      type: z.enum(["multiple_choice", "short_answer"]).optional(),
+      options: z.array(z.string()).optional(),
       answer: z.coerce.number(),
+      answerText: z.string().optional(),
+      explanation: z.string().optional(),
     })
   ),
-  assignment: z.string(),
+  answerKey: z
+    .array(
+      z.object({
+        questionIndex: z.coerce.number(),
+        answer: z.string(),
+        explanation: z.string().optional(),
+      })
+    )
+    .optional(),
+  nextLessonSuggestion: z.string().optional(),
+  assignment: z.string().optional(),
 });
 
 export type TeacherContent = z.infer<typeof teacherSchema>;
@@ -174,10 +214,16 @@ async function aiGenerate(
 }
 
 function hasMeaningfulTeacherContent(content: TeacherContent): boolean {
+  const hasAssignment =
+    (content.assignment && !isInvalidObjectString(content.assignment)) ||
+    (content.researchAssignment?.steps?.length ?? 0) > 0 ||
+    (content.homework?.task && !isInvalidObjectString(content.homework.task));
+  const hasExplanation = !!content.explanation?.trim() || !!content.overview?.trim();
   return (
-    content.assignment.trim().length > 0 ||
+    hasAssignment ||
     content.flashcards.length > 0 ||
-    content.quiz.length > 0
+    content.quiz.length > 0 ||
+    hasExplanation
   );
 }
 
@@ -213,23 +259,58 @@ function parseExplorationResponse(raw: string) {
 
 function teacherFallback(topic: string): TeacherContent {
   return {
+    title: `Introduction to ${topic}`,
+    overview: `This is a basic offline lesson about ${topic}. Connect to the AI when available for a fuller session.`,
+    whyItMatters: `${topic} connects to everyday curiosity and practical understanding.`,
+    learningObjectives: [`Understand the basics of ${topic}`, "Know where to look next"],
+    explanation: `Start by defining ${topic} in your own words. Look for one reliable source and one example from daily life.`,
+    researchAssignment: {
+      steps: [
+        `Search for a beginner-friendly explanation of ${topic}`,
+        "Write three bullet points in your own words",
+        "Note one question you still have",
+      ],
+      expectedOutcome: "A short summary you could explain to a friend",
+      estimatedTimeMinutes: 20,
+    },
+    homework: {
+      task: `Explore ${topic} for 20 minutes`,
+      instructions: ["Pick one source", "Write one surprising sentence"],
+    },
     flashcards: [
       {
         front: `What is ${topic}?`,
-        back: "Explore this topic through reading and observation.",
+        back: "A topic worth exploring through reading and observation.",
       },
     ],
     quiz: [
       {
         question: `Which approach helps you learn about ${topic}?`,
+        type: "multiple_choice",
         options: ["Curious reading", "Giving up", "Ignoring it", "Rushing"],
         answer: 0,
+        answerText: "Curious reading",
       },
     ],
     assignment: `Spend 20 minutes researching ${topic}. Write one sentence about what surprised you.`,
+    reflectionPrompt: `What is one thing about ${topic} you want to understand better?`,
   };
 }
 
+export type TeacherGenerationOptions = {
+  personalContext?: string;
+  libraryContext?: string;
+  difficulty?: TeacherDifficulty;
+  length?: TeacherLength;
+};
+
+export class TeacherAiUnavailableError extends Error {
+  constructor(message = "AI is unavailable. Check Settings or your local model.") {
+    super(message);
+    this.name = "TeacherAiUnavailableError";
+  }
+}
+
 export async function generateQuests(context: Record<string, unknown>, userId?: string) {
   const uid = userId ?? (await getUserId());
   const raw = await aiGenerate(
@@ -321,7 +402,7 @@ export async function generateMentorReview(context: Record<string, unknown>, use
 export async function generateTeacherContent(
   topic: string,
   userId?: string,
-  personalContext?: string
+  options: TeacherGenerationOptions = {}
 ): Promise<TeacherGenerationResult> {
   const trimmed = topic.trim();
   if (!trimmed) {
@@ -332,12 +413,28 @@ export async function generateTeacherContent(
   const behavior = await getAiBehaviorConfig(uid);
   const availability = await getAiAvailability(uid);
 
+  if (!availability.canUse || !availability.online) {
+    throw new TeacherAiUnavailableError();
+  }
+
+  const difficulty = options.difficulty ?? "beginner";
+  const length = options.length ?? "standard";
+  const contextParts = [options.personalContext ?? ""];
+  if (options.libraryContext) contextParts.push(options.libraryContext);
+  const combinedContext = contextParts.filter(Boolean).join("\n\n");
+
   const raw = await aiGenerate(
     uid,
     "homework_generation",
     "system_core",
     "system_teacher",
-    { topic: trimmed, context: personalContext ?? "" }
+    {
+      topic: trimmed,
+      context: combinedContext,
+      library_context: options.libraryContext ?? "Library not available.",
+      difficulty,
+      length,
+    }
   );
 
   if (raw) {
@@ -350,20 +447,29 @@ export async function generateTeacherContent(
       canUse: availability.canUse,
       rawLen: raw.length,
     });
-    if (behavior.strictMode && availability.canUse && availability.online) {
+    if (behavior.strictMode) {
       throw new Error("AI returned invalid lesson content. Try again.");
     }
-  } else {
+    return {
-    debugAiLog("ai.ts:generateTeacherContent", "no raw response", {
+      content: teacherFallback(trimmed),
-      online: availability.online,
+      source: "fallback",
-      canUse: availability.canUse,
+      fallbackReason: "parse_failed",
-    });
+    };
-    if (behavior.strictMode && availability.canUse && availability.online) {
-      throw new Error("AI generation failed");
-    }
   }
 
-  return { content: teacherFallback(trimmed), source: "fallback", fallbackReason: lastAiFallbackReason ?? "generation_failed" };
+  debugAiLog("ai.ts:generateTeacherContent", "no raw response", {
+    online: availability.online,
+    canUse: availability.canUse,
+  });
+  if (behavior.strictMode) {
+    throw new Error("AI generation failed");
+  }
+
+  return {
+    content: teacherFallback(trimmed),
+    source: "fallback",
+    fallbackReason: lastAiFallbackReason ?? "generation_failed",
+  };
 }
 
 export async function isOllamaAvailable(): Promise<boolean> {

apps/web/src/lib/services/library-context.test.ts

@@ -0,0 +1,90 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+
+vi.mock("./calibre", () => ({
+  getCalibreStatus: vi.fn(),
+  listCalibreBooks: vi.fn(),
+}));
+
+vi.mock("./calibre-reading", () => ({
+  getReadingProgress: vi.fn(),
+}));
+
+import { getCalibreStatus, listCalibreBooks } from "./calibre";
+import { getReadingProgress } from "./calibre-reading";
+import {
+  formatLibraryContextForPrompt,
+  getLibraryContextForTopic,
+  shouldIncludeLibraryContextInChat,
+} from "./library-context";
+
+describe("library-context", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+  });
+
+  it("returns empty payload when Calibre unavailable", async () => {
+    vi.mocked(getCalibreStatus).mockResolvedValue({
+      configured: false,
+      online: false,
+      bookCount: 0,
+      lastCheckAt: new Date().toISOString(),
+    });
+
+    const payload = await getLibraryContextForTopic("user-1", "Ottoman history");
+    expect(payload.available).toBe(false);
+    expect(payload.relevantBooks).toEqual([]);
+  });
+
+  it("limits and ranks relevant books for a topic", async () => {
+    vi.mocked(getCalibreStatus).mockResolvedValue({
+      configured: true,
+      online: true,
+      bookCount: 2,
+      lastCheckAt: new Date().toISOString(),
+    });
+    vi.mocked(getReadingProgress).mockResolvedValue([]);
+    vi.mocked(listCalibreBooks).mockResolvedValue([
+      {
+        id: 1,
+        uuid: "a",
+        title: "The Ottoman Empire",
+        authors: ["Author A"],
+        tags: ["history", "ottoman"],
+        comment: "A long ".repeat(50),
+        series: null,
+        seriesIndex: null,
+        rating: null,
+        formats: ["EPUB"],
+        hasCover: true,
+      },
+      {
+        id: 2,
+        uuid: "b",
+        title: "Cooking Basics",
+        authors: ["Chef"],
+        tags: ["food"],
+        comment: null,
+        series: null,
+        seriesIndex: null,
+        rating: null,
+        formats: ["EPUB"],
+        hasCover: false,
+      },
+    ]);
+
+    const payload = await getLibraryContextForTopic("user-1", "Ottoman history", { limit: 3 });
+    expect(payload.available).toBe(true);
+    expect(payload.relevantBooks.length).toBeGreaterThan(0);
+    expect(payload.relevantBooks[0]?.title).toBe("The Ottoman Empire");
+    expect(payload.relevantBooks[0]?.description?.length).toBeLessThanOrEqual(200);
+    const formatted = formatLibraryContextForPrompt(payload);
+    expect(formatted).toContain("Ottoman Empire");
+    expect(formatted).not.toMatch(/\/home\//);
+    expect(formatted).not.toContain("uuid");
+  });
+
+  it("detects chat messages about reading", () => {
+    expect(shouldIncludeLibraryContextInChat("What book should I read about history?")).toBe(true);
+    expect(shouldIncludeLibraryContextInChat("How is my day going?")).toBe(false);
+  });
+});

apps/web/src/lib/services/library-context.ts

@@ -0,0 +1,202 @@
+import type { CalibreBook } from "./calibre";
+import { getCalibreStatus, listCalibreBooks } from "./calibre";
+import { getReadingProgress } from "./calibre-reading";
+
+const MAX_DESCRIPTION = 200;
+const DEFAULT_RELEVANT_LIMIT = 6;
+const DEFAULT_READING_LIMIT = 3;
+
+export type LibraryBookContext = {
+  title: string;
+  authors: string[];
+  tags: string[];
+  series?: string | null;
+  description?: string;
+  status?: "unread" | "reading" | "finished";
+  progressPercent?: number;
+};
+
+export type LibraryContextPayload = {
+  available: boolean;
+  relevantBooks: LibraryBookContext[];
+  currentlyReading: LibraryBookContext[];
+};
+
+function trimDescription(comment: string | null | undefined): string | undefined {
+  if (!comment?.trim()) return undefined;
+  const trimmed = comment.trim().replace(/\s+/g, " ");
+  if (trimmed.length <= MAX_DESCRIPTION) return trimmed;
+  return `${trimmed.slice(0, MAX_DESCRIPTION - 1)}…`;
+}
+
+function toBookContext(
+  book: CalibreBook,
+  progress?: { status?: string | null; currentPage?: number | null; totalPages?: number | null }
+): LibraryBookContext {
+  const total = Math.max(progress?.totalPages ?? 1, 1);
+  const current = progress?.currentPage ?? 0;
+  const status = (progress?.status as LibraryBookContext["status"]) ?? "unread";
+  return {
+    title: book.title,
+    authors: book.authors,
+    tags: book.tags,
+    series: book.series,
+    description: trimDescription(book.comment),
+    status,
+    progressPercent: progress ? Math.round((current / total) * 100) : undefined,
+  };
+}
+
+function scoreBookForTopic(book: CalibreBook, keywords: string[]): number {
+  if (keywords.length === 0) return 0;
+  const haystack = [
+    book.title,
+    book.authors.join(" "),
+    book.tags.join(" "),
+    book.series ?? "",
+    book.comment ?? "",
+  ]
+    .join(" ")
+    .toLowerCase();
+
+  let score = 0;
+  for (const kw of keywords) {
+    if (haystack.includes(kw)) score += kw.length > 3 ? 3 : 1;
+  }
+  return score;
+}
+
+function topicKeywords(topic: string): string[] {
+  return topic
+    .toLowerCase()
+    .split(/[\s,;/]+/)
+    .map((w) => w.trim())
+    .filter((w) => w.length > 2);
+}
+
+export async function getCurrentlyReadingBooks(
+  userId: string,
+  limit = DEFAULT_READING_LIMIT
+): Promise<LibraryBookContext[]> {
+  try {
+    const status = await getCalibreStatus();
+    if (!status.configured || !status.online) return [];
+
+    const progress = await getReadingProgress(userId);
+    const reading = progress.filter((p) => p.status === "reading" && p.calibreBookId);
+    if (reading.length === 0) return [];
+
+    const books = await listCalibreBooks({ limit: 500 });
+    const bookMap = new Map(books.map((b) => [b.id, b]));
+
+    return reading
+      .slice(0, limit)
+      .map((p) => {
+        const book = bookMap.get(p.calibreBookId!);
+        if (!book) return null;
+        return toBookContext(book, p);
+      })
+      .filter((b): b is LibraryBookContext => b != null);
+  } catch {
+    return [];
+  }
+}
+
+export async function getLibraryContextForTopic(
+  userId: string,
+  topic: string,
+  options?: { limit?: number }
+): Promise<LibraryContextPayload> {
+  const limit = options?.limit ?? DEFAULT_RELEVANT_LIMIT;
+  const empty: LibraryContextPayload = {
+    available: false,
+    relevantBooks: [],
+    currentlyReading: [],
+  };
+
+  try {
+    const status = await getCalibreStatus();
+    if (!status.configured || !status.online) return empty;
+
+    const currentlyReading = await getCurrentlyReadingBooks(userId);
+    const keywords = topicKeywords(topic);
+    const progress = await getReadingProgress(userId);
+    const progressMap = new Map(progress.map((p) => [p.calibreBookId, p]));
+
+    let candidates: CalibreBook[] = [];
+    if (keywords.length > 0) {
+      const primary = keywords[0]!;
+      candidates = await listCalibreBooks({ search: primary, limit: 50 });
+      if (candidates.length < limit && keywords.length > 1) {
+        const extra = await listCalibreBooks({ search: keywords.slice(0, 3).join(" "), limit: 50 });
+        const seen = new Set(candidates.map((b) => b.id));
+        for (const book of extra) {
+          if (!seen.has(book.id)) candidates.push(book);
+        }
+      }
+    } else {
+      candidates = await listCalibreBooks({ limit: 50 });
+    }
+
+    const ranked = candidates
+      .map((book) => ({ book, score: scoreBookForTopic(book, keywords) }))
+      .filter((entry) => entry.score > 0 || keywords.length === 0)
+      .sort((a, b) => b.score - a.score)
+      .slice(0, limit)
+      .map(({ book }) => toBookContext(book, progressMap.get(book.id)));
+
+    return {
+      available: true,
+      relevantBooks: ranked,
+      currentlyReading,
+    };
+  } catch {
+    return empty;
+  }
+}
+
+export function formatLibraryContextForPrompt(payload: LibraryContextPayload): string {
+  if (!payload.available) {
+    return "Library: not available (no matching books from user's Calibre library).";
+  }
+
+  const lines: string[] = ["User's Calibre library (metadata only — cite ONLY these titles if relevant):"];
+
+  if (payload.currentlyReading.length > 0) {
+    lines.push("Currently reading:");
+    for (const book of payload.currentlyReading) {
+      lines.push(
+        `- "${book.title}" by ${book.authors.join(", ") || "unknown"}${book.tags.length ? ` [${book.tags.slice(0, 4).join(", ")}]` : ""}`
+      );
+    }
+  }
+
+  if (payload.relevantBooks.length > 0) {
+    lines.push("Books possibly relevant to this topic:");
+    for (const book of payload.relevantBooks) {
+      const desc = book.description ? ` — ${book.description}` : "";
+      lines.push(
+        `- "${book.title}" by ${book.authors.join(", ") || "unknown"}${book.tags.length ? ` [${book.tags.slice(0, 4).join(", ")}]` : ""}${desc}`
+      );
+    }
+  } else {
+    lines.push("No matching library books found for this topic.");
+  }
+
+  lines.push("Do NOT invent books the user owns. If none match, say so and give general reading guidance.");
+  return lines.join("\n");
+}
+
+export function shouldIncludeLibraryContextInChat(message: string): boolean {
+  const lower = message.toLowerCase();
+  const patterns = [
+    /\bbook(s)?\b/,
+    /\bread(ing)?\b/,
+    /\blibrary\b/,
+    /\bshelf\b/,
+    /\brecommend\b.*\bread/,
+    /\bwhat should i read\b/,
+    /\bown(s)?\b.*\bbook/,
+  ];
+  return patterns.some((p) => p.test(lower));
+}

apps/web/src/lib/services/teacher.ts

@@ -1,21 +1,36 @@
-import { generateTeacherContent } from "./ai";
+import {
+  generateTeacherContent,
+  TeacherAiUnavailableError,
+} from "./ai";
 import { buildMentorContext, formatContextForPrompt } from "./ai-context";
+import {
+  formatLibraryContextForPrompt,
+  getLibraryContextForTopic,
+} from "./library-context";
 import {
   listTeacherContent,
   findTeacherContentById,
   insertTeacherContent,
   updateTeacherContent,
 } from "@/lib/repositories/teacher.repository";
+import { wrapTeacherContent, unwrapTeacherContent } from "@/lib/teacher/teacher-content";
 import type { TeacherCreateBody } from "@/lib/validation/schemas";
 
+function mapTeacherRow(row: Awaited<ReturnType<typeof listTeacherContent>>[number]) {
+  const stored = row.content as Record<string, unknown>;
+  const { content, source, fallbackReason } = unwrapTeacherContent(stored);
+  return { ...row, content, source, fallbackReason };
+}
+
 export async function getTeacherHistory(userId: string) {
-  return listTeacherContent(userId);
+  const rows = await listTeacherContent(userId);
+  return rows.map(mapTeacherRow);
 }
 
 export async function getTeacherLesson(userId: string, id: string) {
   const row = await findTeacherContentById(id);
   if (!row || row.userId !== userId) return null;
-  return row;
+  return mapTeacherRow(row);
 }
 
 export async function createTeacherLesson(
@@ -27,18 +42,42 @@ export async function createTeacherLesson(
     throw new Error("Topic is required");
   }
 
-  const ctx = await buildMentorContext(userId, { feature: "teacher", topic, userMessage: topic });
+  const ctx = await buildMentorContext(userId, {
-  const { content, source, fallbackReason } = await generateTeacherContent(topic, userId, formatContextForPrompt(ctx));
+    feature: "teacher",
+    topic,
+    userMessage: topic,
+  });
+
+  let libraryContext = "";
+  if (input.includeLibraryContext !== false) {
+    try {
+      const payload = await getLibraryContextForTopic(userId, topic);
+      libraryContext = formatLibraryContextForPrompt(payload);
+    } catch {
+      libraryContext = "Library: not available.";
+    }
+  }
+
+  const { content, source, fallbackReason } = await generateTeacherContent(topic, userId, {
+    personalContext: formatContextForPrompt(ctx),
+    libraryContext,
+    difficulty: input.difficulty,
+    length: input.length,
+  });
+
+  const storedContent = wrapTeacherContent(content, { source, fallbackReason });
   const row = await insertTeacherContent({
     userId,
     topic,
     explorationId: input.explorationId,
-    content,
+    content: storedContent as Record<string, unknown>,
     status: "active",
   });
-  return { ...row, source, fallbackReason };
+  return { ...mapTeacherRow({ ...row, content: storedContent as Record<string, unknown> }) };
 }
 
+export { TeacherAiUnavailableError };
+
 export async function completeTeacherLesson(
   userId: string,
   id: string,
@@ -53,5 +92,5 @@ export async function completeTeacherLesson(
     completedAt: new Date(),
   });
   if (!updated) throw new Error("Lesson not found");
-  return updated;
+  return mapTeacherRow(updated);
 }

apps/web/src/lib/teacher/extract-text.test.ts

@@ -0,0 +1,46 @@
+import { describe, it, expect } from "vitest";
+import {
+  extractText,
+  extractStringList,
+  isObjectObject,
+  normalizeQuizAnswer,
+} from "./extract-text";
+
+describe("extractText", () => {
+  it("returns empty for object without known fields instead of [object Object]", () => {
+    expect(extractText({ foo: "bar" })).toBe("");
+    expect(extractText({ task: "Research DNS" })).toBe("Research DNS");
+  });
+
+  it("extracts nested assignment objects", () => {
+    expect(
+      extractText({
+        task: "Write a summary",
+        steps: ["Open docs", "Take notes"],
+      })
+    ).toContain("Write a summary");
+  });
+});
+
+describe("extractStringList", () => {
+  it("maps object steps to strings", () => {
+    expect(
+      extractStringList([{ step: "Read chapter 1" }, "Search Wikipedia"])
+    ).toEqual(["Read chapter 1", "Search Wikipedia"]);
+  });
+});
+
+describe("normalizeQuizAnswer", () => {
+  it("maps letter B to index 1", () => {
+    const result = normalizeQuizAnswer("B", ["A opt", "B opt", "C opt"]);
+    expect(result.answerIndex).toBe(1);
+    expect(result.answerText).toBe("B opt");
+  });
+});
+
+describe("isObjectObject", () => {
+  it("detects invalid coerced strings", () => {
+    expect(isObjectObject("[object Object]")).toBe(true);
+    expect(isObjectObject("real text")).toBe(false);
+  });
+});

apps/web/src/lib/teacher/extract-text.ts

@@ -0,0 +1,83 @@
+const OBJECT_OBJECT = "[object Object]";
+
+export function isObjectObject(value: string | undefined | null): boolean {
+  return value?.trim() === OBJECT_OBJECT;
+}
+
+/** Extract human-readable text from AI fields that may be strings or nested objects. */
+export function extractText(value: unknown): string {
+  if (value == null) return "";
+  if (typeof value === "string") {
+    const trimmed = value.trim();
+    return isObjectObject(trimmed) ? "" : trimmed;
+  }
+  if (typeof value === "number" || typeof value === "boolean") {
+    return String(value);
+  }
+  if (Array.isArray(value)) {
+    return value.map((item) => extractText(item)).filter(Boolean).join("; ");
+  }
+  if (typeof value === "object") {
+    const o = value as Record<string, unknown>;
+    const parts: string[] = [];
+    for (const key of ["task", "text", "description", "content", "summary", "goal", "step"]) {
+      const part = extractText(o[key]);
+      if (part) parts.push(part);
+    }
+    if (Array.isArray(o.steps)) {
+      const steps = o.steps.map((s) => extractText(s)).filter(Boolean);
+      if (steps.length) parts.push(steps.join("; "));
+    }
+    if (Array.isArray(o.instructions)) {
+      const instructions = o.instructions.map((s) => extractText(s)).filter(Boolean);
+      if (instructions.length) parts.push(instructions.join("; "));
+    }
+    return parts.join(" — ").trim();
+  }
+  return "";
+}
+
+export function extractStringList(value: unknown): string[] {
+  if (!Array.isArray(value)) return [];
+  return value.map((item) => extractText(item)).filter(Boolean);
+}
+
+export function normalizeQuizAnswer(
+  rawAnswer: unknown,
+  options: string[]
+): { answerIndex: number; answerText: string } {
+  if (options.length === 0) {
+    const text = extractText(rawAnswer);
+    return { answerIndex: 0, answerText: text || "See explanation" };
+  }
+
+  if (typeof rawAnswer === "number" && Number.isFinite(rawAnswer)) {
+    const idx = Math.min(Math.max(0, rawAnswer), options.length - 1);
+    return { answerIndex: idx, answerText: options[idx] ?? "" };
+  }
+
+  const asString = extractText(rawAnswer).trim();
+  if (!asString) return { answerIndex: 0, answerText: options[0] ?? "" };
+
+  const asNum = Number(asString);
+  if (Number.isFinite(asNum) && asNum >= 0 && asNum < options.length) {
+    return { answerIndex: asNum, answerText: options[asNum] ?? "" };
+  }
+
+  const letterMatch = /^[A-Da-d]$/.exec(asString);
+  if (letterMatch) {
+    const idx = letterMatch[0].toUpperCase().charCodeAt(0) - 65;
+    if (idx >= 0 && idx < options.length) {
+      return { answerIndex: idx, answerText: options[idx] ?? "" };
+    }
+  }
+
+  const optionIdx = options.findIndex(
+    (opt) => opt.toLowerCase() === asString.toLowerCase()
+  );
+  if (optionIdx >= 0) {
+    return { answerIndex: optionIdx, answerText: options[optionIdx] ?? "" };
+  }
+
+  return { answerIndex: 0, answerText: asString };
+}

apps/web/src/lib/teacher/teacher-content.test.ts

@@ -0,0 +1,19 @@
+import { describe, it, expect } from "vitest";
+import { wrapTeacherContent, unwrapTeacherContent } from "./teacher-content";
+
+describe("teacher-content envelope", () => {
+  it("round-trips source metadata", () => {
+    const wrapped = wrapTeacherContent(
+      {
+        flashcards: [],
+        quiz: [],
+        assignment: "Read",
+      },
+      { source: "fallback", fallbackReason: "parse_failed" }
+    );
+    const unwrapped = unwrapTeacherContent(wrapped as Record<string, unknown>);
+    expect(unwrapped.source).toBe("fallback");
+    expect(unwrapped.fallbackReason).toBe("parse_failed");
+    expect(unwrapped.content.assignment).toBe("Read");
+  });
+});

apps/web/src/lib/teacher/teacher-content.ts

@@ -0,0 +1,34 @@
+import type { AiFallbackReason, AiContentSource } from "@/lib/services/ai";
+import type { TeacherLessonContent } from "@adventureos/shared";
+
+const META_KEY = "_meta";
+
+type StoredTeacherMeta = {
+  source?: AiContentSource;
+  fallbackReason?: AiFallbackReason;
+};
+
+export type StoredTeacherContent = TeacherLessonContent & {
+  [META_KEY]?: StoredTeacherMeta;
+};
+
+export function wrapTeacherContent(
+  content: TeacherLessonContent,
+  meta: StoredTeacherMeta
+): StoredTeacherContent {
+  return { ...content, [META_KEY]: meta };
+}
+
+export function unwrapTeacherContent(stored: Record<string, unknown>): {
+  content: TeacherLessonContent;
+  source?: AiContentSource;
+  fallbackReason?: AiFallbackReason;
+} {
+  const meta = stored[META_KEY] as StoredTeacherMeta | undefined;
+  const { [META_KEY]: _, ...rest } = stored;
+  return {
+    content: rest as TeacherLessonContent,
+    source: meta?.source,
+    fallbackReason: meta?.fallbackReason,
+  };
+}

apps/web/src/lib/teacher/teacher-render.test.ts

@@ -0,0 +1,39 @@
+import { describe, it, expect } from "vitest";
+import {
+  resolveResearchAssignmentDisplay,
+  hasMeaningfulResearchAssignment,
+} from "./teacher-render";
+
+describe("resolveResearchAssignmentDisplay", () => {
+  it("prefers structured researchAssignment", () => {
+    const display = resolveResearchAssignmentDisplay({
+      researchAssignment: {
+        steps: ["Step one", "Step two"],
+        expectedOutcome: "A summary",
+        estimatedTimeMinutes: 20,
+      },
+    });
+    expect(display?.kind).toBe("structured");
+    if (display?.kind === "structured") {
+      expect(display.data.steps).toHaveLength(2);
+      expect(display.data.expectedOutcome).toBe("A summary");
+    }
+  });
+
+  it("falls back to string assignment", () => {
+    const display = resolveResearchAssignmentDisplay({
+      assignment: "Write one paragraph about DNS",
+    });
+    expect(display).toEqual({
+      kind: "string",
+      text: "Write one paragraph about DNS",
+    });
+  });
+
+  it("never returns [object Object]", () => {
+    const display = resolveResearchAssignmentDisplay({
+      assignment: "[object Object]",
+    });
+    expect(hasMeaningfulResearchAssignment(display)).toBe(false);
+  });
+});

apps/web/src/lib/teacher/teacher-render.ts

@@ -0,0 +1,42 @@
+import type {
+  TeacherLessonContent,
+  TeacherResearchAssignment,
+} from "@adventureos/shared";
+
+export type ResearchAssignmentDisplay =
+  | { kind: "string"; text: string }
+  | { kind: "structured"; data: TeacherResearchAssignment };
+
+export function resolveResearchAssignmentDisplay(
+  content: Pick<
+    TeacherLessonContent,
+    "assignment" | "researchAssignment" | "readingSteps"
+  >
+): ResearchAssignmentDisplay | null {
+  if (content.researchAssignment?.steps?.length) {
+    return { kind: "structured", data: content.researchAssignment };
+  }
+
+  if (content.assignment?.trim()) {
+    return { kind: "string", text: content.assignment.trim() };
+  }
+
+  if (content.readingSteps?.length) {
+    return {
+      kind: "structured",
+      data: { steps: content.readingSteps },
+    };
+  }
+
+  return null;
+}
+
+export function hasMeaningfulResearchAssignment(
+  display: ResearchAssignmentDisplay | null
+): boolean {
+  if (!display) return false;
+  if (display.kind === "string") {
+    return display.text.length > 0 && display.text !== "[object Object]";
+  }
+  return display.data.steps.length > 0;
+}

apps/web/src/lib/validation/schemas.test.ts

@@ -13,14 +13,19 @@ describe("teacherCreateSchema", () => {
     expect(result.success).toBe(true);
   });
 
-  it("accepts null explorationId", () => {
+  it("accepts optional difficulty and length", () => {
     const result = teacherCreateSchema.safeParse({
-      topic: "Rust ownership",
+      topic: "DNS",
-      explorationId: null,
+      difficulty: "intermediate",
+      length: "deep",
+      includeLibraryContext: false,
     });
     expect(result.success).toBe(true);
     if (result.success) {
-      expect(normalizeTeacherCreateBody(result.data).explorationId).toBeUndefined();
+      const body = normalizeTeacherCreateBody(result.data);
+      expect(body.difficulty).toBe("intermediate");
+      expect(body.length).toBe("deep");
+      expect(body.includeLibraryContext).toBe(false);
     }
   });
 });

apps/web/src/lib/validation/schemas.ts

@@ -3,11 +3,17 @@ import { z } from "zod";
 export const teacherCreateSchema = z.object({
   topic: z.string().min(1, "Topic is required"),
   explorationId: z.union([z.string().uuid(), z.null()]).optional(),
+  difficulty: z.enum(["beginner", "intermediate", "advanced"]).optional(),
+  length: z.enum(["short", "standard", "deep"]).optional(),
+  includeLibraryContext: z.boolean().optional(),
 });
 
 export type TeacherCreateBody = {
   topic: string;
   explorationId?: string;
+  difficulty?: "beginner" | "intermediate" | "advanced";
+  length?: "short" | "standard" | "deep";
+  includeLibraryContext?: boolean;
 };
 
 export function normalizeTeacherCreateBody(
@@ -16,6 +22,9 @@ export function normalizeTeacherCreateBody(
   return {
     topic: body.topic,
     explorationId: body.explorationId ?? undefined,
+    difficulty: body.difficulty ?? "beginner",
+    length: body.length ?? "standard",
+    includeLibraryContext: body.includeLibraryContext ?? true,
   };
 }
 

packages/shared/src/types.ts

@@ -206,16 +206,63 @@ export interface StatsOverview {
   xpByCategory: { category: string; amount: number }[];
 }
 
+export type TeacherDifficulty = "beginner" | "intermediate" | "advanced";
+export type TeacherLength = "short" | "standard" | "deep";
+
+export interface TeacherResearchAssignment {
+  steps: string[];
+  expectedOutcome?: string;
+  estimatedTimeMinutes?: number;
+}
+
+export interface TeacherHomework {
+  task: string;
+  instructions: string[];
+}
+
+export interface TeacherCalibreSuggestion {
+  title: string;
+  authors: string[];
+  reason: string;
+}
+
 export interface TeacherQuizQuestion {
   question: string;
-  options: string[];
+  type?: "multiple_choice" | "short_answer";
+  options?: string[];
+  /** 0-based index for multiple choice (legacy + normalized MC) */
   answer: number;
+  answerText?: string;
+  explanation?: string;
+}
+
+export interface TeacherAnswerKeyEntry {
+  questionIndex: number;
+  answer: string;
+  explanation?: string;
 }
 
 export interface TeacherLessonContent {
+  title?: string;
+  /** Alias kept for legacy stored lessons */
+  introduction?: string;
+  overview?: string;
+  whyItMatters?: string;
+  /** Alias kept for legacy stored lessons */
+  objectives?: string[];
+  learningObjectives?: string[];
+  explanation?: string;
+  researchAssignment?: TeacherResearchAssignment;
+  readingSteps?: string[];
+  calibreSuggestions?: TeacherCalibreSuggestion[];
+  externalReading?: string[];
+  homework?: TeacherHomework;
   flashcards: { front: string; back: string }[];
   quiz: TeacherQuizQuestion[];
-  assignment: string;
+  assignment?: string;
+  reflectionPrompt?: string;
+  answerKey?: TeacherAnswerKeyEntry[];
+  nextLessonSuggestion?: string;
 }
 
 export interface TeacherLessonData {
@@ -226,4 +273,11 @@ export interface TeacherLessonData {
   explorationId?: string | null;
   completedNote?: string | null;
   createdAt: string;
+  source?: "ai" | "fallback";
+  fallbackReason?:
+    | "offline"
+    | "model_unavailable"
+    | "parse_failed"
+    | "generation_failed"
+    | "timeout";
 }