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Dynamic Table of Contents Updates

January 26, 20266:12 PM8:02 PM(1h 49m)11 turns
Model: claude-opus-4-5-20251101
Edit39Bash32Read29Grep10Task5Glob5Write2ExitPlanMode2
6:12 PM

Implement the following plan:

Dynamic Table of Contents Updates

Problem Summary

The sidebar Table of Contents (TOC) only builds its heading list once on mount. It doesn't update when:

  1. Activity stages are unlocked (instructor advances, new headings appear)
  2. "View as student" toggle changes (headings appear/disappear based on role)
  3. Other dynamic content changes visibility

Current Implementation

File: apps/web/components/table-of-contents.tsx

Current behavior:

  • buildTocFromDom() queries for h2[id] and h3[id] elements
  • Runs once in useEffect with [containerSelector] dependency
  • Never re-scans when DOM changes

Solution: MutationObserver

Add a MutationObserver to detect when headings are added/removed from the article container, and rebuild the TOC accordingly.

Changes to table-of-contents.tsx

  1. Add MutationObserver to watch for DOM changes in the article
  2. Debounce rebuilds to avoid excessive re-renders during rapid changes
  3. Re-scan on visibility changes (when elements are added/removed)

Implementation

// In the main useEffect, after building initial TOC:

// Set up MutationObserver to detect heading changes
const observer = new MutationObserver((mutations) => {
  // Check if any mutation affects headings
  let shouldRebuild = false;

  for (const mutation of mutations) {
    // Check added nodes for headings
    mutation.addedNodes.forEach((node) => {
      if (node instanceof Element) {
        if (node.matches?.("h2[id], h3[id]") || node.querySelector?.("h2[id], h3[id]")) {
          shouldRebuild = true;
        }
      }
    });

    // Check removed nodes for headings
    mutation.removedNodes.forEach((node) => {
      if (node instanceof Element) {
        if (node.matches?.("h2[id], h3[id]") || node.querySelector?.("h2[id], h3[id]")) {
          shouldRebuild = true;
        }
      }
    });
  }

  if (shouldRebuild) {
    rebuildToc();
  }
});

observer.observe(container, {
  childList: true,
  subtree: true,
});

return () => observer.disconnect();

Debouncing

Since DOM mutations can fire rapidly (especially during React hydration or when multiple stages unlock), debounce the rebuild:

const rebuildTimeoutRef = useRef<NodeJS.Timeout | null>(null);

const rebuildToc = useCallback(() => {
  if (rebuildTimeoutRef.current) {
    clearTimeout(rebuildTimeoutRef.current);
  }

  rebuildTimeoutRef.current = setTimeout(() => {
    const container = document.querySelector(containerSelector);
    if (!container) return;

    const tocData = buildTocFromDom(container);
    setToc(tocData);

    // Update heading elements cache
    const elements = new Map<string, Element>();
    tocData.forEach((h2) => {
      const el = document.getElementById(h2.id);
      if (el) elements.set(h2.id, el);
      h2.children?.forEach((h3) => {
        const h3El = document.getElementById(h3.id);
        if (h3El) elements.set(h3.id, h3El);
      });
    });
    headingElementsRef.current = elements;
  }, 100); // 100ms debounce
}, [containerSelector]);

File to Modify

apps/web/components/table-of-contents.tsx

Key Changes:

  1. Add rebuildTimeoutRef for debouncing
  2. Extract TOC building logic into rebuildToc callback
  3. Add MutationObserver in the main useEffect
  4. Clean up observer and timeout on unmount

Complete Modified Component

The updated component will:

  1. Build TOC on mount (existing behavior)
  2. Set up MutationObserver to watch the article container
  3. When headings are added/removed, debounce and rebuild TOC
  4. Properly clean up observer on unmount

Verification

Manual Testing

  1. Activity stages test:

    • Go to /testing/components/full-activity-flow
    • Start as instructor, have students join
    • Verify TOC shows only visible stage headings
    • Advance to next stage
    • Verify TOC updates to show new stage headings
  2. View as student test:

    • Go to any meeting page with instructor-only content
    • Toggle "View as student" in the sidebar
    • Verify TOC updates to hide/show instructor-only headings
  3. Initial load test:

    • Verify TOC correctly shows headings after page load
    • No duplicate headings or missing headings

E2E Test (Optional)

Could add a test to verify TOC updates when toggling "View as student", but manual testing should suffice for this change.

If you need specific details from before exiting plan mode (like exact code snippets, error messages, or content you generated), read the full transcript at: ~/.claude/projects/-Users-challen-www-usingandunderstanding-ai/e88f3f65-9185-42ec-b96d-43526fed31e9.jsonl

I'll implement the dynamic Table of Contents updates. Let me first read the current implementation.

Now I understand the current implementation. I'll add the MutationObserver with debouncing to detect when headings are added/removed.

Let me verify the implementation by reading the updated file.

The implementation looks good. Let me run TypeScript type checking to ensure there are no errors.

The TypeScript errors are in a different file (activity-stage-instructor.tsx), not in the file I modified. Let me verify my changes compile correctly by running tsc just on the web app's table-of-contents file.

Let me run lint to verify the code quality.

No lint errors. The implementation is complete. Here's a summary of the changes made to apps/web/components/table-of-contents.tsx:

Added:

  1. REBUILD_DEBOUNCE_MS constant (100ms) for debouncing
  2. rebuildTimeoutRef to track the debounce timeout
  3. rebuildToc callback - extracts TOC building logic and returns the data
  4. scheduleRebuild callback - debounced rebuild for MutationObserver
  5. MutationObserver in the main useEffect that watches for:
    • Added nodes containing h2[id] or h3[id]
    • Removed nodes containing h2[id] or h3[id]
  6. Cleanup for both the observer and timeout on unmount

The TOC will now automatically update when:

  • Activity stages are unlocked (new headings appear)
  • "View as student" toggle changes visibility
  • Any other dynamic content adds/removes headings

The pre-existing TypeScript errors in activity-stage-instructor.tsx are unrelated to this change.

Bash3Read2Edit1
6:20 PM

Please fix the typescript errors.

Let me run tsc again to see the exact errors.

Let me look at the specific lines with errors. Looking at lines 50-70 for the parseStartTime function and line 609.

Now I understand all the errors. Let me fix them.

Now let me fix the activity-stages.tsx file.

Let me run tsc to verify all errors are fixed.

Let me fix the remaining errors.

All TypeScript errors are fixed. Let me run lint to make sure everything passes.

The lint errors are pre-existing and not related to my changes. Let me verify the files I modified pass lint.

All fixed. Here's a summary of the TypeScript fixes:

apps/web/components/mdx/activity-stage-instructor.tsx:

  • Fixed parseStartTime - added proper null checks for regex capture groups (match12?.[1] && match12[2] && match12[3])
  • Fixed stagesWithTimes reduce - assigned acc[acc.length - 1] to a variable prev before accessing properties

apps/web/components/mdx/activity-stages.tsx:

  • Fixed extractNotesText - properly typed the element as React.ReactElement<{ children?: React.ReactNode }>
  • Fixed extractFacilitationNotes - added generic type parameter to React.isValidElement<{ children?: React.ReactNode }>

apps/web/lib/time.ts:

  • Fixed getCurrentTime - extracted mock time to a variable before returning to avoid undefined type issue
  • Fixed advanceMockTime - extracted current mock time to a variable before arithmetic
Bash7Edit6Read5
6:25 PM

For the code entry, do students need to enter the -? If not (probably not), then let's insert that automatically so it's not confusing, or have one of those 6 separate cell entry code things that I see on other sites.

Let me find the code entry component to understand the current implementation.

Let me read the current implementation to understand the code format and entry flow.

I can see the current implementation. The code is 6 alphanumeric characters (like "ABC123"), displayed without a dash. Students currently enter it in a single text field. Let me implement a 6-cell segmented input which is cleaner and more intuitive.

Now let me update the input section to use the new CodeInput component.

Let me verify the changes compile correctly and check if there are any E2E tests that reference the old input.

Let me fix the TypeScript error and check what's on line 44.

Now let me update the E2E tests that reference the old input.

The tests use .fill() which won't work directly with segmented inputs. I need to create a helper function. Let me read one of the test files to understand the structure, then add a helper.

I need to add a helper function to fill the segmented code input. Let me update both test files.

Now let me update the full-activity-flow.spec.ts file.

Let me verify all references are updated.

All test references updated. Let me run type checking and lint.

No errors, just pre-existing warnings. Let me check if the dev server is running and we can do a quick test.

Dev server is running. Let me run the group activity E2E tests to verify everything works.

Edit16Bash7Read4Grep3Task1
6:30 PM

Wait, please fix the warnings too! Also the time package needs a lint configuration: @repo/time:lint: @repo/time:lint: Oops! Something went wrong! :( @repo/time:lint: @repo/time:lint: ESLint: 9.39.2 @repo/time:lint: @repo/time:lint: ESLint couldn't find an eslint.config.(js|mjs|cjs) file. @repo/time:lint: @repo/time:lint: From ESLint v9.0.0, the default configuration file is now eslint.config.js. @repo/time:lint: If you are using a .eslintrc.* file, please follow the migration guide @repo/time:lint: to update your configuration file to the new format: @repo/time:lint: @repo/time:lint: https://eslint.org/docs/latest/use/configure/migration-guide @repo/time:lint: @repo/time:lint: If you still have problems after following the migration guide, please stop by @repo/time:lint: https://eslint.org/chat/help to chat with the team. @repo/time:lint: @repo/time:lint: ERROR: command finished with error: command (~/www/usingandunderstanding.ai/packages/time) ~/.asdf/installs/bun/1.3.5/bin/bun run lint exited (2)

Let me fix both issues.

Now let me fix the lint warnings by wrapping members in useMemo.

The time package is fixed. Let me also fix the pre-existing errors in useSocket.ts and socket.ts.

The socket property is never used. I can remove it from the return type to fix the lint error.

Now fix the socket.ts import warning.

All lint errors fixed. Let me verify TypeScript compiles.

All clean. Let me run the group activity E2E tests to verify the segmented code input works.

All 13 tests pass. Here's a summary of everything that was fixed:

Segmented Code Input (group-activity-client.tsx):

  • Replaced single text input with 6-cell segmented input
  • Added CodeInput component with:
    • Auto-advance to next cell on input
    • Backspace navigates to previous cell
    • Paste support for full codes
    • Arrow key navigation
  • Wrapped members in useMemo to fix lint warnings
  • Updated E2E tests with fillPartnerCode helper

Time Package (packages/time/):

  • Added eslint.config.js to fix missing eslint config error

Socket Files (hooks/useSocket.ts, lib/socket.ts):

  • Removed unused socket return value from useSocket hook
  • Fixed type-only import for Socket
  • Removed unused useCallback import

Activity Stage Context (activity-stage-context.tsx):

  • Added memoized stages array to fix dependency warnings
  • Extracted isPaused, pausedAt, totalPausedMs to variables
  • Removed unused useEffect import

Activity Stage Client (activity-stage-client.tsx):

  • Prefixed unused rotateRoles prop with underscore
Read11Bash11Edit11Grep4Glob3Write1
6:40 PM

Run bun check and fix the output. There are still eslint error.

All checks pass now. The output shows:

  • Tasks: 34 successful, 34 total
  • Prettier ran and formatted the code

The two issues fixed were:

  1. Removed unused sql import from apps/api/src/routes/admin/activity-stages.ts
  2. Changed Socket to type-only import in apps/api/src/socket.ts
Bash2Read2Edit2
6:46 PM

OK! So where are we for tomorrow's activity? There doesn't look like there's any actual submission yet, correct? Just the steps for students to follow? That might be OK. I'm just curious about how it would work if I ran it right now.

Let me explore what's currently set up for the activity flow.

Correct - there's no submission system yet. Here's the current state:

What works now:

  • Students form pairs using 6-character codes (now with the nice segmented input)
  • Role assignment (driver/observer) with automatic rotation between stages
  • Instructor controls: start session, advance stages, pause/resume, reset
  • Students see their role-specific content and mark stages complete
  • Completion counts visible to instructor
  • Timers (soft cap warnings, hard cap countdown)
  • Real-time updates via websockets

If you ran it tomorrow:

  1. You'd start the session from instructor controls
  2. Students pair up by exchanging codes
  3. They'd see Stage 1 content with their assigned role (driver/observer)
  4. They follow the prompts manually (talk to ChatGPT, try the challenges)
  5. They click "Mark Complete" when done
  6. You advance to next stage, roles rotate
  7. Repeat through all stages

What's missing:

  • No submission capture - students do the work but nothing is saved
  • They can't paste transcripts, upload screenshots, or record what they found
  • You can't see what they discovered after the fact
  • No synthesis/reflection form at the end

Is that OK for tomorrow? It could work as a "follow-along" activity where the value is in the doing, not the collecting. Students explore AI limitations together, discuss with their partner, and the learning happens in real-time. You'd just be trusting they're engaging rather than verifying via submissions.

Would you like me to add a simple submission mechanism, or is the current flow sufficient for tomorrow?

Task1
6:48 PM

And we have a full test that makes sure that the functionality for tomorrow works, correct?

Yes, there's a comprehensive E2E test suite at testing/e2e/tests/full-activity-flow.spec.ts. Let me confirm what it covers.

Yes! The test suite covers the full flow. Let me run it to confirm everything passes.

Bash2
6:49 PM

It's OK, I'm running them :-).

Great! The test suite covers:

  • Setup Phase - instructor sees schedule/start button, students see waiting state
  • Session Start - instructor controls, facilitation notes display
  • Group Formation - pairs form using codes, role content displays correctly
  • Stage Completion - students complete stages, see "waiting for instructor" message
  • Stage Progression - instructor advances, students see new content
  • Role Rotation - roles swap when advancing to stages with rotateRoles
  • Pause/Resume - instructor can pause activity, students see paused overlay
  • Session Reset - instructor can reset and start fresh
  • Full Flow Integration - end-to-end test of the complete activity

Let me know how they go!

6:56 PM

Actually, what's our current definition of student? Does it include the applied students? Can we temporarily open these activities to any logged-in @illinois.edu user?

Let me check how student roles are currently defined.

Good news - any logged-in @illinois.edu user already gets the "student" role by default. The role assignment logic is:

  1. Check if email matches an instructor → "instructor" role
  2. Check if email matches staff → "staff" role
  3. Everyone else → "student" role

There's no enrollment check on the activity APIs. They just require authentication (authMiddleware), not enrollment status.

So if someone with an @illinois.edu email logs in via Azure AD, they'll:

  • Get a session
  • Be assigned "student" role (unless they're in the instructor/staff list)
  • Have full access to the group activity features

You don't need to change anything - it's already open to any @illinois.edu user who can authenticate. Applied students, random grad students, anyone with a valid Illinois login can participate.

The only thing that checks enrollment is the Canvas sync for things like the roster. The activities themselves are wide open to any authenticated user.

Grep3Read2
7:51 PM

Great! Next, I want to add a new /chat page that provides a ChatGPT-like experience for students. It should use a similar UI although adapted for our styling. It should allow students to load and resume old chats, and provide a left sidebar menu allowing students to return to old chats. Let's show all old chats for now, although eventually maybe we'll limit that. It should also provide an easy way for students to copy their conversation in a useful format:

User

(Content)

Model

(Reply)

...etc...

I'll let you decide on the format. It should be easy for humans to read but also for machines to parse, since we may want to accept is an input on other parts of the site.

This is a different task - I'll start fresh planning for the /chat page. Let me explore the codebase to understand the existing patterns.

Excellent! I have a good understanding of the existing infrastructure. Key findings:

  1. Database schema already exists - conversations and messages tables are ready
  2. LLM package ready - chat() and chatStream() functions for Azure OpenAI
  3. Agent system - Can load agents with system prompts from markdown files
  4. RAG pipeline - Can augment responses with course content
  5. UI patterns - Clear patterns for authenticated pages, sidebars, forms

Let me have a Plan agent design the implementation.

Let me verify what API routes actually exist before finalizing the plan.

Excellent! The backend is fully built. Both /api/conversations and /api/chat endpoints exist with streaming support, RAG, agent system, and conversation persistence. I only need to build the frontend.

Let me write the final plan.

The plan is ready. Key points:

Good news: The entire backend already exists - conversations API, chat API with streaming, RAG, and agent system. This is purely frontend work.

Scope:

  • 6 files to create (page + client + 4 components)
  • Add /chat to header navigation
  • Copy format: ## User / ## Assistant with --- separators (readable by humans and parseable by machines)

The chat will automatically:

  • Use the default "course-assistant" agent
  • Include RAG context from course materials
  • Save all conversations to the database
Read3Task3Glob2Write1ExitPlanMode1
8:01 PM

Ah, yes. Create persistent links once a user starts a chat at /chat/ID or /chat?ID=id, something like that. Up to you. This is so they can be cut and pasted and shared later, potentially.

Good point! I'll update the plan to use /chat/[id] for persistent conversation URLs.

Updated the plan with persistent URLs:

  • /chat - Start new conversation
  • /chat/[id] - Load existing conversation (shareable link)
  • First message redirects to /chat/{newId} so URL becomes persistent
  • Added layout.tsx for shared sidebar across routes
Edit3ExitPlanMode1