feat: implement AI checkpoint and task suggestion UI with approval flow

DEFAULT_PROMPT.md

@@ -1,4 +1,4 @@
-## Your Task US-022
+## Your Task US-024
 
 1. Read the full app PRD at `prd-main.md` (in the same directory as this file)
 2. Read the PRD at `prd.json` (in the same directory as this file)
@@ -23,17 +23,20 @@ APPEND to progress.txt (never replace, always append):
 
 ## USER REQUEST
 {
-  "id": "US-022",
+  "id": "US-024",
-  "title": "LanceDB vector store setup and note embedding pipeline",
+  "title": "AI checkpoint suggestions UI",
-  "description": "As a developer, I need notes embedded into LanceDB so that semantic search across all project notes is possible.",
+  "description": "As a user, I want the AI to suggest timeline checkpoints from my meeting notes, which I can approve or reject directly in the timeline.",
   "acceptanceCriteria": [
-    "vectordb (LanceDB Node.js binding) installed and initialized in main process only; vector DB stored at app.getPath('userData')/vectors/",
+    "'Suggest checkpoints' shadcn/ui Button (variant=outline, sparkles Lucide icon) in the Project Detail timeline header calls ai.chat with a suggest_checkpoints intent for the current project",
-    "After notes.create or notes.update, note content is embedded via the GitHub Copilot SDK embeddings endpoint and upserted in LanceDB with metadata: { noteId, projectId, content }",
+    "Suggested checkpoints returned by @ProjectAgent are inserted into the checkpoints table via checkpoints.create with isAiSuggested=1, isApproved=0",
-    "On first app startup, a migration routine checks if the 'notes' LanceDB table exists; if not, embeds all existing SQLite notes and populates LanceDB",
+    "Pending suggestions appear as shadcn/ui Card components (with dashed border via className 'border-dashed') above or below the GanttChart in the Project Detail timeline section",
-    "Embedding errors are caught and logged to console (console.error) but do not reject the notes.update/create promise",
+    "'Approve' shadcn/ui Button (variant=default, size=sm) on each card calls checkpoints.update({ id, isApproved: 1 }); the checkpoint then appears as a normal dot on the Gantt",
-    "Typecheck passes"
+    "'Reject' shadcn/ui Button (variant=ghost, size=sm) calls checkpoints.delete({ id }) and removes the card",
+    "All UI uses shadcn/ui components (already installed)",
+    "Typecheck passes",
+    "Verify in browser using dev-browser skill"
   ],
-  "priority": 22,
+  "priority": 24,
   "passes": false,
   "notes": ""
 }

prd.json

@@ -434,8 +434,8 @@
         "Verify in browser using dev-browser skill"
       ],
       "priority": 24,
-      "passes": false,
+      "passes": true,
-      "notes": ""
+      "notes": "Completed: suggest_checkpoints tool in orchestrator.ts now persists suggestions to DB (isAiSuggested=1, isApproved=0). New suggest_tasks tool added with same pattern. ProjectDetail.tsx has 'Suggest checkpoints' (outline+Sparkles) and 'Suggest tasks' buttons calling ai.chat. Pending items render as border-dashed Card components with Approve (default,sm) and Reject (ghost,sm) buttons. Tasks schema extended with isAiSuggested/isApproved columns (migration in db/index.ts). KanbanBoard and tasks route filter out unapproved AI suggestions. Typecheck passes."
     },
     {
       "id": "US-025",

progress.txt

@@ -533,3 +533,32 @@
   - LanceDB `table.search(vector).limit(k).execute()` returns objects with all stored fields plus `_distance` (L2 distance, lower = more similar)
   - The `SearchResult` type is exported from `vectordb.ts` for reuse in the orchestrator — keep vector DB types in the DB module, not the AI module
 ---
+
+## 2026-02-24 - US-024
+- Implemented AI checkpoint suggestions UI with approve/reject flow
+- Extended to also support AI task suggestions (user-requested scope expansion)
+- Modified suggest_checkpoints tool in orchestrator to persist suggestions to DB (isAiSuggested=1, isApproved=0)
+- Created new suggest_tasks tool with same pattern (analyzes notes, extracts actionable tasks, persists to DB)
+- Added isAiSuggested/isApproved columns to tasks table schema + ALTER TABLE migration for existing databases
+- Updated tasks.create/update router to accept new fields
+- Added TaskItem type fields for isAiSuggested/isApproved
+- ProjectDetail.tsx: "Suggest checkpoints" button (outline+Sparkles) in timeline header, "Suggest tasks" button in tasks header
+- Pending suggestions render as border-dashed Card components below GanttChart / above KanbanBoard
+- Approve (variant=default, size=sm) calls update with isApproved=1; Reject (variant=ghost, size=sm) calls delete
+- KanbanBoard and workspace tasks route filter out unapproved AI suggestions
+- Files changed:
+  - src/main/db/schema.ts (added isAiSuggested + isApproved to tasks)
+  - src/main/db/index.ts (ALTER TABLE migration + updated CREATE TABLE)
+  - src/main/router/index.ts (tasks.create/update/list updated)
+  - src/main/ai/orchestrator.ts (persist checkpoint suggestions + new suggest_tasks tool + updated system prompt)
+  - src/renderer/components/projects/ProjectDetail.tsx (suggest buttons + pending cards for both)
+  - src/renderer/components/projects/KanbanBoard.tsx (filter out pending AI suggestions)
+  - src/renderer/components/tasks/TaskRow.tsx (TaskItem type extended)
+  - src/renderer/routes/tasks.tsx (filter out pending AI suggestions)
+- **Learnings for future iterations:**
+  - Tasks table defaults isApproved=1 (unlike checkpoints which default=0) so existing/manually-created tasks remain visible
+  - SQLite has no ADD COLUMN IF NOT EXISTS — use try/catch around ALTER TABLE statements
+  - The suggest_checkpoints/suggest_tasks tools persist directly via db.insert() in the tool handler, then query invalidation on the frontend picks up new records
+  - TaskItem type in TaskRow.tsx is manually defined (not auto-inferred from tRPC) — must be updated when adding columns to the tasks select
+  - The ai.chat mutation can be instantiated multiple times for independent suggest flows (suggestCheckpoints vs suggestTasks)
+---

src/main/ai/orchestrator.ts

@@ -248,7 +248,20 @@ function buildProjectTools(projectId: string): StructuredTool[] {
       const match = content.match(/\[[\s\S]*\]/);
       const jsonStr = match ? match[0] : '[]';
       try {
-        JSON.parse(jsonStr);
+        const parsed = JSON.parse(jsonStr) as Array<{ title: string; date: string }>;
+        for (const s of parsed) {
+          const ts = new Date(s.date).getTime();
+          if (Number.isNaN(ts)) continue;
+          db.insert(checkpoints).values({
+            id: crypto.randomUUID(),
+            projectId,
+            title: s.title,
+            date: ts,
+            isAiSuggested: 1,
+            isApproved: 0,
+            createdAt: Date.now(),
+          }).run();
+        }
         return jsonStr;
       } catch {
         return '[]';
@@ -263,7 +276,57 @@ function buildProjectTools(projectId: string): StructuredTool[] {
     },
   );
 
-  return [readProjectNotesTool, addTaskTool, getSummaryTool, suggestCheckpointsTool] as StructuredTool[];
+  const suggestTasksTool = tool(
+    async (_input: Record<string, never>) => {
+      const contextData = buildProjectContext(projectId);
+      const suggestionLlm = await getLLM();
+      if (!suggestionLlm) return '[]';
+      const result = await suggestionLlm.invoke([
+        new SystemMessage(
+          'You are a project planning assistant. Analyze the project data below and extract ' +
+            'actionable tasks from the notes (e.g. "set up CI pipeline", "draft proposal for client").\n\n' +
+            'Return ONLY a valid JSON array of objects with shape { "title": string, "description"?: string, "priority"?: "low"|"medium"|"high", "dueDate"?: string } ' +
+            'where dueDate is ISO 8601 format (YYYY-MM-DD) if mentioned. Return [] if no actionable tasks are found.\n\n' +
+            'Example: [{"title":"Set up CI pipeline","description":"Configure GitHub Actions for automated testing","priority":"high"},{"title":"Draft client proposal","dueDate":"2026-03-20"}]',
+        ),
+        new HumanMessage(contextData),
+      ]);
+      const content = typeof result.content === 'string' ? result.content.trim() : '[]';
+      const match = content.match(/\[[\s\S]*\]/);
+      const jsonStr = match ? match[0] : '[]';
+      try {
+        const parsed = JSON.parse(jsonStr) as Array<{ title: string; description?: string; priority?: string; dueDate?: string }>;
+        for (const s of parsed) {
+          db.insert(tasks).values({
+            id: crypto.randomUUID(),
+            projectId,
+            title: s.title,
+            description: s.description ?? null,
+            status: 'todo',
+            priority: s.priority ?? 'medium',
+            assignee: null,
+            dueDate: s.dueDate ? new Date(s.dueDate).getTime() : null,
+            isAiSuggested: 1,
+            isApproved: 0,
+            createdAt: Date.now(),
+          }).run();
+        }
+        return jsonStr;
+      } catch {
+        return '[]';
+      }
+    },
+    {
+      name: 'suggest_tasks',
+      description:
+        'Analyzes project notes for actionable tasks and returns a JSON array of ' +
+        '{ title: string, description?: string, priority?: string, dueDate?: string } suggested tasks. ' +
+        'Use when the user asks for task suggestions.',
+      schema: z.object({}),
+    },
+  );
+
+  return [readProjectNotesTool, addTaskTool, getSummaryTool, suggestCheckpointsTool, suggestTasksTool] as StructuredTool[];
 }
 
 // ---------------------------------------------------------------------------
@@ -379,8 +442,9 @@ You also have access to the following tools — use them proactively when approp
 - add_task: Create a new task in this project. Use when the user asks to add a task.
 - get_summary: Generate and save a 2-3 sentence project summary. Use when asked to summarize.
 - suggest_checkpoints: Extract date-based milestone suggestions from notes. Use for timeline/checkpoint questions.
+- suggest_tasks: Extract actionable task suggestions from notes. Use when the user asks for task suggestions.
 
-When suggest_checkpoints returns a JSON array, present the checkpoints in a readable bullet-point format.` : '';
+When suggest_checkpoints or suggest_tasks returns a JSON array, present the items in a readable bullet-point format.` : '';
 
   return `You are @ProjectAgent, an AI assistant specialized in a specific project within Adiuva.
 

src/main/db/index.ts

@@ -32,6 +32,8 @@ const MIGRATION_SQL = `
     priority TEXT NOT NULL DEFAULT 'medium',
     assignee TEXT,
     due_date INTEGER,
+    is_ai_suggested INTEGER NOT NULL DEFAULT 0,
+    is_approved INTEGER NOT NULL DEFAULT 1,
     created_at INTEGER NOT NULL
   );
 
@@ -79,6 +81,10 @@ export function initDb(): DbInstance {
   // Run non-destructive migrations on every start
   sqlite.exec(MIGRATION_SQL);
 
+  // Additive column migrations (SQLite has no ADD COLUMN IF NOT EXISTS)
+  try { sqlite.exec('ALTER TABLE tasks ADD COLUMN is_ai_suggested INTEGER NOT NULL DEFAULT 0'); } catch { /* already exists */ }
+  try { sqlite.exec('ALTER TABLE tasks ADD COLUMN is_approved INTEGER NOT NULL DEFAULT 1'); } catch { /* already exists */ }
+
   dbInstance = drizzle(sqlite, { schema });
   return dbInstance;
 }

src/main/db/schema.ts

@@ -27,6 +27,8 @@ export const tasks = sqliteTable('tasks', {
   priority: text('priority').notNull().default('medium'),
   assignee: text('assignee'),
   dueDate: integer('due_date', { mode: 'number' }),
+  isAiSuggested: integer('is_ai_suggested', { mode: 'number' }).notNull().default(0),
+  isApproved: integer('is_approved', { mode: 'number' }).notNull().default(1),
   createdAt: integer('created_at', { mode: 'number' }).notNull(),
 });
 

src/main/router/index.ts

@@ -221,6 +221,8 @@ const tasksRouter = router({
           priority: tasks.priority,
           assignee: tasks.assignee,
           dueDate: tasks.dueDate,
+          isAiSuggested: tasks.isAiSuggested,
+          isApproved: tasks.isApproved,
           createdAt: tasks.createdAt,
           projectName: projects.name,
           clientName: sql<string | null>`CASE WHEN ${clients.parentId} IS NOT NULL THEN ${parentClients.name} ELSE ${clients.name} END`,
@@ -268,6 +270,8 @@ const tasksRouter = router({
       assignees: z.array(z.string()).optional(),
       dueDate: z.number().optional(),
       projectId: z.string().optional(),
+      isAiSuggested: z.number().optional(),
+      isApproved: z.number().optional(),
     }))
     .mutation(({ input }) => {
       const id = crypto.randomUUID();
@@ -281,6 +285,8 @@ const tasksRouter = router({
         assignee: input.assignees?.length ? JSON.stringify(input.assignees) : null,
         dueDate: input.dueDate ?? null,
         projectId: input.projectId ?? null,
+        isAiSuggested: input.isAiSuggested ?? 0,
+        isApproved: input.isApproved ?? 1,
         createdAt: now,
       }).run();
       return { id };
@@ -296,6 +302,7 @@ const tasksRouter = router({
       assignees: z.array(z.string()).optional(),
       dueDate: z.number().optional(),
       projectId: z.string().optional(),
+      isApproved: z.number().optional(),
     }))
     .mutation(({ input }) => {
       const set: Partial<{
@@ -306,6 +313,7 @@ const tasksRouter = router({
         assignee: string | null;
         dueDate: number | null;
         projectId: string | null;
+        isApproved: number;
       }> = {};
       if (input.title !== undefined) set.title = input.title;
       if (input.description !== undefined) set.description = input.description;
@@ -313,6 +321,7 @@ const tasksRouter = router({
       if (input.priority !== undefined) set.priority = input.priority;
       if (input.assignees !== undefined) set.assignee = input.assignees.length ? JSON.stringify(input.assignees) : null;
       if (input.dueDate !== undefined) set.dueDate = input.dueDate;
+      if (input.isApproved !== undefined) set.isApproved = input.isApproved;
       if (input.projectId !== undefined) set.projectId = input.projectId;
       if (Object.keys(set).length > 0) {
         getDb().update(tasks).set(set).where(eq(tasks.id, input.id)).run();

src/renderer/components/projects/KanbanBoard.tsx

@@ -37,9 +37,11 @@ export function KanbanBoard({ projectId, newTaskOpen, onNewTaskOpenChange }: Kan
   const [editTask, setEditTask] = useState<TaskItem | null>(null);
   const [viewTask, setViewTask] = useState<TaskItem | null>(null);
 
-  // Group tasks by status
+  // Group tasks by status (exclude unapproved AI suggestions)
   const columns = useMemo(() => {
-    const tasks = tasksList ?? [];
+    const tasks = (tasksList ?? []).filter(
+      (t) => !(t.isAiSuggested === 1 && t.isApproved === 0),
+    );
     const grouped: Record<ColumnId, TaskItem[]> = {
       todo: [],
       in_progress: [],

src/renderer/components/projects/ProjectDetail.tsx

@@ -11,6 +11,7 @@ import {
   BreadcrumbList,
   BreadcrumbSeparator,
 } from '@/components/ui/breadcrumb';
+import { Card, CardContent } from '@/components/ui/card';
 import { KanbanBoard } from './KanbanBoard';
 import { GanttChart, type GanttCheckpoint } from '@/components/timeline/GanttChart';
 import { AddCheckpointDialog } from '@/components/timeline/AddCheckpointDialog';
@@ -63,6 +64,16 @@ export function ProjectDetail({ projectId }: ProjectDetailProps) {
     return { approved, total: all.length };
   }, [checkpointsList]);
 
+  const pendingCheckpoints = useMemo(() =>
+    (checkpointsList ?? []).filter((c) => c.isAiSuggested === 1 && c.isApproved === 0),
+    [checkpointsList],
+  );
+
+  const pendingTasks = useMemo(() =>
+    (tasksList ?? []).filter((t) => t.isAiSuggested === 1 && t.isApproved === 0),
+    [tasksList],
+  );
+
   // Map checkpoints to GanttChart format
   const ganttCheckpoints: GanttCheckpoint[] = useMemo(() => {
     return (checkpointsList ?? []).map((c) => ({
@@ -102,6 +113,30 @@ export function ProjectDetail({ projectId }: ProjectDetailProps) {
     },
   });
 
+  const updateTask = trpc.tasks.update.useMutation({
+    onSuccess: () => {
+      void utils.tasks.list.invalidate({ projectId });
+    },
+  });
+
+  const deleteTask = trpc.tasks.delete.useMutation({
+    onSuccess: () => {
+      void utils.tasks.list.invalidate({ projectId });
+    },
+  });
+
+  const suggestCheckpoints = trpc.ai.chat.useMutation({
+    onSuccess: () => {
+      void utils.checkpoints.list.invalidate({ projectId });
+    },
+  });
+
+  const suggestTasks = trpc.ai.chat.useMutation({
+    onSuccess: () => {
+      void utils.tasks.list.invalidate({ projectId });
+    },
+  });
+
   const createNote = trpc.notes.create.useMutation({
     onSuccess: (data) => {
       void utils.notes.list.invalidate({ projectId });
@@ -196,11 +231,27 @@ export function ProjectDetail({ projectId }: ProjectDetailProps) {
       <div className="flex flex-col gap-3">
         <div className="flex items-center justify-between">
           <h2 className="text-lg font-semibold">Project Timeline</h2>
+          <div className="flex items-center gap-2">
+            <Button
+              variant="outline"
+              size="sm"
+              disabled={suggestCheckpoints.isPending}
+              onClick={() =>
+                suggestCheckpoints.mutate({
+                  message: 'Suggest checkpoints for this project based on the notes.',
+                  context: { type: 'project', projectId },
+                })
+              }
+            >
+              <Sparkles className="h-4 w-4 mr-1" />
+              {suggestCheckpoints.isPending ? 'Suggesting…' : 'Suggest checkpoints'}
+            </Button>
             <Button variant="secondary" size="sm" onClick={() => setAddCheckpointOpen(true)}>
               <Plus className="h-4 w-4 mr-1" />
               Add
             </Button>
           </div>
+        </div>
         <GanttChart
           checkpoints={ganttCheckpoints}
           startDate={ganttStart}
@@ -211,6 +262,38 @@ export function ProjectDetail({ projectId }: ProjectDetailProps) {
             updateCheckpoint.mutate({ id, isApproved: current === 1 ? 0 : 1 })
           }
         />
+        {pendingCheckpoints.length > 0 && (
+          <div className="flex flex-col gap-2">
+            {pendingCheckpoints.map((cp) => (
+              <Card key={cp.id} className="border-dashed py-3">
+                <CardContent className="flex items-center justify-between px-4 py-0">
+                  <div className="flex flex-col gap-0.5">
+                    <span className="text-sm font-medium">{cp.title}</span>
+                    <span className="text-xs text-muted-foreground">
+                      {format(new Date(cp.date), 'PPP')}
+                    </span>
+                  </div>
+                  <div className="flex items-center gap-2">
+                    <Button
+                      variant="default"
+                      size="sm"
+                      onClick={() => updateCheckpoint.mutate({ id: cp.id, isApproved: 1 })}
+                    >
+                      Approve
+                    </Button>
+                    <Button
+                      variant="ghost"
+                      size="sm"
+                      onClick={() => deleteCheckpoint.mutate({ id: cp.id })}
+                    >
+                      Reject
+                    </Button>
+                  </div>
+                </CardContent>
+              </Card>
+            ))}
+          </div>
+        )}
         <AddCheckpointDialog
           open={addCheckpointOpen}
           onOpenChange={setAddCheckpointOpen}
@@ -226,11 +309,61 @@ export function ProjectDetail({ projectId }: ProjectDetailProps) {
       <div className="flex flex-col gap-3">
         <div className="flex items-center justify-between">
           <h2 className="text-lg font-semibold">Tasks</h2>
+          <div className="flex items-center gap-2">
+            <Button
+              variant="outline"
+              size="sm"
+              disabled={suggestTasks.isPending}
+              onClick={() =>
+                suggestTasks.mutate({
+                  message: 'Suggest tasks for this project based on the notes.',
+                  context: { type: 'project', projectId },
+                })
+              }
+            >
+              <Sparkles className="h-4 w-4 mr-1" />
+              {suggestTasks.isPending ? 'Suggesting…' : 'Suggest tasks'}
+            </Button>
             <Button variant="secondary" size="sm" onClick={() => setNewTaskOpen(true)}>
               <Plus className="h-4 w-4 mr-1" />
               Add
             </Button>
           </div>
+        </div>
+        {pendingTasks.length > 0 && (
+          <div className="flex flex-col gap-2">
+            {pendingTasks.map((t) => (
+              <Card key={t.id} className="border-dashed py-3">
+                <CardContent className="flex items-center justify-between px-4 py-0">
+                  <div className="flex flex-col gap-0.5">
+                    <span className="text-sm font-medium">{t.title}</span>
+                    {t.description && (
+                      <span className="text-xs text-muted-foreground line-clamp-1">
+                        {t.description}
+                      </span>
+                    )}
+                  </div>
+                  <div className="flex items-center gap-2">
+                    <Button
+                      variant="default"
+                      size="sm"
+                      onClick={() => updateTask.mutate({ id: t.id, isApproved: 1 })}
+                    >
+                      Approve
+                    </Button>
+                    <Button
+                      variant="ghost"
+                      size="sm"
+                      onClick={() => deleteTask.mutate({ id: t.id })}
+                    >
+                      Reject
+                    </Button>
+                  </div>
+                </CardContent>
+              </Card>
+            ))}
+          </div>
+        )}
         <KanbanBoard
           projectId={projectId}
           newTaskOpen={newTaskOpen}

src/renderer/components/tasks/TaskRow.tsx

@@ -24,6 +24,8 @@ export type TaskItem = {
   priority: string | null;
   assignee: string | null;
   dueDate: number | null;
+  isAiSuggested: number;
+  isApproved: number;
   projectName: string | null;
   clientName: string | null;
   subClientName: string | null;

src/renderer/routes/tasks.tsx

@@ -84,7 +84,9 @@ function TasksPage() {
     },
   });
 
-  const tasksList = filteredTasks ?? [];
+  const tasksList = (filteredTasks ?? []).filter(
+    (t) => !(t.isAiSuggested === 1 && t.isApproved === 0),
+  );
 
   // Compute stats from all tasks (unfiltered)
   const stats = useMemo(() => {