singularity-forge/src/resources/extensions/sf/tests/plan-milestone.test.ts

import assert from "node:assert/strict";
import {
	existsSync,
	mkdirSync,
	mkdtempSync,
	readFileSync,
	rmSync,
	writeFileSync,
} from "node:fs";
import { tmpdir } from "node:os";
import { join } from "node:path";
import { test } from 'vitest';
import { parseRoadmap } from "../parsers.ts";
import {
	closeDatabase,
	getMilestone,
	getMilestoneSlices,
	getSlice,
	insertMilestone,
	openDatabase,
	updateSliceStatus,
} from "../sf-db.ts";
import {
	handlePlanMilestone,
	type PlanMilestoneParams,
} from "../tools/plan-milestone.ts";

function makeTmpBase(): string {
	const base = mkdtempSync(join(tmpdir(), "sf-plan-milestone-"));
	mkdirSync(join(base, ".sf", "milestones", "M001"), { recursive: true });
	return base;
}

function cleanup(base: string): void {
	try {
		closeDatabase();
	} catch {
		/* noop */
	}
	try {
		rmSync(base, { recursive: true, force: true });
	} catch {
		/* noop */
	}
}

function validParams(): PlanMilestoneParams {
	return {
		milestoneId: "M001",
		title: "DB-backed planning",
		vision: "Make planning write through the database.",
		successCriteria: ["Planning persists", "Roadmap renders from DB"],
		keyRisks: [
			{
				risk: "Renderer mismatch",
				whyItMatters: "Rendered roadmap may stop round-tripping.",
			},
		],
		proofStrategy: [
			{
				riskOrUnknown: "Render correctness",
				retireIn: "S01",
				whatWillBeProven: "ROADMAP output matches DB state.",
			},
		],
		verificationContract: "Contract verification text",
		verificationIntegration: "Integration verification text",
		verificationOperational: "Operational verification text",
		verificationUat: "UAT verification text",
		definitionOfDone: ["Tests pass", "Tool reruns cleanly"],
		requirementCoverage: "Covers R015.",
		boundaryMapMarkdown:
			"| From | To | Produces | Consumes |\n|------|----|----------|----------|\n| S01 | terminal | roadmap | nothing |",
		visionMeeting: {
			trigger:
				"Top-level roadmap spans multiple user, business, and delivery concerns.",
			pm: "Primary product move is making DB-backed planning the real source of truth.",
			userAdvocate:
				"Users need planning artifacts that stay coherent after repeated planning turns.",
			customerPanel:
				"Power users care about fidelity, maintainers care about consistency, and new adopters care about understandable roadmap output.",
			business:
				"The system needs a credible planning surface that can scale to more guided automation.",
			researcher:
				"Comparable planning systems treat requirements, roadmap, and state as a connected contract rather than separate notes.",
			deliveryLead:
				"Keep the first milestone narrow: DB-backed write path, projection, and prompt migration.",
			partner:
				"The proposed roadmap is small enough to land and strong enough to prove the architecture shift.",
			combatant:
				"Do not overbuild planning metadata before the DB-backed write path is working.",
			architect:
				"Persist the meeting and render it into the roadmap so the state machine can reason over it.",
			moderator:
				"Weighted synthesis: preserve the narrow DB-backed milestone, but require explicit stakeholder and market reasoning before execution.",
			weightedSynthesis:
				"User trust, product coherence, and business viability all point to a small but fully real DB-backed planning milestone. The strongest cut is avoiding speculative extra automation in this milestone.",
			confidenceByArea:
				"- User need: high\n- Architecture fit: high\n- Comparable-system fit: medium\n- Sequencing confidence: high",
			recommendedRoute: "planning",
		},
		slices: [
			{
				sliceId: "S01",
				title: "Tool wiring",
				risk: "medium",
				depends: [],
				demo: "The tool writes roadmap state.",
				goal: "Wire the handler.",
				successCriteria: "Handler persists state and renders markdown.",
				proofLevel: "integration",
				integrationClosure: "Downstream callers read rendered roadmap output.",
				observabilityImpact: "Tests expose render and validation failures.",
			},
			{
				sliceId: "S02",
				title: "Prompt migration",
				risk: "low",
				depends: ["S01"],
				demo: "Prompts call the tool.",
				goal: "Migrate prompts to DB-backed path.",
				successCriteria: "Prompt contracts reference the new tool.",
				proofLevel: "integration",
				integrationClosure: "Prompt tests cover the new planning route.",
				observabilityImpact: "Prompt and rogue-write failures become explicit.",
			},
		],
	};
}

test("handlePlanMilestone writes milestone and slice planning state and renders roadmap", async () => {
	const base = makeTmpBase();
	const dbPath = join(base, ".sf", "sf.db");
	openDatabase(dbPath);

	try {
		const result = await handlePlanMilestone(validParams(), base);
		assert.ok(
			!("error" in result),
			`unexpected error: ${"error" in result ? result.error : ""}`,
		);

		const milestone = getMilestone("M001");
		assert.ok(milestone, "milestone should exist");
		assert.equal(
			milestone?.vision,
			"Make planning write through the database.",
		);
		assert.deepEqual(milestone?.success_criteria, [
			"Planning persists",
			"Roadmap renders from DB",
		]);
		assert.equal(
			milestone?.verification_contract,
			"Contract verification text",
		);
		assert.equal(milestone?.vision_meeting?.recommendedRoute, "planning");
		assert.match(
			milestone?.vision_meeting?.customerPanel ?? "",
			/Power users care about fidelity/,
		);

		const slices = getMilestoneSlices("M001");
		assert.equal(slices.length, 2);
		assert.equal(slices[0]?.id, "S01");
		assert.equal(slices[0]?.goal, "Wire the handler.");
		assert.equal(slices[1]?.depends[0], "S01");

		const roadmapPath = join(
			base,
			".sf",
			"milestones",
			"M001",
			"M001-ROADMAP.md",
		);
		assert.ok(existsSync(roadmapPath), "roadmap should be rendered to disk");
		const roadmap = readFileSync(roadmapPath, "utf-8");
		assert.match(roadmap, /# M001: DB-backed planning/);
		assert.match(roadmap, /## Vision/);
		assert.match(roadmap, /Make planning write through the database\./);
		assert.match(roadmap, /## Vision Alignment Meeting/);
		assert.match(roadmap, /### Customer Panel/);
		assert.match(roadmap, /### Weighted Synthesis/);
		assert.match(roadmap, /## Slice Overview/);
		assert.match(roadmap, /\| S01 \| Tool wiring \| medium \|/);
		assert.match(roadmap, /\| S02 \| Prompt migration \| low \| S01 \|/);
	} finally {
		cleanup(base);
	}
});

test("handlePlanMilestone persists weighted roadmap draft even when the meeting routes back to research", async () => {
	const base = makeTmpBase();
	const dbPath = join(base, ".sf", "sf.db");
	openDatabase(dbPath);

	try {
		const baseVisionMeeting = validParams().visionMeeting!;
		const result = await handlePlanMilestone(
			{
				...validParams(),
				visionMeeting: {
					...baseVisionMeeting,
					moderator:
						"Weighted synthesis says comparable-product expectations are still too fuzzy for a final roadmap.",
					confidenceByArea:
						"- User need: high\n- Architecture fit: medium\n- Comparable-system fit: low\n- Sequencing confidence: low",
					recommendedRoute: "researching",
				},
			},
			base,
		);
		assert.ok(
			!("error" in result),
			`unexpected error: ${"error" in result ? result.error : ""}`,
		);

		const milestone = getMilestone("M001");
		assert.equal(milestone?.vision_meeting?.recommendedRoute, "researching");

		const roadmapPath = join(
			base,
			".sf",
			"milestones",
			"M001",
			"M001-ROADMAP.md",
		);
		const roadmap = readFileSync(roadmapPath, "utf-8");
		assert.match(roadmap, /### Recommended Route/);
		assert.match(roadmap, /researching/);
	} finally {
		cleanup(base);
	}
});

test("handlePlanMilestone rejects invalid payloads", async () => {
	const base = makeTmpBase();
	const dbPath = join(base, ".sf", "sf.db");
	openDatabase(dbPath);

	try {
		const params = validParams();
		const result = await handlePlanMilestone({ ...params, slices: [] }, base);
		assert.ok("error" in result);
		assert.match(
			result.error,
			/validation failed: slices must be a non-empty array/,
		);
	} finally {
		cleanup(base);
	}
});

test("handlePlanMilestone rejects leaked JSON fields in nested planning text", async () => {
	const base = makeTmpBase();
	const dbPath = join(base, ".sf", "sf.db");
	openDatabase(dbPath);

	try {
		const params = validParams();
		const result = await handlePlanMilestone(
			{
				...params,
				slices: [
					{
						...params.slices![0]!,
						proofLevel:
							'Contract proof.", "integrationClosure": "leaked field"',
					},
				],
			},
			base,
		);
		assert.ok("error" in result);
		assert.match(
			result.error,
			/validation failed: slices\[0\]\.proofLevel appears to contain leaked JSON fields/,
		);
	} finally {
		cleanup(base);
	}
});

test("handlePlanMilestone normalizes escaped newlines in planning arrays", async () => {
	const base = makeTmpBase();
	const dbPath = join(base, ".sf", "sf.db");
	openDatabase(dbPath);

	try {
		const result = await handlePlanMilestone(
			{
				...validParams(),
				successCriteria: ["First criterion\\nSecond criterion"],
			},
			base,
		);
		assert.ok(
			!("error" in result),
			`unexpected error: ${"error" in result ? result.error : ""}`,
		);
		const milestone = getMilestone("M001");
		assert.deepEqual(milestone?.success_criteria, [
			"First criterion\nSecond criterion",
		]);
	} finally {
		cleanup(base);
	}
});

test("handlePlanMilestone scaffolds common milestone slices from templateId", async () => {
	const base = makeTmpBase();
	const dbPath = join(base, ".sf", "sf.db");
	openDatabase(dbPath);

	try {
		const params = validParams();
		const result = await handlePlanMilestone(
			{
				milestoneId: params.milestoneId,
				title: params.title,
				vision: params.vision,
				templateId: "bugfix",
				successCriteria: params.successCriteria,
			},
			base,
		);
		assert.ok(
			!("error" in result),
			`unexpected error: ${"error" in result ? result.error : ""}`,
		);

		const slices = getMilestoneSlices("M001");
		assert.equal(slices.length, 3);
		assert.equal(slices[0]?.id, "S01");
		assert.equal(slices[1]?.depends[0], "S01");
		assert.match(slices[0]?.goal ?? "", /Capture the failing boundary/i);

		const roadmapPath = join(
			base,
			".sf",
			"milestones",
			"M001",
			"M001-ROADMAP.md",
		);
		const roadmap = readFileSync(roadmapPath, "utf-8");
		assert.match(roadmap, /Reproduce and bound the failure/);
		assert.match(roadmap, /Verify and guard against regression/);
	} finally {
		cleanup(base);
	}
});

test("handlePlanMilestone surfaces render failures and does not clear parse-visible state on failure", async () => {
	const base = makeTmpBase();
	const dbPath = join(base, ".sf", "sf.db");
	openDatabase(dbPath);

	try {
		const fallbackRoadmapPath = join(
			base,
			".sf",
			"milestones",
			"MISSING",
			"MISSING-ROADMAP.md",
		);
		mkdirSync(fallbackRoadmapPath, { recursive: true });

		const result = await handlePlanMilestone(
			{ ...validParams(), milestoneId: "MISSING" },
			base,
		);
		assert.ok("error" in result);
		assert.match(result.error, /render failed:/);

		const existingRoadmapPath = join(
			base,
			".sf",
			"milestones",
			"M001",
			"M001-ROADMAP.md",
		);
		writeFileSync(
			existingRoadmapPath,
			"# M001: Cached roadmap\n\n**Vision:** old value\n\n## Slices\n\n",
			"utf-8",
		);
		const cachedAfter = parseRoadmap(
			readFileSync(existingRoadmapPath, "utf-8"),
		);
		assert.equal(cachedAfter.vision, "old value");
	} finally {
		cleanup(base);
	}
});

test("handlePlanMilestone clears parse-visible roadmap state after successful render", async () => {
	const base = makeTmpBase();
	const dbPath = join(base, ".sf", "sf.db");
	openDatabase(dbPath);

	try {
		const roadmapPath = join(
			base,
			".sf",
			"milestones",
			"M001",
			"M001-ROADMAP.md",
		);
		writeFileSync(
			roadmapPath,
			"# M001: Cached roadmap\n\n**Vision:** old value\n\n## Slices\n\n",
			"utf-8",
		);

		const cachedBefore = parseRoadmap(readFileSync(roadmapPath, "utf-8"));
		assert.equal(cachedBefore.vision, "old value");

		const result = await handlePlanMilestone(validParams(), base);
		assert.ok(!("error" in result));

		const contentAfter = readFileSync(roadmapPath, "utf-8");
		assert.match(contentAfter, /Make planning write through the database\./);
		assert.match(contentAfter, /S01/);
		assert.match(contentAfter, /S02/);
	} finally {
		cleanup(base);
	}
});

test("handlePlanMilestone reruns idempotently and updates existing planning state", async () => {
	const base = makeTmpBase();
	const dbPath = join(base, ".sf", "sf.db");
	openDatabase(dbPath);

	try {
		const first = await handlePlanMilestone(validParams(), base);
		assert.ok(!("error" in first));
		const baseParams = validParams();

		const second = await handlePlanMilestone(
			{
				...baseParams,
				vision: "Updated vision",
				slices: [
					{
						...baseParams.slices![0]!,
						goal: "Updated goal",
						observabilityImpact: "Updated observability",
					},
					baseParams.slices![1]!,
				],
			},
			base,
		);
		assert.ok(!("error" in second));

		const milestone = getMilestone("M001");
		assert.equal(milestone?.vision, "Updated vision");

		const slices = getMilestoneSlices("M001");
		assert.equal(slices.length, 2);
		assert.equal(slices[0]?.goal, "Updated goal");
		assert.equal(slices[0]?.observability_impact, "Updated observability");
	} finally {
		cleanup(base);
	}
});

test("handlePlanMilestone preserves completed slice status on re-plan (#2558)", async () => {
	const base = makeTmpBase();
	const dbPath = join(base, ".sf", "sf.db");
	openDatabase(dbPath);

	try {
		// Initial plan — both slices start as "pending"
		const first = await handlePlanMilestone(validParams(), base);
		assert.ok(
			!("error" in first),
			`unexpected error: ${"error" in first ? first.error : ""}`,
		);
		const _baseParams = validParams();

		// Mark S01 as complete (simulates work done in a worktree)
		updateSliceStatus("M001", "S01", "complete", new Date().toISOString());

		const s01Before = getSlice("M001", "S01");
		assert.equal(
			s01Before?.status,
			"complete",
			"S01 should be complete before re-plan",
		);

		// Re-plan the same milestone — S01 must stay "complete", S02 stays "pending"
		const second = await handlePlanMilestone(validParams(), base);
		assert.ok(
			!("error" in second),
			`unexpected error: ${"error" in second ? second.error : ""}`,
		);

		const s01After = getSlice("M001", "S01");
		assert.equal(
			s01After?.status,
			"complete",
			"S01 status must be preserved as complete after re-plan",
		);

		const s02After = getSlice("M001", "S02");
		assert.equal(s02After?.status, "pending", "S02 should remain pending");
	} finally {
		cleanup(base);
	}
});

test("plan-milestone re-plan preserves completed status and updates slice fields (#2558)", async () => {
	const base = makeTmpBase();
	const dbPath = join(base, ".sf", "sf.db");
	openDatabase(dbPath);

	try {
		// Initial plan — both slices start as "pending"
		const first = await handlePlanMilestone(validParams(), base);
		assert.ok(
			!("error" in first),
			`unexpected error: ${"error" in first ? first.error : ""}`,
		);
		const baseParams = validParams();

		// Mark S01 as complete (simulates work done in worktree, then reconciled)
		updateSliceStatus("M001", "S01", "complete", new Date().toISOString());
		assert.equal(getSlice("M001", "S01")?.status, "complete");

		// Re-plan with updated title for S01.
		// The handler must:
		//   1. NOT downgrade S01 from "complete" to "pending"
		//   2. Update S01's non-status fields (title, risk, depends, demo)
		//   3. Keep S02 as "pending"
		const updatedParams = {
			...baseParams,
			slices: [
				{ ...baseParams.slices![0]!, title: "Updated S01 title", risk: "high" },
				baseParams.slices![1]!,
			],
		};
		const second = await handlePlanMilestone(updatedParams, base);
		assert.ok(
			!("error" in second),
			`unexpected error: ${"error" in second ? second.error : ""}`,
		);

		const s01After = getSlice("M001", "S01");
		assert.equal(
			s01After?.status,
			"complete",
			"completed slice status must survive re-plan",
		);
		assert.equal(
			s01After?.title,
			"Updated S01 title",
			"title should update on re-plan",
		);
		assert.equal(s01After?.risk, "high", "risk should update on re-plan");

		const s02After = getSlice("M001", "S02");
		assert.equal(s02After?.status, "pending", "pending slice stays pending");
	} finally {
		cleanup(base);
	}
});

test("handlePlanMilestone promotes pre-existing queued milestone to active (#3022)", async () => {
	const base = makeTmpBase();
	const dbPath = join(base, ".sf", "sf.db");
	openDatabase(dbPath);

	try {
		// Simulate ensureMilestoneDbRow: pre-create row with status "queued"
		// (this is what sf_milestone_generate_id does)
		insertMilestone({ id: "M001", status: "queued" });

		const before = getMilestone("M001");
		assert.equal(
			before?.status,
			"queued",
			"pre-condition: milestone should start as queued",
		);

		// Now plan the milestone — status should be promoted to "active"
		const result = await handlePlanMilestone(validParams(), base);
		assert.ok(
			!("error" in result),
			`unexpected error: ${"error" in result ? result.error : ""}`,
		);

		const after = getMilestone("M001");
		assert.equal(
			after?.status,
			"active",
			"milestone status should be promoted from queued to active",
		);
		assert.equal(
			after?.title,
			"DB-backed planning",
			"milestone title should be set",
		);
	} finally {
		cleanup(base);
	}
});