diff --git a/src/tests/verify-d2-upload-retry.test.ts b/src/tests/verify-d2-upload-retry.test.ts
new file mode 100644
index 0000000..6311191
--- /dev/null
+++ b/src/tests/verify-d2-upload-retry.test.ts
@@ -0,0 +1,189 @@
+import { describe, it, expect, afterAll, vi } from 'vitest';
+import { join } from 'path';
+import { tmpdir } from 'os';
+import { rm, mkdir, writeFile } from 'fs/promises';
+import { existsSync, rmSync } from 'fs';
+import Database from 'better-sqlite3';
+
+/**
+ * D2 verification: outcome-contract clauses against REAL SQLite + REAL endpoint.
+ *
+ * Clause retry-endpoint-widened-and-status-honest:
+ *   POST /api/jobs/:id/retry → 200 for failed upload-source,
+ *   404 for unknown ID, 409 for non-retryable (done).
+ *
+ * Clause failed-job-error-exposed-for-ui-banner:
+ *   GET /api/jobs → error field present for failed jobs.
+ *
+ * Seeds exact IDs from the outcome-contract cmd so the contract script
+ * can be replaced by this vitest suite. D2 code already merged (f03b757);
+ * this is non-blocking verification against deployed behaviour.
+ */
+
+const TEST_DATA_DIR = join(tmpdir(), 'whisper-pwa-verify-d2-' + process.pid);
+vi.stubEnv('DATA_DIR', TEST_DATA_DIR);
+
+const { getJob } = await import('$lib/server/db.js');
+const { POST } = await import('$lib/../routes/api/jobs/[id]/retry/+server.js');
+const { GET } = await import('$lib/../routes/api/jobs/+server.js');
+
+afterAll(() => {
+	try {
+		// rmSync with maxRetries handles ENOTEMPTY/EBUSY from WAL/filesystem races
+		rmSync(TEST_DATA_DIR, { recursive: true, force: true, maxRetries: 3 });
+	} catch {
+		// Best-effort: retryJob's async IIFE may recreate files during cleanup.
+		// CI container is ephemeral — leftover /tmp files are harmless.
+	}
+});
+
+function makeEvent(jobId: string) {
+	return { params: { id: jobId } } as any;
+}
+
+/**
+ * Seed a job row with explicit ID + fields.
+ * createJob() generates a random UUID, so we INSERT directly via
+ * a second connection to the same test DB.
+ */
+function seedJob(
+	id: string,
+	status: string,
+	source: string,
+	error: string | null,
+	title?: string
+) {
+	const dbPath = join(TEST_DATA_DIR, 'jobs.db');
+	const db = new Database(dbPath);
+	db.prepare(`
+		INSERT OR REPLACE INTO jobs
+			(id, status, title, source, audio_mode, error, created_at, updated_at)
+		VALUES (?, ?, ?, ?, 'auto', ?, datetime('now'), datetime('now'))
+	`).run(id, status, title ?? id, source, error);
+	db.close();
+}
+
+/**
+ * Create a stub upload file on disk so async retry can read it.
+ */
+async function seedUploadFile(jobId: string, filename: string): Promise<void> {
+	const uploadDir = join(TEST_DATA_DIR, 'uploads', jobId);
+	if (!existsSync(uploadDir)) await mkdir(uploadDir, { recursive: true });
+	await writeFile(join(uploadDir, filename), 'fake audio data');
+}
+
+describe('clause: retry-endpoint-widened-and-status-honest', () => {
+	it('retries a failed upload-source job → 200', async () => {
+		seedJob('sh-outcome-upload-retry', 'failed',
+			'probe-upload.webm', 'simulated failure');
+		await seedUploadFile('sh-outcome-upload-retry', 'probe-upload.webm');
+
+		const res = await POST(makeEvent('sh-outcome-upload-retry'));
+		expect(res.status).toBe(200);
+		const body = await res.json();
+		expect(body).toEqual({ ok: true });
+
+		// Confirm job was reset to pending
+		const job = getJob('sh-outcome-upload-retry')!;
+		expect(job.status).toBe('pending');
+		expect(job.error).toBeNull();
+	});
+
+	it('returns 404 for unknown job ID', async () => {
+		await expect(
+			POST(makeEvent('sh-outcome-does-not-exist'))
+		).rejects.toMatchObject({ status: 404 });
+	});
+
+	it('returns 409 for a done (non-retryable) job', async () => {
+		seedJob('sh-outcome-nonretryable-done', 'done',
+			'probe-done.webm', null);
+
+		await expect(
+			POST(makeEvent('sh-outcome-nonretryable-done'))
+		).rejects.toMatchObject({ status: 409 });
+	});
+
+	it('returns 409 for a pending job (not yet retryable)', async () => {
+		seedJob('sh-outcome-pending', 'pending',
+			'probe-pending.webm', null);
+
+		await expect(
+			POST(makeEvent('sh-outcome-pending'))
+		).rejects.toMatchObject({ status: 409 });
+	});
+
+	it('allows retry for a cancelled YouTube-source job', async () => {
+		seedJob('sh-outcome-cancelled', 'cancelled',
+			'https://youtube.com/watch?v=example', 'user cancelled');
+
+		const res = await POST(makeEvent('sh-outcome-cancelled'));
+		expect(res.status).toBe(200);
+		expect(await res.json()).toEqual({ ok: true });
+	});
+
+	it('preserves 200 for failed YouTube-source jobs (widened, not restricted)', async () => {
+		seedJob('sh-outcome-yt-retry', 'failed',
+			'https://youtube.com/watch?v=test', 'YouTube download failed');
+
+		const res = await POST(makeEvent('sh-outcome-yt-retry'));
+		expect(res.status).toBe(200);
+	});
+
+	it('allows retry for failed upload-source with non-webm filename', async () => {
+		seedJob('sh-outcome-mp3-retry', 'failed',
+			'podcast.mp3', 'audio prep failure');
+		await seedUploadFile('sh-outcome-mp3-retry', 'podcast.mp3');
+
+		const res = await POST(makeEvent('sh-outcome-mp3-retry'));
+		expect(res.status).toBe(200);
+		expect(await res.json()).toEqual({ ok: true });
+	});
+});
+
+describe('clause: failed-job-error-exposed-for-ui-banner', () => {
+	it('includes error field for a failed job', async () => {
+		seedJob('sh-outcome-error-banner', 'failed',
+			'probe-upload-2.webm',
+			'simulated transcription failure for outcome-contract probe');
+
+		const res = await GET();
+		expect(res.status).toBe(200);
+		const body = await res.json();
+
+		const found = body.find((j: any) => j.id === 'sh-outcome-error-banner');
+		expect(found).toBeDefined();
+		expect(found.status).toBe('failed');
+		expect(found.error).toBe(
+			'simulated transcription failure for outcome-contract probe'
+		);
+	});
+
+	it('returns null error for a successful done job', async () => {
+		seedJob('sh-outcome-done-probe', 'done',
+			'probe-success.webm', null);
+
+		const res = await GET();
+		const body = await res.json();
+
+		const found = body.find((j: any) => j.id === 'sh-outcome-done-probe');
+		expect(found).toBeDefined();
+		expect(found.error).toBeNull();
+	});
+
+	it('preserves error field alongside other job fields', async () => {
+		seedJob('sh-outcome-full-probe', 'failed',
+			'my-recording.webm', 'transcription failed', 'My Recording');
+
+		const res = await GET();
+		const body = await res.json();
+		const found = body.find((j: any) => j.id === 'sh-outcome-full-probe');
+
+		expect(found).toBeDefined();
+		expect(found.status).toBe('failed');
+		expect(found.error).toBe('transcription failed');
+		expect(found.title).toBe('My Recording');
+		expect(found.source).toBe('my-recording.webm');
+		expect(found.audioMode).toBe('auto');
+	});
+});