Merge pull request #104 from nilenso/jadoo-better-errors

neenaoffline · web-flow · commit 8233a3372254 · 2026-04-29T01:32:39.000+05:30
Improve jadoo error handling
diff --git a/jadoo/src/index.ts b/jadoo/src/index.ts
@@ -7,54 +7,80 @@
 import { Bot } from "./bot.js";
 import { loadAIConfig, loadGoogleCalendarConfig, loadHarvestConfig, loadSlackConfig } from "./config/index.js";
 import { openDatabase, runMigrations } from "./db/index.js";
+import { AdminPlugin } from "./plugins/admin/index.js";
+import { LeavePlugin } from "./plugins/leave/index.js";
 import { PiAIService } from "./services/ai/pi-ai-service.js";
 import { GCalService } from "./services/calendar/gcal-service.js";
 import { HarvestAPIService } from "./services/harvest/harvest-service.js";
 import { BoltSlackService } from "./services/slack/bolt-slack-service.js";
 import { BackgroundWorker } from "./worker.js";
 
-// Load configuration from environment
-const slackConfig = loadSlackConfig();
-const aiConfig = loadAIConfig();
-const gcalConfig = loadGoogleCalendarConfig();
-const harvestConfig = loadHarvestConfig();
+let bot: Bot | undefined;
+let worker: BackgroundWorker | undefined;
+let db: ReturnType<typeof openDatabase> | undefined;
 
-// Database
-const db = openDatabase();
-runMigrations(db);
+async function main(): Promise<void> {
+	try {
+		console.log("[jadoo] loading configuration");
+		const slackConfig = loadSlackConfig();
+		const aiConfig = loadAIConfig();
+		const gcalConfig = loadGoogleCalendarConfig();
+		const harvestConfig = loadHarvestConfig();
 
-// Build services
-const slack = new BoltSlackService(slackConfig);
-const ai = new PiAIService(aiConfig);
-const calendar = new GCalService(gcalConfig);
-const harvest = new HarvestAPIService(harvestConfig);
+		console.log("[jadoo] opening database");
+		db = openDatabase();
+		runMigrations(db);
 
-import { AdminPlugin } from "./plugins/admin/index.js";
-import { LeavePlugin } from "./plugins/leave/index.js";
+		console.log("[jadoo] building services");
+		const slack = new BoltSlackService(slackConfig);
+		const ai = new PiAIService(aiConfig);
+		const calendar = new GCalService(gcalConfig);
+		const harvest = new HarvestAPIService(harvestConfig);
 
-// Assemble bot
-const bot = new Bot({ ai, calendar, harvest, slack });
+		console.log("[jadoo] registering plugins");
+		bot = new Bot({ ai, calendar, harvest, slack });
+		bot.register(new AdminPlugin(db));
+		bot.register(new LeavePlugin(db));
 
-// Register plugins here:
-bot.register(new AdminPlugin(db));
-bot.register(new LeavePlugin(db));
+		worker = new BackgroundWorker({ db, calendar, harvest, slack });
 
-// Background worker — processes confirmed leave actions + expires stale ones
-const worker = new BackgroundWorker({ db, calendar, harvest, slack });
+		console.log("[jadoo] starting bot");
+		await bot.start();
+		worker.start();
+		console.log("🚀 Jadoo is live");
+	} catch (err) {
+		const msg = err instanceof Error ? (err.stack ?? err.message) : String(err);
+		console.error(`[jadoo] fatal startup error: ${msg}`);
 
-await bot.start();
-worker.start();
-console.log("🚀 Jadoo is live");
+		try {
+			worker?.stop();
+			await bot?.stop();
+			db?.close();
+		} catch (cleanupErr) {
+			console.error(`[jadoo] cleanup after startup failure also failed: ${cleanupErr}`);
+		}
 
-// Graceful shutdown
-function shutdown() {
-	console.log("\n[jadoo] shutting down…");
-	worker.stop();
-	bot.stop();
-	db.close();
-	process.exit(0);
+		process.exit(1);
+	}
 }
-process.on("SIGINT", shutdown);
-process.on("SIGTERM", shutdown);
+
+async function shutdown(signal: string): Promise<void> {
+	console.log(`\n[jadoo] shutting down on ${signal}…`);
+
+	try {
+		worker?.stop();
+		await bot?.stop();
+		db?.close();
+		process.exit(0);
+	} catch (err) {
+		console.error(`[jadoo] shutdown failed: ${err}`);
+		process.exit(1);
+	}
+}
+
+process.on("SIGINT", () => void shutdown("SIGINT"));
+process.on("SIGTERM", () => void shutdown("SIGTERM"));
+
+await main();
 
 export { bot, worker };
diff --git a/jadoo/src/services/slack/bolt-slack-service.ts b/jadoo/src/services/slack/bolt-slack-service.ts
@@ -20,6 +20,10 @@ export class BoltSlackService implements SlackService {
 	private app: App;
 	private handlers: MessageHandler[] = [];
 
+	private formatError(err: unknown): string {
+		return err instanceof Error ? err.message : String(err);
+	}
+
 	constructor(config: SlackConfig) {
 		this.app = new BoltApp({
 			token: config.botToken,
@@ -54,9 +58,20 @@ export class BoltSlackService implements SlackService {
 			};
 
 			for (const handler of this.handlers) {
-				const reply = await handler(incoming);
-				if (reply) {
-					await say({ text: reply, thread_ts: msg.thread_ts ?? msg.ts });
+				try {
+					const reply = await handler(incoming);
+					if (reply) {
+						await say({ text: reply, thread_ts: msg.thread_ts ?? msg.ts });
+					}
+				} catch (err) {
+					const errorMessage = this.formatError(err);
+					console.error(
+						`[slack] message handler failed for user=${incoming.userId} channel=${incoming.channelId} ts=${incoming.ts}: ${errorMessage}`,
+					);
+					await say({
+						text: "⚠️ Sorry, something went wrong while processing that message. Please try again or contact an admin if it keeps happening.",
+						thread_ts: msg.thread_ts ?? msg.ts,
+					});
 				}
 			}
 		});
@@ -91,14 +106,35 @@ export class BoltSlackService implements SlackService {
 
 			if (!action?.action_id || !user?.id || !channel?.id || !message?.ts) return;
 
-			await handler({
+			const event = {
 				actionId: action.action_id,
 				value: action.value ?? "",
 				userId: user.id,
 				channelId: channel.id,
 				messageTs: message.ts,
 				threadTs: message.thread_ts,
-			});
+			};
+
+			try {
+				await handler(event);
+			} catch (err) {
+				const errorMessage = this.formatError(err);
+				console.error(
+					`[slack] action handler failed for action=${event.actionId} user=${event.userId} channel=${event.channelId} ts=${event.messageTs}: ${errorMessage}`,
+				);
+				await this.updateMessage(event.channelId, event.messageTs, {
+					text: "⚠️ Sorry, something went wrong while processing that action. Please try again or contact an admin if it keeps happening.",
+					blocks: [
+						{
+							type: "section",
+							text: {
+								type: "mrkdwn",
+								text: "⚠️ *Something went wrong while processing that action.* Please try again or contact an admin if it keeps happening.",
+							},
+						},
+					],
+				});
+			}
 		});
 	}
 
diff --git a/jadoo/src/worker.ts b/jadoo/src/worker.ts
@@ -43,6 +43,12 @@ export interface CancelLeavePayload {
 	dates: string[]; // YYYY-MM-DD
 }
 
+interface LeaveProcessingFailure {
+	date: string;
+	stage: "calendar" | "harvest" | "cancel" | "validation";
+	message: string;
+}
+
 // ─── Config ─────────────────────────────────────────────
 
 export interface WorkerConfig {
@@ -179,10 +185,18 @@ export class BackgroundWorker {
 		if (!user) {
 			console.error(`[worker] user ${action.user_id} not found for action ${action.id}`);
 			updatePendingActionStatus(this.db, action.id, "failed");
+			await this.notifyFailed(action, [
+				{
+					date: payload.dates.join(", "),
+					stage: "validation",
+					message: `User ${action.user_id} no longer exists in Jadoo's database.`,
+				},
+			]);
 			return;
 		}
 
 		let allSucceeded = true;
+		const failures: LeaveProcessingFailure[] = [];
 
 		for (const date of payload.dates) {
 			// Upsert a leave record in 'confirmed' state
@@ -196,6 +210,7 @@ export class BackgroundWorker {
 				status: "confirmed",
 			});
 
+			let stage: LeaveProcessingFailure["stage"] = "calendar";
 			try {
 				// Sync to Calendar
 				const start = new Date(`${date}T00:00:00`);
@@ -210,6 +225,7 @@ export class BackgroundWorker {
 				// Sync to Harvest (only if user has a Harvest mapping)
 				let harvestEntryId: number | null = null;
 				if (user.harvest_user_id) {
+					stage = "harvest";
 					harvestEntryId = await this.harvest.createTimeEntry({
 						harvestUserId: user.harvest_user_id,
 						date,
@@ -229,6 +245,8 @@ export class BackgroundWorker {
 				const msg = err instanceof Error ? err.message : String(err);
 				const retryCount = incrementLeaveRecordRetry(this.db, record.id, msg);
 
+				failures.push({ date, stage, message: msg });
+
 				if (retryCount >= this.maxRetries) {
 					updateLeaveRecordStatus(this.db, record.id, {
 						status: "failed",
@@ -263,7 +281,7 @@ export class BackgroundWorker {
 			} else {
 				// All dates either completed or failed
 				updatePendingActionStatus(this.db, action.id, "failed");
-				await this.notifyFailed(action);
+				await this.notifyFailed(action, failures, payload);
 			}
 		}
 	}
@@ -274,6 +292,13 @@ export class BackgroundWorker {
 		if (!user) {
 			console.error(`[worker] user ${action.user_id} not found for action ${action.id}`);
 			updatePendingActionStatus(this.db, action.id, "failed");
+			await this.notifyFailed(action, [
+				{
+					date: payload.dates.join(", "),
+					stage: "validation",
+					message: `User ${action.user_id} no longer exists in Jadoo's database.`,
+				},
+			]);
 			return;
 		}
 
@@ -289,6 +314,21 @@ export class BackgroundWorker {
 			)
 			.all(user.id, ...payload.dates);
 
+		if (records.length === 0) {
+			updatePendingActionStatus(this.db, action.id, "failed");
+			await this.notifyFailed(
+				action,
+				payload.dates.map((date) => ({
+					date,
+					stage: "validation",
+					message: "No matching leave record was found to cancel.",
+				})),
+			);
+			return;
+		}
+
+		const failures: LeaveProcessingFailure[] = [];
+
 		for (const record of records) {
 			try {
 				if (record.calendar_event_id) {
@@ -301,13 +341,20 @@ export class BackgroundWorker {
 			} catch (err) {
 				const msg = err instanceof Error ? err.message : String(err);
 				console.error(`[worker] failed to cancel leave record ${record.id}: ${msg}`);
+				failures.push({ date: record.date, stage: "cancel", message: msg });
 				updateLeaveRecordStatus(this.db, record.id, {
 					status: "failed",
 					errorMessage: msg,
 				});
 			}
 		}
 
+		if (failures.length > 0) {
+			updatePendingActionStatus(this.db, action.id, "failed");
+			await this.notifyFailed(action, failures);
+			return;
+		}
+
 		updatePendingActionStatus(this.db, action.id, "completed");
 		await this.notifyCancelled(action, payload);
 	}
@@ -338,20 +385,47 @@ export class BackgroundWorker {
 		}
 	}
 
-	private async notifyFailed(action: DbPendingAction): Promise<void> {
+	private async notifyFailed(
+		action: DbPendingAction,
+		failures: LeaveProcessingFailure[],
+		payload?: CreateLeavePayload,
+	): Promise<void> {
 		const channel = action.slack_channel_id;
 		const ts = action.slack_bot_message_ts;
 		if (!channel || !ts) return;
 
+		const totalDates = payload?.dates.length;
+		const uniqueFailures = failures.slice(0, 5).map((failure) => {
+			const stageLabel =
+				failure.stage === "calendar"
+					? "Calendar"
+					: failure.stage === "harvest"
+						? "Harvest"
+						: failure.stage === "cancel"
+							? "Cancellation"
+							: "Validation";
+			return `• ${failure.date}: ${stageLabel} — ${failure.message}`;
+		});
+		const summary =
+			totalDates && totalDates > failures.length
+				? `Some dates may have succeeded, but ${failures.length} date(s) failed.`
+				: "The request could not be completed.";
+		const message = [
+			"❌ Leave processing failed.",
+			summary,
+			"Please try again or contact an admin.",
+			...uniqueFailures,
+		].join("\n");
+
 		try {
 			await this.slack.updateMessage(channel, ts, {
-				text: "❌ Leave sync failed after retries. Please contact an admin.",
+				text: message,
 				blocks: [
 					{
 						type: "section",
 						text: {
 							type: "mrkdwn",
-							text: "❌ *Leave sync failed* after retries. Please contact an admin.",
+							text: `❌ *Leave processing failed*\n${summary}\nPlease try again or contact an admin.${uniqueFailures.length ? `\n\n${uniqueFailures.join("\n")}` : ""}`,
 						},
 					},
 				],
diff --git a/jadoo/test/worker.test.ts b/jadoo/test/worker.test.ts
@@ -189,6 +189,8 @@ describe("processTick — create_leave", () => {
 		expect(slack.updatedMessages.length).toBeGreaterThanOrEqual(1);
 		const lastUpdate = slack.updatedMessages[slack.updatedMessages.length - 1];
 		expect(lastUpdate.options.text).toContain("❌");
+		expect(lastUpdate.options.text).toContain("Calendar");
+		expect(lastUpdate.options.text).toContain("2026-04-01");
 	});
 
 	it("still processes leave for a deactivated user", async () => {
@@ -333,6 +335,26 @@ describe("processTick — cancel_leave", () => {
 		const records = getLeaveRecordsByStatus(db, "cancelled");
 		expect(records).toHaveLength(1);
 	});
+
+	it("fails cancellation with a helpful message when no matching leave exists", async () => {
+		const action = createPendingAction(db, {
+			userId: user.id,
+			actionType: "cancel_leave",
+			payload: { dates: ["2026-04-09"] },
+			slackChannelId: "C1",
+			expiresAt: futureExpiry(),
+		});
+		updatePendingActionBotMessageTs(db, action.id, "bot-msg-404");
+		updatePendingActionStatus(db, action.id, "confirmed");
+
+		worker = new BackgroundWorker(deps(), { processIntervalMs: 999999, expiryIntervalMs: 999999 });
+		await worker.processTick();
+
+		expect(getPendingActionById(db, action.id)?.status).toBe("failed");
+		expect(slack.updatedMessages).toHaveLength(1);
+		expect(slack.updatedMessages[0].options.text).toContain("No matching leave record");
+		expect(slack.updatedMessages[0].options.text).toContain("2026-04-09");
+	});
 });
 
 // ─── expiryTick ─────────────────────────────────────────
