From fdfb1df0de8d5f6a6f5a0d5cde6919e3cc8f2f8d Mon Sep 17 00:00:00 2001
From: Peter Steinberger <steipete@gmail.com>
Date: Tue, 25 Nov 2025 03:57:50 +0100
Subject: [PATCH] feat: add dry-run options and retry helper

---
 src/cli/program.ts      |  2 ++
 src/commands/up.ts      |  9 ++++++++-
 src/commands/webhook.ts |  4 ++++
 src/infra/retry.ts      | 18 ++++++++++++++++++
 4 files changed, 32 insertions(+), 1 deletion(-)
 create mode 100644 src/infra/retry.ts

diff --git a/src/cli/program.ts b/src/cli/program.ts
index 772dcc199..54575f63a 100644
--- a/src/cli/program.ts
+++ b/src/cli/program.ts
@@ -179,6 +179,7 @@ Examples:
 		.option("--path <path>", "Webhook path", "/webhook/whatsapp")
 		.option("--verbose", "Log inbound and auto-replies", false)
 		.option("-y, --yes", "Auto-confirm prompts when possible", false)
+		.option("--dry-run", "Print planned actions without starting server", false)
 		.addHelpText(
 			"after",
 			`
@@ -220,6 +221,7 @@ With Tailscale:
 		.option("--path <path>", "Webhook path", "/webhook/whatsapp")
 		.option("--verbose", "Verbose logging during setup/webhook", false)
 		.option("-y, --yes", "Auto-confirm prompts when possible", false)
+		.option("--dry-run", "Print planned actions without touching network", false)
 		// istanbul ignore next
 		.action(async (opts) => {
 			setVerbose(Boolean(opts.verbose));
diff --git a/src/commands/up.ts b/src/commands/up.ts
index 165437cbe..c2bff8288 100644
--- a/src/commands/up.ts
+++ b/src/commands/up.ts
@@ -3,7 +3,7 @@ import type { RuntimeEnv } from "../runtime.js";
 import { waitForever as defaultWaitForever } from "../cli/wait.js";
 
 export async function upCommand(
-	opts: { port: string; path: string; verbose?: boolean; yes?: boolean },
+	opts: { port: string; path: string; verbose?: boolean; yes?: boolean; dryRun?: boolean },
 	deps: CliDeps,
 	runtime: RuntimeEnv,
 	waiter: typeof defaultWaitForever = defaultWaitForever,
@@ -15,6 +15,13 @@ export async function upCommand(
 
 	await deps.ensurePortAvailable(port);
 	const env = deps.readEnv(runtime);
+	if (opts.dryRun) {
+		runtime.log(`[dry-run] would enable funnel on port ${port}`);
+		runtime.log(`[dry-run] would start webhook at path ${opts.path}`);
+		runtime.log(`[dry-run] would update Twilio sender webhook`);
+		const publicUrl = `https://dry-run${opts.path}`;
+		return { server: undefined, publicUrl, senderSid: undefined, waiter };
+	}
 	await deps.ensureBinary("tailscale", undefined, runtime);
 	await deps.ensureFunnel(port, undefined, runtime);
 	const host = await deps.getTailnetHostname();
diff --git a/src/commands/webhook.ts b/src/commands/webhook.ts
index 359f61723..5307a4b69 100644
--- a/src/commands/webhook.ts
+++ b/src/commands/webhook.ts
@@ -17,6 +17,10 @@ export async function webhookCommand(
 		throw new Error("Port must be between 1 and 65535");
 	}
 	await deps.ensurePortAvailable(port);
+	if (opts.reply === "dry-run") {
+		runtime.log(`[dry-run] would start webhook on port ${port} path ${opts.path}`);
+		return undefined;
+	}
 	const server = await deps.startWebhook(
 		port,
 		opts.path,
diff --git a/src/infra/retry.ts b/src/infra/retry.ts
new file mode 100644
index 000000000..b32a5fc80
--- /dev/null
+++ b/src/infra/retry.ts
@@ -0,0 +1,18 @@
+export async function retryAsync<T>(
+	fn: () => Promise<T>,
+	attempts = 3,
+	initialDelayMs = 300,
+): Promise<T> {
+	let lastErr: unknown;
+	for (let i = 0; i < attempts; i += 1) {
+		try {
+			return await fn();
+		} catch (err) {
+			lastErr = err;
+			if (i === attempts - 1) break;
+			const delay = initialDelayMs * 2 ** i;
+			await new Promise((r) => setTimeout(r, delay));
+		}
+	}
+	throw lastErr;
+}