diff --git a/README.md b/README.md
index 36169d0f2..0c35918bb 100644
--- a/README.md
+++ b/README.md
@@ -36,6 +36,7 @@ You can also talk to WhatsApp directly with a personal WhatsApp Web session (QR
 ## Common Commands
 
 - Send: `pnpm warelay send --to +12345550000 --message "Hello" --wait 20 --poll 2`
+- Send (JSON output): `pnpm warelay send --to +12345550000 --message "Hello" --json`
 - Send via personal WhatsApp Web: first `pnpm warelay web:login` (alias: `pnpm warelay login`, scan QR), then `pnpm warelay send --provider web --to +12345550000 --message "Hi"`
 - Auto-replies (auto provider): `pnpm warelay relay` (uses web if logged in, otherwise twilio poll)
 - Auto-replies (force web): `pnpm warelay relay --provider web`
diff --git a/docs/refactor/plan.md b/docs/refactor/plan.md
index a25d317e8..c8f45069a 100644
--- a/docs/refactor/plan.md
+++ b/docs/refactor/plan.md
@@ -16,6 +16,7 @@ This is a living note capturing the cleanups underway to keep `warelay` small an
 - README updated to document direct WhatsApp Web support and Claude output handling.
 - Added zod validation for `~/.warelay/warelay.json` and a `--dry-run` flag for `send`.
 - Introduced a tiny logger (`src/logger.ts`) and backoff retry in Twilio polling.
+- Added `--json` for `send`, logger adoption for web/twilio sends, and retries for webhook bring-up.
 
 ## In this pass
 - Wire more modules to the logger; keep colors/verbosity consistent.
diff --git a/src/cli/program.ts b/src/cli/program.ts
index 1cd00de21..48a847049 100644
--- a/src/cli/program.ts
+++ b/src/cli/program.ts
@@ -122,10 +122,7 @@ Examples:
 			const provider = await pickProvider(providerPref as Provider | "auto");
 
 			if (provider === "web") {
-				defaultRuntime.log(
-					info("Provider: web (personal WhatsApp Web session)"),
-				);
-				logWebSelfId();
+				logWebSelfId(defaultRuntime, true);
 				try {
 					await monitorWebProvider(Boolean(opts.verbose));
 					return;
diff --git a/src/commands/up.ts b/src/commands/up.ts
index c2bff8288..cdff293a4 100644
--- a/src/commands/up.ts
+++ b/src/commands/up.ts
@@ -1,6 +1,7 @@
 import type { CliDeps } from "../cli/deps.js";
 import type { RuntimeEnv } from "../runtime.js";
 import { waitForever as defaultWaitForever } from "../cli/wait.js";
+import { retryAsync } from "../infra/retry.js";
 
 export async function upCommand(
 	opts: { port: string; path: string; verbose?: boolean; yes?: boolean; dryRun?: boolean },
@@ -23,17 +24,22 @@ export async function upCommand(
 		return { server: undefined, publicUrl, senderSid: undefined, waiter };
 	}
 	await deps.ensureBinary("tailscale", undefined, runtime);
-	await deps.ensureFunnel(port, undefined, runtime);
+	await retryAsync(() => deps.ensureFunnel(port, undefined, runtime), 3, 500);
 	const host = await deps.getTailnetHostname();
 	const publicUrl = `https://${host}${opts.path}`;
 	runtime.log(`🌐 Public webhook URL (via Funnel): ${publicUrl}`);
 
-	const server = await deps.startWebhook(
-		port,
-		opts.path,
-		undefined,
-		Boolean(opts.verbose),
-		runtime,
+	const server = await retryAsync(
+		() =>
+			deps.startWebhook(
+				port,
+				opts.path,
+				undefined,
+				Boolean(opts.verbose),
+				runtime,
+			),
+		3,
+		300,
 	);
 
 	if (!deps.createClient) {
diff --git a/src/commands/webhook.ts b/src/commands/webhook.ts
index 5307a4b69..42425122e 100644
--- a/src/commands/webhook.ts
+++ b/src/commands/webhook.ts
@@ -1,5 +1,6 @@
 import type { CliDeps } from "../cli/deps.js";
 import type { RuntimeEnv } from "../runtime.js";
+import { retryAsync } from "../infra/retry.js";
 
 export async function webhookCommand(
 	opts: {
@@ -21,12 +22,17 @@ export async function webhookCommand(
 		runtime.log(`[dry-run] would start webhook on port ${port} path ${opts.path}`);
 		return undefined;
 	}
-	const server = await deps.startWebhook(
-		port,
-		opts.path,
-		opts.reply,
-		Boolean(opts.verbose),
-		runtime,
+	const server = await retryAsync(
+		() =>
+			deps.startWebhook(
+				port,
+				opts.path,
+				opts.reply,
+				Boolean(opts.verbose),
+				runtime,
+			),
+		3,
+		300,
 	);
 	return server;
 }
diff --git a/src/provider-web.ts b/src/provider-web.ts
index d339dd82e..469eadd32 100644
--- a/src/provider-web.ts
+++ b/src/provider-web.ts
@@ -364,14 +364,20 @@ function readWebSelfId() {
 	}
 }
 
-export function logWebSelfId(runtime: RuntimeEnv = defaultRuntime) {
+export function logWebSelfId(
+	runtime: RuntimeEnv = defaultRuntime,
+	includeProviderPrefix = false,
+) {
 	// Human-friendly log of the currently linked personal web session.
 	const { e164, jid } = readWebSelfId();
 	const details =
 		e164 || jid
 			? `${e164 ?? "unknown"}${jid ? ` (jid ${jid})` : ""}`
 			: "unknown";
-	runtime.log(info(`Listening on web session: ${details}`));
+	const prefix = includeProviderPrefix
+		? "Provider: web (personal WhatsApp Web session) — "
+		: "";
+	runtime.log(info(`${prefix}Listening on web session: ${details}`));
 }
 
 export async function pickProvider(pref: Provider | "auto"): Promise<Provider> {