diff --git a/src/commands/send.ts b/src/commands/send.ts
index e1ad32e4d..ab370891e 100644
--- a/src/commands/send.ts
+++ b/src/commands/send.ts
@@ -39,14 +39,19 @@ export async function sendCommand(
 		if (waitSeconds !== 0) {
 			runtime.log(info("Wait/poll are Twilio-only; ignored for provider=web."));
 		}
-		const res = await deps.sendMessageWeb(
-			opts.to,
-			opts.message,
-			{
-				verbose: false,
-				mediaUrl: opts.media,
-			},
-		);
+		const res = await deps
+			.sendMessageWeb(
+				opts.to,
+				opts.message,
+				{
+					verbose: false,
+					mediaUrl: opts.media,
+				},
+			)
+			.catch((err) => {
+				runtime.error(`❌ Web send failed: ${String(err)}`);
+				throw err;
+			});
 		if (opts.json) {
 			runtime.log(
 				JSON.stringify(
diff --git a/src/provider-web.ts b/src/provider-web.ts
index 20a3fd161..17fdcb22c 100644
--- a/src/provider-web.ts
+++ b/src/provider-web.ts
@@ -106,6 +106,7 @@ export async function sendMessageWeb(
 ): Promise<{ messageId: string; toJid: string }> {
 	const sock = await createWaSocket(false, options.verbose);
 	try {
+		logInfo("🔌 Connecting to WhatsApp Web…");
 		await waitForWaConnection(sock);
 		const jid = toWhatsappJid(to);
 		try {