diff --git a/src/resources/extensions/ask-user-questions.ts b/src/resources/extensions/ask-user-questions.ts
index 215ad635d..8178fd1b0 100644
--- a/src/resources/extensions/ask-user-questions.ts
+++ b/src/resources/extensions/ask-user-questions.ts
@@ -135,10 +135,14 @@ export default function AskUserQuestions(pi: ExtensionAPI) {
 				}
 			}
 
+			// Try remote first if configured (works in both interactive and headless modes).
+			// tryRemoteQuestions returns null when no remote channel is configured, so
+			// this is a no-op when the user has not set up Slack/Discord/Telegram.
+			const { tryRemoteQuestions } = await import("./remote-questions/manager.js");
+			const remoteResult = await tryRemoteQuestions(params.questions, signal);
+			if (remoteResult) return { ...remoteResult, details: remoteResult.details as unknown };
+
 			if (!ctx.hasUI) {
-				const { tryRemoteQuestions } = await import("./remote-questions/manager.js");
-				const remoteResult = await tryRemoteQuestions(params.questions, signal);
-				if (remoteResult) return { ...remoteResult, details: remoteResult.details as unknown };
 				return errorResult("Error: UI not available (non-interactive mode)", params.questions);
 			}
 
diff --git a/src/resources/extensions/gsd/tests/remote-questions.test.ts b/src/resources/extensions/gsd/tests/remote-questions.test.ts
index 23432a2c0..4cd08b339 100644
--- a/src/resources/extensions/gsd/tests/remote-questions.test.ts
+++ b/src/resources/extensions/gsd/tests/remote-questions.test.ts
@@ -739,6 +739,27 @@ test("config source-level: hydration skips api_key entries with empty keys", ()
   );
 });
 
+test("ask-user-questions source-level: tryRemoteQuestions is called before the hasUI guard", () => {
+  // Regression test for #3480 — remote questions were silently skipped in interactive
+  // mode because tryRemoteQuestions was gated behind `if (!ctx.hasUI)`.
+  // The fix moved the remote call before that guard so configured channels
+  // (Telegram/Slack/Discord) fire regardless of UI availability.
+  const src = readFileSync(
+    join(__dirname, "..", "..", "ask-user-questions.ts"),
+    "utf-8",
+  );
+
+  const remoteCallIdx = src.indexOf("tryRemoteQuestions(params.questions");
+  const hasUIGuardIdx = src.indexOf("if (!ctx.hasUI)");
+
+  assert.ok(remoteCallIdx !== -1, "tryRemoteQuestions call should exist in ask-user-questions.ts");
+  assert.ok(hasUIGuardIdx !== -1, "!ctx.hasUI guard should exist in ask-user-questions.ts");
+  assert.ok(
+    remoteCallIdx < hasUIGuardIdx,
+    "tryRemoteQuestions must be called before the !ctx.hasUI guard — otherwise remote questions are skipped in interactive mode",
+  );
+});
+
 test("config source-level: removeProviderToken uses auth.remove not auth.set with empty key", () => {
   const commandSrc = readFileSync(
     join(__dirname, "..", "..", "remote-questions", "remote-command.ts"),