diff --git a/packages/web/src/lib/config.ts b/packages/web/src/lib/config.ts
index 5ce26ab..f7e8d8f 100644
--- a/packages/web/src/lib/config.ts
+++ b/packages/web/src/lib/config.ts
@@ -7,6 +7,13 @@ const STORE_KEY = "openconcho:instances";
 
 export const HONCHO_CLOUD_URL = "https://api.honcho.dev";
 
+/**
+ * Connection-test timeout. Generous because a cold/idle self-hosted Honcho (DB
+ * pool spin-up, tunnel wake) can take several seconds on its first request — a
+ * tight 5s budget reported live-and-reachable instances as "Connection timed out".
+ */
+export const CONNECTION_TIMEOUT_MS = 15_000;
+
 function normalizeBaseUrl(url: string): string {
 	return url.trim().replace(/\/+$/, "").toLowerCase();
 }
@@ -162,6 +169,7 @@ export type HealthStatus = "ok" | "auth-required" | "unreachable" | "checking";
 export async function checkConnection(
 	baseUrl: string,
 	token?: string,
+	timeoutMs: number = CONNECTION_TIMEOUT_MS,
 ): Promise<{ status: HealthStatus; message: string }> {
 	try {
 		const { baseUrl: base, headers, fetch } = dispatchFor({ baseUrl, token });
@@ -169,7 +177,7 @@ export async function checkConnection(
 			method: "POST",
 			headers,
 			body: JSON.stringify({}),
-			signal: AbortSignal.timeout(5000),
+			signal: AbortSignal.timeout(timeoutMs),
 		});
 
 		const reject = res.headers.get(PROXY_REJECT_HEADER);
diff --git a/packages/web/src/test/check-connection.test.ts b/packages/web/src/test/check-connection.test.ts
index 1e0b8eb..f12f688 100644
--- a/packages/web/src/test/check-connection.test.ts
+++ b/packages/web/src/test/check-connection.test.ts
@@ -45,3 +45,30 @@ describe("checkConnection — web proxy mode", () => {
 		expect(res.message).toMatch(/allowlist/i);
 	});
 });
+
+describe("checkConnection — timeout budget", () => {
+	// A fetch that resolves after `ms`, but rejects early if the abort signal fires —
+	// mirrors how a real slow upstream interacts with AbortSignal.timeout.
+	function delayedFetch(ms: number) {
+		return (_url: string, init: { signal?: AbortSignal }) =>
+			new Promise<Response>((resolve, reject) => {
+				const timer = setTimeout(() => resolve(new Response("{}", { status: 200 })), ms);
+				init.signal?.addEventListener("abort", () => {
+					clearTimeout(timer);
+					reject(new DOMException("The operation timed out", "TimeoutError"));
+				});
+			});
+	}
+
+	it("reports unreachable when the upstream is slower than the timeout budget", async () => {
+		httpFetchMock.mockImplementation(delayedFetch(80));
+		const res = await checkConnection("https://slow.example.net", undefined, 20);
+		expect(res.status).toBe("unreachable");
+	});
+
+	it("succeeds when a slow upstream responds within the (cold-start) budget", async () => {
+		httpFetchMock.mockImplementation(delayedFetch(20));
+		const res = await checkConnection("https://slow.example.net", undefined, 200);
+		expect(res.status).toBe("ok");
+	});
+});