diff --git a/apps/desktop/electron/connection-config.cjs b/apps/desktop/electron/connection-config.cjs
index 0704cd6a2..c10a657d1 100644
--- a/apps/desktop/electron/connection-config.cjs
+++ b/apps/desktop/electron/connection-config.cjs
@@ -65,6 +65,59 @@ function buildGatewayWsUrlWithTicket(baseUrl, ticket) {
   return `${wsScheme}://${parsed.host}${prefix}/api/ws?ticket=${encodeURIComponent(ticket)}`
 }
 
+/**
+ * Build the WS URL the renderer would connect with, so the connection test can
+ * exercise the same transport the app actually uses.
+ *
+ * The OAuth ticket-minter is injected (`mintTicket(baseUrl) -> Promise<ticket>`)
+ * so this stays electron-free and unit-testable; main.cjs passes the real
+ * `mintGatewayWsTicket`.
+ *
+ * Return semantics:
+ *   - token mode + token   → ws(s)://…/api/ws?token=…
+ *   - token mode, no token → null  (genuine skip; nothing to authenticate with)
+ *   - oauth, mint ok       → ws(s)://…/api/ws?ticket=…
+ *   - oauth, mint fails    → THROWS  (NOT a skip)
+ *
+ * The oauth-mint-failure throw is the important case: the real boot path
+ * (resolveRemoteBackend in main.cjs) treats a mint failure as a hard
+ * "session expired" auth error and refuses to connect. Swallowing it here
+ * would re-introduce the exact false-positive this test exists to catch —
+ * HTTP /api/status passes, the test reports "reachable", then the renderer
+ * can't authenticate /api/ws and boot dies with "Could not connect".
+ *
+ * @param {string} baseUrl
+ * @param {'token'|'oauth'} authMode
+ * @param {string|null} token
+ * @param {{ mintTicket: (baseUrl: string) => Promise<string> }} deps
+ * @returns {Promise<string|null>}
+ */
+async function resolveTestWsUrl(baseUrl, authMode, token, deps = {}) {
+  if (authMode === 'oauth') {
+    const mintTicket = deps.mintTicket
+    if (typeof mintTicket !== 'function') {
+      throw new Error('resolveTestWsUrl: a mintTicket function is required in OAuth mode.')
+    }
+    let ticket
+    try {
+      ticket = await mintTicket(baseUrl)
+    } catch (error) {
+      const err = new Error(
+        'Reached the gateway over HTTP, but could not mint a WebSocket ticket for the OAuth session ' +
+          '(it may have expired). Open Settings → Gateway and sign in again.'
+      )
+      err.needsOauthLogin = true
+      err.cause = error
+      throw err
+    }
+    return buildGatewayWsUrlWithTicket(baseUrl, ticket)
+  }
+  if (!token) {
+    return null
+  }
+  return buildGatewayWsUrl(baseUrl, token)
+}
+
 function tokenPreview(value) {
   const raw = String(value || '')
 
@@ -114,5 +167,6 @@ module.exports = {
   cookiesHaveSession,
   normalizeRemoteBaseUrl,
   resolveAuthMode,
+  resolveTestWsUrl,
   tokenPreview
 }
diff --git a/apps/desktop/electron/connection-config.test.cjs b/apps/desktop/electron/connection-config.test.cjs
index 3182bd2ff..33f81f3b6 100644
--- a/apps/desktop/electron/connection-config.test.cjs
+++ b/apps/desktop/electron/connection-config.test.cjs
@@ -21,6 +21,7 @@ const {
   cookiesHaveSession,
   normalizeRemoteBaseUrl,
   resolveAuthMode,
+  resolveTestWsUrl,
   tokenPreview
 } = require('./connection-config.cjs')
 
@@ -159,3 +160,52 @@ test('tokenPreview returns set for short tokens', () => {
 test('tokenPreview returns a masked suffix for long tokens', () => {
   assert.equal(tokenPreview('abcdefghijklmnop'), '...klmnop')
 })
+
+// --- resolveTestWsUrl ---
+//
+// The "Test remote" button must exercise the same WS transport the app uses,
+// and must FAIL (not skip) when an OAuth session can't mint a ws-ticket — that
+// is the exact false-positive PR #39098 set out to eliminate.
+
+test('resolveTestWsUrl (token mode) builds a ?token= URL the WS probe can use', async () => {
+  const url = await resolveTestWsUrl('https://gw.example.com', 'token', 'tok123')
+  assert.equal(url, 'wss://gw.example.com/api/ws?token=tok123')
+})
+
+test('resolveTestWsUrl (token mode, no token) returns null — genuine skip', async () => {
+  assert.equal(await resolveTestWsUrl('https://gw.example.com', 'token', null), null)
+})
+
+test('resolveTestWsUrl (oauth, mint ok) builds a ?ticket= URL', async () => {
+  const url = await resolveTestWsUrl('https://gw.example.com', 'oauth', null, {
+    mintTicket: async () => 'tkt-9'
+  })
+  assert.equal(url, 'wss://gw.example.com/api/ws?ticket=tkt-9')
+})
+
+test('resolveTestWsUrl (oauth, mint FAILS) throws — must NOT skip WS validation', async () => {
+  await assert.rejects(
+    () =>
+      resolveTestWsUrl('https://gw.example.com', 'oauth', null, {
+        mintTicket: async () => {
+          throw new Error('401 ticket mint failed')
+        }
+      }),
+    err => {
+      // Actionable, points the user at re-auth, and preserves the cause + flag
+      // the boot overlay uses to offer a sign-in prompt.
+      assert.match(err.message, /WebSocket ticket/i)
+      assert.match(err.message, /sign in again/i)
+      assert.equal(err.needsOauthLogin, true)
+      assert.ok(err.cause instanceof Error)
+      return true
+    }
+  )
+})
+
+test('resolveTestWsUrl (oauth) requires a mintTicket function', async () => {
+  await assert.rejects(
+    () => resolveTestWsUrl('https://gw.example.com', 'oauth', null),
+    /mintTicket function is required/
+  )
+})
diff --git a/apps/desktop/electron/main.cjs b/apps/desktop/electron/main.cjs
index 5792b1dc2..0a877719e 100644
--- a/apps/desktop/electron/main.cjs
+++ b/apps/desktop/electron/main.cjs
@@ -35,6 +35,7 @@ const {
   cookiesHaveSession,
   normalizeRemoteBaseUrl,
   resolveAuthMode,
+  resolveTestWsUrl,
   tokenPreview
 } = require('./connection-config.cjs')
 const {
@@ -3770,7 +3771,7 @@ async function testDesktopConnectionConfig(input = {}) {
   // false-positive "reachable" while the real boot still failed with "Could not
   // connect to Hermes gateway". Mirror the renderer's connect here so the test
   // reflects the full path the app actually uses.
-  const wsUrl = await resolveTestWsUrl(baseUrl, authMode, token)
+  const wsUrl = await resolveTestWsUrl(baseUrl, authMode, token, { mintTicket: mintGatewayWsTicket })
   // Skip the WS leg only when the runtime genuinely lacks a WebSocket (so an
   // older Electron/Node never fails the test spuriously); Electron's main
   // process ships a global WebSocket on every supported version.
@@ -3791,26 +3792,6 @@ async function testDesktopConnectionConfig(input = {}) {
   }
 }
 
-// Build the WS URL the renderer would connect with, so the connection test can
-// exercise the same transport. OAuth gateways need a freshly minted single-use
-// ticket; token/local gateways carry a long-lived token in the query string. A
-// null return means we can't form a credentialed URL (e.g. OAuth without a live
-// session) and the WS leg of the test is skipped rather than failing spuriously.
-async function resolveTestWsUrl(baseUrl, authMode, token) {
-  if (authMode === 'oauth') {
-    try {
-      const ticket = await mintGatewayWsTicket(baseUrl)
-      return buildGatewayWsUrlWithTicket(baseUrl, ticket)
-    } catch {
-      return null
-    }
-  }
-  if (!token) {
-    return null
-  }
-  return buildGatewayWsUrl(baseUrl, token)
-}
-
 function resetBootProgressForReconnect() {
   updateBootProgress(
     {