diff --git a/ablySpec/RealtimeClientConnection.swift b/ablySpec/RealtimeClientConnection.swift
index ae4be0b02..7f778e22d 100644
--- a/ablySpec/RealtimeClientConnection.swift
+++ b/ablySpec/RealtimeClientConnection.swift
@@ -1197,9 +1197,6 @@ class RealtimeClientConnection: QuickSpec {
 
             // RTN14b
             context("connection request fails") {
-
-                // NOTE: the connection doesn't retry to request a new token if any failure occurs
-
                 it("should not emit error with a renewable token") {
                     let options = AblyTests.commonAppSetup()
                     options.autoConnect = false
@@ -1257,6 +1254,66 @@ class RealtimeClientConnection: QuickSpec {
                     expect(failures[0].error!.code).to(equal(40142)) //Token expired
                 }
 
+                it("should transition to Failed when the token renewal fails") {
+                    let options = AblyTests.commonAppSetup()
+                    options.autoConnect = false
+                    let tokenTtl = 1.0
+                    let tokenDetails = getTestTokenDetails(key: options.key, capability: nil, ttl: tokenTtl)!
+                    options.token = tokenDetails.token
+                    options.authCallback = { tokenParams, callback in
+                        callback(tokenDetails, nil) // Return the same expired token again.
+                    }
+
+                    // Let the token expire
+                    waitUntil(timeout: testTimeout) { done in
+                        delay(tokenTtl) {
+                            done()
+                        }
+                    }
+
+                    let client = ARTRealtime(options: options)
+                    client.setTransportClass(TestProxyTransport.self)
+                    defer {
+                        client.dispose()
+                        client.close()
+                    }
+
+                    var transport: TestProxyTransport!
+
+                    waitUntil(timeout: testTimeout) { done in
+                        client.connection.on { stateChange in
+                            let stateChange = stateChange!
+                            let state = stateChange.current
+                            let errorInfo = stateChange.reason
+                            switch state {
+                            case .Connected:
+                                fail("Should not be connected")
+                                done()
+                            case .Failed, .Disconnected, .Suspended:
+                                guard let errorInfo = errorInfo else {
+                                    fail("ErrorInfo is nil"); done(); return
+                                }
+                                expect(errorInfo.code).to(equal(40142)) //Token expired
+                                done()
+                            default:
+                                break
+                            }
+                        }
+                        client.connect()
+                        transport = client.transport as! TestProxyTransport
+                    }
+
+                    let failures = transport.protocolMessagesReceived.filter({ $0.action == .Error })
+
+                    if failures.count != 2 {
+                        fail("Should have two connection request fail")
+                        return
+                    }
+
+                    expect(failures[0].error!.code).to(equal(40142))
+                    expect(failures[1].error!.code).to(equal(40142))
+                }
+
                 it("should transition to Failed state because the token is invalid and not renewable") {
                     let options = AblyTests.clientOptions()
                     options.autoConnect = false