diff --git a/Xcodes/AppleAPI/Sources/AppleAPI/Client.swift b/Xcodes/AppleAPI/Sources/AppleAPI/Client.swift
index cc135b64..f04f069a 100644
--- a/Xcodes/AppleAPI/Sources/AppleAPI/Client.swift
+++ b/Xcodes/AppleAPI/Sources/AppleAPI/Client.swift
@@ -126,10 +126,10 @@ public class Client {
                     switch urlResponse.statusCode {
                     case 200..<300:
                         return (data, urlResponse)
-                    case 401:
+                    case 400, 401:
                         throw AuthenticationError.incorrectSecurityCode
                     case let code:
-                        throw AuthenticationError.badStatusCode(code, data, urlResponse)
+                        throw AuthenticationError.badStatusCode(statusCode: code, data: data, response: urlResponse)
                     }
                 }
                 .flatMap { (data, response) -> AnyPublisher<AuthenticationState, Error> in
@@ -175,28 +175,36 @@ public enum AuthenticationState: Equatable {
 public enum AuthenticationError: Swift.Error, LocalizedError, Equatable {
     case invalidSession
     case invalidUsernameOrPassword(username: String)
-    case invalidPhoneNumberIndex(min: Int, max: Int, given: String?)
     case incorrectSecurityCode
     case unexpectedSignInResponse(statusCode: Int, message: String?)
     case appleIDAndPrivacyAcknowledgementRequired
     case accountUsesTwoStepAuthentication
     case accountUsesUnknownAuthenticationKind(String?)
-    case badStatusCode(Int, Data, HTTPURLResponse)
+    case badStatusCode(statusCode: Int, data: Data, response: HTTPURLResponse)
 
     public var errorDescription: String? {
         switch self {
-        case .invalidUsernameOrPassword(let username):
-            return "Invalid username and password combination. Attempted to sign in with username \(username)."
+        case .invalidSession:
+            return "Your authentication session is invalid. Try signing in again."
+        case .invalidUsernameOrPassword:
+            return "Invalid username and password combination."
+        case .incorrectSecurityCode:
+            return "The code that was entered is incorrect."
+        case let .unexpectedSignInResponse(statusCode, message):
+            return """
+                Received an unexpected sign in response. If you continue to have problems, please submit a bug report in the Help menu and include the following information:
+
+                Status code: \(statusCode)
+                \(message != nil ? ("Message: " + message!) : "")
+                """
         case .appleIDAndPrivacyAcknowledgementRequired:
             return "You must sign in to https://appstoreconnect.apple.com and acknowledge the Apple ID & Privacy agreement."
-        case .invalidPhoneNumberIndex(let min, let max, let given):
-            return "Not a valid phone number index. Expecting a whole number between \(min)-\(max), but was given \(given ?? "nothing")."
         case .accountUsesTwoStepAuthentication:
-            return "Received a response from Apple that indicates this account has two-step authentication enabled. xcodes currently only supports the newer two-factor authentication, though. Please consider upgrading to two-factor authentication, or open an issue on GitHub explaining why this isn't an option for you here: https://github.com/RobotsAndPencils/xcodes/issues/new"
+            return "Received a response from Apple that indicates this account has two-step authentication enabled. xcodes currently only supports the newer two-factor authentication, though. Please consider upgrading to two-factor authentication, or explain why this isn't an option for you by making a new feature request in the Help menu."
         case .accountUsesUnknownAuthenticationKind:
-            return "Received a response from Apple that indicates this account has two-step or two-factor authentication enabled, but xcodes is unsure how to handle this response:"
-        default:
-            return String(describing: self)
+            return "Received a response from Apple that indicates this account has two-step or two-factor authentication enabled, but xcodes is unsure how to handle this response. If you continue to have problems, please submit a bug report in the Help menu."
+        case let .badStatusCode(statusCode, _, _):
+            return "Received an unexpected status code: \(statusCode). If you continue to have problems, please submit a bug report in the Help menu."
         }
     }
 }
diff --git a/Xcodes/Backend/AppState.swift b/Xcodes/Backend/AppState.swift
index 087bb109..3bf6138c 100644
--- a/Xcodes/Backend/AppState.swift
+++ b/Xcodes/Backend/AppState.swift
@@ -6,6 +6,7 @@ import LegibleError
 import KeychainAccess
 import Path
 import Version
+import os.log
 
 class AppState: ObservableObject {
     private let client = AppleAPI.Client()
@@ -181,7 +182,7 @@ class AppState: ObservableObject {
                 try? Current.keychain.remove(username)
             }
 
-            // This error message is not user friendly... need to extract some meaningful data in the different cases
+            Logger.appState.error("Authentication error: \(error.legibleDescription)")
             self.authError = error
         case .finished:
             switch self.authenticationState {
diff --git a/Xcodes/Frontend/About/AboutView.swift b/Xcodes/Frontend/About/AboutView.swift
index d463f422..a34a8176 100644
--- a/Xcodes/Frontend/About/AboutView.swift
+++ b/Xcodes/Frontend/About/AboutView.swift
@@ -2,6 +2,7 @@ import SwiftUI
 
 struct AboutView: View {
     let showAcknowledgementsWindow: () -> Void
+    @SwiftUI.Environment(\.openURL) var openURL: OpenURLAction
     
     var body: some View {
         HStack {
@@ -18,7 +19,7 @@ struct AboutView: View {
                 
                 HStack(spacing: 32) {
                     Button(action: {
-                        NSWorkspace.shared.open(URL(string: "https://github.com/RobotsAndPencils/XcodesApp/")!)
+                        openURL(URL(string: "https://github.com/RobotsAndPencils/XcodesApp/")!)
                     }) {
                         Label("GitHub Repo", systemImage: "link")
                     }
diff --git a/Xcodes/XcodesApp.swift b/Xcodes/XcodesApp.swift
index 85b0569f..4a8ab645 100644
--- a/Xcodes/XcodesApp.swift
+++ b/Xcodes/XcodesApp.swift
@@ -7,6 +7,7 @@ import SwiftUI
 struct XcodesApp: App {
     @NSApplicationDelegateAdaptor(AppDelegate.self) var appDelegate: AppDelegate
     @SwiftUI.Environment(\.scenePhase) private var scenePhase: ScenePhase
+    @SwiftUI.Environment(\.openURL) var openURL: OpenURLAction
     @StateObject private var appState = AppState()
     
     var body: some Scene {
@@ -51,6 +52,25 @@ struct XcodesApp: App {
             }
 
             XcodeCommands(appState: appState)
+            
+            CommandGroup(replacing: CommandGroupPlacement.help) {
+                Button("Xcodes GitHub Repo") {
+                    let xcodesRepoURL = URL(string: "https://github.com/RobotsAndPencils/XcodesApp/")!
+                    openURL(xcodesRepoURL)
+                }
+                
+                Divider()
+                
+                Button("Report a Bug") {
+                    let bugReportURL = URL(string: "https://github.com/RobotsAndPencils/XcodesApp/issues/new?assignees=&labels=bug&template=bug_report.md&title=")!
+                    openURL(bugReportURL)
+                }
+                
+                Button("Request a New Feature") {
+                    let featureRequestURL = URL(string: "https://github.com/RobotsAndPencils/XcodesApp/issues/new?assignees=&labels=enhancement&template=feature_request.md&title=")!
+                    openURL(featureRequestURL)
+                }
+            }
         }
     }