Further along work towards auto updating. Show release notes for the builds that are more recent than yours.

7 files changed, 788 insertions, 202 deletions

diff --git a/Hotline.xcodeproj/project.pbxproj b/Hotline.xcodeproj/project.pbxproj
index d35440f..642a329 100644
--- a/Hotline.xcodeproj/project.pbxproj
+++ b/Hotline.xcodeproj/project.pbxproj
@@ -36,7 +36,7 @@
 		DA6300972B24036B0034CBFD /* HotlineClient.swift in Sources */ = {isa = PBXBuildFile; fileRef = DA6300962B24036B0034CBFD /* HotlineClient.swift */; };
 		DA65499A2BEC280E00EDB697 /* ServerMessageView.swift in Sources */ = {isa = PBXBuildFile; fileRef = DA6549992BEC280E00EDB697 /* ServerMessageView.swift */; };
 		DA65499C2BEC3FBD00EDB697 /* ServerAgreementView.swift in Sources */ = {isa = PBXBuildFile; fileRef = DA65499B2BEC3FBD00EDB697 /* ServerAgreementView.swift */; };
-		DA65499E2BEC438A00EDB697 /* NSWindowBridge.swift in Sources */ = {isa = PBXBuildFile; fileRef = DA65499D2BEC438A00EDB697 /* NSWindowBridge.swift */; };
+		DA65499E2BEC438A00EDB697 /* NSWindowBridge.swift in Sources */ = {isa = PBXBuildFile; fileRef = DA65499D2BEC438A00EDB697 /* NSWindowBridge.swift */; platformFilters = (macos, ); };
 		DA6980792BF80525003E434B /* TextView.swift in Sources */ = {isa = PBXBuildFile; fileRef = DA6980782BF80525003E434B /* TextView.swift */; };
 		DA69807E2BFD449B003E434B /* MessageBoardEditorView.swift in Sources */ = {isa = PBXBuildFile; fileRef = DA69807D2BFD449B003E434B /* MessageBoardEditorView.swift */; };
 		DA6980832BFFD06C003E434B /* BookmarkDocument.swift in Sources */ = {isa = PBXBuildFile; fileRef = DA6980822BFFD06C003E434B /* BookmarkDocument.swift */; };
@@ -75,6 +75,9 @@
 		DAC002192B21630900A6C290 /* SwiftUIExtensions.swift in Sources */ = {isa = PBXBuildFile; fileRef = DAC002182B21630900A6C290 /* SwiftUIExtensions.swift */; };
 		DAC3D9832BC33FD000A727C9 /* AppState.swift in Sources */ = {isa = PBXBuildFile; fileRef = DAC3D9822BC33FD000A727C9 /* AppState.swift */; };
 		DAC87F072C5010E80060FADF /* HotlineExtensions.swift in Sources */ = {isa = PBXBuildFile; fileRef = DAC87F062C5010E80060FADF /* HotlineExtensions.swift */; };
+		DACCE5E12EABE4B4008CDD92 /* AppUpdate.swift in Sources */ = {isa = PBXBuildFile; fileRef = DACCE5E02EABE4B4008CDD92 /* AppUpdate.swift */; platformFilters = (macos, ); };
+		DACCE5E32EABE86A008CDD92 /* AppUpdateView.swift in Sources */ = {isa = PBXBuildFile; fileRef = DACCE5E22EABE86A008CDD92 /* AppUpdateView.swift */; platformFilters = (macos, ); };
+		DACCE5EF2EAC19C9008CDD92 /* SwiftUIIntrospect in Frameworks */ = {isa = PBXBuildFile; productRef = DACCE5EE2EAC19C9008CDD92 /* SwiftUIIntrospect */; };
 		DADDB28B2B22B31F0024040D /* Tracker.swift in Sources */ = {isa = PBXBuildFile; fileRef = DADDB28A2B22B31F0024040D /* Tracker.swift */; };
 		DADDB28D2B22B5920024040D /* Server.swift in Sources */ = {isa = PBXBuildFile; fileRef = DADDB28C2B22B5920024040D /* Server.swift */; };
 		DADDB28F2B238D850024040D /* Hotline.swift in Sources */ = {isa = PBXBuildFile; fileRef = DADDB28E2B238D850024040D /* Hotline.swift */; };
@@ -159,6 +162,8 @@
 		DAC002182B21630900A6C290 /* SwiftUIExtensions.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = SwiftUIExtensions.swift; sourceTree = "<group>"; };
 		DAC3D9822BC33FD000A727C9 /* AppState.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = AppState.swift; sourceTree = "<group>"; };
 		DAC87F062C5010E80060FADF /* HotlineExtensions.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = HotlineExtensions.swift; sourceTree = "<group>"; };
+		DACCE5E02EABE4B4008CDD92 /* AppUpdate.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = AppUpdate.swift; sourceTree = "<group>"; };
+		DACCE5E22EABE86A008CDD92 /* AppUpdateView.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = AppUpdateView.swift; sourceTree = "<group>"; };
 		DADDB28A2B22B31F0024040D /* Tracker.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = Tracker.swift; sourceTree = "<group>"; };
 		DADDB28C2B22B5920024040D /* Server.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = Server.swift; sourceTree = "<group>"; };
 		DADDB28E2B238D850024040D /* Hotline.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = Hotline.swift; sourceTree = "<group>"; };
@@ -178,6 +183,7 @@
 			isa = PBXFrameworksBuildPhase;
 			buildActionMask = 2147483647;
 			files = (
+				DACCE5EF2EAC19C9008CDD92 /* SwiftUIIntrospect in Frameworks */,
 				DA72A0E02B4DA8CA00A0F48A /* SplitView in Frameworks */,
 				DAB4D8872B4CB3610048A05C /* MarkdownUI in Frameworks */,
 			);
@@ -191,6 +197,7 @@
 			children = (
 				DAC3D9822BC33FD000A727C9 /* AppState.swift */,
 				DA2863D92B37BF6E00A7D050 /* Preferences.swift */,
+				DACCE5E02EABE4B4008CDD92 /* AppUpdate.swift */,
 			);
 			path = State;
 			sourceTree = "<group>";
@@ -362,6 +369,7 @@
 				DA2863D72B37AD1C00A7D050 /* SettingsView.swift */,
 				DAE136B92B9D1147007D8307 /* HotlinePanelView.swift */,
 				DA55AC762BE589F700034857 /* AboutView.swift */,
+				DACCE5E22EABE86A008CDD92 /* AppUpdateView.swift */,
 				DA65499B2BEC3FBD00EDB697 /* ServerAgreementView.swift */,
 				DA6549992BEC280E00EDB697 /* ServerMessageView.swift */,
 				11F8288A2BF9428100216BA0 /* AccountManagerView.swift */,
@@ -388,6 +396,7 @@
 			packageProductDependencies = (
 				DAB4D8862B4CB3610048A05C /* MarkdownUI */,
 				DA72A0DF2B4DA8CA00A0F48A /* SplitView */,
+				DACCE5EE2EAC19C9008CDD92 /* SwiftUIIntrospect */,
 			);
 			productName = Hotline;
 			productReference = DA9CAFB72B126D5700CDA197 /* Hotline.app */;
@@ -420,6 +429,7 @@
 			packageReferences = (
 				DAB4D8852B4CB3610048A05C /* XCRemoteSwiftPackageReference "swift-markdown-ui" */,
 				DA72A0DE2B4DA8CA00A0F48A /* XCRemoteSwiftPackageReference "SplitView" */,
+				DACCE5ED2EAC19C9008CDD92 /* XCRemoteSwiftPackageReference "SwiftUI-Introspect" */,
 			);
 			productRefGroup = DA9CAFB82B126D5700CDA197 /* Products */;
 			projectDirPath = "";
@@ -500,6 +510,7 @@
 				DA72A0DD2B4CD0BF00A0F48A /* NewsEditorView.swift in Sources */,
 				DABFCC292B1530DC009F40D2 /* FoundationExtensions.swift in Sources */,
 				DA57536C2B36BA1D00FAC277 /* TextDocument.swift in Sources */,
+				DACCE5E12EABE4B4008CDD92 /* AppUpdate.swift in Sources */,
 				DA77253F2B21176D006C5ABB /* NewsView.swift in Sources */,
 				DA99218E2C51AA5D0058FA6C /* HotlineDataBuilder.swift in Sources */,
 				DA872B132BDDBF78008B1012 /* HotlinePanel.swift in Sources */,
@@ -522,6 +533,7 @@
 				DA6980832BFFD06C003E434B /* BookmarkDocument.swift in Sources */,
 				DAB4D87E2B4C8BCA0048A05C /* FilePreviewTextView.swift in Sources */,
 				DA4F2C012B1A558E00D8ADDC /* ChatView.swift in Sources */,
+				DACCE5E32EABE86A008CDD92 /* AppUpdateView.swift in Sources */,
 				DA32CD492B2931640053B98B /* User.swift in Sources */,
 			);
 			runOnlyForDeploymentPostprocessing = 0;
@@ -656,7 +668,7 @@
 				CODE_SIGN_ENTITLEMENTS = Hotline/Hotline.entitlements;
 				"CODE_SIGN_IDENTITY[sdk=macosx*]" = "Apple Development";
 				CODE_SIGN_STYLE = Automatic;
-				CURRENT_PROJECT_VERSION = 23;
+				CURRENT_PROJECT_VERSION = 24;
 				DEVELOPMENT_ASSET_PATHS = "\"Hotline/Preview Content\"";
 				DEVELOPMENT_TEAM = 5AEEV7QB2U;
 				"ENABLE_HARDENED_RUNTIME[sdk=macosx*]" = YES;
@@ -675,7 +687,7 @@
 					"$(inherited)",
 					"@executable_path/Frameworks",
 				);
-				MACOSX_DEPLOYMENT_TARGET = 14.3;
+				MACOSX_DEPLOYMENT_TARGET = 15.6;
 				MARKETING_VERSION = 1.0;
 				PRODUCT_BUNDLE_IDENTIFIER = co.goodmake.hotline;
 				PRODUCT_NAME = "$(TARGET_NAME)";
@@ -696,7 +708,7 @@
 				CODE_SIGN_ENTITLEMENTS = Hotline/Hotline.entitlements;
 				"CODE_SIGN_IDENTITY[sdk=macosx*]" = "Apple Development";
 				CODE_SIGN_STYLE = Automatic;
-				CURRENT_PROJECT_VERSION = 23;
+				CURRENT_PROJECT_VERSION = 24;
 				DEVELOPMENT_ASSET_PATHS = "\"Hotline/Preview Content\"";
 				DEVELOPMENT_TEAM = 5AEEV7QB2U;
 				"ENABLE_HARDENED_RUNTIME[sdk=macosx*]" = YES;
@@ -715,7 +727,7 @@
 					"$(inherited)",
 					"@executable_path/Frameworks",
 				);
-				MACOSX_DEPLOYMENT_TARGET = 14.3;
+				MACOSX_DEPLOYMENT_TARGET = 15.6;
 				MARKETING_VERSION = 1.0;
 				PRODUCT_BUNDLE_IDENTIFIER = co.goodmake.hotline;
 				PRODUCT_NAME = "$(TARGET_NAME)";
@@ -768,6 +780,14 @@
 				minimumVersion = 2.3.0;
 			};
 		};
+		DACCE5ED2EAC19C9008CDD92 /* XCRemoteSwiftPackageReference "SwiftUI-Introspect" */ = {
+			isa = XCRemoteSwiftPackageReference;
+			repositoryURL = "https://github.com/siteline/SwiftUI-Introspect";
+			requirement = {
+				kind = upToNextMajorVersion;
+				minimumVersion = 26.0.0;
+			};
+		};
 /* End XCRemoteSwiftPackageReference section */
 
 /* Begin XCSwiftPackageProductDependency section */
@@ -781,6 +801,11 @@
 			package = DAB4D8852B4CB3610048A05C /* XCRemoteSwiftPackageReference "swift-markdown-ui" */;
 			productName = MarkdownUI;
 		};
+		DACCE5EE2EAC19C9008CDD92 /* SwiftUIIntrospect */ = {
+			isa = XCSwiftPackageProductDependency;
+			package = DACCE5ED2EAC19C9008CDD92 /* XCRemoteSwiftPackageReference "SwiftUI-Introspect" */;
+			productName = SwiftUIIntrospect;
+		};
 /* End XCSwiftPackageProductDependency section */
 	};
 	rootObject = DA9CAFAF2B126D5700CDA197 /* Project object */;
diff --git a/Hotline.xcodeproj/project.xcworkspace/xcshareddata/swiftpm/Package.resolved b/Hotline.xcodeproj/project.xcworkspace/xcshareddata/swiftpm/Package.resolved
index 28a7003..f112b32 100644
--- a/Hotline.xcodeproj/project.xcworkspace/xcshareddata/swiftpm/Package.resolved
+++ b/Hotline.xcodeproj/project.xcworkspace/xcshareddata/swiftpm/Package.resolved
@@ -1,5 +1,5 @@
 {
-  "originHash" : "e60904df125ffbce75adea70452a77ae65a068371a6b6c4cfe0e6c155c4bdcee",
+  "originHash" : "26db0d070cfc8e002044ea1380ec5e675c0718ebf212f6e8a57f12cc6c295723",
   "pins" : [
     {
       "identity" : "networkimage",
@@ -36,6 +36,15 @@
         "revision" : "5f613358148239d0292c0cef674a3c2314737f9e",
         "version" : "2.4.1"
       }
+    },
+    {
+      "identity" : "swiftui-introspect",
+      "kind" : "remoteSourceControl",
+      "location" : "https://github.com/siteline/SwiftUI-Introspect",
+      "state" : {
+        "revision" : "a08b87f96b41055577721a6e397562b21ad52454",
+        "version" : "26.0.0"
+      }
     }
   ],
   "version" : 3
diff --git a/Hotline/MacApp.swift b/Hotline/MacApp.swift
index a4ff3cb..a91df52 100644
--- a/Hotline/MacApp.swift
+++ b/Hotline/MacApp.swift
@@ -61,6 +61,10 @@ class AppDelegate: NSObject, NSApplicationDelegate {
 //        NotificationCenter.default.removeObserver(token)
 //      }
 //    }
+
+    Task {
+      await AppUpdate.shared.checkForUpdatesOnLaunch()
+    }
   }
   
   func applicationWillTerminate(_ notification: Notification) {
@@ -78,6 +82,7 @@ struct Application: App {
   
   @State private var hotlinePanel: HotlinePanel? = nil
   @State private var selection: TrackerSelection? = nil
+  @Bindable private var update = AppUpdate.shared
 
   @FocusedValue(\.activeHotlineModel) private var activeHotline: Hotline?
   @FocusedValue(\.activeServerState) private var activeServerState: ServerState?
@@ -112,15 +117,43 @@ struct Application: App {
         }
       }
     }
+    .onChange(of: self.update.showWindow) {
+      if self.update.showWindow {
+        self.openWindow(id: "update")
+      }
+    }
     
     // MARK: About Box
     Window("About", id: "about") {
       AboutView()
-        .ignoresSafeArea()
-        .background(Color.hotlineRed)
+        .background(Color.hotlineRed, ignoresSafeAreaEdges: .all)
+        .windowFullScreenBehavior(.disabled)
+        .toolbar(removing: .title)
+        .gesture(WindowDragGesture())
+        .background(
+          WindowConfigurator { window in
+            window.titlebarAppearsTransparent = true
+            window.titlebarSeparatorStyle = .none
+            window.isMovableByWindowBackground = true
+            
+            if let closeButton = window.standardWindowButton(.closeButton) {
+              closeButton.isHidden = false   // make sure it’s visible
+              closeButton.isEnabled = true
+            }
+            
+            if let btn = window.standardWindowButton(.zoomButton) {
+              btn.isHidden = true
+            }
+            
+            if let btn = window.standardWindowButton(.miniaturizeButton) {
+              btn.isHidden = true
+            }
+          }
+        )
     }
     .windowResizability(.contentSize)
     .windowStyle(.hiddenTitleBar)
+    .restorationBehavior(.disabled)
     .defaultPosition(.center)
     .commandsRemoved() // Remove About that was automatically added to Window menu.
     .commands {
@@ -128,9 +161,26 @@ struct Application: App {
         Button("About Hotline") {
           openWindow(id: "about")
         }
+                
+        Button("Check for Updates...") {
+          Task {
+            await AppUpdate.shared.checkForUpdatesManually()
+          }
+        }
       }
     }
     
+    // MARK: Update Window
+    Window("New Update", id: "update") {
+      AppUpdateView()
+        .windowFullScreenBehavior(.disabled)
+    }
+    .windowResizability(.contentSize)
+    .windowStyle(.hiddenTitleBar)
+    .restorationBehavior(.disabled)
+    .defaultPosition(.center)
+    .commandsRemoved()
+    
     // MARK: Server Window
     WindowGroup(id: "server", for: Server.self) { server in
       ServerView(server: server)
@@ -189,7 +239,7 @@ struct Application: App {
           }
         }
         Divider()
-        Button("Download Latest...") {
+        Button("Open Latest Release Page...") {
           if let url = URL(string: "https://github.com/mierau/hotline/releases/latest") {
             openURL(url)
           }
diff --git a/Hotline/State/AppUpdate.swift b/Hotline/State/AppUpdate.swift
new file mode 100644
index 0000000..601859e
--- /dev/null
+++ b/Hotline/State/AppUpdate.swift
@@ -0,0 +1,341 @@
+import Foundation
+import Observation
+import AppKit
+
+struct UpdateReleaseInfo: Equatable {
+  let tagName: String
+  let displayVersion: String
+  let versionNumber: Double
+  let buildNumber: Int
+  let notes: String
+  let downloadURL: URL
+  let assetName: String
+}
+
+struct AppUpdateMessage: Equatable {
+  enum Kind {
+    case info
+    case success
+    case error
+  }
+  
+  let title: String
+  let detail: String
+  let kind: Kind
+}
+
+@Observable
+final class AppUpdate {
+  static let shared = AppUpdate()
+  
+  private init() {}
+  
+  private enum CheckTrigger {
+    case automatic
+    case manual
+  }
+  
+  // MARK: - Public State
+  
+  var isChecking = false
+  var isDownloading = false
+  var showWindow = false
+  var release: UpdateReleaseInfo?
+  var releases: [UpdateReleaseInfo] = []
+  var message: AppUpdateMessage?
+  var userInitiated = false
+  var releaseNotesCombined: String?
+  
+  // MARK: - Configuration
+  
+  private let releasesURL = URL(string: "https://api.github.com/repos/mierau/hotline/releases?per_page=100")!
+  private let remindInterval: TimeInterval = 60 * 60 * 24 * 14
+  
+  private let defaults = UserDefaults.standard
+  private let remindDateKey = "update.remind.date"
+  private let lastPromptedVersionKey = "update.last.prompt.version"
+  
+  // MARK: - Public API
+  
+  func checkForUpdatesOnLaunch() async {
+    await checkForUpdates(trigger: .automatic)
+  }
+  
+  func checkForUpdatesManually() async {
+    await checkForUpdates(trigger: .manual)
+  }
+  
+  @MainActor
+  func startDownload() {
+    guard let release, isDownloading == false else { return }
+    
+    isDownloading = true
+    message = nil
+    
+    Task(priority: .userInitiated) {
+      await self.downloadRelease(release)
+    }
+  }
+  
+  @MainActor
+  func remindLater() {
+    guard let release else {
+      resetAndCloseWindow()
+      return
+    }
+    
+    recordPrompt(for: release, remindLater: true)
+    resetAndCloseWindow()
+  }
+  
+  @MainActor
+  func acknowledgeMessage() {
+    resetAndCloseWindow()
+  }
+  
+  @MainActor
+  func handleWindowDismissed() {
+    guard showWindow else { return }
+    
+    resetAndCloseWindow()
+  }
+  
+  // MARK: - Internal Logic
+  
+  private func checkForUpdates(trigger: CheckTrigger) async {
+    await MainActor.run {
+      self.isChecking = true
+      self.userInitiated = (trigger == .manual)
+      self.message = nil
+      self.releases = []
+      self.release = nil
+      self.releaseNotesCombined = nil
+      self.isDownloading = false
+      if trigger == .manual {
+        self.showWindow = false
+      }
+    }
+    
+    do {
+      let newerReleases = try await fetchNewerReleases()
+      let latestRelease = newerReleases.first
+      let shouldShow: Bool
+      switch trigger {
+      case .manual:
+        shouldShow = latestRelease != nil
+      case .automatic:
+        if let latestRelease {
+          shouldShow = shouldPrompt(for: latestRelease)
+        } else {
+          shouldShow = false
+        }
+      }
+      
+      await MainActor.run {
+        self.isChecking = false
+        if shouldShow, let latestRelease {
+          self.release = latestRelease
+          self.releases = newerReleases
+          self.releaseNotesCombined = combinedReleaseNotes(from: newerReleases)
+          self.isDownloading = false
+          self.message = nil
+          self.showWindow = true
+        } else {
+          self.release = nil
+          self.releases = []
+          self.releaseNotesCombined = nil
+          self.isDownloading = false
+          if trigger == .manual {
+            self.message = AppUpdateMessage(
+              title: "Hotline is up to date",
+              detail: "You're running the latest and greatest.",
+              kind: .success
+            )
+            self.showWindow = true
+          } else {
+            self.message = nil
+            self.showWindow = false
+          }
+        }
+      }
+    } catch {
+      await MainActor.run {
+        self.isChecking = false
+        self.release = nil
+        self.releases = []
+        self.releaseNotesCombined = nil
+        self.isDownloading = false
+        if trigger == .manual {
+          self.message = AppUpdateMessage(
+            title: "Unable to Check for Updates",
+            detail: error.localizedDescription,
+            kind: .error
+          )
+          self.showWindow = true
+        }
+      }
+    }
+  }
+  
+  private func fetchNewerReleases() async throws -> [UpdateReleaseInfo] {
+    let (data, _) = try await URLSession.shared.data(from: releasesURL)
+    guard let jsonArray = try JSONSerialization.jsonObject(with: data, options: []) as? [[String: Any]] else {
+      throw NSError(domain: "AppUpdate", code: -10, userInfo: [NSLocalizedDescriptionKey: "Malformed GitHub releases response."])
+    }
+    
+    let parsed = jsonArray.compactMap(parseRelease)
+    let newer = parsed.filter(isReleaseNewer)
+    return newer
+  }
+  
+  private func parseRelease(_ json: [String: Any]) -> UpdateReleaseInfo? {
+    guard let tagName = json["tag_name"] as? String else {
+      return nil
+    }
+    
+    let notes = (json["body"] as? String) ?? ""
+    guard
+      let assets = json["assets"] as? [[String: Any]],
+      let asset = assets.first,
+      let downloadString = asset["browser_download_url"] as? String,
+      let downloadURL = URL(string: downloadString)
+    else {
+      return nil
+    }
+    
+    let assetName = (asset["name"] as? String) ?? downloadURL.lastPathComponent
+    
+    let versionPattern = #"^([0-9\.]+)beta([0-9]+)"#
+    guard let regex = try? NSRegularExpression(pattern: versionPattern, options: []) else {
+      return nil
+    }
+    
+    let range = NSRange(location: 0, length: tagName.utf16.count)
+    guard let match = regex.firstMatch(in: tagName, options: [], range: range),
+          match.numberOfRanges >= 3,
+          let versionRange = Range(match.range(at: 1), in: tagName),
+          let buildRange = Range(match.range(at: 2), in: tagName),
+          let versionNumber = Double(String(tagName[versionRange])),
+          let buildNumber = Int(String(tagName[buildRange]))
+    else {
+      return nil
+    }
+    
+    let versionComponent = String(tagName[versionRange])
+    let buildComponent = String(tagName[buildRange])
+    let displayVersion = "\(versionComponent)b\(buildComponent)"
+    
+    return UpdateReleaseInfo(
+      tagName: tagName,
+      displayVersion: displayVersion,
+      versionNumber: versionNumber,
+      buildNumber: buildNumber,
+      notes: notes,
+      downloadURL: downloadURL,
+      assetName: assetName
+    )
+  }
+  
+  private func combinedReleaseNotes(from releases: [UpdateReleaseInfo]) -> String? {
+    guard let firstRelease = releases.first else { return nil }
+    
+    let firstNotes = firstRelease.notes.trimmingCharacters(in: .whitespacesAndNewlines)
+    let firstBody = firstNotes.isEmpty ? "_No release notes provided._" : firstNotes
+    
+    guard releases.count > 1 else {
+      return firstBody
+    }
+    
+    let olderSections = releases.dropFirst().map { release -> String in
+      let trimmed = release.notes.trimmingCharacters(in: .whitespacesAndNewlines)
+      let body = trimmed.isEmpty ? "_No release notes provided._" : trimmed
+      return "## Hotline \(release.displayVersion)\n\n\(body)"
+    }
+    
+    let olderCombined = olderSections.joined(separator: "\n\n---\n\n")
+    return "\(firstBody)\n\n---\n\n\(olderCombined)"
+  }
+  
+  private func downloadRelease(_ release: UpdateReleaseInfo) async {
+    do {
+      let (temporaryURL, _) = try await URLSession.shared.download(from: release.downloadURL)
+      let downloadsDirectory = FileManager.default.urls(for: .downloadsDirectory, in: .userDomainMask).first!
+      let destinationURL = downloadsDirectory.appendingPathComponent(release.assetName)
+      
+      if FileManager.default.fileExists(atPath: destinationURL.path) {
+        try? FileManager.default.removeItem(at: destinationURL)
+      }
+      
+      try FileManager.default.moveItem(at: temporaryURL, to: destinationURL)
+      
+      await MainActor.run {
+        self.isDownloading = false
+        NSWorkspace.shared.activateFileViewerSelecting([destinationURL])
+        self.resetAndCloseWindow()
+      }
+    } catch {
+      await MainActor.run {
+        self.isDownloading = false
+        self.message = AppUpdateMessage(
+          title: "Download Failed",
+          detail: error.localizedDescription,
+          kind: .error
+        )
+        self.showWindow = true
+      }
+    }
+  }
+  
+  private func currentApplicationVersion() -> (version: Double, build: Int) {
+    let info = Bundle.main.infoDictionary ?? [:]
+    let versionString = info["CFBundleShortVersionString"] as? String ?? "0"
+    let buildString = info["CFBundleVersion"] as? String ?? "0"
+    let version = Double(versionString) ?? 0
+    let build = Int(buildString) ?? 0
+    return (version, build)
+  }
+  
+  private func isReleaseNewer(_ release: UpdateReleaseInfo) -> Bool {
+    let current = currentApplicationVersion()
+    if release.versionNumber > current.version {
+      return true
+    }
+    if release.versionNumber == current.version {
+      return release.buildNumber > current.build
+    }
+    return false
+  }
+  
+  private func shouldPrompt(for release: UpdateReleaseInfo) -> Bool {
+    if defaults.string(forKey: lastPromptedVersionKey) != release.tagName {
+      return true
+    }
+    guard let remindDate = defaults.object(forKey: remindDateKey) as? Date else {
+      return true
+    }
+    return remindDate <= Date()
+  }
+  
+  @MainActor
+  private func recordPrompt(for release: UpdateReleaseInfo, remindLater: Bool) {
+    defaults.set(release.tagName, forKey: lastPromptedVersionKey)
+    if remindLater {
+      let nextReminder = Date().addingTimeInterval(remindInterval)
+      defaults.set(nextReminder, forKey: remindDateKey)
+    } else {
+      defaults.removeObject(forKey: remindDateKey)
+    }
+  }
+  
+  @MainActor
+  private func resetAndCloseWindow() {
+    isChecking = false
+    isDownloading = false
+    release = nil
+    releases = []
+    releaseNotesCombined = nil
+    message = nil
+    userInitiated = false
+    showWindow = false
+  }
+}
diff --git a/Hotline/Utility/NSWindowBridge.swift b/Hotline/Utility/NSWindowBridge.swift
index 5cd7197..8f766d9 100644
--- a/Hotline/Utility/NSWindowBridge.swift
+++ b/Hotline/Utility/NSWindowBridge.swift
@@ -23,3 +23,24 @@ public struct NSWindowAccessor: NSViewRepresentable {
   public func makeNSView(context: Context) -> NSView   { return NSWindowAccessorView( configCode ) }
   public func updateNSView(_ nsView: NSView, context: Context) {}
 }
+
+
+//import SwiftUI
+
+  /// A helper view you can embed once per window to run a closure
+/// with the underlying NSWindow reference.
+struct WindowConfigurator: NSViewRepresentable {
+  let configure: (NSWindow) -> Void
+  
+  func makeNSView(context: Context) -> NSView {
+    let view = NSView()
+    DispatchQueue.main.async {
+      if let window = view.window {
+        configure(window)
+      }
+    }
+    return view
+  }
+  
+  func updateNSView(_ nsView: NSView, context: Context) { }
+}
diff --git a/Hotline/macOS/AboutView.swift b/Hotline/macOS/AboutView.swift
index baafcf8..57f855e 100644
--- a/Hotline/macOS/AboutView.swift
+++ b/Hotline/macOS/AboutView.swift
@@ -1,11 +1,5 @@
 import SwiftUI
-
-enum VersionCheckState {
-  case needToCheck
-  case checking
-  case upToDate
-  case updateAvailable(version: String)
-}
+import SwiftUIIntrospect
 
 struct AboutContributor: Identifiable {
   let id: UUID = UUID()
@@ -14,164 +8,66 @@ struct AboutContributor: Identifiable {
   let pictureURL: URL?
 }
 
-struct AboutView: View {
+struct AboutContributorView: View {
   @Environment(\.openURL) private var openURL
   
-  @State private var versionCheck: VersionCheckState = .needToCheck
-  @State private var downloadURL: String = "https://github.com/mierau/hotline/releases/latest"
-  @State private var contributors: [AboutContributor] = []
+  let contributor: AboutContributor
   
   var body: some View {
-    HStack(alignment: .center, spacing: 0) {
-      VStack(alignment: .center, spacing: 0) {
-        Spacer()
-        
-        Image("About Hotline")
-          .padding(.top, 44)
-        
-        Text("Hotline")
-          .font(.system(size: 28))
-          .fontWeight(.bold)
-          .padding(.top, 12)
-          .kerning(-1.0)
-          .foregroundColor(.white)
-        
-        let appDetails = getAppVersionAndBuild()
-        Text("Version \(String(format: "%.1f", appDetails.version))b\(appDetails.build)")
-          .foregroundColor(.white)
-          .opacity(0.4)
-        
-        HStack(alignment: .center) {
-          switch versionCheck {
-          case .needToCheck:
-            Button("Check for Updates") {
-              Task {
-                await checkForUpdate()
-              }
-            }
-            .controlSize(.small)
-          case .checking:
-            HStack(spacing: 8) {
-              ProgressView()
-                .controlSize(.small)
-              Text("Checking for updates...")
-                .fontWeight(.semibold)
-            }
-            .foregroundStyle(.white)
-            .tint(.white)
-          case .upToDate:
-            Label("Hotline is up to date.", systemImage: "checkmark.circle.fill")
-              .foregroundStyle(.white)
-              .fontWeight(.semibold)
-              .tint(.white)
-              .onTapGesture {
-                versionCheck = .needToCheck
-              }
-          case .updateAvailable(let version):
-            Button("Download Latest \(version)") {
-              if let url = URL(string: downloadURL) {
-                openURL(url)
-              }
-            }
-            .controlSize(.small)
+    HStack {
+      if let pictureURL = contributor.pictureURL {
+        AsyncImage(url: pictureURL) { phase in
+          if let image = phase.image {
+            image
+              .interpolation(.high)
+              .resizable()
+              .scaledToFit()
+              .background(.white)
+              .frame(width: 32, height: 32)
+          } else if phase.error != nil {
+            Color.clear
+              .frame(width: 32, height: 32)
+          } else {
+            Color.white
+              .opacity(0.2)
+              .frame(width: 32, height: 32)
           }
         }
-        .frame(height: 40)
-
-        Spacer()
+        .frame(width: 32, height: 32)
+        .clipShape(Circle())
       }
-      .frame(width: 250)
       
-      Spacer()
-      
-      ScrollView(.vertical) {
-        VStack(alignment: .leading, spacing: 16) {
-          
-          VStack(alignment: .leading, spacing: 4) {
-            Link(destination: URL(string: "https://github.com/mierau/hotline")!) {
-              HStack(alignment: .center, spacing: 4) {
-                Text("Contributors")
-                  .lineLimit(1)
-                  .font(.system(size: 16))
-                  .fontWeight(.semibold)
-                  .foregroundStyle(.black)
-                  .opacity(0.75)
+      VStack(alignment: .leading, spacing: 2) {
+        Text(contributor.username)
+          .fontWeight(.semibold)
+          .foregroundStyle(.white)
+          .lineLimit(1)
+        
+        Text(contributor.webURL.absoluteString)
+          .lineLimit(1)
+          .truncationMode(.middle)
+          .font(.system(size: 11))
+          .foregroundStyle(.white.opacity(0.4))
+      }
+    }
+//    }
+//    .accessibilityAddTraits(.isLink)
+//    .pointerStyle(.link)
+  }
+}
 
-                Image(systemName: "arrow.forward.circle.fill")
-                  .resizable()
-                  .fontWeight(.bold)
-                  .scaledToFit()
-                  .frame(width: 12, height: 12)
-                  .foregroundStyle(.black)
-                  .opacity(0.75)
-              }
-            }
-            .padding(.top, 24)
-            
-            Text("Hotline is an open source project made possible by its contributors.")
-              .font(.system(size: 11))
-              .foregroundStyle(.black)
-              .blendMode(.overlay)
-              .padding(.trailing, 32)
-          }
-          .padding(.bottom, 8)
-          
-          ForEach(contributors) { contributor in
-            Link(destination: contributor.webURL) {
-              HStack {
-                if let pictureURL = contributor.pictureURL {
-                  AsyncImage(url: pictureURL) { phase in
-                    if let image = phase.image {
-                      image
-                        .interpolation(.high)
-                        .resizable()
-                        .scaledToFit()
-                        .background(.white)
-                        .frame(width: 32, height: 32)
-                    } else if phase.error != nil {
-                      Color.clear
-                        .frame(width: 32, height: 32)
-                    } else {
-                      Color.white
-                        .opacity(0.2)
-                        .frame(width: 32, height: 32)
-                    }
-                  }
-                  .frame(width: 32, height: 32)
-                  .clipShape(Circle())
-                  
-//                  AsyncImage(url: pictureURL) { img in
-//                    img
-//                      .interpolation(.high)
-//                      .resizable()
-//                      .scaledToFit()
-//                      .background(.white)
-//                  } placeholder: {
-//                    Color.white.opacity(0.2)
-//                      .frame(width: 32, height: 32)
-//                  }
-//                  .frame(width: 32, height: 32)
-//                  .clipShape(Circle())
-                }
-                
-                VStack(alignment: .leading, spacing: 2) {
-                  Text(contributor.username)
-                    .fontWeight(.semibold)
-                    .foregroundStyle(.white)
-                    .lineLimit(1)
-                  
-                  Text(contributor.webURL.absoluteString)
-                    .lineLimit(1)
-                    .truncationMode(.middle)
-                    .font(.system(size: 11))
-                    .foregroundStyle(.white.opacity(0.4))
-                }
-              }
-            }
-          }
+struct AboutView: View {
+  @Environment(\.openURL) private var openURL
+  
+  @State private var contributors: [AboutContributor] = []
+  
+  var body: some View {
+    HStack(alignment: .center, spacing: 0) {
+      self.brandView
+      self.contributorsList
+        .background {
+          Color.black.blendMode(.softLight).opacity(0.3).ignoresSafeArea()
         }
-      }
-      .scrollClipDisabled()
     }
     .frame(width: 570, height: 330)
     .background(
@@ -184,12 +80,105 @@ struct AboutView: View {
         .offset(x: 250)
       }
     )
-    .background(Color.hotlineRed)
     .task {
       await loadContributors()
     }
   }
   
+  private var brandView: some View {
+    VStack(alignment: .center, spacing: 4) {
+      Spacer()
+      
+      Image("About Hotline")
+      
+      Text("Hotline")
+        .font(.system(size: 28))
+        .fontWeight(.bold)
+        .padding(.top, 12)
+        .kerning(-1.0)
+        .foregroundColor(.white)
+      
+      let appDetails = getAppVersionAndBuild()
+      Button {
+        self.openURL(URL(string: "https://github.com/mierau/hotline/releases/tag/\(appDetails.version)beta\(appDetails.build)")!)
+      } label: {
+        
+        Text("Version \(String(format: "%.1f", appDetails.version))b\(appDetails.build)")
+          .foregroundColor(.white.opacity(0.756))
+          .padding(.vertical, 4)
+          .padding(.horizontal, 12)
+          .background {
+            Capsule()
+              .fill(.white.opacity(0.5))
+              .blendMode(.softLight)
+          }
+      }
+      .buttonStyle(.plain)
+      .buttonBorderShape(.capsule)
+      .padding(.bottom, 16)
+
+      Spacer()
+    }
+    .frame(width: 250)
+  }
+  
+  private var contributorsList: some View {
+    ScrollView(.vertical) {
+      VStack(alignment: .leading, spacing: 16) {
+        self.contributorHeaderView
+        ForEach(self.contributors) { contributor in
+          Button {
+            self.openURL(contributor.webURL)
+          } label: {
+            AboutContributorView(contributor: contributor)
+          }
+          .buttonStyle(.plain)
+          .accessibilityAddTraits(.isLink)
+          .pointerStyle(.link)
+        }
+      }
+      .frame(maxWidth: .infinity)
+      .padding()
+    }
+    .scrollClipDisabled()
+    .scrollContentBackground(.hidden)
+//    .introspect(.scrollView, on: .macOS(.v10_15, .v11, .v12, .v13, .v14, .v15, .v26)) { v in
+//      v.automaticallyAdjustsContentInsets = false
+//    }
+  }
+  
+  private var contributorHeaderView: some View {
+    VStack(alignment: .leading, spacing: 4) {
+      Link(destination: URL(string: "https://github.com/mierau/hotline")!) {
+        HStack(alignment: .center, spacing: 4) {
+          Text("Contributors")
+            .lineLimit(1)
+            .font(.system(size: 16))
+            .fontWeight(.semibold)
+            .foregroundStyle(.black)
+            .opacity(0.8)
+
+          Image(systemName: "arrow.forward.circle.fill")
+            .resizable()
+            .fontWeight(.bold)
+            .scaledToFit()
+            .frame(width: 12, height: 12)
+            .foregroundStyle(.black)
+            .opacity(0.4)
+        }
+      }
+      .accessibilityAddTraits(.isLink)
+      .pointerStyle(.link)
+      
+      Text("Hotline is an open source project made possible by its contributors.")
+        .font(.system(size: 11))
+        .foregroundStyle(.black)
+        .opacity(0.5)
+        .padding(.trailing, 32)
+    }
+    .padding(.bottom, 8)
+  }
+  
   func loadContributors() async {
     var newContributors: [AboutContributor] = []
     
@@ -214,43 +203,7 @@ struct AboutView: View {
       contributors = newContributors
     }
   }
-  
-  func checkForUpdate() async {
-    let appDetails = getAppVersionAndBuild()
-    
-    self.versionCheck = .checking
-    
-    do {
-      let url = URL(string: "https://api.github.com/repos/mierau/hotline/releases/latest")!
-      let (data, _) = try await URLSession.shared.data(from: url)
-      let versionExpression = /^([0-9\.]+)beta([0-9]+)/
-      
-      if let json = try JSONSerialization.jsonObject(with: data, options: []) as? [String: Any],
-         let tagName = json["tag_name"] as? String,
-         let assets = json["assets"] as? [[String: Any]],
-         let firstAsset = assets.first,
-         let assetDownloadURL = firstAsset["browser_download_url"] as? String,
-         let versionMatches = try? versionExpression.wholeMatch(in: tagName) {
-        if let versionNumber = Double(versionMatches.1),
-           let buildNumber = Int(versionMatches.2),
-           versionNumber > appDetails.version || buildNumber > appDetails.build {
-            let versionString = "\(versionMatches.1)b\(versionMatches.2)"
-            self.versionCheck = .updateAvailable(version: versionString)
-            downloadURL = assetDownloadURL
-        }
-        else {
-          self.versionCheck = .upToDate
-        }
-      }
-      else {
-        self.versionCheck = .needToCheck
-      }
-    }
-    catch {
-      self.versionCheck = .needToCheck
-    }
-  }
-  
+
   func getAppVersionAndBuild() -> (version: Double, build: Int) {
     let infoDictionary = Bundle.main.infoDictionary!
     let version = Double(infoDictionary["CFBundleShortVersionString"]! as! String)!
diff --git a/Hotline/macOS/AppUpdateView.swift b/Hotline/macOS/AppUpdateView.swift
new file mode 100644
index 0000000..89312fc
--- /dev/null
+++ b/Hotline/macOS/AppUpdateView.swift
@@ -0,0 +1,187 @@
+import SwiftUI
+import MarkdownUI
+import AppKit
+import Observation
+
+struct AppUpdateView: View {
+  @Environment(\.dismiss) private var dismiss
+  @Bindable private var update = AppUpdate.shared
+  
+  var body: some View {
+    VStack(alignment: .leading, spacing: 20) {
+      if let message = update.message {
+        messageOnlyView(message)
+      }
+      else if update.release != nil {
+        headerSection
+        releaseNotesSection
+        actionRow
+      }
+      else {
+        defaultPlaceholder
+      }
+    }
+    .padding(.horizontal, 24)
+    .padding(.bottom, 24)
+    .padding(.top, 8)
+    .frame(width: update.message != nil ? 380 : 520)
+    .frame(idealHeight: 360)
+    .onChange(of: update.showWindow) { _, show in
+      if !show {
+        dismiss()
+      }
+    }
+    .onDisappear {
+      update.handleWindowDismissed()
+    }
+  }
+  
+  private var headerSection: some View {
+    HStack(alignment: .center, spacing: 8) {
+      Image(nsImage: NSApplication.shared.applicationIconImage)
+        .resizable()
+        .scaledToFit()
+        .frame(width: 56, height: 56)
+        .shadow(color: Color.black.mix(with: .red, by: 0.4).opacity(0.15), radius: 3, y: 1.5)
+      
+      VStack(alignment: .leading, spacing: 2) {
+        if let release = update.release {
+          Text("Hotline \(release.displayVersion)")
+            .font(.title2)
+            .fontWeight(.semibold)
+        }
+        Text("A new version of Hotline is available. 🎉")
+          .foregroundStyle(.secondary)
+      }
+    }
+  }
+  
+  private var releaseNotesSection: some View {
+    ScrollView(.vertical) {
+      Markdown(releaseNotesMarkdown())
+        .textSelection(.enabled)
+        .markdownTheme(.gitHub.text(text: {
+          FontSize(.em(0.85))
+        }))
+        .font(.system(size: 14))
+        .frame(maxWidth: .infinity, alignment: .leading)
+        .padding(.vertical, 12)
+        .padding(.horizontal, 12)
+    }
+    .frame(minHeight: 220, maxHeight: 260)
+    .background(
+      RoundedRectangle(cornerRadius: 12)
+        .stroke(Color(nsColor: .separatorColor), lineWidth: 1)
+    )
+  }
+  
+  private var actionRow: some View {
+    HStack {
+      Button("Not Now") {
+        update.remindLater()
+      }
+      .buttonBorderShape(.capsule)
+      .keyboardShortcut(.escape, modifiers: [])
+      .controlSize(.large)
+      .disabled(update.isDownloading)
+      
+      Spacer()
+      
+      if update.isDownloading {
+        ProgressView()
+          .controlSize(.small)
+          .padding(.trailing, 12)
+      }
+      
+      Button("Download") {
+        update.startDownload()
+      }
+      .buttonBorderShape(.capsule)
+      .keyboardShortcut(.defaultAction)
+      .controlSize(.large)
+      .disabled(update.isDownloading)
+    }
+  }
+  
+  @ViewBuilder
+  private func messageOnlyView(_ message: AppUpdateMessage) -> some View {
+    let iconName = {
+      switch message.kind {
+      case .info:
+        return "info.circle"
+      case .success:
+        return "checkmark.circle.fill"
+      case .error:
+        return "exclamationmark.triangle.fill"
+      }
+    }()
+    
+    HStack(alignment: .center, spacing: 12) {
+      
+      if message.kind == .success {
+        Text("👍")
+          .font(.system(size: 42))
+          .shadow(color: .yellow.mix(with: .black, by: 0.3).opacity(0.2), radius: 4, y: 1.5)
+      }
+      else {
+        Image(systemName: iconName)
+          .resizable()
+          .scaledToFit()
+          .symbolRenderingMode(.multicolor)
+          .frame(width: 48, height: 48)
+      }
+      
+      VStack(alignment: .leading, spacing: 2) {
+        Text(message.title)
+          .font(.title2)
+          .fontWeight(.semibold)
+        Text(message.detail)
+          .foregroundStyle(.secondary)
+      }
+      
+      Spacer()
+    }
+  }
+  
+  private var defaultPlaceholder: some View {
+    VStack(alignment: .center, spacing: 12) {
+      Text("No update information available.")
+        .font(.headline)
+      Button("Close") {
+        update.acknowledgeMessage()
+      }
+      .keyboardShortcut(.defaultAction)
+    }
+    .frame(maxWidth: .infinity, maxHeight: .infinity)
+  }
+  
+  private func releaseNotesMarkdown() -> String {
+    if let combined = update.releaseNotesCombined?
+      .trimmingCharacters(in: .whitespacesAndNewlines),
+       combined.isEmpty == false {
+      return combined
+    }
+    
+    let fallback = update.release?.notes.trimmingCharacters(in: .whitespacesAndNewlines) ?? ""
+    return fallback.isEmpty ? "_No release notes provided._" : fallback
+  }
+}
+
+#Preview {
+  AppUpdate.shared.release = UpdateReleaseInfo(
+    tagName: "1.0beta1",
+    displayVersion: "1.0b1",
+    versionNumber: 1.0,
+    buildNumber: 1,
+    notes: """
+    - Added support for release notes in Markdown.
+    - Improved the update workflow for macOS users.
+    """,
+    downloadURL: URL(string: "https://example.com")!,
+    assetName: "Hotline.zip"
+  )
+  AppUpdate.shared.releases = [AppUpdate.shared.release!]
+  AppUpdate.shared.releaseNotesCombined = nil
+  AppUpdate.shared.showWindow = true
+  return AppUpdateView()
+}