iStorry · Oct 29, 2026 · Oct 29, 2026 · Oct 29, 2026 · Oct 29, 2026 · Oct 29, 2026
diff --git a/.github/workflows/CI.yml b/.github/workflows/CI.yml
@@ -43,6 +43,9 @@ jobs:
           path: .build/SourcePackages
           key: spm-${{ hashFiles('Whisky.xcodeproj/project.xcworkspace/xcshareddata/swiftpm/Package.resolved', 'WhiskyKit/Package.swift') }}
 
+      - name: Test WhiskyKit
+        run: swift test --package-path WhiskyKit
+
       - name: Build Whisky
         run: xcodebuild build -project Whisky.xcodeproj -scheme Whisky -configuration Release
           -clonedSourcePackagesDirPath .build/SourcePackages -disableAutomaticPackageResolution

diff --git a/.github/workflows/Release.yml b/.github/workflows/Release.yml
diff --git a/Whisky.xcodeproj/project.pbxproj b/Whisky.xcodeproj/project.pbxproj
@@ -36,6 +36,7 @@
 		6E5B61B62AC34E6D007B1913 /* SemanticVersion in Frameworks */ = {isa = PBXBuildFile; productRef = 6E5B61B52AC34E6D007B1913 /* SemanticVersion */; };
 		6E621CEF2A5F631300C9AAB3 /* Winetricks.swift in Sources */ = {isa = PBXBuildFile; fileRef = 6E621CEE2A5F631200C9AAB3 /* Winetricks.swift */; };
 		6E6C0CF22A419A6800356232 /* WelcomeView.swift in Sources */ = {isa = PBXBuildFile; fileRef = 6E6C0CF12A419A6800356232 /* WelcomeView.swift */; };
+		6E7A1F012F00000000000001 /* SetupFailureView.swift in Sources */ = {isa = PBXBuildFile; fileRef = 6E7A1F012F00000000000002 /* SetupFailureView.swift */; };
 		6E6C0CF42A419A7600356232 /* RosettaView.swift in Sources */ = {isa = PBXBuildFile; fileRef = 6E6C0CF32A419A7600356232 /* RosettaView.swift */; };
 		6E6C0CF62A419A8300356232 /* WhiskyWineDownloadView.swift in Sources */ = {isa = PBXBuildFile; fileRef = 6E6C0CF52A419A8300356232 /* WhiskyWineDownloadView.swift */; };
 		6E6C0CF82A419A8C00356232 /* WhiskyWineInstallView.swift in Sources */ = {isa = PBXBuildFile; fileRef = 6E6C0CF72A419A8C00356232 /* WhiskyWineInstallView.swift */; };
@@ -138,6 +139,7 @@
 		6E50D98429CDF25B008C39F6 /* BottleCreationView.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = BottleCreationView.swift; sourceTree = "<group>"; };
 		6E621CEE2A5F631200C9AAB3 /* Winetricks.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = Winetricks.swift; sourceTree = "<group>"; };
 		6E6C0CF12A419A6800356232 /* WelcomeView.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = WelcomeView.swift; sourceTree = "<group>"; };
+		6E7A1F012F00000000000002 /* SetupFailureView.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = SetupFailureView.swift; sourceTree = "<group>"; };
 		6E6C0CF32A419A7600356232 /* RosettaView.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = RosettaView.swift; sourceTree = "<group>"; };
 		6E6C0CF52A419A8300356232 /* WhiskyWineDownloadView.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = WhiskyWineDownloadView.swift; sourceTree = "<group>"; };
 		6E6C0CF72A419A8C00356232 /* WhiskyWineInstallView.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = WhiskyWineInstallView.swift; sourceTree = "<group>"; };
@@ -368,6 +370,7 @@
 			children = (
 				6EF557972A410599001A4F09 /* SetupView.swift */,
 				6E6C0CF12A419A6800356232 /* WelcomeView.swift */,
+				6E7A1F012F00000000000002 /* SetupFailureView.swift */,
 				6E6C0CF32A419A7600356232 /* RosettaView.swift */,
 				6E6C0CF52A419A8300356232 /* WhiskyWineDownloadView.swift */,
 				6E6C0CF72A419A8C00356232 /* WhiskyWineInstallView.swift */,
@@ -618,6 +621,7 @@
 				6E49E0212AECB7DB00009CAC /* SettingsView.swift in Sources */,
 				6E7C07C02AAF570100F6E66B /* FileOpenView.swift in Sources */,
 				6E6C0CF22A419A6800356232 /* WelcomeView.swift in Sources */,
+				6E7A1F012F00000000000001 /* SetupFailureView.swift in Sources */,
 				6E40498129CCA8B0006E3F1B /* BottleView.swift in Sources */,
 				6E355E5E29D7D85D002D83BE /* ProgramView.swift in Sources */,
 			);

diff --git a/Whisky/Localizable.xcstrings b/Whisky/Localizable.xcstrings
@@ -8164,6 +8164,56 @@
         }
       }
     },
+    "create.error.message.%@.%@" : {
+      "localizations" : {
+        "en" : {
+          "stringUnit" : {
+            "state" : "translated",
+            "value" : "“%1$@” could not be created. %2$@"
+          }
+        }
+      }
+    },
+    "create.error.prefixNotCreated.%@" : {
+      "localizations" : {
+        "en" : {
+          "stringUnit" : {
+            "state" : "translated",
+            "value" : "Wine did not set up the bottle. Wine output: %@"
+          }
+        }
+      }
+    },
+    "create.error.title" : {
+      "localizations" : {
+        "en" : {
+          "stringUnit" : {
+            "state" : "translated",
+            "value" : "Couldn't Create Bottle"
+          }
+        }
+      }
+    },
+    "create.error.unsupportedLocation.%@" : {
+      "localizations" : {
+        "en" : {
+          "stringUnit" : {
+            "state" : "translated",
+            "value" : "Wine can't use folders whose names end with a period. Choose a different location than %@."
+          }
+        }
+      }
+    },
+    "create.error.whiskyWineNotInstalled" : {
+      "localizations" : {
+        "en" : {
+          "stringUnit" : {
+            "state" : "translated",
+            "value" : "WhiskyWine is not installed. Install it from Whisky > Setup, then try again."
+          }
+        }
+      }
+    },
     "create.name" : {
       "localizations" : {
         "ar" : {
@@ -17298,6 +17348,16 @@
         }
       }
     },
+    "setup.whiskywine.download.failed" : {
+      "localizations" : {
+        "en" : {
+          "stringUnit" : {
+            "state" : "translated",
+            "value" : "Download Failed"
+          }
+        }
+      }
+    },
     "setup.whiskywine.download.subtitle" : {
       "localizations" : {
         "ar" : {
@@ -17706,6 +17766,16 @@
         }
       }
     },
+    "setup.whiskywine.install.failed" : {
+      "localizations" : {
+        "en" : {
+          "stringUnit" : {
+            "state" : "translated",
+            "value" : "Installation Failed"
+          }
+        }
+      }
+    },
     "setup.whiskywine.install.subtitle" : {
       "localizations" : {
         "ar" : {

diff --git a/Whisky/View Models/BottleVM.swift b/Whisky/View Models/BottleVM.swift
@@ -17,62 +17,107 @@
 //
 
 import Foundation
+import os
 import SemanticVersion
 import WhiskyKit
 
+enum BottleCreationError: LocalizedError {
+    case whiskyWineNotInstalled
+    case unsupportedLocation(URL)
+    case prefixNotCreated(wineOutput: String)
+
+    var errorDescription: String? {
+        switch self {
+        case .whiskyWineNotInstalled:
+            return String(localized: "create.error.whiskyWineNotInstalled")
+        case .unsupportedLocation(let url):
+            return String(localized: "create.error.unsupportedLocation.\(url.prettyPath())")
+        case .prefixNotCreated(let wineOutput):
+            return String(localized: "create.error.prefixNotCreated.\(wineOutput.suffix(1000).description)")
+        }
+    }
+}
+
+struct BottleCreationFailure: Identifiable {
+    let id = UUID()
+    let bottleName: String
+    let error: Error
+}
+
 // swiftlint:disable:next todo
 // TODO: Don't use unchecked!
 final class BottleVM: ObservableObject, @unchecked Sendable {
     @MainActor static let shared = BottleVM()
 
     var bottlesList = BottleData()
     @Published var bottles: [Bottle] = []
+    @Published var bottleCreationFailure: BottleCreationFailure?
 
+    /// Bottles still being created are not in the bottle list yet, so they are kept across reloads
     @MainActor
     func loadBottles() {
-        bottles = bottlesList.loadBottles()
+        let bottlesInCreation = bottles.filter { $0.inFlight && !bottlesList.paths.contains($0.url) }
+        bottles = bottlesList.loadBottles() + bottlesInCreation
     }
 
     func countActive() -> Int {
         return bottles.filter { $0.isAvailable == true }.count
     }
 
+    @MainActor
     func createNewBottle(bottleName: String, winVersion: WinVersion, bottleURL: URL) -> URL {
         let newBottleDir = bottleURL.appending(path: UUID().uuidString)
 
-        Task.detached {
-            var bottleId: Bottle?
+        Task {
             do {
-                try FileManager.default.createDirectory(atPath: newBottleDir.path(percentEncoded: false),
-                                                        withIntermediateDirectories: true)
-                let bottle = Bottle(bottleUrl: newBottleDir, inFlight: true)
-                bottleId = bottle
-
-                await MainActor.run {
-                    self.bottles.append(bottle)
-                }
-
-                bottle.settings.windowsVersion = winVersion
-                bottle.settings.name = bottleName
-                try await Wine.changeWinVersion(bottle: bottle, win: winVersion)
-                let wineVer = try await Wine.wineVersion()
-                bottle.settings.wineVersion = SemanticVersion(wineVer) ?? SemanticVersion(0, 0, 0)
-                // Add record
-                await MainActor.run {
-                    self.bottlesList.paths.append(newBottleDir)
-                    self.loadBottles()
-                }
+                try await setUpBottle(at: newBottleDir, name: bottleName, winVersion: winVersion)
             } catch {
-                print("Failed to create new bottle: \(error)")
-                if let bottle = bottleId {
-                    await MainActor.run {
-                        if let index = self.bottles.firstIndex(of: bottle) {
-                            self.bottles.remove(at: index)
-                        }
-                    }
-                }
+                Logger.wineKit.error("Failed to create bottle `\(bottleName)`: \(error)")
+                discardBottle(at: newBottleDir)
+                bottleCreationFailure = BottleCreationFailure(bottleName: bottleName, error: error)
             }
         }
         return newBottleDir
     }
+
+    @MainActor
+    private func setUpBottle(at bottleDir: URL, name: String, winVersion: WinVersion) async throws {
+        guard WhiskyWineInstaller.isWhiskyWineInstalled() else {
+            throw BottleCreationError.whiskyWineNotInstalled
+        }
+        // Wine drops trailing dots when mapping Unix paths to Windows ones, so the prefix cannot load
+        guard !bottleDir.pathComponents.contains(where: { $0.hasSuffix(".") }) else {
+            throw BottleCreationError.unsupportedLocation(bottleDir)
+        }
+
+        try FileManager.default.createDirectory(at: bottleDir, withIntermediateDirectories: true)
+        let bottle = Bottle(bottleUrl: bottleDir, inFlight: true)
+        bottles.append(bottle)
+
+        bottle.settings.windowsVersion = winVersion
+        bottle.settings.name = name
+        let wineOutput = try await Wine.changeWinVersion(bottle: bottle, win: winVersion)
+        guard FileManager.default.fileExists(atPath: bottleDir.appending(path: "drive_c").path(percentEncoded: false))
+        else {
+            throw BottleCreationError.prefixNotCreated(wineOutput: wineOutput)
+        }
+
+        let wineVer = try await Wine.wineVersion()
+        bottle.settings.wineVersion = SemanticVersion(wineVer) ?? SemanticVersion(0, 0, 0)
+        bottlesList.paths.append(bottleDir)
+        loadBottles()
+    }
+
+    @MainActor
+    private func discardBottle(at bottleDir: URL) {
+        bottles.removeAll { $0.url == bottleDir }
+        guard FileManager.default.fileExists(atPath: bottleDir.path(percentEncoded: false)) else { return }
+        do {
+            try FileManager.default.removeItem(at: bottleDir)
+        } catch {
+            Logger.wineKit.error(
+                "Failed to remove incomplete bottle `\(bottleDir.path(percentEncoded: false))`: \(error)"
+            )
+        }
+    }
 }
diff --git a/Whisky/Views/ContentView.swift b/Whisky/Views/ContentView.swift
@@ -20,6 +20,7 @@ import SwiftUI
 import UniformTypeIdentifiers
 import WhiskyKit
 import SemanticVersion
+import os
 
 struct ContentView: View {
     @AppStorage("selectedBottleURL") private var selectedBottleURL: URL?
@@ -28,6 +29,7 @@ struct ContentView: View {
 
     @State private var selected: URL?
     @State private var showBottleCreation: Bool = false
+    @State private var showWhiskyWineUpdate: Bool = false
     @State private var bottlesLoaded: Bool = false
     @State private var showBottleSelection: Bool = false
     @State private var newlyCreatedBottleURL: URL?
@@ -77,6 +79,17 @@ struct ContentView: View {
         .sheet(isPresented: $showSetup) {
             SetupView(showSetup: $showSetup, firstTime: false)
         }
+        .sheet(isPresented: $showWhiskyWineUpdate) {
+            SetupView(showSetup: $showWhiskyWineUpdate, firstTime: false, initialPath: [.whiskyWineDownload])
+        }
+        .alert(
+            "create.error.title",
+            isPresented: isShowingBottleCreationFailure,
+            presenting: bottleVM.bottleCreationFailure
+        ) { _ in
+        } message: { failure in
+            Text("create.error.message.\(failure.bottleName).\(failure.error.localizedDescription)")
+        }
         .sheet(item: $openedFileURL) { url in
             FileOpenView(fileURL: url,
                          currentBottle: selected,
@@ -104,28 +117,39 @@ struct ContentView: View {
             if !WhiskyWineInstaller.isWhiskyWineInstalled() {
                 showSetup = true
             }
-            let task = Task.detached {
-                return await WhiskyWineInstaller.shouldUpdateWhiskyWine()
-            }
-            let updateInfo = await task.value
-            if updateInfo.0 {
-                let alert = NSAlert()
-                alert.messageText = String(localized: "update.whiskywine.title")
-                alert.informativeText = String(format: String(localized: "update.whiskywine.description"),
-                                               String(WhiskyWineInstaller.whiskyWineVersion()
-                                                      ?? SemanticVersion(0, 0, 0)),
-                                               String(updateInfo.1))
-                alert.alertStyle = .warning
-                alert.addButton(withTitle: String(localized: "update.whiskywine.update"))
-                alert.addButton(withTitle: String(localized: "button.removeAlert.cancel"))
+            await offerWhiskyWineUpdate()
+        }
+    }
 
-                let response = alert.runModal()
+    private var isShowingBottleCreationFailure: Binding<Bool> {
+        Binding(
+            get: { bottleVM.bottleCreationFailure != nil },
+            set: { if !$0 { bottleVM.bottleCreationFailure = nil } }
+        )
+    }
 
-                if response == .alertFirstButtonReturn {
-                    WhiskyWineInstaller.uninstall()
-                    showSetup = true
-                }
-            }
+    private func offerWhiskyWineUpdate() async {
+        let remoteVersion: SemanticVersion?
+        do {
+            remoteVersion = try await WhiskyWineInstaller.availableUpdate()
+        } catch {
+            Logger.wineKit.error("Failed to check for a WhiskyWine update: \(error)")
+            return
+        }
+        guard let remoteVersion else { return }
+
+        let alert = NSAlert()
+        alert.messageText = String(localized: "update.whiskywine.title")
+        alert.informativeText = String(format: String(localized: "update.whiskywine.description"),
+                                       String(WhiskyWineInstaller.whiskyWineVersion()
+                                              ?? SemanticVersion(0, 0, 0)),
+                                       String(remoteVersion))
+        alert.alertStyle = .warning
+        alert.addButton(withTitle: String(localized: "update.whiskywine.update"))
+        alert.addButton(withTitle: String(localized: "button.removeAlert.cancel"))
+
+        if alert.runModal() == .alertFirstButtonReturn {
+            showWhiskyWineUpdate = true
         }
     }