diff --git a/cmd/vinegar/binary.go b/cmd/vinegar/binary.go
index 1f672919..a1b8d00f 100644
--- a/cmd/vinegar/binary.go
+++ b/cmd/vinegar/binary.go
@@ -111,7 +111,7 @@ func (b *Binary) Main(args ...string) error {
 
 	logFile, err := LogFile(b.Type.String())
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to init log file: %w", err)
 	}
 	defer logFile.Close()
 
@@ -170,7 +170,7 @@ func (b *Binary) Main(args ...string) error {
 		}
 
 		if err != nil {
-			return err
+			return fmt.Errorf("failed to init %s prefix: %w", b.Type, err)
 		}
 	}
 
@@ -223,7 +223,7 @@ func (b *Binary) Run(args ...string) error {
 
 	cmd, err := b.Command(args...)
 	if err != nil {
-		return err
+		return fmt.Errorf("%s command: %w", b.Type, err)
 	}
 
 	// Act as the signal holder, as roblox/wine will not do anything with the INT signal.
@@ -272,10 +272,9 @@ func (b *Binary) Run(args ...string) error {
 			}
 		}
 
-		// Blocks and tails file forever until roblox is dead
-		if err := b.Tail(lf); err != nil {
-			log.Println(err)
-		}
+		// Blocks and tails file forever until roblox is dead, unless
+		// if finding the log file had failed.
+		b.Tail(lf)
 	}()
 
 	if err := cmd.Run(); err != nil {
@@ -324,10 +323,11 @@ func RobloxLogFile(pfx *wine.Prefix) (string, error) {
 	}
 }
 
-func (b *Binary) Tail(name string) error {
+func (b *Binary) Tail(name string) {
 	t, err := tail.TailFile(name, tail.Config{Follow: true})
 	if err != nil {
-		return err
+		log.Printf("WARNING: failed to tail roblox log file: %s", err)
+		return
 	}
 
 	for line := range t.Lines {
@@ -339,8 +339,6 @@ func (b *Binary) Tail(name string) error {
 			}
 		}
 	}
-
-	return nil
 }
 
 func (b *Binary) Command(args ...string) (*exec.Cmd, error) {
diff --git a/cmd/vinegar/binary_setup.go b/cmd/vinegar/binary_setup.go
index 8fed3f94..6281147b 100644
--- a/cmd/vinegar/binary_setup.go
+++ b/cmd/vinegar/binary_setup.go
@@ -27,7 +27,7 @@ func (b *Binary) FetchDeployment() error {
 
 	d, err := boot.FetchDeployment(b.Type, b.Config.Channel)
 	if err != nil {
-		return err
+		return fmt.Errorf("fetch %s %s deployment: %w", b.Type, b.Config.Channel, err)
 	}
 
 	b.Deploy = &d
@@ -46,7 +46,7 @@ func (b *Binary) Setup() error {
 		log.Printf("Installing %s (%s -> %s)", b.Name, b.State.Version, b.Deploy.GUID)
 
 		if err := b.Install(); err != nil {
-			return err
+			return fmt.Errorf("install %s: %w", b.Deploy.GUID, err)
 		}
 	} else {
 		log.Printf("%s is up to date (%s)", b.Name, b.Deploy.GUID)
@@ -56,19 +56,23 @@ func (b *Binary) Setup() error {
 
 	log.Println("Using Renderer:", b.Config.Renderer)
 	if err := b.Config.FFlags.Apply(b.Dir); err != nil {
-		return err
+		return fmt.Errorf("apply fflags: %w", err)
 	}
 
 	if err := dirs.OverlayDir(b.Dir); err != nil {
-		return err
+		return fmt.Errorf("overlay dir: %w", err)
 	}
 
 	if err := b.SetupDxvk(); err != nil {
-		return err
+		return fmt.Errorf("setup dxvk: %w", err)
 	}
 
 	b.Splash.SetProgress(1.0)
-	return b.GlobalState.Save()
+	if err := b.GlobalState.Save(); err != nil {
+		return fmt.Errorf("save state: %w", err)
+	}
+
+	return nil
 }
 
 func (b *Binary) Install() error {
@@ -80,11 +84,7 @@ func (b *Binary) Install() error {
 
 	pm, err := boot.FetchPackageManifest(b.Deploy)
 	if err != nil {
-		return err
-	}
-
-	if err := dirs.Mkdirs(dirs.Downloads); err != nil {
-		return err
+		return fmt.Errorf("fetch %s package manifest: %w", b.Deploy.GUID, err)
 	}
 
 	// Prioritize smaller files first, to have less pressure
@@ -97,12 +97,12 @@ func (b *Binary) Install() error {
 
 	b.Splash.SetMessage("Downloading " + b.Alias)
 	if err := b.DownloadPackages(&pm); err != nil {
-		return err
+		return fmt.Errorf("download %s packages: %w", b.Deploy.GUID, err)
 	}
 
 	b.Splash.SetMessage("Extracting " + b.Alias)
 	if err := b.ExtractPackages(&pm); err != nil {
-		return err
+		return fmt.Errorf("extract %s packages: %w", b.Deploy.GUID, err)
 	}
 
 	if b.Type == roblox.Studio {
@@ -115,16 +115,20 @@ func (b *Binary) Install() error {
 	}
 
 	if err := boot.WriteAppSettings(b.Dir); err != nil {
-		return err
+		return fmt.Errorf("appsettings: %w", err)
 	}
 
 	b.State.Add(&pm)
 
 	if err := b.GlobalState.CleanPackages(); err != nil {
-		return err
+		return fmt.Errorf("clean packages: %w", err)
+	}
+
+	if err := b.GlobalState.CleanVersions(); err != nil {
+		return fmt.Errorf("clean versions: %w", err)
 	}
 
-	return b.GlobalState.CleanVersions()
+	return nil
 }
 
 func (b *Binary) PerformPackages(pm *boot.PackageManifest, fn func(boot.Package) error) error {
@@ -179,7 +183,7 @@ func (b *Binary) SetupDxvk() error {
 		(!b.GlobalConfig.Player.Dxvk && !b.GlobalConfig.Studio.Dxvk) {
 		b.Splash.SetMessage("Uninstalling DXVK")
 		if err := dxvk.Remove(b.Prefix); err != nil {
-			return err
+			return fmt.Errorf("remove dxvk: %w", err)
 		}
 
 		b.State.DxvkVersion = ""