diff --git a/cmd/candy/cmd/launch_darwin.go b/cmd/candy/cmd/launch_darwin.go
index 00b840e6..41a4425a 100644
--- a/cmd/candy/cmd/launch_darwin.go
+++ b/cmd/candy/cmd/launch_darwin.go
@@ -3,6 +3,7 @@
 package cmd
 
 import (
+	"context"
 	"fmt"
 	"os"
 	"path/filepath"
@@ -49,6 +50,7 @@ func launchRunE(c *cobra.Command, args []string) error {
 		}
 
 		for _, proxy := range proxies {
+			proxy := proxy
 			g.Add(func() error {
 				return proxy.Run()
 			}, func(err error) {
@@ -58,9 +60,11 @@ func launchRunE(c *cobra.Command, args []string) error {
 	}
 
 	{
+		ctx, cancel := context.WithCancel(context.Background())
 		g.Add(func() error {
-			return startServer(c)
+			return startServer(c, ctx)
 		}, func(err error) {
+			cancel()
 		})
 	}
 
diff --git a/cmd/candy/cmd/root.go b/cmd/candy/cmd/root.go
index c143ac98..302fea91 100644
--- a/cmd/candy/cmd/root.go
+++ b/cmd/candy/cmd/root.go
@@ -25,34 +25,33 @@ var (
 )
 
 func init() {
-	var err error
-	homeDir, err = userHomeDir()
-	if err != nil {
-		candy.Log().Fatal("error getting user home directory", zap.Error(err))
-	}
-
-	rootCmd.PersistentFlags().StringVar(&flagRootCfgFile, "config", filepath.Join(homeDir, ".candyconfig"), "Config file")
+	rootCmd.PersistentFlags().StringVar(&flagRootCfgFile, "config", filepath.Join(userHomeDir(), ".candyconfig"), "Config file")
 }
 
-func userHomeDir() (string, error) {
+func userHomeDir() string {
+	if homeDir != "" {
+		return homeDir
+	}
+
 	var (
 		sudo = os.Getenv("SUDO_USER")
 		euid = os.Geteuid()
+		err  error
 	)
 
 	if sudo != "" && euid == 0 {
 		u, err := user.Lookup(sudo)
 		if err != nil {
-			return "", nil
+			candy.Log().Fatal("error looking up sudo user", zap.String("user", sudo), zap.Error(err))
 		}
 
-		return u.HomeDir, nil
+		return u.HomeDir
 	}
 
-	homeDir, err := os.UserHomeDir()
+	homeDir, err = os.UserHomeDir()
 	if err != nil {
-		return "", err
+		candy.Log().Fatal("error getting user home directory", zap.Error(err))
 	}
 
-	return homeDir, nil
+	return homeDir
 }
diff --git a/cmd/candy/cmd/run.go b/cmd/candy/cmd/run.go
index 75b91a33..9322972f 100644
--- a/cmd/candy/cmd/run.go
+++ b/cmd/candy/cmd/run.go
@@ -32,7 +32,7 @@ func init() {
 }
 
 func addServerFlags(cmd *cobra.Command) {
-	cmd.Flags().String("host-root", filepath.Join(homeDir, ".candy"), "Path to the directory containing applications that will be served by Candy")
+	cmd.Flags().String("host-root", filepath.Join(userHomeDir(), ".candy"), "Path to the directory containing applications that will be served by Candy")
 	cmd.Flags().StringSlice("domain", defaultDomains, "The top-level domains for which Candy will respond to DNS queries")
 	cmd.Flags().String("http-addr", ":28080", "The Proxy server HTTP address")
 	cmd.Flags().String("https-addr", ":28443", "The Proxy server HTTPS address")
@@ -42,10 +42,10 @@ func addServerFlags(cmd *cobra.Command) {
 }
 
 func runRunE(c *cobra.Command, args []string) error {
-	return startServer(c)
+	return startServer(c, context.Background())
 }
 
-func startServer(c *cobra.Command) error {
+func startServer(c *cobra.Command, ctx context.Context) error {
 	var cfg server.Config
 	if err := candy.LoadConfig(
 		flagRootCfgFile,
@@ -66,10 +66,10 @@ func startServer(c *cobra.Command) error {
 	candy.Log().Info("using config", zap.Any("cfg", cfg))
 
 	if err := os.MkdirAll(cfg.HostRoot, 0o0755); err != nil {
-		return fmt.Errorf("failed to create host directory: %w", err)
+		return fmt.Errorf("failed to create host directory %s: %w", cfg.HostRoot, err)
 	}
 
 	svr := server.New(cfg)
 
-	return svr.Run(context.Background())
+	return svr.Run(ctx)
 }