diff --git a/codeserver.go b/codeserver.go
index f2559da..afefe2c 100644
--- a/codeserver.go
+++ b/codeserver.go
@@ -24,7 +24,7 @@ import (
 func loadCodeServer(ctx context.Context) (string, error) {
 	start := time.Now()
 
-	const cachePath = "/tmp/sail-code-server-cache/code-server"
+	cachePath := filepath.Join(os.TempDir(), "sail-code-server-cache/code-server")
 
 	// downloadURLPath stores the download URL, so we know whether we should update
 	// the binary.
diff --git a/config.go b/config.go
index 5468eb4..4a1f653 100644
--- a/config.go
+++ b/config.go
@@ -18,15 +18,14 @@ func resolvePath(homedir string, path string) string {
 		return path
 	}
 
-	list := strings.Split(path, string(filepath.Separator))
-
-	for i, seg := range list {
-		if seg == "~" {
-			list[i] = homedir
-		}
+	// Replace tilde notation in path with homedir.
+	if path == "~" {
+		path = homedir
+	} else if strings.HasPrefix(path, "~/") {
+		path = filepath.Join(homedir, path[2:])
 	}
 
-	return filepath.Join(list...)
+	return filepath.Clean(path)
 }
 
 // config describes the config.toml.
diff --git a/runner.go b/runner.go
index 75802d1..d8199a3 100644
--- a/runner.go
+++ b/runner.go
@@ -236,12 +236,12 @@ func (r *runner) mounts(mounts []mount.Mount, image string) ([]mount.Mount, erro
 	// Mount in VS Code configs.
 	mounts = append(mounts, mount.Mount{
 		Type:   "bind",
-		Source: "~/.config/Code",
+		Source: vscodeConfigDir(),
 		Target: "~/.config/Code",
 	})
 	mounts = append(mounts, mount.Mount{
 		Type:   "bind",
-		Source: "~/.vscode/extensions",
+		Source: vscodeExtensionsDir(),
 		Target: hostExtensionsDir,
 	})
 
@@ -251,8 +251,7 @@ func (r *runner) mounts(mounts []mount.Mount, image string) ([]mount.Mount, erro
 	// socket to the container allows for using the user's existing setup for
 	// ssh authentication instead of having to create a new keys or explicity
 	// pass them in.
-	sshAuthSock, exists := os.LookupEnv("SSH_AUTH_SOCK")
-	if exists {
+	if sshAuthSock, exists := os.LookupEnv("SSH_AUTH_SOCK"); exists {
 		mounts = append(mounts, mount.Mount{
 			Type:   "bind",
 			Source: sshAuthSock,
diff --git a/vscode.go b/vscode.go
new file mode 100644
index 0000000..b76a8d3
--- /dev/null
+++ b/vscode.go
@@ -0,0 +1,33 @@
+package main
+
+import (
+	"os"
+	"path/filepath"
+	"runtime"
+)
+
+const (
+	vsCodeConfigDirEnv     = "VSCODE_CONFIG_DIR"
+	vsCodeExtensionsDirEnv = "VSCODE_EXTENSIONS_DIR"
+)
+
+func vscodeConfigDir() string {
+	if env, ok := os.LookupEnv(vsCodeConfigDirEnv); ok {
+		return os.ExpandEnv(env)
+	}
+
+	path := os.ExpandEnv("$HOME/.config/Code/")
+	if runtime.GOOS == "darwin" {
+		path = os.ExpandEnv("$HOME/Library/Application Support/Code/")
+	}
+	return filepath.Clean(path)
+}
+
+func vscodeExtensionsDir() string {
+	if env, ok := os.LookupEnv(vsCodeExtensionsDirEnv); ok {
+		return os.ExpandEnv(env)
+	}
+
+	path := os.ExpandEnv("$HOME/.vscode/extensions/")
+	return filepath.Clean(path)
+}