Improve error messages with context wrapping

internal/auth/auth.go

@@ -26,7 +26,7 @@ func TokenPath() (string, error) {
 func LoadToken() (*StoredAuth, error) {
 	path, err := TokenPath()
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("load token: %w", err)
 	}
 	data, err := os.ReadFile(path)
 	if err != nil {
@@ -51,7 +51,7 @@ func LoadToken() (*StoredAuth, error) {
 func SaveToken(auth *StoredAuth) error {
 	path, err := TokenPath()
 	if err != nil {
-		return err
+		return fmt.Errorf("save token: %w", err)
 	}
 
 	dir := filepath.Dir(path)
@@ -74,7 +74,7 @@ func SaveToken(auth *StoredAuth) error {
 func DeleteToken() error {
 	path, err := TokenPath()
 	if err != nil {
-		return err
+		return fmt.Errorf("delete token: %w", err)
 	}
 	err = os.Remove(path)
 	if err != nil && !os.IsNotExist(err) {

internal/auth/auth_test.go

@@ -258,6 +258,10 @@ func TestDeleteToken_FileNotExist(t *testing.T) {
 }
 
 func TestDeleteToken_PermissionError(t *testing.T) {
+	if os.Geteuid() == 0 {
+		t.Skip("root bypasses filesystem permission checks")
+	}
+
 	tmpDir := t.TempDir()
 	authDir := filepath.Join(tmpDir, ".openboot")
 	authFile := filepath.Join(authDir, "auth.json")
@@ -378,6 +382,10 @@ func TestStoredAuth_JSONMarshaling(t *testing.T) {
 }
 
 func TestLoadToken_ReadPermissionError(t *testing.T) {
+	if os.Geteuid() == 0 {
+		t.Skip("root bypasses filesystem permission checks")
+	}
+
 	tmpDir := t.TempDir()
 	authDir := filepath.Join(tmpDir, ".openboot")
 	authFile := filepath.Join(authDir, "auth.json")

internal/auth/login_test.go

@@ -521,6 +521,9 @@ func TestLoginInteractive_InvalidExpirationFormat(t *testing.T) {
 }
 
 func TestLoginInteractive_SaveTokenError(t *testing.T) {
+	if os.Geteuid() == 0 {
+		t.Skip("root bypasses filesystem permission checks")
+	}
 	withFastPoll(t)
 	withNoBrowser(t)
 	tmpDir := t.TempDir()

internal/cli/login_test.go

@@ -90,6 +90,9 @@ func TestLogoutCmd_WhenNotAuthenticated(t *testing.T) {
 }
 
 func TestLogoutCmd_DeleteError(t *testing.T) {
+	if os.Geteuid() == 0 {
+		t.Skip("root bypasses filesystem permission checks")
+	}
 	tmpDir := setupTestAuth(t, true)
 	authDir := filepath.Join(tmpDir, ".openboot")
 

internal/dotfiles/dotfiles.go

@@ -43,15 +43,18 @@ func Clone(repoURL string, dryRun bool) error {
 
 	home, err := system.HomeDir()
 	if err != nil {
-		return err
+		return fmt.Errorf("clone dotfiles: %w", err)
 	}
 	dotfilesPath := filepath.Join(home, defaultDotfilesDir)
 
 	if _, err := os.Stat(dotfilesPath); err == nil {
 		// Dotfiles directory already exists — sync or re-clone as appropriate.
 		needsClone, err := handleExistingDotfiles(dotfilesPath, repoURL, dryRun)
-		if err != nil || !needsClone {
-			return err
+		if err != nil {
+			return fmt.Errorf("handle existing dotfiles: %w", err)
+		}
+		if !needsClone {
+			return nil
 		}
 	}
 
@@ -210,7 +213,7 @@ func confirmResetIfDirty(dotfilesPath, branch string) bool {
 func Link(dryRun bool) error {
 	home, err := system.HomeDir()
 	if err != nil {
-		return err
+		return fmt.Errorf("link dotfiles: %w", err)
 	}
 	dotfilesPath := filepath.Join(home, defaultDotfilesDir)
 
@@ -332,17 +335,17 @@ func backupConflicts(pkgDir, targetDir string) ([][2]string, error) {
 
 func linkWithStow(dotfilesPath string, dryRun bool) error {
 	if err := ensureStow(dryRun); err != nil {
-		return err
+		return fmt.Errorf("ensure stow: %w", err)
 	}
 
 	entries, err := os.ReadDir(dotfilesPath)
 	if err != nil {
-		return err
+		return fmt.Errorf("read dotfiles dir: %w", err)
 	}
 
 	home, err := system.HomeDir()
 	if err != nil {
-		return err
+		return fmt.Errorf("link with stow: %w", err)
 	}
 
 	var errs []error
@@ -399,12 +402,12 @@ func linkWithStow(dotfilesPath string, dryRun bool) error {
 func linkDirect(dotfilesPath string, dryRun bool) error {
 	home, err := system.HomeDir()
 	if err != nil {
-		return err
+		return fmt.Errorf("link direct: %w", err)
 	}
 
 	entries, err := os.ReadDir(dotfilesPath)
 	if err != nil {
-		return err
+		return fmt.Errorf("read dotfiles dir: %w", err)
 	}
 
 	for _, entry := range entries {

internal/npm/npm.go

@@ -124,7 +124,7 @@ func Install(packages []string, dryRun bool) error {
 
 	failed, err := installBatch(toInstall)
 	if err != nil {
-		return err
+		return fmt.Errorf("install npm packages: %w", err)
 	}
 
 	if len(failed) > 0 {

internal/shell/shell.go

@@ -119,7 +119,7 @@ func EnsureBrewShellenv(dryRun bool) error {
 
 	home, err := system.HomeDir()
 	if err != nil {
-		return err
+		return fmt.Errorf("ensure brew shellenv: %w", err)
 	}
 	zshrcPath := filepath.Join(home, ".zshrc")
 
@@ -129,7 +129,10 @@ func EnsureBrewShellenv(dryRun bool) error {
 			fmt.Printf("[DRY-RUN] Would create %s with Homebrew shellenv\n", zshrcPath)
 			return nil
 		}
-		return os.WriteFile(zshrcPath, []byte(brewShellenvLine+"\n"), 0600)
+		if err := os.WriteFile(zshrcPath, []byte(brewShellenvLine+"\n"), 0600); err != nil {
+			return fmt.Errorf("create .zshrc: %w", err)
+		}
+		return nil
 	}
 
 	raw, err := os.ReadFile(zshrcPath)
@@ -262,7 +265,7 @@ func RestoreFromSnapshot(ohMyZsh bool, theme string, plugins []string, dryRun bo
 
 	home, err := system.HomeDir()
 	if err != nil {
-		return err
+		return fmt.Errorf("configure zshrc: %w", err)
 	}
 	zshrcPath := filepath.Join(home, ".zshrc")
 
@@ -272,11 +275,11 @@ func RestoreFromSnapshot(ohMyZsh bool, theme string, plugins []string, dryRun bo
 			return nil
 		}
 		if err := validateShellIdentifier(theme, "ZSH_THEME"); err != nil {
-			return err
+			return fmt.Errorf("validate theme: %w", err)
 		}
 		for _, p := range plugins {
 			if err := validateShellIdentifier(p, "plugin"); err != nil {
-				return err
+				return fmt.Errorf("validate plugin: %w", err)
 			}
 		}
 		template := fmt.Sprintf(`export ZSH="$HOME/.oh-my-zsh"

internal/state/reminder_test.go

@@ -176,6 +176,9 @@ func TestRoundTrip_DefaultState(t *testing.T) {
 }
 
 func TestLoadState_ReadError(t *testing.T) {
+	if os.Geteuid() == 0 {
+		t.Skip("root bypasses filesystem permission checks")
+	}
 	tmpDir := t.TempDir()
 	statePath := filepath.Join(tmpDir, "state.json")
 

internal/system/system.go

@@ -77,8 +77,7 @@ func RunCommandOutput(name string, args ...string) (string, error) {
 //	curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh | sha256sum
 const knownBrewInstallHash = "dfd5145fe2aa5956a600e35848765273f5798ce6def01bd08ecec088a1268d91"
 
-// brewInstallURL is a var so tests can redirect it without a real server.
-var brewInstallURL = "https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh"
+const brewInstallURL = "https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh"
 
 // brewHTTPClient is a var so tests can inject a mock transport.
 var brewHTTPClient *http.Client = http.DefaultClient