diff --git a/environment/sudo.go b/environment/sudo.go
new file mode 100644
index 0000000..afd196d
--- /dev/null
+++ b/environment/sudo.go
@@ -0,0 +1,175 @@
+package environment
+
+import (
+	"fmt"
+	"log/slog"
+	"os"
+	"os/user"
+	"path/filepath"
+	"strconv"
+	"strings"
+)
+
+// RestoreOriginalUserEnvironment detects if running under sudo and restores
+// the original user's environment variables that are important for subprocess execution.
+func RestoreOriginalUserEnvironment(logger *slog.Logger) map[string]string {
+	restoredEnv := make(map[string]string)
+
+	// Check if running under sudo by looking for SUDO_USER
+	sudoUser := os.Getenv("SUDO_USER")
+	if sudoUser == "" {
+		logger.Debug("Not running under sudo, no environment restoration needed")
+		return restoredEnv
+	}
+
+	logger.Debug("Detected sudo execution, restoring original user environment", "sudo_user", sudoUser)
+
+	// Get original user information
+	originalUser, err := user.Lookup(sudoUser)
+	if err != nil {
+		logger.Warn("Failed to lookup original user, skipping environment restoration", "sudo_user", sudoUser, "error", err)
+		return restoredEnv
+	}
+
+	// Restore basic user identity variables
+	restoredEnv["USER"] = sudoUser
+	restoredEnv["LOGNAME"] = sudoUser
+	restoredEnv["HOME"] = originalUser.HomeDir
+
+	// Restore original user's UID and GID if available
+	if sudoUID := os.Getenv("SUDO_UID"); sudoUID != "" {
+		restoredEnv["UID"] = sudoUID
+	}
+	if sudoGID := os.Getenv("SUDO_GID"); sudoGID != "" {
+		restoredEnv["GID"] = sudoGID
+	}
+
+	// Try to restore a reasonable PATH for the original user
+	// This is a best-effort attempt since the original PATH might be complex
+	restoredPath := restoreUserPath(originalUser, logger)
+	if restoredPath != "" {
+		restoredEnv["PATH"] = restoredPath
+	}
+
+	// Restore XDG directories for the original user
+	restoreXDGEnvironment(originalUser, restoredEnv)
+
+	// Log what we're restoring
+	logger.Debug("Restored environment variables for original user", 
+		"user", sudoUser, 
+		"home", originalUser.HomeDir,
+		"restored_vars", len(restoredEnv))
+
+	return restoredEnv
+}
+
+// restoreUserPath attempts to construct a reasonable PATH for the original user
+func restoreUserPath(originalUser *user.User, logger *slog.Logger) string {
+	// Start with comprehensive system paths (in order of preference)
+	systemPaths := []string{
+		"/usr/local/bin",
+		"/usr/bin",
+		"/bin",
+		"/usr/local/sbin",
+		"/usr/sbin",
+		"/sbin",
+	}
+
+	// Add user-specific paths
+	userPaths := []string{
+		filepath.Join(originalUser.HomeDir, ".local", "bin"),
+		filepath.Join(originalUser.HomeDir, "bin"),
+		filepath.Join(originalUser.HomeDir, ".cargo", "bin"),     // Rust tools
+		filepath.Join(originalUser.HomeDir, "go", "bin"),         // Go tools
+		filepath.Join(originalUser.HomeDir, ".npm-global", "bin"), // npm global tools
+	}
+
+	// Check if user paths exist and add them
+	var validUserPaths []string
+	for _, path := range userPaths {
+		if _, err := os.Stat(path); err == nil {
+			validUserPaths = append(validUserPaths, path)
+			logger.Debug("Found user path", "path", path)
+		}
+	}
+
+	// Try to preserve paths from current PATH that might be user-specific or important
+	var preservedPaths []string
+	currentPath := os.Getenv("PATH")
+	if currentPath != "" {
+		for _, path := range strings.Split(currentPath, ":") {
+			// Include paths that contain the user's home directory
+			if strings.Contains(path, originalUser.HomeDir) {
+				if _, err := os.Stat(path); err == nil {
+					preservedPaths = append(preservedPaths, path)
+					logger.Debug("Preserved user-specific path from current PATH", "path", path)
+				}
+			}
+			// Also preserve common tool paths that might not be in system paths
+			if strings.Contains(path, "/opt/") || strings.Contains(path, "/snap/bin") {
+				if _, err := os.Stat(path); err == nil {
+					preservedPaths = append(preservedPaths, path)
+					logger.Debug("Preserved tool path from current PATH", "path", path)
+				}
+			}
+		}
+	}
+
+	// Combine all paths: preserved user paths + valid user paths + system paths
+	allPaths := append(preservedPaths, validUserPaths...)
+	allPaths = append(allPaths, systemPaths...)
+
+	// Remove duplicates while preserving order
+	seen := make(map[string]bool)
+	var uniquePaths []string
+	for _, path := range allPaths {
+		if !seen[path] {
+			seen[path] = true
+			uniquePaths = append(uniquePaths, path)
+		}
+	}
+
+	restoredPath := strings.Join(uniquePaths, ":")
+	logger.Debug("Restored PATH for user", "user", originalUser.Username, "path", restoredPath)
+	return restoredPath
+}
+
+// restoreXDGEnvironment restores XDG Base Directory variables for the original user
+func restoreXDGEnvironment(originalUser *user.User, restoredEnv map[string]string) {
+	homeDir := originalUser.HomeDir
+
+	// Set XDG directories according to the specification
+	// https://specifications.freedesktop.org/basedir-spec/basedir-spec-latest.html
+	restoredEnv["XDG_DATA_HOME"] = filepath.Join(homeDir, ".local", "share")
+	restoredEnv["XDG_CONFIG_HOME"] = filepath.Join(homeDir, ".config")
+	restoredEnv["XDG_STATE_HOME"] = filepath.Join(homeDir, ".local", "state")
+	restoredEnv["XDG_CACHE_HOME"] = filepath.Join(homeDir, ".cache")
+
+	// XDG_RUNTIME_DIR is typically /run/user/{uid} but we'll leave it as-is
+	// since it requires the actual UID and proper permissions
+}
+
+// GetEffectiveUID returns the effective UID that should be used for the subprocess
+// This helps determine if we need to drop privileges when running under sudo
+func GetEffectiveUID() (int, error) {
+	if sudoUID := os.Getenv("SUDO_UID"); sudoUID != "" {
+		uid, err := strconv.Atoi(sudoUID)
+		if err != nil {
+			return 0, fmt.Errorf("invalid SUDO_UID: %v", err)
+		}
+		return uid, nil
+	}
+	return os.Getuid(), nil
+}
+
+// GetEffectiveGID returns the effective GID that should be used for the subprocess
+func GetEffectiveGID() (int, error) {
+	if sudoGID := os.Getenv("SUDO_GID"); sudoGID != "" {
+		gid, err := strconv.Atoi(sudoGID)
+		if err != nil {
+			return 0, fmt.Errorf("invalid SUDO_GID: %v", err)
+		}
+		return gid, nil
+	}
+	return os.Getgid(), nil
+}
diff --git a/network/linux.go b/network/linux.go
index 82eacc2..9e22c80 100644
--- a/network/linux.go
+++ b/network/linux.go
@@ -9,6 +9,8 @@ import (
 	"os/exec"
 	"syscall"
 	"time"
+
+	"github.com/coder/jail/environment"
 )
 
 const (
@@ -92,6 +94,12 @@ func (l *LinuxJail) Execute(command []string, extraEnv map[string]string) error
 	l.logger.Debug("Setting up environment")
 	env := os.Environ()
 
+	// Restore original user environment if running under sudo
+	restoredUserEnv := environment.RestoreOriginalUserEnvironment(l.logger)
+	for key, value := range restoredUserEnv {
+		env = append(env, fmt.Sprintf("%s=%s", key, value))
+	}
+
 	// Add extra environment variables (including CA cert if provided)
 	for key, value := range extraEnv {
 		env = append(env, fmt.Sprintf("%s=%s", key, value))
@@ -102,6 +110,27 @@ func (l *LinuxJail) Execute(command []string, extraEnv map[string]string) error
 	cmd.Stdout = os.Stdout
 	cmd.Stderr = os.Stderr
 
+	// Drop privileges to original user if running under sudo
+	if sudoUser := os.Getenv("SUDO_USER"); sudoUser != "" {
+		uid, err := environment.GetEffectiveUID()
+		if err != nil {
+			l.logger.Warn("Failed to get effective UID, subprocess will run as root", "error", err)
+		} else {
+			gid, err := environment.GetEffectiveGID()
+			if err != nil {
+				l.logger.Warn("Failed to get effective GID, subprocess will run as root", "error", err)
+			} else {
+				cmd.SysProcAttr = &syscall.SysProcAttr{
+					Credential: &syscall.Credential{
+						Uid: uint32(uid),
+						Gid: uint32(gid),
+					},
+				}
+				l.logger.Debug("Dropping privileges to original user", "uid", uid, "gid", gid, "user", sudoUser)
+			}
+		}
+	}
+
 	// Start command
 	l.logger.Debug("Starting command", "path", cmd.Path, "args", cmd.Args)
 	err := cmd.Start()
diff --git a/network/macos.go b/network/macos.go
index 79f8097..a4927c2 100644
--- a/network/macos.go
+++ b/network/macos.go
@@ -10,6 +10,8 @@ import (
 	"strconv"
 	"strings"
 	"syscall"
+
+	"github.com/coder/jail/environment"
 )
 
 const (
@@ -79,6 +81,12 @@ func (m *MacOSNetJail) Execute(command []string, extraEnv map[string]string) err
 	m.logger.Debug("Setting up environment")
 	env := os.Environ()
 
+	// Restore original user environment if running under sudo
+	restoredUserEnv := environment.RestoreOriginalUserEnvironment(m.logger)
+	for key, value := range restoredUserEnv {
+		env = append(env, fmt.Sprintf("%s=%s", key, value))
+	}
+
 	// Add extra environment variables (including CA cert if provided)
 	for key, value := range extraEnv {
 		env = append(env, fmt.Sprintf("%s=%s", key, value))
@@ -89,11 +97,33 @@ func (m *MacOSNetJail) Execute(command []string, extraEnv map[string]string) err
 	cmd.Stderr = os.Stderr
 	cmd.Stdin = os.Stdin
 
-	// Set group ID using syscall (like httpjail does)
-	cmd.SysProcAttr = &syscall.SysProcAttr{
-		Credential: &syscall.Credential{
-			Gid: uint32(m.groupID),
-		},
+	// Drop privileges to original user if running under sudo
+	if sudoUser := os.Getenv("SUDO_USER"); sudoUser != "" {
+		uid, err := environment.GetEffectiveUID()
+		if err != nil {
+			m.logger.Warn("Failed to get effective UID, subprocess will run as root", "error", err)
+		} else {
+			gid, err := environment.GetEffectiveGID()
+			if err != nil {
+				m.logger.Warn("Failed to get effective GID, subprocess will run as root", "error", err)
+			} else {
+				// Set group ID using syscall (like httpjail does)
+				cmd.SysProcAttr = &syscall.SysProcAttr{
+					Credential: &syscall.Credential{
+						Uid: uint32(uid),
+						Gid: uint32(gid),
+					},
+				}
+				m.logger.Debug("Dropping privileges to original user", "uid", uid, "gid", gid, "user", sudoUser)
+			}
+		}
+	} else {
+		// Set group ID using syscall (like httpjail does) - original behavior for non-sudo
+		cmd.SysProcAttr = &syscall.SysProcAttr{
+			Credential: &syscall.Credential{
+				Gid: uint32(m.groupID),
+			},
+		}
 	}
 
 	// Start and wait for command to complete
@@ -334,4 +364,4 @@ func (m *MacOSNetJail) cleanupTempFiles() {
 	if m.mainRulesPath != "" {
 		os.Remove(m.mainRulesPath)
 	}
-}
+}
\ No newline at end of file
diff --git a/tls/tls.go b/tls/tls.go
index a9e51b0..8f66040 100644
--- a/tls/tls.go
+++ b/tls/tls.go
@@ -12,6 +12,7 @@ import (
 	"math/big"
 	"net"
 	"os"
+	"os/user"
 	"path/filepath"
 	"sync"
 	"time"
@@ -295,9 +296,28 @@ func (cm *CertificateManager) generateServerCertificate(hostname string) (*tls.C
 
 // GetConfigDir returns the configuration directory path
 func GetConfigDir() (string, error) {
-	homeDir, err := os.UserHomeDir()
-	if err != nil {
-		return "", fmt.Errorf("failed to get user home directory: %v", err)
+	// When running under sudo, use the original user's home directory
+	// so the subprocess can access the CA certificate files
+	var homeDir string
+	if sudoUser := os.Getenv("SUDO_USER"); sudoUser != "" {
+		// Get original user's home directory
+		if user, err := user.Lookup(sudoUser); err == nil {
+			homeDir = user.HomeDir
+		} else {
+			// Fallback to current user if lookup fails
+			var err2 error
+			homeDir, err2 = os.UserHomeDir()
+			if err2 != nil {
+				return "", fmt.Errorf("failed to get user home directory: %v", err2)
+			}
+		}
+	} else {
+		// Normal case - use current user's home
+		var err error
+		homeDir, err = os.UserHomeDir()
+		if err != nil {
+			return "", fmt.Errorf("failed to get user home directory: %v", err)
+		}
 	}
 
 	// Use platform-specific config directory