fix(server): improve error message for encrypted TLS private keys (#4742)

Added TLS certificate validation that detects encrypted (password-protected)
private keys and provides a clear error message with instructions on how to
decrypt them using openssl. This addresses user confusion when Go's standard
library fails with the cryptic 'tls: failed to parse private key' error.

Changes:
- Added validateTLSCertificates function to validate certs before server start
- Added isEncryptedPEM helper to detect both PKCS#8 and legacy encrypted keys
- Added comprehensive tests for TLS validation including encrypted key detection
- Added integration test that starts server with TLS and verifies HTTPS works
- Added test certificates (valid for 100 years) with SAN for localhost

Signed-off-by: Deluan <deluan@navidrome.org>

server/server.go

@@ -1,8 +1,11 @@
 package server
 
 import (
+	"bytes"
 	"cmp"
 	"context"
+	"crypto/tls"
+	"encoding/pem"
 	"errors"
 	"fmt"
 	"net"
@@ -69,6 +72,13 @@ func (s *Server) Run(ctx context.Context, addr string, port int, tlsCert string,
 	// Determine if TLS is enabled
 	tlsEnabled := tlsCert != "" && tlsKey != ""
 
+	// Validate TLS certificates before starting the server
+	if tlsEnabled {
+		if err := validateTLSCertificates(tlsCert, tlsKey); err != nil {
+			return err
+		}
+	}
+
 	// Create a listener based on the address type (either Unix socket or TCP)
 	var listener net.Listener
 	var err error
@@ -89,17 +99,17 @@ func (s *Server) Run(ctx context.Context, addr string, port int, tlsCert string,
 	// Start the server in a new goroutine and send an error signal to errC if there's an error
 	errC := make(chan error)
 	go func() {
+		var err error
 		if tlsEnabled {
 			// Start the HTTPS server
 			log.Info("Starting server with TLS (HTTPS) enabled", "tlsCert", tlsCert, "tlsKey", tlsKey)
-			if err := server.ServeTLS(listener, tlsCert, tlsKey); !errors.Is(err, http.ErrServerClosed) {
-				errC <- err
-			}
+			err = server.ServeTLS(listener, tlsCert, tlsKey)
 		} else {
 			// Start the HTTP server
-			if err := server.Serve(listener); !errors.Is(err, http.ErrServerClosed) {
-				errC <- err
-			}
+			err = server.Serve(listener)
+		}
+		if !errors.Is(err, http.ErrServerClosed) {
+			errC <- err
 		}
 	}()
 
@@ -249,3 +259,56 @@ func AbsoluteURL(r *http.Request, u string, params url.Values) string {
 	}
 	return buildUrl.String()
 }
+
+// validateTLSCertificates validates the TLS certificate and key files before starting the server.
+// It provides detailed error messages for common issues like encrypted private keys.
+func validateTLSCertificates(certFile, keyFile string) error {
+	// Read the key file to check for encryption
+	keyData, err := os.ReadFile(keyFile)
+	if err != nil {
+		return fmt.Errorf("reading TLS key file: %w", err)
+	}
+
+	// Parse PEM blocks and check for encryption
+	block, _ := pem.Decode(keyData)
+	if block == nil {
+		return errors.New("TLS key file does not contain a valid PEM block")
+	}
+
+	// Check for encrypted private key indicators
+	if isEncryptedPEM(block, keyData) {
+		return errors.New("TLS private key is encrypted (password-protected). " +
+			"Navidrome does not support encrypted private keys. " +
+			"Please decrypt your key using: openssl pkey -in <encrypted-key> -out <decrypted-key>")
+	}
+
+	// Try to load the certificate pair to validate it
+	_, err = tls.LoadX509KeyPair(certFile, keyFile)
+	if err != nil {
+		return fmt.Errorf("loading TLS certificate/key pair: %w", err)
+	}
+
+	return nil
+}
+
+// isEncryptedPEM checks if a PEM block represents an encrypted private key.
+func isEncryptedPEM(block *pem.Block, rawData []byte) bool {
+	// Check for PKCS#8 encrypted format (BEGIN ENCRYPTED PRIVATE KEY)
+	if block.Type == "ENCRYPTED PRIVATE KEY" {
+		return true
+	}
+
+	// Check for legacy encrypted format with Proc-Type header
+	if block.Headers != nil {
+		if procType, ok := block.Headers["Proc-Type"]; ok && strings.Contains(procType, "ENCRYPTED") {
+			return true
+		}
+	}
+
+	// Also check raw data for DEK-Info header (in case pem.Decode doesn't parse headers correctly)
+	if bytes.Contains(rawData, []byte("DEK-Info:")) || bytes.Contains(rawData, []byte("Proc-Type: 4,ENCRYPTED")) {
+		return true
+	}
+
+	return false
+}

server/server_test.go

@@ -1,13 +1,20 @@
 package server
 
 import (
+	"context"
+	"crypto/tls"
+	"crypto/x509"
+	"fmt"
 	"io/fs"
 	"net/http"
 	"net/url"
 	"os"
 	"path/filepath"
+	"time"
 
 	"github.com/navidrome/navidrome/conf"
+	"github.com/navidrome/navidrome/conf/configtest"
+	"github.com/navidrome/navidrome/tests"
 	. "github.com/onsi/ginkgo/v2"
 	. "github.com/onsi/gomega"
 )
@@ -107,3 +114,146 @@ var _ = Describe("createUnixSocketFile", func() {
 		})
 	})
 })
+
+var _ = Describe("TLS support", func() {
+	Describe("validateTLSCertificates", func() {
+		const testDataDir = "server/testdata"
+
+		When("certificate and key are valid and unencrypted", func() {
+			It("returns nil", func() {
+				certFile := filepath.Join(testDataDir, "test_cert.pem")
+				keyFile := filepath.Join(testDataDir, "test_key.pem")
+				err := validateTLSCertificates(certFile, keyFile)
+				Expect(err).ToNot(HaveOccurred())
+			})
+		})
+
+		When("private key is encrypted with PKCS#8 format", func() {
+			It("returns an error with helpful message", func() {
+				certFile := filepath.Join(testDataDir, "test_cert_encrypted.pem")
+				keyFile := filepath.Join(testDataDir, "test_key_encrypted.pem")
+				err := validateTLSCertificates(certFile, keyFile)
+				Expect(err).To(HaveOccurred())
+				Expect(err.Error()).To(ContainSubstring("encrypted"))
+				Expect(err.Error()).To(ContainSubstring("openssl"))
+			})
+		})
+
+		When("private key is encrypted with legacy format (Proc-Type header)", func() {
+			It("returns an error with helpful message", func() {
+				certFile := filepath.Join(testDataDir, "test_cert.pem")
+				keyFile := filepath.Join(testDataDir, "test_key_encrypted_legacy.pem")
+				err := validateTLSCertificates(certFile, keyFile)
+				Expect(err).To(HaveOccurred())
+				Expect(err.Error()).To(ContainSubstring("encrypted"))
+				Expect(err.Error()).To(ContainSubstring("openssl"))
+			})
+		})
+
+		When("key file does not exist", func() {
+			It("returns an error", func() {
+				certFile := filepath.Join(testDataDir, "test_cert.pem")
+				keyFile := filepath.Join(testDataDir, "nonexistent.pem")
+				err := validateTLSCertificates(certFile, keyFile)
+				Expect(err).To(HaveOccurred())
+				Expect(err.Error()).To(ContainSubstring("reading TLS key file"))
+			})
+		})
+
+		When("key file does not contain valid PEM", func() {
+			It("returns an error", func() {
+				// Create a temp file with invalid PEM content
+				tmpFile, err := os.CreateTemp("", "invalid_key*.pem")
+				Expect(err).ToNot(HaveOccurred())
+				DeferCleanup(func() {
+					_ = os.Remove(tmpFile.Name())
+				})
+				_, err = tmpFile.WriteString("not a valid PEM file")
+				Expect(err).ToNot(HaveOccurred())
+				_ = tmpFile.Close()
+
+				certFile := filepath.Join(testDataDir, "test_cert.pem")
+				err = validateTLSCertificates(certFile, tmpFile.Name())
+				Expect(err).To(HaveOccurred())
+				Expect(err.Error()).To(ContainSubstring("valid PEM block"))
+			})
+		})
+
+		When("certificate file does not exist", func() {
+			It("returns an error from tls.LoadX509KeyPair", func() {
+				certFile := filepath.Join(testDataDir, "nonexistent_cert.pem")
+				keyFile := filepath.Join(testDataDir, "test_key.pem")
+				err := validateTLSCertificates(certFile, keyFile)
+				Expect(err).To(HaveOccurred())
+				Expect(err.Error()).To(ContainSubstring("loading TLS certificate/key pair"))
+			})
+		})
+	})
+
+	Describe("Server TLS", func() {
+		const testDataDir = "server/testdata"
+
+		When("server is started with valid TLS certificates", func() {
+			It("accepts HTTPS connections", func() {
+				DeferCleanup(configtest.SetupConfig())
+
+				// Create server with mock dependencies
+				ds := &tests.MockDataStore{}
+				server := New(ds, nil, nil)
+
+				// Load the test certificate to create a trusted CA pool
+				certFile := filepath.Join(testDataDir, "test_cert.pem")
+				keyFile := filepath.Join(testDataDir, "test_key.pem")
+				caCert, err := os.ReadFile(certFile)
+				Expect(err).ToNot(HaveOccurred())
+
+				caCertPool := x509.NewCertPool()
+				caCertPool.AppendCertsFromPEM(caCert)
+
+				// Create an HTTPS client that trusts our test certificate
+				httpClient := &http.Client{
+					Timeout: 5 * time.Second,
+					Transport: &http.Transport{
+						TLSClientConfig: &tls.Config{
+							RootCAs:    caCertPool,
+							MinVersion: tls.VersionTLS12,
+						},
+					},
+				}
+
+				// Start the server in a goroutine
+				ctx, cancel := context.WithCancel(GinkgoT().Context())
+				defer cancel()
+
+				errChan := make(chan error, 1)
+				go func() {
+					errChan <- server.Run(ctx, "127.0.0.1", 14534, certFile, keyFile)
+				}()
+
+				Eventually(func() error {
+					// Make an HTTPS request to the server
+					resp, err := httpClient.Get("https://127.0.0.1:14534/ping")
+					if err != nil {
+						return err
+					}
+					defer resp.Body.Close()
+					if resp.StatusCode != http.StatusOK {
+						return fmt.Errorf("unexpected status code: %d", resp.StatusCode)
+					}
+					return nil
+				}, 2*time.Second, 100*time.Millisecond).Should(Succeed())
+
+				// Stop the server
+				cancel()
+
+				// Wait for server to stop (with timeout)
+				select {
+				case <-errChan:
+					// Server stopped
+				case <-time.After(2 * time.Second):
+					Fail("Server did not stop in time")
+				}
+			})
+		})
+	})
+})

server/testdata/test_cert.pem

@@ -0,0 +1,23 @@
+-----BEGIN CERTIFICATE-----
+MIIDwzCCAqugAwIBAgIUXqdUxUOo8kmsDe71iTR+Vr7btP8wDQYJKoZIhvcNAQEL
+BQAwYjELMAkGA1UEBhMCVVMxDTALBgNVBAgMBFRlc3QxDTALBgNVBAcMBFRlc3Qx
+EjAQBgNVBAoMCU5hdmlkcm9tZTENMAsGA1UECwwEVGVzdDESMBAGA1UEAwwJbG9j
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+TmF2aWRyb21lMQ0wCwYDVQQLDARUZXN0MRIwEAYDVQQDDAlsb2NhbGhvc3QwggEi
+MA0GCSqGSIb3DQEBAQUAA4IBDwAwggEKAoIBAQCkB/TQgl5ei5KRSHt5OJim8rKS
+MzRlkK4BjSEM4D9ESbebdpEVjX48QuBYACrCvgvVp7mQGF5anl8Hm89trvd8ooVQ
+x9IPQQ6gRKM+4gLrt9FHvFGGzZQS8UTQXN5oBi11E+8/Vs47HLUNXC2TRtRLCMyK
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+OHC4L3B36QN3+VQ2yDjsp1PVAPX07UnzXO3Oj7uGYnMQxwprGMEubm3nADDxAgMB
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+TXYurWPYsQ==
+-----END CERTIFICATE-----

server/testdata/test_cert_encrypted.pem

@@ -0,0 +1,22 @@
+-----BEGIN CERTIFICATE-----
+MIIDpzCCAo+gAwIBAgIUEa7gEJYwJqYEJjTY7otQ+oUyELwwDQYJKoZIhvcNAQEL
+BQAwYjELMAkGA1UEBhMCVVMxDTALBgNVBAgMBFRlc3QxDTALBgNVBAcMBFRlc3Qx
+EjAQBgNVBAoMCU5hdmlkcm9tZTENMAsGA1UECwwEVGVzdDESMBAGA1UEAwwJbG9j
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+2yP4mpMKurgKOv7unTDLwvjQRa6ZTYJCsYtvC6hbyqlGc7AfNTu6DKz8r35/2/V5
+hPsG5lNb91HhvHE839mLAvpi02LoFH2Sr8BR7s6qxfNKYcP8PUOJQXltJ6yAa8YJ
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+Hy1L5a2vUDbsdONdvRkYZRHqMpG4bdD8D3j2
+-----END CERTIFICATE-----

server/testdata/test_key.pem

@@ -0,0 +1,28 @@
+-----BEGIN PRIVATE KEY-----
+MIIEvQIBADANBgkqhkiG9w0BAQEFAASCBKcwggSjAgEAAoIBAQCkB/TQgl5ei5KR
+SHt5OJim8rKSMzRlkK4BjSEM4D9ESbebdpEVjX48QuBYACrCvgvVp7mQGF5anl8H
+m89trvd8ooVQx9IPQQ6gRKM+4gLrt9FHvFGGzZQS8UTQXN5oBi11E+8/Vs47HLUN
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+PVR/YeAhVdz/OHC4L3B36QN3+VQ2yDjsp1PVAPX07UnzXO3Oj7uGYnMQxwprGMEu
+bm3nADDxAgMBAAECggEABqJFvesP2v4FEvgd+kSWM+ZL34rPmy3zQ5/MDuPA20ep
+89EjQ/5hdRl1TknPcOnTu7PZVuENa9fM2xdrl7GEU9eU0bQLJE/KwiOUgJYObS8V
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+f14sRNV7kWnPZsDPlqn8p9SKmpnj3RW97uWeMCtiyx6/+VHm8ljts/GaY1zT2s1r
+KqrPNfNDWQmU3MljNeqbh9lOTWK/xEVy0gzB31MNAoGAQNWrZvVdAbL95XW6STUu
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+ytEIUnvn5YmmbI7PDz80XpU=
+-----END PRIVATE KEY-----

server/testdata/test_key_encrypted.pem

@@ -0,0 +1,30 @@
+-----BEGIN ENCRYPTED PRIVATE KEY-----
+MIIFNTBfBgkqhkiG9w0BBQ0wUjAxBgkqhkiG9w0BBQwwJAQQPH9PYzryCI3smm81
+J8rm+QICCAAwDAYIKoZIhvcNAgkFADAdBglghkgBZQMEASoEEI+9XxNfKSiMYIVB
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+BmvLMnswa23yw9egYRG5jOXyCgIr+1rnNcph1HGJsvxvgJ2gwwo5NKCG8SC6LcZQ
+fbDjX+ssmobLE3ktN03FZPMp32/ciexzuZoamfyiPXh7xE++ckifNEKJlNhx+kCG
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+8JG/ilG4I8uMxUwhGj7amrWXUlJBd1by7e1EAL+utCo14/Tx3otB9/JtqY+lm9Ey
+1ptPhMRQxvDNWrCmYM2kyrGghdNfEMir6GKDWI6PY9cwAFv/PLOxr1c=
+-----END ENCRYPTED PRIVATE KEY-----

server/testdata/test_key_encrypted_legacy.pem

@@ -0,0 +1,30 @@
+-----BEGIN RSA PRIVATE KEY-----
+Proc-Type: 4,ENCRYPTED
+DEK-Info: AES-256-CBC,3C969050EAB73F121B7F0E6B75C42525
+
+V6pSaAsrn9CQNo4p88QshJLbg8zkQJEom81dPbYSVqQSZa9YlPtpLZ9YtuLj/Ay0
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+hA96AIbPOwc76iCuvsKHPKU9MlEmjGipmk/C2RQLHCZJ3WkiDRgCM8KQ7vKhfACT
+w908yj4cB1e/P0JPq8t/3F7kPJ+6SVM1vMEffHl0otQR3rAyrK8QikwJ0K9qX62d
+cqchTVlEyyZBYovR8DrRRUDbsXS5j1ZmX3NQpvTSTFowr+33fMrY+4Oz8sdR4yx1
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+U+wpkRjf3zS6ZaUU0NKdOcop4YX33i99/tZF2RNR1i7ETLYph+/LCf09286Bi3u/
+UCCuWedyECPdz0c6j0s27Fdfc/HEK90OEzeWh/fc+H2gJZhqJYK9V47HPTQNNMnB
+U1a6FsJlrKE3E6nfSnTLxrSx9m/XTV7HV+HkgX+q8VhN7Q2VHUqkPzE7ZOPYpZ+A
+dQzsm1TmEMxym6osYqFzQScXR1NZasrV2MTQ2J16dUgCdGAM2YMUD9JaoJR+u77M
+WAjYzDiRg84rLr/KbJPAwHbsfo2KpiapJGSBBEDhz4W1/LOrFhsjaqIMSy4yZDGm
+1KqXGHIlqmuHI7v4fD8vuzhj7GUujRx85HSZWakE/uc6s5WrhkSeVKYJWPfpsxTv
+dT3oLOGJ+nRzWxM3aFtuJghX0nIGdKxT4EAUNXz0/vLT3OP1QCZR+oELrriFzmtj
++O30bGH2SAFZEQJ/uTQg6celoNh89IzH4DJkcn67hqpX6mUiU9CrIr/eR9C/en8Q
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++wdIrUtf55Lw51JCpLGl70mg4b/zBj5hqBkU2YvAAnz/htjfH/wrD6ZAF1TCdlRO
+gyODrJjGRnLd/v0XLk0wp+RkAjBcSlRlkUvZY5BtugL7dIdwiNGGQPcOni9IVeG0
+6vDUEQnDOLYDj4d/JcckTLuHdrP+SW+0RQl2HK5+/w1hScGXN4O48gccu7yR/MN8
+DmpCg5rD/nq8sxJosmSt07GrN36KppYt8LCXQbSg3NG2Ad715caS2C+0Qtdm5MPD
+rM1UyTXQYSJXgUN9yZS/pmzlguCywnnvsBPU6j3ljZwcoD41QJ/1OU09/W6sIMQR
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+wp7/y39KirnlTl99i3XiOJ4WF4gIU2IaSlqMo4+e/A32h2JFi9QfNyfItXe6Fm1X
+d0j2XGHzwMfHEFKdWyrgtVZwc38/1d6xWYAhs02b2basV/0AQhFTaKf5Z268eBNJ
+-----END RSA PRIVATE KEY-----