Files
Charon/backend/internal/services/mail_service_test.go

1498 lines
42 KiB
Go

package services
import (
"bufio"
"bytes"
"context"
"crypto/rand"
"crypto/rsa"
"crypto/tls"
"crypto/x509"
"crypto/x509/pkix"
"encoding/pem"
"errors"
"fmt"
"math/big"
"net"
"net/mail"
"os"
"path/filepath"
"strconv"
"strings"
"sync"
"testing"
"time"
"github.com/Wikid82/charon/backend/internal/models"
"github.com/stretchr/testify/assert"
"github.com/stretchr/testify/require"
"gorm.io/driver/sqlite"
"gorm.io/gorm"
"gorm.io/gorm/logger"
)
// TestMain sets up the SSL_CERT_FILE environment variable globally BEFORE any tests run.
// This ensures x509.SystemCertPool() initializes with our test CA, which is critical for
// parallel test execution with -race flag where cert pool initialization timing matters.
func TestMain(m *testing.M) {
// Initialize shared test CA and write stable cert file
initializeTestCAForSuite()
// Set SSL_CERT_FILE globally so cert pool initialization uses our CA
if err := os.Setenv("SSL_CERT_FILE", testCAFile); err != nil {
panic("failed to set SSL_CERT_FILE: " + err.Error())
}
// Run tests
exitCode := m.Run()
// Cleanup (optional, OS will clean /tmp on reboot)
_ = os.Remove(testCAFile)
os.Exit(exitCode)
}
// initializeTestCAForSuite is called once by TestMain to set up the shared CA infrastructure.
func initializeTestCAForSuite() {
testCAOnce.Do(func() {
var err error
testCAKey, err = rsa.GenerateKey(rand.Reader, 2048)
if err != nil {
panic("GenerateKey failed: " + err.Error())
}
testCATemplate = &x509.Certificate{
SerialNumber: big.NewInt(1),
Subject: pkix.Name{
CommonName: "charon-test-ca",
},
NotBefore: time.Now().Add(-time.Hour),
NotAfter: time.Now().Add(24 * 365 * time.Hour), // 24 years
KeyUsage: x509.KeyUsageCertSign | x509.KeyUsageCRLSign,
BasicConstraintsValid: true,
IsCA: true,
}
caDER, err := x509.CreateCertificate(rand.Reader, testCATemplate, testCATemplate, &testCAKey.PublicKey, testCAKey)
if err != nil {
panic("CreateCertificate failed: " + err.Error())
}
testCAPEM = pem.EncodeToMemory(&pem.Block{Type: "CERTIFICATE", Bytes: caDER})
testCAFile = filepath.Join(os.TempDir(), "charon-test-ca-mail-service.pem")
if err := os.WriteFile(testCAFile, testCAPEM, 0o600); err != nil {
panic("WriteFile failed: " + err.Error())
}
})
}
func setupMailTestDB(t *testing.T) *gorm.DB {
db, err := gorm.Open(sqlite.Open(":memory:"), &gorm.Config{
Logger: logger.Default.LogMode(logger.Silent),
})
require.NoError(t, err)
err = db.AutoMigrate(&models.Setting{})
require.NoError(t, err)
return db
}
func TestMailService_SaveAndGetSMTPConfig(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
config := &SMTPConfig{
Host: "smtp.example.com",
Port: 587,
Username: "user@example.com",
Password: "secret123",
FromAddress: "noreply@example.com",
Encryption: "starttls",
}
err := svc.SaveSMTPConfig(config)
require.NoError(t, err)
retrieved, err := svc.GetSMTPConfig()
require.NoError(t, err)
assert.Equal(t, config.Host, retrieved.Host)
assert.Equal(t, config.Port, retrieved.Port)
assert.Equal(t, config.Username, retrieved.Username)
assert.Equal(t, config.Password, retrieved.Password)
assert.Equal(t, config.FromAddress, retrieved.FromAddress)
assert.Equal(t, config.Encryption, retrieved.Encryption)
}
func TestMailService_UpdateSMTPConfig(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
config := &SMTPConfig{
Host: "smtp.example.com",
Port: 587,
Username: "user@example.com",
Password: "secret123",
FromAddress: "noreply@example.com",
Encryption: "starttls",
}
err := svc.SaveSMTPConfig(config)
require.NoError(t, err)
config.Host = "smtp.newhost.com"
config.Port = 465
config.Encryption = "ssl"
err = svc.SaveSMTPConfig(config)
require.NoError(t, err)
retrieved, err := svc.GetSMTPConfig()
require.NoError(t, err)
assert.Equal(t, "smtp.newhost.com", retrieved.Host)
assert.Equal(t, 465, retrieved.Port)
assert.Equal(t, "ssl", retrieved.Encryption)
}
func TestMailService_IsConfigured(t *testing.T) {
tests := []struct {
name string
config *SMTPConfig
expected bool
}{
{
name: "configured with all fields",
config: &SMTPConfig{
Host: "smtp.example.com",
Port: 587,
FromAddress: "noreply@example.com",
Encryption: "starttls",
},
expected: true,
},
{
name: "not configured - missing host",
config: &SMTPConfig{
Port: 587,
FromAddress: "noreply@example.com",
},
expected: false,
},
{
name: "not configured - missing from address",
config: &SMTPConfig{
Host: "smtp.example.com",
Port: 587,
},
expected: false,
},
}
for _, tt := range tests {
t.Run(tt.name, func(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
err := svc.SaveSMTPConfig(tt.config)
require.NoError(t, err)
result := svc.IsConfigured()
assert.Equal(t, tt.expected, result)
})
}
}
func TestMailService_GetSMTPConfig_Defaults(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
config, err := svc.GetSMTPConfig()
require.NoError(t, err)
assert.Equal(t, 587, config.Port)
assert.Equal(t, "starttls", config.Encryption)
assert.Empty(t, config.Host)
}
func TestMailService_BuildEmail(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
fromAddr, err := mail.ParseAddress("sender@example.com")
require.NoError(t, err)
toAddr, err := mail.ParseAddress("recipient@example.com")
require.NoError(t, err)
// Encode subject as SendEmail would
encodedSubject, err := encodeSubject("Test Subject")
require.NoError(t, err)
msg, err := svc.buildEmail(fromAddr, toAddr, nil, encodedSubject, "<html><body>Test Body</body></html>")
require.NoError(t, err)
msgStr := string(msg)
// Addresses are RFC-formatted and may include angle brackets
assert.Contains(t, msgStr, "From:")
assert.Contains(t, msgStr, "sender@example.com")
assert.Contains(t, msgStr, "To:")
// After CodeQL remediation, To: header uses undisclosed recipients
assert.Contains(t, msgStr, "undisclosed-recipients:;")
assert.Contains(t, msgStr, "Subject:")
assert.Contains(t, msgStr, "Content-Type: text/html")
assert.Contains(t, msgStr, "Test Body")
}
func TestParseEmailAddressForHeader(t *testing.T) {
tests := []struct {
name string
email string
wantErr bool
}{
{"valid email", "user@example.com", false},
{"valid email with name", "User Name <user@example.com>", false},
{"empty email", "", true},
{"invalid format", "not-an-email", true},
{"missing domain", "user@", true},
{"injection attempt", "user@example.com\r\nBcc: evil@hacker.com", true},
}
for _, tc := range tests {
t.Run(tc.name, func(t *testing.T) {
_, err := parseEmailAddressForHeader("to", tc.email)
if tc.wantErr {
assert.Error(t, err)
} else {
assert.NoError(t, err)
}
})
}
}
func TestMailService_BuildEmail_RejectsCRLFInSubject(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
fromAddr, err := mail.ParseAddress("sender@example.com")
require.NoError(t, err)
toAddr, err := mail.ParseAddress("recipient@example.com")
require.NoError(t, err)
_, err = svc.buildEmail(fromAddr, toAddr, nil, "Normal\r\nBcc: attacker@evil.com", "<p>Body</p>")
assert.Error(t, err)
}
func TestMailService_BuildEmail_RejectsCRLFInReplyTo(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
fromAddr, err := mail.ParseAddress("sender@example.com")
require.NoError(t, err)
toAddr, err := mail.ParseAddress("recipient@example.com")
require.NoError(t, err)
// Create reply-to address with CRLF injection attempt in the name field
replyToAddr := &mail.Address{
Name: "Attacker\r\nBcc: evil@example.com",
Address: "attacker@example.com",
}
_, err = svc.buildEmail(fromAddr, toAddr, replyToAddr, "Test Subject", "<p>Body</p>")
assert.Error(t, err, "Should reject CRLF in reply-to name")
}
func TestMailService_SMTPDotStuffing(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
fromAddr, err := mail.ParseAddress("from@example.com")
require.NoError(t, err)
toAddr, err := mail.ParseAddress("to@example.com")
require.NoError(t, err)
tests := []struct {
name string
htmlBody string
shouldContain string
}{
{
name: "body with leading period on line",
htmlBody: "Line 1\n.Line 2 starts with period\nLine 3",
shouldContain: "Line 1\n..Line 2 starts with period\nLine 3",
},
{
name: "body with SMTP terminator sequence",
htmlBody: "Some text\n.\nMore text",
shouldContain: "Some text\n..\nMore text",
},
{
name: "body with multiple leading periods",
htmlBody: ".First\n..Second\nNormal",
shouldContain: "..First\n...Second\nNormal",
},
{
name: "body without leading periods",
htmlBody: "Normal line\nAnother normal line",
shouldContain: "Normal line\nAnother normal line",
},
}
for _, tc := range tests {
t.Run(tc.name, func(t *testing.T) {
msg, err := svc.buildEmail(fromAddr, toAddr, nil, "Test", tc.htmlBody)
require.NoError(t, err)
msgStr := string(msg)
parts := strings.Split(msgStr, "\r\n\r\n")
require.Len(t, parts, 2, "Email should have headers and body")
body := parts[1]
assert.Contains(t, body, tc.shouldContain, "Body should contain dot-stuffed content")
})
}
}
func TestSanitizeEmailBody(t *testing.T) {
tests := []struct {
name string
input string
expected string
}{
{"single leading period", ".test", "..test"},
{"period in middle", "test.com", "test.com"},
{"multiple lines with periods", "line1\n.line2\nline3", "line1\n..line2\nline3"},
{"SMTP terminator", "text\n.\nmore", "text\n..\nmore"},
{"no periods", "clean text", "clean text"},
{"empty string", "", ""},
}
for _, tc := range tests {
t.Run(tc.name, func(t *testing.T) {
result := sanitizeEmailBody(tc.input)
assert.Equal(t, tc.expected, result)
})
}
}
func TestMailService_TestConnection_NotConfigured(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
err := svc.TestConnection()
assert.Error(t, err)
assert.Contains(t, err.Error(), "not configured")
}
func TestMailService_SendEmail_NotConfigured(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
err := svc.SendEmail(context.Background(), []string{"test@example.com"}, "Subject", "<p>Body</p>")
assert.Error(t, err)
assert.Contains(t, err.Error(), "not configured")
}
func TestMailService_SendEmail_RejectsCRLFInSubject(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
config := &SMTPConfig{
Host: "smtp.example.com",
Port: 587,
FromAddress: "noreply@example.com",
}
require.NoError(t, svc.SaveSMTPConfig(config))
err := svc.SendEmail(context.Background(), []string{"recipient@example.com"}, "Hello\r\nBcc: evil@example.com", "Body")
assert.Error(t, err)
assert.Contains(t, err.Error(), "invalid subject")
}
func TestSMTPConfigSerialization(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
config := &SMTPConfig{
Host: "smtp.example.com",
Port: 587,
Username: "user@example.com",
Password: "p@$$w0rd!#$%",
FromAddress: "Charon <noreply@example.com>",
Encryption: "starttls",
}
err := svc.SaveSMTPConfig(config)
require.NoError(t, err)
retrieved, err := svc.GetSMTPConfig()
require.NoError(t, err)
assert.Equal(t, config.Password, retrieved.Password)
assert.Equal(t, config.FromAddress, retrieved.FromAddress)
}
func TestMailService_SendInvite_Template(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
err := svc.SendInvite("test@example.com", "abc123token", "TestApp", "https://example.com")
assert.Error(t, err)
assert.Contains(t, err.Error(), "not configured")
}
func BenchmarkMailService_IsConfigured(b *testing.B) {
db, _ := gorm.Open(sqlite.Open(":memory:"), &gorm.Config{
Logger: logger.Default.LogMode(logger.Silent),
})
_ = db.AutoMigrate(&models.Setting{})
svc := NewMailService(db)
config := &SMTPConfig{
Host: "smtp.example.com",
Port: 587,
FromAddress: "noreply@example.com",
}
_ = svc.SaveSMTPConfig(config)
b.ResetTimer()
for i := 0; i < b.N; i++ {
svc.IsConfigured()
}
}
func BenchmarkMailService_BuildEmail(b *testing.B) {
db, _ := gorm.Open(sqlite.Open(":memory:"), &gorm.Config{
Logger: logger.Default.LogMode(logger.Silent),
})
svc := NewMailService(db)
fromAddr, _ := mail.ParseAddress("sender@example.com")
toAddr, _ := mail.ParseAddress("recipient@example.com")
b.ResetTimer()
for i := 0; i < b.N; i++ {
_, _ = svc.buildEmail(fromAddr, toAddr, nil, "Test Subject", "<html><body>Test Body</body></html>")
}
}
func TestMailService_SendInvite_InvalidBaseURL_CRLF(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
err := svc.SendInvite("test@example.com", "token123", "TestApp", "https://example.com\r\nBcc: attacker@example.com")
assert.Error(t, err)
assert.Contains(t, err.Error(), "baseURL")
}
func TestMailService_SendInvite_InvalidBaseURL_Path(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
err := svc.SendInvite("test@example.com", "token123", "TestApp", "https://example.com/sneaky")
assert.Error(t, err)
assert.Contains(t, err.Error(), "baseURL")
}
func TestMailService_Integration(t *testing.T) {
if testing.Short() {
t.Skip("Skipping integration test in short mode")
}
t.Skip("Integration test requires SMTP server")
}
func TestMailService_SendInvite_TokenFormat(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
config := &SMTPConfig{
Host: "smtp.example.com",
Port: 587,
FromAddress: "noreply@example.com",
}
_ = svc.SaveSMTPConfig(config)
err := svc.SendInvite("test@example.com", "token123", "Charon", "https://charon.local/")
assert.Error(t, err)
err = svc.SendInvite("test@example.com", "token123", "Charon", "https://charon.local")
assert.Error(t, err)
}
func TestMailService_SaveSMTPConfig_Concurrent(t *testing.T) {
t.Skip("In-memory SQLite doesn't support concurrent writes - test real DB in integration")
}
func TestMailService_SendEmail_InvalidRecipient(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
config := &SMTPConfig{
Host: "smtp.example.com",
Port: 587,
FromAddress: "noreply@example.com",
}
require.NoError(t, svc.SaveSMTPConfig(config))
err := svc.SendEmail(context.Background(), []string{"invalid\r\nemail"}, "Subject", "Body")
assert.Error(t, err)
assert.Contains(t, err.Error(), "invalid recipient")
}
func TestMailService_SendEmail_InvalidFromAddress(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
config := &SMTPConfig{
Host: "smtp.example.com",
Port: 587,
FromAddress: "invalid\r\nfrom@example.com",
}
require.NoError(t, svc.SaveSMTPConfig(config))
err := svc.SendEmail(context.Background(), []string{"test@example.com"}, "Subject", "Body")
assert.Error(t, err)
assert.Contains(t, err.Error(), "invalid from address")
}
func TestMailService_SendEmail_EncryptionModes(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
tests := []struct {
name string
encryption string
}{
{"ssl", "ssl"},
{"starttls", "starttls"},
{"none", "none"},
{"empty", ""},
}
for _, tt := range tests {
t.Run(tt.name, func(t *testing.T) {
config := &SMTPConfig{
Host: "smtp.example.com",
Port: 587,
Username: "user",
Password: "pass",
FromAddress: "test@example.com",
Encryption: tt.encryption,
}
require.NoError(t, svc.SaveSMTPConfig(config))
err := svc.SendEmail(context.Background(), []string{"recipient@example.com"}, "Test", "Body")
assert.Error(t, err)
})
}
}
// TestMailService_SendEmail_CRLFInjection_Comprehensive tests CRLF injection prevention
// across all email header fields (CodeQL go/email-injection remediation)
func TestMailService_SendEmail_CRLFInjection_Comprehensive(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
config := &SMTPConfig{
Host: "smtp.example.com",
Port: 587,
FromAddress: "noreply@example.com",
Encryption: "starttls",
}
require.NoError(t, svc.SaveSMTPConfig(config))
tests := []struct {
name string
to string
subject string
fromAddress string
description string
}{
{
name: "CRLF in recipient address",
to: "victim@example.com\r\nBcc: attacker@evil.com",
subject: "Normal Subject",
fromAddress: "noreply@example.com",
description: "Reject CRLF in To header",
},
{
name: "CRLF in subject line",
to: "victim@example.com",
subject: "Test\r\nBcc: attacker@evil.com",
fromAddress: "noreply@example.com",
description: "Reject CRLF in Subject header",
},
{
name: "LF only in recipient",
to: "victim@example.com\nBcc: attacker@evil.com",
subject: "Normal Subject",
fromAddress: "noreply@example.com",
description: "Reject LF in To header",
},
{
name: "LF only in subject",
to: "victim@example.com",
subject: "Test\nBcc: attacker@evil.com",
fromAddress: "noreply@example.com",
description: "Reject LF in Subject header",
},
{
name: "CR only in recipient",
to: "victim@example.com\rBcc: attacker@evil.com",
subject: "Normal Subject",
fromAddress: "noreply@example.com",
description: "Reject CR in To header",
},
{
name: "multiple CRLF sequences",
to: "victim@example.com",
subject: "Test\r\nBcc: evil1@attacker.com\r\nCc: evil2@attacker.com",
fromAddress: "noreply@example.com",
description: "Reject multiple CRLF attempts",
},
}
for _, tc := range tests {
t.Run(tc.name, func(t *testing.T) {
// Update config with potentially malicious from address if specified
if tc.fromAddress != config.FromAddress {
testConfig := *config
testConfig.FromAddress = tc.fromAddress
require.NoError(t, svc.SaveSMTPConfig(&testConfig))
}
err := svc.SendEmail(context.Background(), []string{tc.to}, tc.subject, "<p>Normal body</p>")
assert.Error(t, err, tc.description)
assert.Contains(t, err.Error(), "invalid", "Error should indicate invalid input")
})
}
}
// TestMailService_SendInvite_CRLFInjection tests CRLF injection prevention in invite emails
// TestMailService_BuildEmail_UndisclosedRecipients verifies that buildEmail uses
// "undisclosed-recipients:;" in the To: header instead of the actual recipient address.
// This prevents request-derived data from appearing in message headers (CodeQL go/email-injection).
func TestMailService_BuildEmail_UndisclosedRecipients(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
fromAddr, err := mail.ParseAddress("sender@example.com")
require.NoError(t, err)
toAddr, err := mail.ParseAddress("recipient@example.com")
require.NoError(t, err)
// Encode subject as SendEmail would
encodedSubject, err := encodeSubject("Test Subject")
require.NoError(t, err)
msg, err := svc.buildEmail(fromAddr, toAddr, nil, encodedSubject, "<html><body>Test Body</body></html>")
require.NoError(t, err)
msgStr := string(msg)
// MUST contain undisclosed recipients header
assert.Contains(t, msgStr, "To: undisclosed-recipients:;", "To header must use undisclosed recipients")
// MUST NOT contain the actual recipient email address in headers
// Split message into headers and body
parts := strings.Split(msgStr, "\r\n\r\n")
require.Len(t, parts, 2, "Email should have headers and body sections")
headers := parts[0]
assert.NotContains(t, headers, "recipient@example.com", "Recipient email must not appear in message headers")
}
// TestMailService_SendInvite_HTMLTemplateEscaping verifies that the HTML template
// properly escapes special characters in user-controlled fields like appName.
func TestMailService_SendInvite_HTMLTemplateEscaping(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
config := &SMTPConfig{
Host: "smtp.example.com",
Port: 587,
FromAddress: "noreply@example.com",
Encryption: "starttls",
}
require.NoError(t, svc.SaveSMTPConfig(config))
// Use appName with HTML tags that should be escaped
maliciousAppName := "<b>XSS</b><script>alert('test')</script>"
baseURL := "https://example.com"
token := "testtoken123"
// SendInvite will fail because SMTP isn't actually configured,
// but we can test the template rendering by calling the internal logic
// directly through a helper or by examining the error path.
// For now, we'll test that the appName validation rejects CRLF
// (HTML injection in templates is handled by html/template auto-escaping)
err := svc.SendInvite("test@example.com", token, maliciousAppName, baseURL)
assert.Error(t, err) // Will fail due to SMTP not actually running
// The key security property is that html/template auto-escapes {{.AppName}}
// This is verified by the template engine itself, not by our code
}
func TestMailService_SendInvite_CRLFInjection(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
config := &SMTPConfig{
Host: "smtp.example.com",
Port: 587,
FromAddress: "noreply@example.com",
Encryption: "starttls",
}
require.NoError(t, svc.SaveSMTPConfig(config))
tests := []struct {
name string
email string
token string
appName string
baseURL string
description string
}{
{
name: "CRLF in email address",
email: "victim@example.com\r\nBcc: attacker@evil.com",
token: "token123",
appName: "TestApp",
baseURL: "https://example.com",
description: "Reject CRLF in invite email address",
},
{
name: "CRLF in baseURL",
email: "user@example.com",
token: "token123",
appName: "TestApp",
baseURL: "https://example.com\r\nBcc: attacker@evil.com",
description: "Reject CRLF in invite baseURL",
},
{
name: "CRLF in app name (subject)",
email: "user@example.com",
token: "token123",
appName: "TestApp\r\nBcc: attacker@evil.com",
baseURL: "https://example.com",
description: "Reject CRLF in app name used in subject",
},
}
for _, tc := range tests {
t.Run(tc.name, func(t *testing.T) {
err := svc.SendInvite(tc.email, tc.token, tc.appName, tc.baseURL)
assert.Error(t, err, tc.description)
})
}
}
func TestRejectCRLF(t *testing.T) {
t.Parallel()
require.NoError(t, rejectCRLF("normal-value"))
require.ErrorIs(t, rejectCRLF("bad\r\nvalue"), errEmailHeaderInjection)
}
func TestNormalizeBaseURLForInvite(t *testing.T) {
t.Parallel()
tests := []struct {
name string
raw string
want string
wantErr bool
}{
{name: "valid https", raw: "https://example.com", want: "https://example.com", wantErr: false},
{name: "valid http with slash path", raw: "https://discord.com/api/webhooks/123/abc/", want: "https://discord.com/api/webhooks/123/abc", wantErr: false},
{name: "empty", raw: "", wantErr: true},
{name: "invalid scheme", raw: "ftp://example.com", wantErr: true},
{name: "with path", raw: "https://example.com/path", wantErr: true},
{name: "with query", raw: "https://example.com?x=1", wantErr: true},
{name: "with fragment", raw: "https://example.com#frag", wantErr: true},
{name: "with user info", raw: "https://user@example.com", wantErr: true},
{name: "with header injection", raw: "https://example.com\r\nX-Test: 1", wantErr: true},
}
for _, tt := range tests {
t.Run(tt.name, func(t *testing.T) {
got, err := normalizeBaseURLForInvite(tt.raw)
if tt.wantErr {
require.Error(t, err)
require.ErrorIs(t, err, errInvalidBaseURLForInvite)
return
}
require.NoError(t, err)
require.Equal(t, tt.want, got)
})
}
}
func TestEncodeSubject_RejectsCRLF(t *testing.T) {
t.Parallel()
_, err := encodeSubject("Hello\r\nWorld")
require.Error(t, err)
require.ErrorIs(t, err, errEmailHeaderInjection)
}
// Shared test CA infrastructure to work around Go's cert pool caching.
// When tests run with -count=N, Go caches x509.SystemCertPool() after the first run.
// Generating a new CA per test causes failures because cached pool references old CA.
// Solution: Generate CA once, reuse across runs, and use stable cert file path.
var (
testCAOnce sync.Once
testCAPEM []byte
testCAKey *rsa.PrivateKey
testCATemplate *x509.Certificate
testCAFile string
)
func initTestCA(t *testing.T) {
t.Helper()
// Delegate to the suite-level initialization (already called by TestMain)
initializeTestCAForSuite()
}
func newTestTLSConfigShared(t *testing.T) (*tls.Config, []byte) {
t.Helper()
// Ensure shared CA is initialized
initTestCA(t)
// Generate leaf certificate signed by shared CA
leafKey, err := rsa.GenerateKey(rand.Reader, 2048)
require.NoError(t, err)
leafTemplate := &x509.Certificate{
SerialNumber: big.NewInt(time.Now().UnixNano()), // Unique serial per leaf
Subject: pkix.Name{
CommonName: "127.0.0.1",
},
NotBefore: time.Now().Add(-time.Hour),
NotAfter: time.Now().Add(24 * time.Hour),
KeyUsage: x509.KeyUsageDigitalSignature | x509.KeyUsageKeyEncipherment,
ExtKeyUsage: []x509.ExtKeyUsage{x509.ExtKeyUsageServerAuth},
BasicConstraintsValid: true,
DNSNames: []string{"localhost"},
IPAddresses: []net.IP{net.ParseIP("127.0.0.1")},
}
leafDER, err := x509.CreateCertificate(rand.Reader, leafTemplate, testCATemplate, &leafKey.PublicKey, testCAKey)
require.NoError(t, err)
leafCertPEM := pem.EncodeToMemory(&pem.Block{Type: "CERTIFICATE", Bytes: leafDER})
leafKeyPEM := pem.EncodeToMemory(&pem.Block{Type: "RSA PRIVATE KEY", Bytes: x509.MarshalPKCS1PrivateKey(leafKey)})
cert, err := tls.X509KeyPair(leafCertPEM, leafKeyPEM)
require.NoError(t, err)
return &tls.Config{Certificates: []tls.Certificate{cert}, MinVersion: tls.VersionTLS12}, testCAPEM
}
func TestMailService_GetSMTPConfig_DBError(t *testing.T) {
t.Parallel()
db := setupMailTestDB(t)
svc := NewMailService(db)
sqlDB, err := db.DB()
require.NoError(t, err)
require.NoError(t, sqlDB.Close())
_, err = svc.GetSMTPConfig()
assert.Error(t, err)
assert.Contains(t, err.Error(), "failed to load SMTP settings")
}
func TestMailService_GetSMTPConfig_InvalidPortFallback(t *testing.T) {
t.Parallel()
db := setupMailTestDB(t)
svc := NewMailService(db)
require.NoError(t, db.Create(&models.Setting{Key: "smtp_host", Value: "smtp.example.com", Type: "string", Category: "smtp"}).Error)
require.NoError(t, db.Create(&models.Setting{Key: "smtp_port", Value: "invalid", Type: "string", Category: "smtp"}).Error)
require.NoError(t, db.Create(&models.Setting{Key: "smtp_from_address", Value: "noreply@example.com", Type: "string", Category: "smtp"}).Error)
config, err := svc.GetSMTPConfig()
require.NoError(t, err)
assert.Equal(t, 587, config.Port)
}
func TestMailService_BuildEmail_NilAddressValidation(t *testing.T) {
t.Parallel()
db := setupMailTestDB(t)
svc := NewMailService(db)
toAddr, err := mail.ParseAddress("recipient@example.com")
require.NoError(t, err)
_, err = svc.buildEmail(nil, toAddr, nil, "Subject", "Body")
assert.Error(t, err)
assert.Contains(t, err.Error(), "from address is required")
fromAddr, err := mail.ParseAddress("sender@example.com")
require.NoError(t, err)
_, err = svc.buildEmail(fromAddr, nil, nil, "Subject", "Body")
assert.Error(t, err)
assert.Contains(t, err.Error(), "to address is required")
}
func TestWriteEmailHeader_RejectsCRLFValue(t *testing.T) {
t.Parallel()
var buf bytes.Buffer
err := writeEmailHeader(&buf, headerSubject, "bad\r\nvalue")
assert.Error(t, err)
}
func TestMailService_sendSSL_DialFailure(t *testing.T) {
t.Parallel()
db := setupMailTestDB(t)
svc := NewMailService(db)
err := svc.sendSSL(
"127.0.0.1:1",
&SMTPConfig{Host: "127.0.0.1"},
nil,
"from@example.com",
"to@example.com",
[]byte("test"),
)
assert.Error(t, err)
assert.Contains(t, err.Error(), "SSL connection failed")
}
func TestMailService_sendSTARTTLS_DialFailure(t *testing.T) {
t.Parallel()
db := setupMailTestDB(t)
svc := NewMailService(db)
err := svc.sendSTARTTLS(
"127.0.0.1:1",
&SMTPConfig{Host: "127.0.0.1"},
nil,
"from@example.com",
"to@example.com",
[]byte("test"),
)
assert.Error(t, err)
assert.Contains(t, err.Error(), "SMTP connection failed")
}
func TestMailService_TestConnection_StartTLSSuccessWithAuth(t *testing.T) {
t.Parallel()
tlsConf, _ := newTestTLSConfigShared(t)
trustTestCertificate(t, nil)
addr, cleanup := startMockSMTPServer(t, tlsConf, true, true)
defer cleanup()
host, portStr, err := net.SplitHostPort(addr)
require.NoError(t, err)
port, err := strconv.Atoi(portStr)
require.NoError(t, err)
db := setupMailTestDB(t)
svc := NewMailService(db)
require.NoError(t, svc.SaveSMTPConfig(&SMTPConfig{
Host: host,
Port: port,
Username: "user",
Password: "pass",
FromAddress: "sender@example.com",
Encryption: "starttls",
}))
require.NoError(t, svc.TestConnection())
}
func TestMailService_TestConnection_NoneSuccess(t *testing.T) {
t.Parallel()
tlsConf, _ := newTestTLSConfig(t)
addr, cleanup := startMockSMTPServer(t, tlsConf, false, false)
defer cleanup()
host, portStr, err := net.SplitHostPort(addr)
require.NoError(t, err)
port, err := strconv.Atoi(portStr)
require.NoError(t, err)
db := setupMailTestDB(t)
svc := NewMailService(db)
require.NoError(t, svc.SaveSMTPConfig(&SMTPConfig{
Host: host,
Port: port,
FromAddress: "sender@example.com",
Encryption: "none",
}))
require.NoError(t, svc.TestConnection())
}
func TestMailService_SendEmail_STARTTLSSuccess(t *testing.T) {
t.Parallel()
tlsConf, _ := newTestTLSConfigShared(t)
trustTestCertificate(t, nil)
addr, cleanup := startMockSMTPServer(t, tlsConf, true, true)
defer cleanup()
host, portStr, err := net.SplitHostPort(addr)
require.NoError(t, err)
port, err := strconv.Atoi(portStr)
require.NoError(t, err)
db := setupMailTestDB(t)
svc := NewMailService(db)
require.NoError(t, svc.SaveSMTPConfig(&SMTPConfig{
Host: host,
Port: port,
Username: "user",
Password: "pass",
FromAddress: "sender@example.com",
Encryption: "starttls",
}))
// With fixed cert trust, STARTTLS connection and email send succeed
err = svc.SendEmail(context.Background(), []string{"recipient@example.com"}, "Subject", "Body")
require.NoError(t, err)
}
func TestMailService_SendEmail_SSLSuccess(t *testing.T) {
t.Parallel()
tlsConf, _ := newTestTLSConfigShared(t)
trustTestCertificate(t, nil)
addr, cleanup := startMockSSLSMTPServer(t, tlsConf, true)
defer cleanup()
host, portStr, err := net.SplitHostPort(addr)
require.NoError(t, err)
port, err := strconv.Atoi(portStr)
require.NoError(t, err)
db := setupMailTestDB(t)
svc := NewMailService(db)
require.NoError(t, svc.SaveSMTPConfig(&SMTPConfig{
Host: host,
Port: port,
Username: "user",
Password: "pass",
FromAddress: "sender@example.com",
Encryption: "ssl",
}))
// With fixed cert trust, SSL connection and email send succeed
err = svc.SendEmail(context.Background(), []string{"recipient@example.com"}, "Subject", "Body")
require.NoError(t, err)
}
func TestMailService_SendEmail_ContextCancelled(t *testing.T) {
t.Parallel()
db := setupMailTestDB(t)
svc := NewMailService(db)
require.NoError(t, svc.SaveSMTPConfig(&SMTPConfig{
Host: "127.0.0.1",
Port: 2525,
FromAddress: "sender@example.com",
Encryption: "none",
}))
ctx, cancel := context.WithCancel(context.Background())
cancel() // cancel immediately
err := svc.SendEmail(ctx, []string{"recipient@example.com"}, "Test Subject", "<p>Body</p>")
require.Error(t, err)
assert.Contains(t, err.Error(), "context cancelled")
}
func TestSanitizeAndNormalizeHTMLBody_EmptyInput(t *testing.T) {
t.Parallel()
assert.Equal(t, "", sanitizeAndNormalizeHTMLBody(""))
}
func TestSanitizeAndNormalizeHTMLBody_SingleLine(t *testing.T) {
t.Parallel()
result := sanitizeAndNormalizeHTMLBody("Hello World")
assert.Equal(t, "<p>Hello World</p>", result)
}
func TestSanitizeAndNormalizeHTMLBody_HTMLEscaping(t *testing.T) {
t.Parallel()
result := sanitizeAndNormalizeHTMLBody("<script>alert('xss')</script>")
assert.NotContains(t, result, "<script>")
assert.Contains(t, result, "&lt;script&gt;")
}
func newTestTLSConfig(t *testing.T) (*tls.Config, []byte) {
t.Helper()
caKey, err := rsa.GenerateKey(rand.Reader, 2048)
require.NoError(t, err)
caTemplate := &x509.Certificate{
SerialNumber: big.NewInt(1),
Subject: pkix.Name{
CommonName: "charon-test-ca",
},
NotBefore: time.Now().Add(-time.Hour),
NotAfter: time.Now().Add(24 * time.Hour),
KeyUsage: x509.KeyUsageCertSign | x509.KeyUsageCRLSign,
BasicConstraintsValid: true,
IsCA: true,
}
caDER, err := x509.CreateCertificate(rand.Reader, caTemplate, caTemplate, &caKey.PublicKey, caKey)
require.NoError(t, err)
caPEM := pem.EncodeToMemory(&pem.Block{Type: "CERTIFICATE", Bytes: caDER})
leafKey, err := rsa.GenerateKey(rand.Reader, 2048)
require.NoError(t, err)
leafTemplate := &x509.Certificate{
SerialNumber: big.NewInt(2),
Subject: pkix.Name{
CommonName: "127.0.0.1",
},
NotBefore: time.Now().Add(-time.Hour),
NotAfter: time.Now().Add(24 * time.Hour),
KeyUsage: x509.KeyUsageDigitalSignature | x509.KeyUsageKeyEncipherment,
ExtKeyUsage: []x509.ExtKeyUsage{x509.ExtKeyUsageServerAuth},
BasicConstraintsValid: true,
DNSNames: []string{"localhost"},
IPAddresses: []net.IP{net.ParseIP("127.0.0.1")},
}
leafDER, err := x509.CreateCertificate(rand.Reader, leafTemplate, caTemplate, &leafKey.PublicKey, caKey)
require.NoError(t, err)
leafCertPEM := pem.EncodeToMemory(&pem.Block{Type: "CERTIFICATE", Bytes: leafDER})
leafKeyPEM := pem.EncodeToMemory(&pem.Block{Type: "RSA PRIVATE KEY", Bytes: x509.MarshalPKCS1PrivateKey(leafKey)})
cert, err := tls.X509KeyPair(leafCertPEM, leafKeyPEM)
require.NoError(t, err)
return &tls.Config{Certificates: []tls.Certificate{cert}, MinVersion: tls.VersionTLS12}, caPEM
}
func trustTestCertificate(t *testing.T, _ []byte) {
t.Helper()
// SSL_CERT_FILE is already set globally by TestMain.
// This function kept for API compatibility but no longer needs to set environment.
initTestCA(t) // Ensure CA is initialized (already done by TestMain, but safe to call)
}
func startMockSMTPServer(t *testing.T, tlsConf *tls.Config, supportStartTLS bool, requireAuth bool) (string, func()) {
t.Helper()
listener, err := net.Listen("tcp", "127.0.0.1:0")
require.NoError(t, err)
done := make(chan struct{})
var wg sync.WaitGroup
var connsMu sync.Mutex
var conns []net.Conn
go func() {
defer close(done)
for {
conn, acceptErr := listener.Accept()
if acceptErr != nil {
// Expected shutdown path: listener closed
if errors.Is(acceptErr, net.ErrClosed) || strings.Contains(acceptErr.Error(), "use of closed network connection") {
return
}
// Unexpected accept error - signal test failure
t.Errorf("unexpected accept error: %v", acceptErr)
return
}
connsMu.Lock()
conns = append(conns, conn)
connsMu.Unlock()
wg.Add(1)
go func(c net.Conn) {
defer wg.Done()
defer func() { _ = c.Close() }()
handleSMTPConn(c, tlsConf, supportStartTLS, requireAuth)
}(conn)
}
}()
cleanup := func() {
_ = listener.Close()
// Close all active connections to unblock handlers
connsMu.Lock()
for _, conn := range conns {
_ = conn.Close()
}
connsMu.Unlock()
// Wait for accept-loop exit and active handlers with timeout
cleanupDone := make(chan struct{})
go func() {
<-done
wg.Wait()
close(cleanupDone)
}()
select {
case <-cleanupDone:
// Success
case <-time.After(2 * time.Second):
t.Errorf("cleanup timeout: server did not shut down cleanly")
}
}
return listener.Addr().String(), cleanup
}
func startMockSSLSMTPServer(t *testing.T, tlsConf *tls.Config, requireAuth bool) (string, func()) {
t.Helper()
listener, err := tls.Listen("tcp", "127.0.0.1:0", tlsConf)
require.NoError(t, err)
done := make(chan struct{})
var wg sync.WaitGroup
var connsMu sync.Mutex
var conns []net.Conn
go func() {
defer close(done)
for {
conn, acceptErr := listener.Accept()
if acceptErr != nil {
// Expected shutdown path: listener closed
if errors.Is(acceptErr, net.ErrClosed) || strings.Contains(acceptErr.Error(), "use of closed network connection") {
return
}
// Unexpected accept error - signal test failure
t.Errorf("unexpected accept error: %v", acceptErr)
return
}
connsMu.Lock()
conns = append(conns, conn)
connsMu.Unlock()
wg.Add(1)
go func(c net.Conn) {
defer wg.Done()
defer func() { _ = c.Close() }()
handleSMTPConn(c, tlsConf, false, requireAuth)
}(conn)
}
}()
cleanup := func() {
_ = listener.Close()
// Close all active connections to unblock handlers
connsMu.Lock()
for _, conn := range conns {
_ = conn.Close()
}
connsMu.Unlock()
// Wait for accept-loop exit and active handlers with timeout
cleanupDone := make(chan struct{})
go func() {
<-done
wg.Wait()
close(cleanupDone)
}()
select {
case <-cleanupDone:
// Success
case <-time.After(2 * time.Second):
t.Errorf("cleanup timeout: server did not shut down cleanly")
}
}
return listener.Addr().String(), cleanup
}
func handleSMTPConn(conn net.Conn, tlsConf *tls.Config, supportStartTLS bool, requireAuth bool) {
reader := bufio.NewReader(conn)
writer := bufio.NewWriter(conn)
writeLine := func(line string) {
_, _ = writer.WriteString(line + "\r\n")
_ = writer.Flush()
}
writeLine("220 localhost ESMTP")
tlsUpgraded := false
for {
line, err := reader.ReadString('\n')
if err != nil {
return
}
command := strings.ToUpper(strings.TrimSpace(line))
switch {
case strings.HasPrefix(command, "EHLO") || strings.HasPrefix(command, "HELO"):
if supportStartTLS && !tlsUpgraded {
writeLine("250-localhost")
writeLine("250-STARTTLS")
writeLine("250 AUTH PLAIN")
} else {
writeLine("250-localhost")
writeLine("250 AUTH PLAIN")
}
case strings.HasPrefix(command, "STARTTLS"):
if !supportStartTLS || tlsUpgraded {
writeLine("454 TLS not available")
continue
}
writeLine("220 Ready to start TLS")
tlsConn := tls.Server(conn, tlsConf)
if handshakeErr := tlsConn.Handshake(); handshakeErr != nil {
return
}
conn = tlsConn
reader = bufio.NewReader(conn)
writer = bufio.NewWriter(conn)
tlsUpgraded = true
case strings.HasPrefix(command, "AUTH"):
if requireAuth {
writeLine("235 Authentication successful")
} else {
writeLine("235 Authentication accepted")
}
case strings.HasPrefix(command, "MAIL FROM"):
writeLine("250 OK")
case strings.HasPrefix(command, "RCPT TO"):
writeLine("250 OK")
case strings.HasPrefix(command, "DATA"):
writeLine("354 End data with <CR><LF>.<CR><LF>")
for {
dataLine, readErr := reader.ReadString('\n')
if readErr != nil {
return
}
if dataLine == ".\r\n" {
break
}
}
writeLine("250 Message accepted")
case strings.HasPrefix(command, "QUIT"):
writeLine("221 Bye")
return
default:
writeLine("250 OK")
}
}
}
func TestValidateEmailRecipients_Empty(t *testing.T) {
err := validateEmailRecipients([]string{})
assert.NoError(t, err)
}
func TestValidateEmailRecipients_Valid(t *testing.T) {
err := validateEmailRecipients([]string{"a@b.com", "c@d.org"})
assert.NoError(t, err)
}
func TestValidateEmailRecipients_TooMany(t *testing.T) {
recipients := make([]string, 21)
for i := range recipients {
recipients[i] = "a@b.com"
}
err := validateEmailRecipients(recipients)
assert.ErrorIs(t, err, ErrTooManyRecipients)
}
func TestValidateEmailRecipients_CRLFInRecipient(t *testing.T) {
err := validateEmailRecipients([]string{"victim@example.com\r\nBcc: evil@bad.com"})
assert.ErrorIs(t, err, ErrInvalidRecipient)
}
func TestValidateEmailRecipients_InvalidFormat(t *testing.T) {
err := validateEmailRecipients([]string{"not-an-email"})
assert.ErrorIs(t, err, ErrInvalidRecipient)
}
func TestValidateEmailRecipients_ExactlyTwenty(t *testing.T) {
recipients := make([]string, 20)
for i := range recipients {
recipients[i] = "a@b.com"
}
err := validateEmailRecipients(recipients)
assert.NoError(t, err)
}
func TestSendEmail_TooManyRecipients(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
cfg := &SMTPConfig{Host: "smtp.example.com", Port: 587, FromAddress: "from@example.com"}
require.NoError(t, svc.SaveSMTPConfig(cfg))
recipients := make([]string, 21)
for i := range recipients {
recipients[i] = fmt.Sprintf("user%d@example.com", i)
}
err := svc.SendEmail(context.Background(), recipients, "Subject", "<p>Body</p>")
require.Error(t, err)
assert.ErrorIs(t, err, ErrTooManyRecipients)
}
func TestSendEmail_HeaderInjectionInRecipient(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
cfg := &SMTPConfig{Host: "smtp.example.com", Port: 587, FromAddress: "from@example.com"}
require.NoError(t, svc.SaveSMTPConfig(cfg))
err := svc.SendEmail(context.Background(), []string{"bad\r\naddr@test.com"}, "Subject", "<p>Body</p>")
require.Error(t, err)
assert.ErrorIs(t, err, ErrInvalidRecipient)
}
func TestSendEmail_InvalidRFC5322Recipient(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
cfg := &SMTPConfig{Host: "smtp.example.com", Port: 587, FromAddress: "from@example.com"}
require.NoError(t, svc.SaveSMTPConfig(cfg))
err := svc.SendEmail(context.Background(), []string{"notanemail"}, "Subject", "<p>Body</p>")
require.Error(t, err)
assert.ErrorIs(t, err, ErrInvalidRecipient)
}
func TestSendEmail_ValidMultipleRecipients(t *testing.T) {
db := setupMailTestDB(t)
svc := NewMailService(db)
// Use a mock SMTP server to capture the connection attempt.
// Since we're not running a real SMTP server, the actual send will fail,
// but validation (the part being tested) must pass — error must NOT be ErrInvalidRecipient or ErrTooManyRecipients.
cfg := &SMTPConfig{Host: "127.0.0.1", Port: 19999, FromAddress: "from@example.com"}
require.NoError(t, svc.SaveSMTPConfig(cfg))
err := svc.SendEmail(context.Background(),
[]string{"alice@example.com", "bob@example.com", "carol@example.com"},
"Test Subject", "<p>Hello</p>",
)
// Validation must pass; connection refused error expected (no SMTP server running)
if err != nil {
assert.NotErrorIs(t, err, ErrInvalidRecipient)
assert.NotErrorIs(t, err, ErrTooManyRecipients)
}
}