normalize email from

.env.example

@@ -70,8 +70,13 @@ ACCOUNT_CONFIRMATION_REQUIRED=false
 SHARE_CONFIRMATION_REQUIRED=true
 
 # smtp mailing
+# port 465 → tls
+# port 587 → starttls
 PUBLIC_URL=https://pad.example.com
 # SMTP_HOST=smtp.example.com
+#SMTP_SECURITY=none
+SMTP_SECURITY=starttls
+#SMTP_SECURITY=tls
 SMTP_PORT=587
 SMTP_USERNAME=
 SMTP_PASSWORD=

Cargo.lock

@@ -2581,7 +2581,7 @@ dependencies = [
 
 [[package]]
 name = "rustpad"
-version = "0.1.8"
+version = "0.1.9"
 dependencies = [
  "argon2",
  "aws-config",

Cargo.toml

@@ -1,6 +1,6 @@
 [package]
 name = "rustpad"
-version = "0.1.8"
+version = "0.1.9"
 edition = "2024"
 rust-version = "1.94"
 description = "Collaborative Markdown notepad built with Axum, WebSockets and SQLite, PostgreSQL and MySQL"

README.md

@@ -121,7 +121,7 @@ Migrations are stored in `migrations/sqlite`, `migrations/postgres`, and `migrat
 
 Nicknames can be used anonymously while they remain unregistered. Registering a nickname reserves it and requires a valid login session before it can be used in editor WebSocket connections.
 
-Configure `PUBLIC_URL`, `SMTP_HOST`, `SMTP_PORT`, `SMTP_USERNAME`, `SMTP_PASSWORD`, and `SMTP_FROM` to enable password-reset emails. `SMTP_FROM` accepts both `RustPad <no-reply@example.com>` and a value wrapped in one matching pair of single or double quotes, as may be passed literally by container env-file implementations. Reset links expire after 30 minutes and can be used only once.
+Configure `PUBLIC_URL`, `SMTP_HOST`, `SMTP_PORT`, `SMTP_SECURITY`, `SMTP_USERNAME`, `SMTP_PASSWORD`, and `SMTP_FROM` to enable password-reset emails. `SMTP_FROM` accepts both `RustPad <no-reply@example.com>` and a value wrapped in one matching pair of single or double quotes, as may be passed literally by container env-file implementations. `SMTP_SECURITY` accepts `none` (plain SMTP, typically an internal relay on port 25), `starttls`, or `tls` (implicit TLS, commonly port 465). When omitted, it defaults to `tls` for port 465 and `starttls` for other ports. Reset links expire after 30 minutes and can be used only once.
 
 ## Diagnostics and logging
 

src/auth/mod.rs

@@ -25,7 +25,7 @@ use tracing::{debug, info, warn};
 
 use crate::{
     queries,
-    state::{SharedState, SmtpConfig},
+    state::{SharedState, SmtpConfig, SmtpSecurity},
 };
 
 const MIN_PASSWORD: usize = 8;
@@ -2098,15 +2098,19 @@ async fn send_share_invitation(
 }
 
 async fn send_message(smtp: &SmtpConfig, message: Message, label: &str) -> Result<(), AuthError> {
-    let mut builder = if smtp.port == 465 {
+    let mut builder = match smtp.security {
-        AsyncSmtpTransport::<Tokio1Executor>::relay(&smtp.host)
+        SmtpSecurity::None => AsyncSmtpTransport::<Tokio1Executor>::builder_dangerous(&smtp.host),
-    } else {
+        SmtpSecurity::StartTls => AsyncSmtpTransport::<Tokio1Executor>::starttls_relay(&smtp.host)
-        AsyncSmtpTransport::<Tokio1Executor>::starttls_relay(&smtp.host)
+            .map_err(|error| {
+                tracing::error!(error = %error, host = %smtp.host, port = smtp.port, security = ?smtp.security, "invalid SMTP configuration");
+                AuthError::internal("Invalid SMTP configuration.")
+            })?,
+        SmtpSecurity::Tls => AsyncSmtpTransport::<Tokio1Executor>::relay(&smtp.host)
+            .map_err(|error| {
+                tracing::error!(error = %error, host = %smtp.host, port = smtp.port, security = ?smtp.security, "invalid SMTP configuration");
+                AuthError::internal("Invalid SMTP configuration.")
+            })?,
     }
-    .map_err(|error| {
-        tracing::error!(error = %error, host = %smtp.host, port = smtp.port, "invalid SMTP configuration");
-        AuthError::internal("Invalid SMTP configuration.")
-    })?
     .port(smtp.port);
 
     if !smtp.username.is_empty() {

src/config.rs

@@ -121,6 +121,10 @@ impl Config {
             Some(crate::state::SmtpConfig {
                 host,
                 port: values.get("SMTP_PORT", "587").parse()?,
+                security: parse_smtp_security(&values.get(
+                    "SMTP_SECURITY",
+                    if values.get("SMTP_PORT", "587") == "465" { "tls" } else { "starttls" },
+                ))?,
                 username: values.get("SMTP_USERNAME", ""),
                 password: values.get("SMTP_PASSWORD", ""),
                 from: normalize_smtp_from(
@@ -187,6 +191,15 @@ impl Config {
 
 
 
+fn parse_smtp_security(value: &str) -> Result<crate::state::SmtpSecurity, Box<dyn std::error::Error>> {
+    match value.trim().to_ascii_lowercase().as_str() {
+        "none" | "plain" => Ok(crate::state::SmtpSecurity::None),
+        "starttls" => Ok(crate::state::SmtpSecurity::StartTls),
+        "tls" | "ssl" | "smtps" => Ok(crate::state::SmtpSecurity::Tls),
+        _ => Err("SMTP_SECURITY must be one of: none, starttls, tls".into()),
+    }
+}
+
 fn normalize_smtp_from(value: String) -> Result<String, Box<dyn std::error::Error>> {
     let trimmed = value.trim();
     if trimmed.is_empty() {
@@ -225,7 +238,7 @@ const KNOWN_CONFIG_KEYS: &[&str] = &[
     "FRONTEND_LOG_LEVEL", "ANONYMOUS_ACCESS_TOKEN_TTL_DAYS", "USER_SESSION_TTL_DAYS",
     "UNCONFIRMED_ACCOUNT_TTL_DAYS", "AUTHORIZATION_TYPE",
     "S3_ENDPOINT", "S3_REGION", "S3_BUCKET", "S3_ACCESS_KEY", "S3_SECRET_KEY",
-    "S3_FORCE_PATH_STYLE", "SMTP_HOST", "SMTP_PORT", "SMTP_USERNAME", "SMTP_PASSWORD",
+    "S3_FORCE_PATH_STYLE", "SMTP_HOST", "SMTP_PORT", "SMTP_SECURITY", "SMTP_USERNAME", "SMTP_PASSWORD",
     "SMTP_FROM", "PUBLIC_URL", "LDAP_URL", "LDAP_STARTTLS", "LDAP_BIND_DN",
     "LDAP_BIND_PASSWORD", "LDAP_BASE_DN", "LDAP_USER_FILTER", "LDAP_USERNAME_ATTRIBUTE",
     "LDAP_EMAIL_ATTRIBUTE", "LDAP_DISPLAY_NAME_ATTRIBUTE", "LDAP_EXTERNAL_ID_ATTRIBUTE",
@@ -387,7 +400,20 @@ fn parse_yaml_scalar(value: &str) -> Result<String, String> {
 
 #[cfg(test)]
 mod tests {
-    use super::normalize_smtp_from;
+    use super::{normalize_smtp_from, parse_smtp_security};
+    use crate::state::SmtpSecurity;
+
+    #[test]
+    fn smtp_security_accepts_supported_modes() {
+        assert_eq!(parse_smtp_security("none").unwrap(), SmtpSecurity::None);
+        assert_eq!(parse_smtp_security("starttls").unwrap(), SmtpSecurity::StartTls);
+        assert_eq!(parse_smtp_security("tls").unwrap(), SmtpSecurity::Tls);
+    }
+
+    #[test]
+    fn smtp_security_rejects_unknown_mode() {
+        assert!(parse_smtp_security("auto").is_err());
+    }
 
     #[test]
     fn smtp_from_accepts_unquoted_value() {

src/state.rs

@@ -11,10 +11,18 @@ use tokio::sync::{RwLock, broadcast};
 
 const CHANNEL_CAPACITY: usize = 256;
 
+#[derive(Debug, Clone, Copy, PartialEq, Eq)]
+pub enum SmtpSecurity {
+    None,
+    StartTls,
+    Tls,
+}
+
 #[derive(Debug, Clone)]
 pub struct SmtpConfig {
     pub host: String,
     pub port: u16,
+    pub security: SmtpSecurity,
     pub username: String,
     pub password: String,
     pub from: String,