diff --git a/.env b/.env
index 735724ee..475df852 100644
--- a/.env
+++ b/.env
@@ -41,3 +41,10 @@
 # ROCKET_ADDRESS=0.0.0.0 # Enable this to test mobile app
 # ROCKET_PORT=8000
 # ROCKET_TLS={certs="/path/to/certs.pem",key="/path/to/key.pem"}
+
+## Mail specific settings, if SMTP_HOST is specified, SMTP_USERNAME and SMTP_PASSWORD are mandatory
+# SMTP_HOST=smtp.domain.tld
+# SMTP_PORT=587
+# SMTP_SSL=true
+# SMTP_USERNAME=username
+# SMTP_PASSWORD=password
\ No newline at end of file
diff --git a/Cargo.toml b/Cargo.toml
index fb5adafb..537b4e1e 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -58,6 +58,10 @@ lazy_static = "1.0.1"
 num-traits = "0.2.5"
 num-derive = "0.2.2"
 
+lettre = "0.8.2"
+lettre_email = "0.8.2"
+native-tls = "0.1.5"
+
 [patch.crates-io]
  # Make jwt use ring 0.11, to match rocket
 jsonwebtoken = { path = "libs/jsonwebtoken" }
diff --git a/src/api/core/accounts.rs b/src/api/core/accounts.rs
index e45c08dc..bc018f1e 100644
--- a/src/api/core/accounts.rs
+++ b/src/api/core/accounts.rs
@@ -5,6 +5,7 @@ use db::models::*;
 
 use api::{PasswordData, JsonResult, EmptyResult, JsonUpcase, NumberOrString};
 use auth::Headers;
+use mail;
 
 use CONFIG;
 
@@ -258,15 +259,23 @@ struct PasswordHintData {
 fn password_hint(data: JsonUpcase<PasswordHintData>, conn: DbConn) -> EmptyResult {
     let data: PasswordHintData = data.into_inner().data;
 
-    if !CONFIG.show_password_hint {
-        return Ok(())
+    let user = User::find_by_mail(&data.Email, &conn);
+    if user.is_none() {
+        return Ok(());
+    }
+
+    let user = user.unwrap();
+    let hint = user.password_hint.to_owned().unwrap_or("You don't have any...".to_string());
+
+    if let Some(ref mail_config) = CONFIG.mail {
+        if let Err(e) = mail::send_password_hint(&user.email, &hint, mail_config) {
+            err!(format!("There have been a problem sending the email: {}", e));
+        }
     }
 
-    match User::find_by_mail(&data.Email, &conn) {
-        Some(user) => {
-            let hint = user.password_hint.to_owned().unwrap_or_default();
-            err!(format!("Your password hint is: {}", hint))
-        },
-        None => Ok(()),
+    if !CONFIG.show_password_hint {
+        err!(format!("Your password hint is: {}", &hint));
     }
+
+    Ok(())
 }
diff --git a/src/mail.rs b/src/mail.rs
new file mode 100644
index 00000000..7faa791f
--- /dev/null
+++ b/src/mail.rs
@@ -0,0 +1,47 @@
+use std::error::Error;
+use native_tls::TlsConnector;
+use native_tls::{Protocol};
+use lettre::{EmailTransport, SmtpTransport, ClientTlsParameters, ClientSecurity};
+use lettre::smtp::{ConnectionReuseParameters, SmtpTransportBuilder};
+use lettre::smtp::authentication::{Credentials, Mechanism};
+use lettre_email::EmailBuilder;
+
+use MailConfig;
+
+fn mailer(config: &MailConfig) -> SmtpTransport {
+    let client_security = if config.smtp_ssl {
+        let mut tls_builder = TlsConnector::builder().unwrap();
+        tls_builder.supported_protocols(&[
+            Protocol::Tlsv10, Protocol::Tlsv11, Protocol::Tlsv12
+        ]).unwrap();
+
+        ClientSecurity::Required(
+            ClientTlsParameters::new(config.smtp_host.to_owned(), tls_builder.build().unwrap())
+        )
+    } else {
+        ClientSecurity::None
+    };
+
+    SmtpTransportBuilder::new((config.smtp_host.to_owned().as_str(), config.smtp_port), client_security)
+        .unwrap()
+        .credentials(Credentials::new(config.smtp_username.to_owned(), config.smtp_password.to_owned()))
+        .authentication_mechanism(Mechanism::Login)
+        .smtp_utf8(true)
+        .connection_reuse(ConnectionReuseParameters::ReuseUnlimited)
+        .build()
+}
+
+pub fn send_password_hint(address: &str, hint: &str, config: &MailConfig) -> Result<(), String> {
+    let email = EmailBuilder::new()
+        .to(address)
+        .from((config.smtp_from.to_owned(), "Bitwarden-rs"))
+        .subject("Your Master Password Hint")
+        .body(hint)
+        .build().unwrap();
+
+    match mailer(config).send(&email) {
+        Ok(_) => Ok(()),
+        Err(e) => Err(e.description().to_string()),
+    }
+}
+        
diff --git a/src/main.rs b/src/main.rs
index e506e05e..8f39057f 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -26,6 +26,9 @@ extern crate lazy_static;
 #[macro_use]
 extern crate num_derive;
 extern crate num_traits;
+extern crate lettre;
+extern crate lettre_email;
+extern crate native_tls;
 
 use std::{env, path::Path, process::{exit, Command}};
 use rocket::Rocket;
@@ -37,6 +40,7 @@ mod api;
 mod db;
 mod crypto;
 mod auth;
+mod mail;
 
 fn init_rocket() -> Rocket {
     rocket::ignite()
@@ -155,10 +159,10 @@ lazy_static! {
 
 #[derive(Debug)]
 pub struct MailConfig {
-    reply_to_email: Option<String>,
     smtp_host: String,
     smtp_port: u16,
     smtp_ssl: bool,
+    smtp_from: String,
     smtp_username: String,
     smtp_password: String,
 }
@@ -172,22 +176,23 @@ impl MailConfig {
             return None
         }
 
-        let smtp_ssl = util::parse_option_string(env::var("SMTP_SSL").ok()).unwrap_or(false);
+        let smtp_ssl = util::parse_option_string(env::var("SMTP_SSL").ok()).unwrap_or(true);
         let smtp_port = util::parse_option_string(env::var("SMTP_PORT").ok())
             .unwrap_or_else(|| {
                 if smtp_ssl {
-                    465u16
+                    587u16
                 } else {
                     25u16
                 }
             });
 
         Some(MailConfig {
-            reply_to_email: util::parse_option_string(env::var("REPLY_TO_EMAIL").ok()),
             smtp_host: smtp_host.unwrap(),
             smtp_port: smtp_port,
             smtp_ssl: smtp_ssl,
-            // If username or password is not specified, and SMTP support seems to be wanted,
+            smtp_from: util::parse_option_string(env::var("SMTP_FROM").ok())
+                .unwrap_or("bitwarden@localhost".to_string()),
+            // If username or password is not specified and SMTP support seems to be wanted,
             // don't let the app start: the configuration is clearly incomplete.
             smtp_username: util::parse_option_string(env::var("SMTP_USERNAME").ok())
                 .unwrap_or_else(|| {