Enable working TLS to smtp.office365.com

docker-compose.yml

@@ -21,10 +21,11 @@ services:
 
       - SMTP=false                                    ## true = enable mail notifications via smtp
       - SMTP_HOST=smtp.gmail.com                      ## smtp Server - smtp.gmail.com for google
-      - SMTP_PORT=465                                 ## smtp Server Port - 465 for google
+      - SMTP_PORT=587                                 ## smtp Server Port - 587 for TLS, 465 for SSL, 25 for unsecured
       - SMTP_USERNAME=max.mustermann@gmail.com        ## smtp Login - your EMail for google
       - SMTP_PASSWORD=                                ## smtp Login Password - your Login PW for google
-      - SMTP_TLS=true                                 ## enable TLS - true for google and most smtp servers
+      - SMTP_TLS=true                                 ## enable TLS
+      - SMTP_SSL=false                                ## enable SSL
       - SMTP_SENDER=max.mustermann@gmail.com          ## sender adress - same as Login for google and most smtp servers
       - SMTP_RECIPIENT=max.mustermann@gmail.com       ## recipient for notifications - can be the same as sender
       #-SMTP_SUBJECT=                                 ## Subject and Body options are optional.

sample.env

@@ -14,10 +14,11 @@ TGTG_USER_ID=
 
 SMTP=false
 SMTP_HOST=smtp.gmail.com
-SMTP_PORT=465
+SMTP_PORT=587
 SMTP_USERNAME=
 SMTP_PASSWORD=
 SMTP_TLS=true
+SMTP_SSL=false
 SMTP_SENDER=
 SMTP_RECIPIENT=
 

src/config.sample.ini

@@ -29,12 +29,13 @@ Username =
 ## Subject and Body options are optional.
 ## Subject and Body options can use variables as described below
 ## The Body option is interpreted as HTML
-enabled = true
+enabled = false
 Host = smtp.gmail.com
-Port = 465
+Port = 587
 Username = max.mustermann@gmail.com
 Password = 
-TLS = true 
+TLS = true
+SSL = false
 Sender = max.mustermann@gmail.com
 Recipient = max.mustermann@gmail.com
 # cron = 

src/models/config.py

@@ -92,6 +92,7 @@ def _ini_reader(self, file: str) -> None:
                 "host": config["SMTP"].get("Host"),
                 "port": config["SMTP"].getint("Port"),
                 "tls": config["SMTP"].getboolean("TLS"),
+                "ssl": config["SMTP"].getboolean("SSL"),
                 "username": config["SMTP"].get("Username"),
                 "password": config["SMTP"].get("Password"),
                 "cron": config["SMTP"].get("cron", '* * * * *'),
@@ -167,6 +168,7 @@ def _env_reader(self) -> None:
                 "host": environ.get("SMTP_HOST", None),
                 "port": int(environ.get("SMTP_PORT", 25)),
                 "tls": environ.get("SMTP_TLS", "false").lower() in ('true', '1', 't'),
+                "ssl": environ.get("SMTP_SSL", "false").lower() in ('true', '1', 't'),
                 "username": environ.get("SMTP_USERNAME", ""),
                 "password": environ.get("SMTP_PASSWORD", ""),
                 "sender": environ.get("SMTP_SENDER", None),

src/notifiers/smtp.py

@@ -20,6 +20,7 @@ def __init__(self, config: Config):
         self.host = config.smtp["host"]
         self.port = config.smtp["port"]
         self.tls = config.smtp["tls"]
+        self.ssl = config.smtp["ssl"]
         self.username = config.smtp["username"]
         self.password = config.smtp["password"]
         self.sender = config.smtp["sender"]
@@ -39,7 +40,7 @@ def __init__(self, config: Config):
             try:
                 self._connect()
             except Exception as exc:
-                raise SMTPConfigurationError() from exc
+                raise SMTPConfigurationError(exc) from exc
 
     def __del__(self):
         """Closes SMTP connection when shutdown"""
@@ -51,10 +52,12 @@ def __del__(self):
 
     def _connect(self) -> None:
         """Connect to SMTP Server"""
-        if self.tls:
+        if self.ssl:
             self.server = smtplib.SMTP_SSL(self.host, self.port)
         else:
             self.server = smtplib.SMTP(self.host, self.port)
+        if self.tls:
+            self.server.starttls()
         self.server.set_debuglevel(self.debug)
         self.server.ehlo()
         if self.username and self.password: