- Add support for local SMTP

- Ignore venv in flake8

DOCUMENTATION.md

@@ -1548,15 +1548,27 @@ Port to connect to SMTP server.
 
 Default:
 
+##### smtp_security
+
+Use encryption on the SMTP connection. none, tls, starttls
+
+Default: none
+
+##### smtp_ssl_verify_mode
+
+The certificate verification mode. Works for tls and starttls. NONE, OPTIONAL or REQUIRED
+
+Default: REQUIRED
+
 ##### smtp_username
 
-Username to authenticate with SMTP server.
+Username to authenticate with SMTP server. Leave empty to disable authentication (e.g. using local mail server).
 
 Default:
 
 ##### smtp_password
 
-Password to authenticate with SMTP server.
+Password to authenticate with SMTP server. Leave empty to disable authentication (e.g. using local mail server).
 
 Default:
 

config

@@ -305,13 +305,15 @@
 [hook]
 
 # Hook types
-# Value: none | rabbitmq
+# Value: none | rabbitmq | email
 #type = none
 #rabbitmq_endpoint =
 #rabbitmq_topic =
 #rabbitmq_queue_type = classic
-#smtp_server =
-#smtp_port = 587
+#smtp_server = localhost
+#smtp_port = 25
+#smtp_security = starttls
+#smtp_ssl_verify_mode = REQUIRED
 #smtp_username =
 #smtp_password =
 #from_email =

radicale/config.py

@@ -38,6 +38,7 @@ from typing import (Any, Callable, ClassVar, Iterable, List, Optional,
                     Sequence, Tuple, TypeVar, Union)
 
 from radicale import auth, hook, rights, storage, types, web
+from radicale.hook import email
 from radicale.item import check_and_sanitize_props
 
 DEFAULT_CONFIG_PATH: str = os.pathsep.join([
@@ -85,6 +86,7 @@ def list_of_ip_address(value: Any) -> List[Tuple[str, int]]:
             return address.strip(string.whitespace + "[]"), int(port)
         except ValueError:
             raise ValueError("malformed IP address: %r" % value)
+
     return [ip_address(s) for s in value.split(",")]
 
 
@@ -445,6 +447,16 @@ DEFAULT_CONFIG_SCHEMA: types.CONFIG_SCHEMA = OrderedDict([
             "value": "",
             "help": "SMTP server port",
             "type": str}),
+        ("smtp_security", {
+            "value": "none",
+            "help": "SMTP security mode: *none*|tls|starttls",
+            "type": str,
+            "internal": email.SMTP_SECURITY_TYPES}),
+        ("smtp_ssl_verify_mode", {
+            "value": "REQUIRED",
+            "help": "The certificate verification mode. Works for tls and starttls: NONE, OPTIONAL, default is REQUIRED",
+            "type": str,
+            "internal": email.SMTP_SSL_VERIFY_MODES}),
         ("smtp_username", {
             "value": "",
             "help": "SMTP server username",
@@ -606,7 +618,6 @@ _Self = TypeVar("_Self", bound="Configuration")
 
 
 class Configuration:
-
     SOURCE_MISSING: ClassVar[types.CONFIG] = {}
 
     _schema: types.CONFIG_SCHEMA

radicale/hook/email/__init__.py

@@ -1,16 +1,17 @@
 # This file is related to Radicale - CalDAV and CardDAV server
 # for email notifications
 # Copyright © 2025-2025 Nate Harris
-
+import enum
 import re
 import smtplib
+import ssl
 from datetime import datetime, timedelta
 from email.encoders import encode_base64
 from email.mime.base import MIMEBase
 from email.mime.multipart import MIMEMultipart
 from email.mime.text import MIMEText
 from email.utils import formatdate
-from typing import Any, Dict, List, Optional, Tuple
+from typing import Any, Dict, List, Optional, Sequence, Tuple
 
 import vobject
 
@@ -28,6 +29,14 @@ PLUGIN_CONFIG_SCHEMA = {
             "value": "",
             "type": str
         },
+        "smtp_security": {
+            "value": "none",
+            "type": str,
+        },
+        "smtp_ssl_verify_mode": {
+            "value": "REQUIRED",
+            "type": str,
+        },
         "smtp_username": {
             "value": "",
             "type": str
@@ -82,6 +91,44 @@ MESSAGE_TEMPLATE_VARIABLES = [
 ]
 
 
+class SMTP_SECURITY_TYPE_ENUM(enum.Enum):
+    EMPTY = ""
+    NONE = "none"
+    STARTTLS = "starttls"
+    TLS = "tls"
+
+    @classmethod
+    def from_string(cls, value):
+        """Convert a string to the corresponding enum value."""
+        for member in cls:
+            if member.value == value:
+                return member
+        raise ValueError(f"Invalid security type: {value}. Allowed values are: {[m.value for m in cls]}")
+
+
+class SMTP_SSL_VERIFY_MODE_ENUM(enum.Enum):
+    EMPTY = ""
+    NONE = "NONE"
+    OPTIONAL = "OPTIONAL"
+    REQUIRED = "REQUIRED"
+
+    @classmethod
+    def from_string(cls, value):
+        """Convert a string to the corresponding enum value."""
+        for member in cls:
+            if member.value == value:
+                return member
+        raise ValueError(f"Invalid SSL verify mode: {value}. Allowed values are: {[m.value for m in cls]}")
+
+
+SMTP_SECURITY_TYPES: Sequence[str] = (SMTP_SECURITY_TYPE_ENUM.NONE.value,
+                                      SMTP_SECURITY_TYPE_ENUM.STARTTLS.value,
+                                      SMTP_SECURITY_TYPE_ENUM.TLS.value)
+SMTP_SSL_VERIFY_MODES: Sequence[str] = (SMTP_SSL_VERIFY_MODE_ENUM.NONE.value,
+                                        SMTP_SSL_VERIFY_MODE_ENUM.OPTIONAL.value,
+                                        SMTP_SSL_VERIFY_MODE_ENUM.REQUIRED.value)
+
+
 def ics_contents_contains_invited_event(contents: str):
     """
     Check if the ICS contents contain an event (versus a VTODO or VJOURNAL).
@@ -543,6 +590,8 @@ class EmailConfig:
     def __init__(self,
                  host: str,
                  port: int,
+                 security: str,
+                 ssl_verify_mode: str,
                  username: str,
                  password: str,
                  from_email: str,
@@ -551,6 +600,8 @@ class EmailConfig:
                  removed_template: MessageTemplate):
         self.host = host
         self.port = port
+        self.security = SMTP_SECURITY_TYPE_ENUM.from_string(value=security)
+        self.ssl_verify_mode = SMTP_SSL_VERIFY_MODE_ENUM.from_string(value=ssl_verify_mode)
         self.username = username
         self.password = password
         self.from_email = from_email
@@ -567,6 +618,9 @@ class EmailConfig:
         return f"EmailConfig(host={self.host}, port={self.port}, username={self.username}, " \
                f"from_email={self.from_email}, send_mass_emails={self.send_mass_emails})"
 
+    def __repr__(self):
+        return self.__str__()
+
     def send_added_email(self, attendees: List[Attendee], event: EmailEvent) -> bool:
         """
         Send a notification for added attendees.
@@ -644,6 +698,23 @@ class EmailConfig:
 
             return not failure_encountered  # Return True if all emails were sent successfully
 
+    def _build_context(self) -> ssl.SSLContext:
+        """
+        Build the SSL context based on the configured security and SSL verify mode.
+        :return: An SSLContext object configured for the SMTP connection.
+        """
+        context = ssl.create_default_context()
+        if self.ssl_verify_mode == SMTP_SSL_VERIFY_MODE_ENUM.REQUIRED:
+            context.check_hostname = True
+            context.verify_mode = ssl.CERT_REQUIRED
+        elif self.ssl_verify_mode == SMTP_SSL_VERIFY_MODE_ENUM.OPTIONAL:
+            context.check_hostname = True
+            context.verify_mode = ssl.CERT_OPTIONAL
+        else:
+            context.check_hostname = False
+            context.verify_mode = ssl.CERT_NONE
+        return context
+
     def _send_email(self,
                     subject: str,
                     body: str,
@@ -681,11 +752,25 @@ class EmailConfig:
         text = message.as_string()
 
         try:
-            server = smtplib.SMTP(host=self.host, port=self.port)
-            server.ehlo()  # Identify self to server
-            server.starttls()  # Start TLS connection
-            server.ehlo()  # Identify again after starting TLS
-            server.login(user=self.username, password=self.password)
+            if self.security == SMTP_SECURITY_TYPE_ENUM.EMPTY:
+                logger.warning("SMTP security type is empty, raising ValueError.")
+                raise ValueError("SMTP security type cannot be empty. Please specify a valid security type.")
+            elif self.security == SMTP_SECURITY_TYPE_ENUM.NONE:
+                server = smtplib.SMTP(host=self.host, port=self.port)
+            elif self.security == SMTP_SECURITY_TYPE_ENUM.STARTTLS:
+                context = self._build_context()
+                server = smtplib.SMTP(host=self.host, port=self.port)
+                server.ehlo()  # Identify self to server
+                server.starttls(context=context)  # Start TLS connection
+                server.ehlo()  # Identify again after starting TLS
+            elif self.security == SMTP_SECURITY_TYPE_ENUM.TLS:
+                context = self._build_context()
+                server = smtplib.SMTP_SSL(host=self.host, port=self.port, context=context)
+
+            if self.username and self.password:
+                logger.debug("Logging in to SMTP server with username: %s", self.username)
+                server.login(user=self.username, password=self.password)
+
             errors: Dict[str, Tuple[int, bytes]] = server.sendmail(from_addr=self.from_email, to_addrs=to_addresses,
                                                                    msg=text)
             logger.debug("Email sent successfully to %s", to_addresses)
@@ -701,12 +786,6 @@ class EmailConfig:
 
         return True
 
-    def __repr__(self):
-        return f'EmailConfig(host={self.host}, port={self.port}, from_email={self.from_email})'
-
-    def __str__(self):
-        return f'{self.from_email} ({self.host}:{self.port})'
-
 
 def _read_event(vobject_data: str) -> EmailEvent:
     """
@@ -729,6 +808,8 @@ class Hook(BaseHook):
         self.email_config = EmailConfig(
             host=self.configuration.get("hook", "smtp_server"),
             port=self.configuration.get("hook", "smtp_port"),
+            security=self.configuration.get("hook", "smtp_security"),
+            ssl_verify_mode=self.configuration.get("hook", "smtp_ssl_verify_mode"),
             username=self.configuration.get("hook", "smtp_username"),
             password=self.configuration.get("hook", "smtp_password"),
             from_email=self.configuration.get("hook", "from_email"),

setup.cfg

@@ -3,4 +3,22 @@
 # DNE: DOES-NOT-EXIST
 select = E,F,W,C90,DNE000
 ignore = E121,E123,E126,E226,E24,E704,W503,W504,DNE000,E501,E261
+exclude = .git,
+    __pycache__,
+    build,
+    dist,
+    *.egg,
+    *.egg-info,
+    *.eggs,
+    *.pyc,
+    *.pyo,
+    *.pyd,
+    .tox,
+    venv,
+    venv3,
+    .venv,
+    .venv3,
+    .env,
+    .mypy_cache,
+    .pytest_cache
 extend-exclude = build