Add support for SMTP SSL port (465) (jaymzh#140)

Adds an option (--ssl) to use SSL instead of STARTTLS to gain support of
mail servers supporting only this auth method.

According to [RFC8314](https://datatracker.ietf.org/doc/html/rfc8314)
implicit SSL is recommended over STARTTLS for mail submission now.

README.md

@@ -44,7 +44,7 @@ There are a variety of other options that you may want:
 * customize mail hostname and port (-H and -P respectively)
 * customize the email message (-M)
 * don't use PGP/Mime in the email (-O, implies -e)
-* specify a SMTPAUTH or STARTTLS for SMTP (-u and -S)
+* specify SMTPAUTH (-u) and either STARTTLS (-S) or SSL (--ssl) for SMTP
 
 And more! See the '-h' option for more.
 

libpius/mailer.py

@@ -31,6 +31,7 @@ def __init__(
         port,
         user,
         tls,
+        ssl,
         no_mime,
         override,
         msg_text,
@@ -43,6 +44,7 @@ def __init__(
         self.user = user
         self.password = ""
         self.tls = tls
+        self.ssl = ssl
         self.no_pgp_mime = no_mime
         self.address_override = override
         self.message_text = msg_text
@@ -77,6 +79,7 @@ def add_options(parser, group=None):
             mail_host=DEFAULT_MAIL_HOST,
             mail_port=DEFAULT_MAIL_PORT,
             mail_tls=True,
+            mail_ssl=False,
         )
         group.add_option(
             "-D",
@@ -103,6 +106,12 @@ def add_options(parser, group=None):
             dest="mail_tls",
             help="Do not use STARTTLS when talking to the SMTP" " server.",
         )
+        group.add_option(
+            "--ssl",
+            action="store_true",
+            dest="mail_ssl",
+            help="Use SSL when talking to the SMTP server.",
+        )
         group.add_option(
             "-P",
             "--mail-port",
@@ -175,7 +184,10 @@ def get_pass(self):
     def verify_pass(self):
         """Verify the password we got works for SMTPAUTH."""
         try:
-            smtp = smtplib.SMTP(self.host, self.port)
+            if self.ssl:
+                smtp = smtplib.SMTP_SSL(self.host, self.port)
+            else:
+                smtp = smtplib.SMTP(self.host, self.port)
         except socket.error as msg:
             raise MailSendError(msg)
 
@@ -188,13 +200,14 @@ def verify_pass(self):
         # So, in order be secure on older pythons we ehlo() and then check the
         # response before attempting startls.
         try:
-            smtp.ehlo()
-            if not smtp.has_extn("STARTTLS"):
-                # Emulate 2.6 behavior
-                raise smtplib.SMTPException("Server does not support STARTTLS")
-            smtp.starttls()
-            # must ehlo after startls
-            smtp.ehlo()
+            if not self.ssl:
+                smtp.ehlo()
+                if not smtp.has_extn("STARTTLS"):
+                    # Emulate 2.6 behavior
+                    raise smtplib.SMTPException("Server does not support STARTTLS")
+                smtp.starttls()
+                # must ehlo after startls
+                smtp.ehlo()
             smtp.login(self.user, self.password)
         except smtplib.SMTPAuthenticationError:
             return False
@@ -374,27 +387,32 @@ def _send_mail(self, to, msg):
         msg["Date"] = formatdate(localtime=True)
 
         try:
-            smtp = smtplib.SMTP(self.host, self.port)
+            if self.ssl:
+                smtp = smtplib.SMTP_SSL(self.host, self.port)
+            else:
+                smtp = smtplib.SMTP(self.host, self.port)
             if self.tls:
-                # NOTE WELL: SECURITY IMPORTANT NOTE!
-                #
-                # In python 2.6 if you attempt to starttls() and the server
-                # doesn't understand an exception is raised. However before
-                # that, it just carried on and one could attempt to auth over a
-                # plain-text session.  This is BAD!
-                #
-                # So, in order be secure on older pythons we ehlo() and then
-                # check the response before attempting startls.
-                smtp.ehlo()
-                if not smtp.has_extn("STARTTLS"):
-                    # Emulate 2.6 behavior
-                    raise smtplib.SMTPException(
-                        "Server does not support STARTTLS"
-                    )
-                smtp.starttls()
-                # must re-ehlo after STARTTLS
-                smtp.ehlo()
-                # Don't want to send auth information unless we're TLS'd
+                if not self.ssl:
+                    # NOTE WELL: SECURITY IMPORTANT NOTE!
+                    #
+                    # In python 2.6 if you attempt to starttls() and the server
+                    # doesn't understand an exception is raised. However before
+                    # that, it just carried on and one could attempt to auth over a
+                    # plain-text session.  This is BAD!
+                    #
+                    # So, in order be secure on older pythons we ehlo() and then
+                    # check the response before attempting startls.
+                    smtp.ehlo()
+                    if not smtp.has_extn("STARTTLS"):
+                        # Emulate 2.6 behavior
+                        raise smtplib.SMTPException(
+                            "Server does not support STARTTLS"
+                        )
+                    smtp.starttls()
+                    # must re-ehlo after STARTTLS
+                    smtp.ehlo()
+
+                    # Don't want to send auth information unless we're TLS'd
                 if self.user:
                     smtp.login(self.user, self.password)
             if self.address_override:

pius

@@ -88,10 +88,13 @@ def check_options(parser, options, args):
         print("NOTE: -O and -m are present, turning on -e")
         options.encrypt_outfiles = True
 
-    if options.mail_user and not options.mail_tls:
-        print("NOTE: -u is present, turning off -S.")
+    if options.mail_user and not (options.mail_tls or options.mail_ssl):
+        print("NOTE: -u (SMTPAUTH) is present, enabling TLS. Either TLS or SSL is required with SMTPAUTH")
         options.mail_tls = True
 
+    if options.mail_tls and options.mail_ssl:
+        parser.error("ERROR: TLS and SSL cannot be used at the same time.")
+
     if options.mail_text and not options.mail:
         parser.error("ERROR: -M requires -m")
 
@@ -300,6 +303,7 @@ def main():
             options.mail_port,
             options.mail_user,
             options.mail_tls,
+            options.mail_ssl,
             options.mail_no_pgp_mime,
             options.mail_override,
             options.mail_text,

pius-keyring-mgr

@@ -862,6 +862,7 @@ There are no options"""
                     options.mail_port,
                     options.mail_user,
                     options.mail_tls,
+                    options.mail_ssl,
                     options.mail_no_pgp_mime,
                     options.mail_override,
                     options.mail_text,

pius-report

@@ -550,6 +550,7 @@ def main():
             options.mail_port,
             options.mail_user,
             options.mail_tls,
+            options.mail_ssl,
             options.mail_no_pgp_mime,
             options.mail_override,
             options.mail_text,