feat: Add Outlook settings to .env.example

fix: Force `smtp_starttls` depending on `SSLError`
fix: Uncommented line that prevents multiple "Re: " prefixes

.env.example

@@ -12,7 +12,7 @@ SYSTEM_PROMPT=
 # Set to "true" to redact email addresses or you can remove it (or set it to "false") to not redact email addresses
 REDACT_EMAIL_ADDRESSES=true
 
-OPENAI_API_KEY=""
+OPENAI_API_KEY="..."
 # At least when writing this, openrouter.ai has a free tier
 OPENAI_BASE_URL="https://openrouter.ai/api/v1"
 # The model to use for OpenAI
@@ -24,7 +24,7 @@ IMAP_HOST=imap.gmail.com
 IMAP_PORT=993
 IMAP_USERNAME=[email protected]
 # You'll probably need to use an app password if you're using Gmail, thought it might only be required instead of an account password if you have 2FA
-IMAP_PASSWORD=
+IMAP_PASSWORD=...
 # Using All Mail for Gmail works the best as the program should be able to see sent emails as well as received emails
 # If you're using a different email provider that doesn't have an All Mail folder, you might need to change this
 # You can get a list of folders by running `llmail list-folders`
@@ -37,6 +37,17 @@ SMTP_PORT=465
 SMTP_USERNAME=[email protected]
 # Like with IMAP, you might need an app password
 SMTP_PASSWORD=
+# Outlook
+# IMAP_HOST=imap-mail.outlook.com
+# IMAP_PORT=993
+# [email protected]
+# IMAP_PASSWORD=...
+# FOLDER="Inbox,Sent"
+# SMTP_HOST=smtp-mail.outlook.com
+# SMTP_PORT=587
+# [email protected]
+# SMTP_PASSWORD=...
+
 # MESSAGE_ID_DOMAIN is the domain used in the Message-ID header
 # Leave it empty or remove it if you don't want to use it as I'm not sure what the point would even be but it's here if you need it
 MESSAGE_ID_DOMAIN=""

llmail/__main__.py

@@ -10,6 +10,7 @@
 from datetime import timezone
 import time
 import re
+from ssl import SSLError
 
 
 from llmail.utils.cli_args import argparser
@@ -95,6 +96,7 @@ def main():
             # Set up logging
             set_primary_logger(args.log_level, args.redact_email_addresses)
             logger.debug(args)
+            logger.info(f"Looking for emails that match the subject key \"{args.subject_key}\"")
             if args.watch_interval:
                 logger.info(
                     f"Watching for new emails every {args.watch_interval} seconds"
@@ -480,16 +482,42 @@ def send_reply(
         host=args.smtp_host,
         port=int(args.smtp_port),
     )
-    yag.send(
-        to=sender,
-        # subject=f"Re: {subject}" if not subject.startswith("Re: ") else subject,
-        subject=f"Re: {subject}",
-        headers={"In-Reply-To": message_id, "References": " ".join(references_ids)},
-        contents=generated_response,
-        message_id=make_msgid(
-            domain=args.message_id_domain if args.message_id_domain else "llmail"
-        ),
-    )
+    try:
+        yag.send(
+            to=sender,
+            subject=f"Re: {subject}" if not subject.startswith("Re: ") else subject,
+            # subject=f"Re: {subject}",
+            headers={"In-Reply-To": message_id, "References": " ".join(references_ids)},
+            contents=generated_response,
+            message_id=make_msgid(
+                domain=args.message_id_domain if args.message_id_domain else "llmail"
+            ),
+        )
+    except SSLError as e:
+        if "WRONG_VERSION_NUMBER" in str(e):
+            logger.info(
+                "SSL error occurred. Trying to connect with starttls=True instead."
+            )
+            yag = yagmail.SMTP(
+                user={args.smtp_username: alias} if alias else args.smtp_username,
+                password=args.smtp_password,
+                host=args.smtp_host,
+                port=int(args.smtp_port),
+                smtp_starttls=True,
+                smtp_ssl=False
+            )
+            yag.send(
+                to=sender,
+                subject=f"Re: {subject}" if not subject.startswith("Re: ") else subject,
+                # subject=f"Re: {subject}",
+                headers={"In-Reply-To": message_id, "References": " ".join(references_ids)},
+                contents=generated_response,
+                message_id=make_msgid(
+                    domain=args.message_id_domain if args.message_id_domain else "llmail"
+                ),
+            )
+        else:
+            raise e
     # thread_from_msg_id = get_thread_history(client, msg_id)
     # logger.debug(f"Thread history (message_identifier): {thread_from_msg_id}")
     # logger.debug(f"Thread history length (message_identifier): {len(thread_from_msg_id)}")