Davmail Compatibility

[bmclean2]

Let me preface this by saying that this very well could be a davmail issue, but I thought I'd put it here for discussion purposes. I use davmail in SMTP/IMAP server mode to connect to exchange servers with msmtp, NeoMutt, isync, calendars, etc. When I use the following config for mailmerge...

[smtp_server]
host = localhost
port = 1025
username = MYDOMAIN\johnny.smith

...I get the following error: "localhost:1025 failed to send message: (530, b'Authentication required', 'My Self [email protected]')"

I don't get a password prompt. I'm not sure if the error is happening with mailmerge or davmail. Maybe some of you can chime in. Is there a hidden verbose mode in mailmerge that can be accessed?

[awdeorio]

Would it help to use the `security` parameter? There are several examples in `mailmerge_server.conf`, which you can produce with `mailmerge --sample`.

…

On Fri, Oct 9, 2020 at 9:42 PM bmclean2 ***@***.***> wrote: Let me preface this by saying that this very well could be a davmail issue, but I thought I'd put it here for discussion purposes. I use davmail in SMTP/IMAP server mode to connect to exchange servers with msmtp, NeoMutt, isync, calendars, etc. When I use the following config for mailmerge... [smtp_server] host = localhost port = 1025 username = MYDOMAIN\johnny.smith ...I get the following error: "localhost:1025 failed to send message: (530, b'Authentication required', 'My Self ***@***.***')" I don't get a password prompt. I'm not sure if the error is happening with mailmerge or davmail. Maybe some of you can chime in. Is there a hidden verbose mode in mailmerge that can be accessed? — You are receiving this because you are subscribed to this thread. Reply to this email directly, view it on GitHub <#106>, or unsubscribe <https://github.com/notifications/unsubscribe-auth/ABZHZHJ667B7HTWHEM7Z54LSJ63ZPANCNFSM4SKWZTFQ> .

[bmclean2]

The security parameter is not required for davmail since you are just communicating with a localhost smtp server. The security between davmail and the exchange server, on the other hand, is automatically handled.

[awdeorio]

The SMTP library API has no password when using no security. Let me know if there's a security option (password but no encryption) that mailmerge is missing.

[bmclean2]

I think that's the issue. To connect to davmail, you need the security option of password but no encryption. Are you saying the SMTP library API doesn't offer that, or just that it hasn't been implemented in mailmerge?

[awdeorio]

I do not know whether the Python SMTP library offers the option of a password but no encryption. Feel free to take a look!

[awdeorio]

Here's an idea you could try. Let me know if this works for you.

1. Create mailmerge_server.conf like this. Change the port if you need to.

[smtp_server]
host = YOUR_HOST_HERE
port = 25
security = STARTTLS
username = YOUR_USERNAME_HERE

1. Remove these two lines to disable TLS.
2. Try sending a message with mailmerge

If that works, then we could use it as the basis for creating a localhost only no-password option.

[bmclean2]

It works! Thank you!

[awdeorio]

Awesome! Would you be willing to implement a new server config to handle this? It would be more-or-less a clone of the STARTTLS configuration, minus the lines we discussed earlier. In summary:

• Add a new else to this if statement for a new security configuration. Maybe call it CLEARTEXT or UNENCRYPTED?
• Add a new section to the sample server config generated by mailmerge --sample
• Add a unit test to test_sendmail_client.py, mimic test_security_starttls() for a starting point.

[bmclean2]

Sure! I'm not familiar with python, but I will give it a try on my machine and test it out. The only caveat is that won't get to it for a while.