Sending EMail using SMTP with OAUTH

[Julian Ford]

Hello, all.

I have a few clients who have Hotmail, or Microsoft Live EMail accounts,

and these do not support the use of STARTTLS, to send EMails.

They do, however, support XOAUTH2.

I am using the EMan goodie to send EMails, and I have also been adding to that

goodie for the last few years.

Has anyone built an EMail client using OAUTH?

Any pointers, or a starting direction, would be greatly appreciated..

Thanks in advance....

And stay safe and healthy!

Regards,

Julian

[Seth Berman]

Hi Julian,

Since 9.2, the mail application includes an authentication framework to implement SASL.
It supports CRAM-MD5, SCRAM-SHA-1, SCRAM-SHA-256, LOGIN, XOAUTH2 or a custom protocol you can define and hook into SASL.

Load the ST:Server Smalltalk (SST) - Mail (IMAP/SMTP) feature and review the SstMailAuthenticationApp for some idea.

If you want see how that looks from a protocol conversation standpoint...run some of the SstSmtpClientExample>>exampleSasl* examples which has logging enabled and prints these out to the Transcript.  You can then switch out the sasl authenticator used in the example with a SstSaslOAuth2Authenticator which requies a user and access token.

VAST just handles the SASL conversation and encoding for XOAUTH2...there are still specifics to understand with each provider (gmail, hotmail, yahoo...).

Of course, I know what we have in VAST is not EMan, but hopefully it may point you in the right direction.

-------------------------------------------------------------------------------------

Back to your original problem, you said that they don't support a STARTTLS upgrade.
But what about just an initial SSL connection?  If you login to their SSL/TLS port for Microsoft Live...what CAPABILITY listing does it answer?

- Seth

[Seth Berman]

BTW, I would get 9.2.1 if you are going to experiment.
There were some SMTP fixes that were necessary for certain SMTP servers.

- Seth

[Julian Ford]

Thanks, Seth....

I will try what you have suggested.

And yes, I am already using 9.2.1, so should have what I need.

Greatly appreciate the response!

Julian

[Seth Berman]

Hi Julian,

Sure. Just reach out to me if you get stuck.

- Seth

[Julian Ford]

Sorry....missed the second part of your message....

After the EHLO, the capabilities listing I receive is as follows:

250-SIZE 157286400

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-AUTH LOGIN XOAUTH2

250-8BITMIME

250-BINARYMIME

250-CHUNKING

250 SMTPUTF8

Julian

On Sunday, May 24, 2020 at 1:06:47 PM UTC-4, Seth Berman wrote:

[Seth Berman]

Hi Julian,

So it supports LOGIN?  Can you just use that?
@see SstSaslLoginAuthenticator

- Seth