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.
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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