Please test Thunderbird as client to the SendGrid relay service?
I just discovered a great service which has saved me from the multiple sites that have draconian policies and consider my VPS providers (1nd1.com and OVH) to be of "poor reputation".
There is a problem when you try to open two similar accounts in Thunderbird. I want one to send my messages to SendGrid (smtp.sendgrid.net) and the other to my own VPS. The fact that both accounts share the same IMAP server seems to confuse TBird. I got messages like "that account exists already", then I removed one and both were gone. The names of the accounts in one display (external) were inconsistent with the other (internal). See screenshot.
After some struggle, I managed to make this work, with a single account and 2 identities (one with outgoing server smtp.sendgrid.net and the other to my domain smtp.jfknumbers.org).
I think that the "uniqueness" of an account is not being based on the account name (as it should) but in the IMAP server. Two accounts should be able to have the same IMAP server, shouldn't they?
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Allow me to rephrase. Now I understand what T-Bird was trying to tell me:
"No, no, you don't do it that way. Do not use two accounts, only one based on your IMAP server. If you need different SMTP/outgoing servers, you handle that with identities"
However, in the process of "telling" me that, T-Bird became rather confused, with inconsistent displays and other unusual behaviors.