My application started randomly experiencing deliverability issues when sending mail to Outlook and Hotmail addresses. I'm sending mail in java 8 through the mail API Transport.send(msg). This uses a dynamic range of IPs to send mail and I've found the at least 3 of them are blacklisted currently. I guess this could be a big reason for why I am experiencing this issue. Has anyone experienced this before and how have you been able to overcome this issue?
In the meantime I'm trying to explore other avenues like using a Gmail SMTP relay.