Question: I've been using MaxBulk Mailer for years and love it but can't get a connection with upgrade 8.6.1. Here are the settings I've been using:
SMTP Host smtp.mail.me.com:587 or 25 or 2525. The latter is the only one that doesn't prompt an immediate authentication error message. 2525 doesn't do that but nothing happens - negative or positive.
Security TLS v1 Exp
Authentication ESMTP Login (have tried Plain too)
Account ID •••••••••@icloud.com
Password ••••••••• (just created for MaxBulk Mailer for icloud)
Group mails 200
Interval 24:00.00 - have also tried shorter intervals
Name ••••••••• •••••••••
Indeed a custom app-specific password is required for MobileMe/iCloud accounts. If your password is not accepted just turn off the two-factor authentication option here or better create a password for MaxBulk Mailer from the same page by clicking on 'Generate Password' (in Security, below APP-SPECIFIC PASSWORDS). A pop-up box will open, just enter MaxBulk Mailer (or any name you choose). Apple will then generate a secure password. Copy this password into the Settings > Password box in MaxBulk Mailer.
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