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With Lets Encrypt, it would be nice to incorporate Dovecot SNI configuration through ISPConfig. Send and Receive works with my installation across a number of domains when using Outlook 2007 and iPhone4 (iOS7). My iPhone complains about the LE certificate, but after accepting it, all mail functions work fine.

My VPS system: (Ubuntu 14.04 LTS, Kernel 3.15.4-x86_64, Apache 2.4.7, MariaDB Server 5.5.40, MariaDB Client 5.5.41, PHP 5.5.9, ISPConfig 3.0.5.4p8, Webmin, PureFTP & Quota, phpMyAdmin, postfix, dovecot, amavis, clamav, spamassassin, awstats, fail2ban, Jailkit, bind9, vlogger, webalizer)