Outgoing Mail Server in Roundcube for ISPConfig 3.

[Sterngate]

Dear all,

Please can someone point me in the right direction. I have Roundcube installed on ISPConfig 3 mail server used only for emails for my clients and customers. I have one customer who has to use Roundcube webmail but for a workaround, I need to change the outgoing mail server settings due to emails going into Hotmail/AOL spam/junk folders. I did see there is a file called config.inc.php and in there is a section to enter SMTP mail server, username and password. Am I correct, if I enter the outgoing mail server details, it will route this SMTP server. The issue why I am doing this is anyone who emails out through our ISPConfig mail server, the email drops into the junk folders of Hotmail/AOL. Before you ask, I have correctly configured our hostname/domain with proper rDNS that resolves correctly from public IP address to hostname.domain.com. The SMTP banner is all correct and does not have any DNS Mismatch and SPF/TXT records all have correct Sender ID and IP address entered in the SPF (TXT Record) because I checked with SPF/TXT record look up. We also have CA certificate of authority with Comodo SSL installed on Postfix and Dovecot which works great for port 995 and 465 but just problems of outgoing email delivery into peoples HOtmail/AOL junk folder and not inbox. Customers and clients who use Outlook 2010 or 2016, I changed the outgoing mail server to our dedicated postfix SMTP server only that I created 2 years ago which works like a charm for Hotmail/AOL but not on this ISPConfig/Roundcube server I built this year.   

Thank you

Harvey Sharman

[SKaero]

Most likely the server ip is in a blacklist somewhere that is causing the mail to get dropped into spam.

[Sterngate]

Most likely the server ip is in a blacklist somewhere that is causing the mail to get dropped into spam.

Thank you Skaero, no it is a dedicated static IP address specific on a commercial level and no blacklist database is not listed at all. I tried all from MXToolbox, Whatismyipaddress but all clean. Even if I run an email diagnostic to mail-tester.com and comers back everything is all good 9/10. Tells me I am not blacklisted, SPF record is valid, SpamAssassin is good, no broken links nor spammy html headers, fully authenticated through sender ID and SPF, successfully associated with my domain,  my domain is assigned to a mail server all good. Bloody Microsoft servers and AOL, what the hell is hell on. My dedicated SMTP postfix server does not have issues and all emails route properly into AOL and Hotmail. The postfix or something must be injecting something for AOL and Hotmail not to like incoming emails but if I can change the outgoing mail that will be good.

Harvey Sharman

[SKaero]

I have had the same problem that has ended up being the ip, hotmail does run there own blacklists.