sending email always going into gmail SPAM (Outlook)

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#1 Wed, 02/22/2017 - 17:23
anthonyinit2012

sending email always going into gmail SPAM (Outlook)

Hello,

I have a VPS with virtualmin installed i have a big issue with my email server, why is that all my emails that i send from my end going to SPAM Folder ? i have configured my emails server and using Outlook.

when i contact the hosting provider they recommended this link https://contabo.com/?show=tutorials&tutorial=prevent-e-mails-marked-spam

but im so confused how to configure everything in virtualmin

Please i really need help

Thank you

Thu, 02/23/2017 - 03:43
Diabolico
Diabolico's picture

There are three kind of records what must be present for the email to validate as not spam plus one extra as it comes handy. The most important are rDNS (or reverse DNS), SPF, DKIM and the extra one is DMARC. Gmail, Hotmail and others will immediately mark your email as spam if they are missing any one of the first three records. DMARC is somehow "optional" but like i already said its good to have it.

There are many online tools to check all your records but i find this one to be easy to use and understand: http://www.mail-tester.com.

- I often come to the conclusion that my brain has too many tabs open. -
Failing at desktop publishing & graphic design since 1994.

Thu, 02/23/2017 - 06:29
unborn
unborn's picture

hey, you should deploy spf, dkim and dmarc - those are dns settings and all you would ever need, which means it will take some time to propagate out.. give it at least 27 hours before testing it again. rdns or reverse dns is not need it. I do not use them and it all works fine, if your hostname of your server is setup correctly then dns would work correctly - semiautomatic. Just check those things and also make sure youre server is not blacklisted in spamhouse and other corporations like it - if it is just do removal requests and follow those corporations guidelines and you should be good to go.

Configuring/troubleshooting Debian servers is always great fun

Thu, 02/23/2017 - 07:32
Diabolico
Diabolico's picture

@unborn: Sorry but you are wrong with rDNS. Without this record Gmail will mark your email as spam, Hotmail too and i'm sure most of other mail servers. Servers of my clients would not even accept the email without valid rDNS. If you didnt set rDNS it could be your host as i know some of them do this automatically.

Actually i think Gmail will even bounce back your email without valid rDNS.

- I often come to the conclusion that my brain has too many tabs open. -
Failing at desktop publishing & graphic design since 1994.

Thu, 02/23/2017 - 17:21
anthonyinit2012

hello all, thank you for your reply but please help me how to configure these records in virtualmin i'm lost here

thank you so much

Sat, 02/25/2017 - 15:56
Diabolico
Diabolico's picture

Ok, so the list goes:
1. rDNS - only the owner of the IP can set/change rDNS, so that would be your host. Majority of them will leave this to you to set up over their control panel (e.g. SolusVM). If you are hosting from home your ISP will never give you this option so if this is your case you will never be able to set it up.
2. SPF - This record can be set in your DNS and doesnt require anything else than Bind or DNS manager from your registrar. You have this option inside Virtualmin - Virtual server - Server Configuration.
3. DKIM - Again, same as SPF this is another record you can set in your DNS alone. Like SPF can be set up within Virtualmin.

So this are the "holly trinity" of email delivery. Without any of this records your emails will fail or at minimum be marked as spam. Not good to send emails without this records because pretty soon your IP and/or domain will be listed with every major RBL.

There is one optional thing, doesnt directly affect your sender score but it can help a lot in case of someone trying to spoof your email server or address:
3. DMARC - This record is used to instruct other mail server how to handle emails originating from you or someone else with missing one of the above records. Thats why is important to have it in case someone else is trying to spoof your mail server, otherwise your IP could end in some RBL.

Steps:
1. First lover your TTL to 300 seconds, it will help down the line when you are testing/changing your DNS. Note: For new TTL to take effect the old TTL must expire, so if your old TTL was one day you will need to wait one day and 5 minutes (300 seconds) for new TTL to come into play. Remember this or you will find yourself changing DNS and wondering why nothing happens.
2. Set SPF with ~all (softfail) first and proceed with next step.
3. Set DKIM. Both 2 and 3 can be done from Virtualmin but you can always "fine tune" as you need or want by changing it directly in your DNS.
4. Double-triple check if everything is ok. There are many tools online but if you want one what is easy to use and understand, try this one: http://www.mail-tester.com.
5. If after 24 hours (to be sure) everything still works and its in order change SPF from ~all (softfail) to -all (fail). Note: Difference is ~ and -.
6. Now is time for DMARC. Dont set this record before you are 100% sure everything else is perfectly ok or you will instruct other servers to reject/quarantine your own emails.

More or less thats it.

- I often come to the conclusion that my brain has too many tabs open. -
Failing at desktop publishing & graphic design since 1994.

Wed, 03/08/2017 - 11:12 (Reply to #6)
anthonyinit2012

Thank you so much for your reply,

i'm using cloudflare DNS and i have changed all my records accordingly. i tested everything with mail-tester.com and got pass every records except for rDNS.

my ISP given me a option to change my PTR and i did change it to something like mail.mydomain.com.au then i when i check again with the mail-tester but it gave me error as follows

" Your IP address 80.xxx.xxx.163 is associated with the domain mail.mydomain.com.au. Nevertheless your message appears to be sent from vmi.contabo.host.

You may want to change your pointer (PTR type) DNS record and the host name of your server to the same value.

Here are the tested values for this check: IP: 80.xxx.xxx.163 HELO: vmi.contabo.host rDNS: mail.mydomain.com.au"

Please help me here . am i doing something wrong?

Note: mydomain is not the actual name of my domain name and my ip address also i have marked with xxx for my safety :)

Wed, 03/08/2017 - 15:41
Diabolico
Diabolico's picture

Your rDNS doesnt match and you will need to sort it out. So if you host doesnt offer this option you will need to open a ticket and ask them to change it.

Now the ugly part - what is wrong with all of you using Vmin to end hosting from home or with most shittiest hosting companies you could find on the web? Just this year Contabo got tons of negative reviews and based on other people experience they are holding the money e.g. no refunds, oversold servers and support worth nothing... so good luck with them, you will need it. On the other hand, you could be that "lucky client" who gets things sorted out.

- I often come to the conclusion that my brain has too many tabs open. -
Failing at desktop publishing & graphic design since 1994.

Wed, 11/01/2017 - 07:05
TechnicalAnnie
TechnicalAnnie's picture

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Wed, 11/01/2017 - 19:21
anthonyinit2012

this issue is fixed... thank you for your reply :) i fix my "dkim" "rdns" "spf" 3 main issue

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