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Need recommendations for low volume mail relay that delivers to inbox on yahoo and outlook.com
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Need recommendations for low volume mail relay that delivers to inbox on yahoo and outlook.com

After many years of running a very tight ship on my private mail server, I find that every mail I send to Outlook.com and Yahoo goes to the spam folder. After a couple of weeks or making a pedantically correct server configuration even more pedantically correct, I caved in and setup Mailgun as my "smarthost".

Only to discover that delivery is actually worse. Mail to yahoo still goes to the spam folder. Mail to outlook.com seems to be blocked entirely.

So that exercise was pointless. Is there a better (i.e. useful) smart host for a low volume mail server that sends no bulk at all?

Comments

  • deankdeank Member, Troll

    What's the nature (or content) of the mails?

  • Plain old person to person emails, along with some test messages. I first noticed the problem went I sent out an invitation to a handful of people for dinner.

  • WolfWolf Member

    Yeah. Always got that problem when I mail my relatives. Big family eh? ;)

  • deankdeank Member, Troll
    edited July 2019

    I've never sent emails to invite people for dinner. I simply text one or two and ask them to spread the news.

    Thanked by 1Janevski
  • ITLabsITLabs Member

    I usually send pigeons with little messages.

  • raindog308raindog308 Administrator, Veteran

    subhacker said: Is there a better (i.e. useful) smart host for a low volume mail server that sends no bulk at all?

    https://www.lowendtalk.com/discussion/158888/need-a-mail-relay-from-home-best-way

    I've been using Amazon SES.

    Thanked by 1uptime
  • If your still using your own mail server what are the message codes/responses when you send?

    Might be worth checking your status with SNDS/JMRP & Postmaster to clear up any deliverability issues.

  • intovpsintovps Member, Host Rep

    @subhacker said:
    After many years of running a very tight ship on my private mail server, I find that every mail I send to Outlook.com and Yahoo goes to the spam folder. After a couple of weeks or making a pedantically correct server configuration even more pedantically correct, I caved in and setup Mailgun as my "smarthost".

    Only to discover that delivery is actually worse. Mail to yahoo still goes to the spam folder. Mail to outlook.com seems to be blocked entirely.

    So that exercise was pointless. Is there a better (i.e. useful) smart host for a low volume mail server that sends no bulk at all?

    The way I see it there are three ingredients to this:

    1. High reputation provider / IP prefix
    2. Good settings check list like SPF, DKIM, DMARC etc. etc.
    3. Watch the content for spam triggering words like free, discount, linking obscure web sites etc. etc. This has a level of uncontrollable items, since, just like in SEO, not everything is publicly known

    To get better feedback and for others to get inspiration: what have you done in these areas?

    Thanked by 1uptime
  • MikePTMikePT Moderator, Patron Provider, Veteran

    You can signup for our webhosting plans and use it to relay. We are using MailChannels to deliver all emails.

    Thanked by 2intovps ashkulz
  • intovps, I did all that years ago. I have fully validated SPF/DKIM/DMARC. SNDS reports normal status. JMRP has never reported anything. It is entirely plausible that my IP has been given a poor reputation for no good reason but there is no way to get this information directly and my investigation found nothing nefarious had occurred recently in the IP block that it resides. By extension, this is no way to know if the next IP (if I were to move) has not been secretly given a poor reputation score by yahoo and outlook.com without setting up a server there and sending mail.

    Thanked by 1AlwaysSkint
  • intovpsintovps Member, Host Rep
    edited July 2019

    @subhacker said:
    By extension, this is no way to know if the next IP (if I were to move) has not been secretly given a poor reputation score by yahoo and outlook.com without setting up a server there and sending mail.

    I have a hunch that if you move to another provider/IP you may just get slightly lower reputation just because your domain is new as sender from that IP.

    All this includes a lot of FUD.

    At some point we had a /24 prefix that was graylisted for years by Yahoo and the MTF's didn't give us any clear answer or resolution, just some rubbish intentionally vague responses. And NO spam has been sent from that IP for the last some years (since we got the prefix).

    We somehow found out that years ago some ISP had a large prefix, that included our own /24 and some spam has been sent, like from any other home user ISP a decade ago.

    We just stopped using the /24 for anything that sends email, we used it just for web servers.

    Yahoo cleared it at some point.

    So, looks like I have no useful info for you. :)

    I assume sysadmins from Mailchimp and services like that have some more insights in the mail service providers FUD.

    Thanked by 1vimalware
  • JanevskiJanevski Member
    edited July 2019

    @deank said:
    I've never sent emails to invite people for dinner. I simply text one or two and ask them to spread the news.

    @ITLabs said:
    I usually send pigeons with little messages.

    Sorry, confusion, thought pigeon was the dinner...

    Thanked by 2uptime ITLabs
  • @raindog308 said:

    subhacker said: Is there a better (i.e. useful) smart host for a low volume mail server that sends no bulk at all?

    https://www.lowendtalk.com/discussion/158888/need-a-mail-relay-from-home-best-way

    I've been using Amazon SES.

    Have you tried sending mail to outlook.com and yahoo recently?

  • raindog308raindog308 Administrator, Veteran

    subhacker said: Have you tried sending mail to outlook.com and yahoo recently?

    No - don't use either of those services. Works fine to Gmail but that's all I can report.

  • sanvitsanvit Member
    edited July 2019

    @MikePT said:
    You can signup for our webhosting plans and use it to relay. We are using MailChannels to deliver all emails.

    Curently using mix of MXroute/SES/Postmark/MailChannels (via MikePT). It's working great :)

    @subhacker said:

    @raindog308 said:

    subhacker said: Is there a better (i.e. useful) smart host for a low volume mail server that sends no bulk at all?

    https://www.lowendtalk.com/discussion/158888/need-a-mail-relay-from-home-best-way

    I've been using Amazon SES.

    Have you tried sending mail to outlook.com and yahoo recently?

    Haven't tried outlook.com, but sending to university mail addresses which uses Outlook worked fine. If you PM me a test email address, I can send a test message to that address using SES/MXroute/MailChannels/Postmark.

    Thanked by 1MikePT
  • JunJun Member

    sanvit said: Curently using mix of MXroute/SES/MailChannels (via MikePT). It's working great

    Could you elaborate how this mix works? They look mutually exclusive to me. Did you find some pattern in email deliverability that you choose your relay based on some heuristics? Why do you pay for all three different services?

  • sanvitsanvit Member
    edited July 2019

    @Jun said:

    sanvit said: Curently using mix of MXroute/SES/MailChannels (via MikePT). It's working great

    Could you elaborate how this mix works? They look mutually exclusive to me. Did you find some pattern in email deliverability that you choose your relay based on some heuristics?

    I just manually change when I want to. All relays work pretty nice.

    e.g. most emails go through MXroute since they don't edit return-path (so DKIM signed from my server works fine). SES and Postmark does sign DKIM by themselves so not a biggie. Just prefer DKIM signed by my server over DKIM signed by 3rd party :)
    When I need to send mass mails (friends/family, nothing spammy. Just invitations, etc.) I prefer using SES just to make sure MXroute's cost is minimum when managng their services (more mails = more MailChannel fees in case it fails delivery by their own relay)
    Postmark was my main relay until I got approved from SES. It is now a backup just in case other services fails (most unlikely)

    Why do you pay for all three different services?

    It isn't that expensive to manage them. I am a postmark legacy PAYG user and still have around 35K free emails left. I hwve a lifetime deal with @MikePT which covers MailChannels, and I have some mailboxes with MXroute (which costs me $5/y). SES is PAYG ($0.1/1K emails + outbound bandwidth fee), and I still have some free credits left which I got as a student and participating in ceminars. So my real cost is $5/y MXroute + €9.99 one time to MYW (MikePT).

    Thanked by 2Jun MikePT
  • @MikePT said:
    You can signup for our webhosting plans and use it to relay. We are using MailChannels to deliver all emails.

    Thanks, signed up for the offer listed in the mega thread -- I wasn't sure would be available, but was :smile:

    Thanked by 1MikePT
  • @sanvit said:

    Have you tried sending mail to outlook.com and yahoo recently?

    Haven't tried outlook.com, but sending to university mail addresses which uses Outlook worked fine. If you PM me a test email address, I can send a test message to that address using SES/MXroute/MailChannels/Postmark.

    Be aware that Office365 has a different spam filter than Outlook.com. In my case, only Outlook.com sends my mail to the spam folder. I will send you a PM with some test mail accounts.

  • MikePTMikePT Moderator, Patron Provider, Veteran

    @sanvit said:

    @Jun said:

    sanvit said: Curently using mix of MXroute/SES/MailChannels (via MikePT). It's working great

    Could you elaborate how this mix works? They look mutually exclusive to me. Did you find some pattern in email deliverability that you choose your relay based on some heuristics?

    I just manually change when I want to. All relays work pretty nice.

    e.g. most emails go through MXroute since they don't edit return-path (so DKIM signed from my server works fine). SES and Postmark does sign DKIM by themselves so not a biggie. Just prefer DKIM signed by my server over DKIM signed by 3rd party :)
    When I need to send mass mails (friends/family, nothing spammy. Just invitations, etc.) I prefer using SES just to make sure MXroute's cost is minimum when managng their services (more mails = more MailChannel fees in case it fails delivery by their own relay)
    Postmark was my main relay until I got approved from SES. It is now a backup just in case other services fails (most unlikely)

    Why do you pay for all three different services?

    It isn't that expensive to manage them. I am a postmark legacy PAYG user and still have around 35K free emails left. I hwve a lifetime deal with @MikePT which covers MailChannels, and I have some mailboxes with MXroute (which costs me $5/y). SES is PAYG ($0.1/1K emails + outbound bandwidth fee), and I still have some free credits left which I got as a student and participating in ceminars. So my real cost is $5/y MXroute + €9.99 one time to MYW (MikePT).

    Thanks mate!!!

    Btw the emails you relay to MailChannels should be signed by the server as well, feel free to open a ticket to investigate further! 😁

    @ashkulz said:

    @MikePT said:
    You can signup for our webhosting plans and use it to relay. We are using MailChannels to deliver all emails.

    Thanks, signed up for the offer listed in the mega thread -- I wasn't sure would be available, but was :smile:

    Not much stock available so instead of expiring the coupon I just let it run while stock lasts. Welcome aboard! 😁

    Thanked by 1sanvit
  • sanvitsanvit Member

    @MikePT said:
    Btw the emails you relay to MailChannels should be signed by the server as well, feel free to open a ticket to investigate further! 😁

    I disabled DKIM signing on DA since my server signs it before handing it over to the relay :)

    Thanked by 1MikePT
  • MikePTMikePT Moderator, Patron Provider, Veteran

    @sanvit said:

    @MikePT said:
    Btw the emails you relay to MailChannels should be signed by the server as well, feel free to open a ticket to investigate further! 😁

    I disabled DKIM signing on DA since my server signs it before handing it over to the relay :)

    Ahh okay, makes sense! :)

    Thanked by 1sanvit
  • Sanvit sent test mails via SES/MXroute/MailChannels/Postmark to some test accounts I have. Two were are yahoo. One is outlook.com. All arrived in my inbox except for Mailchannels -> outlook.com. That one went into the spam folder. Which goes to show that there is no certainty even with the best providers.

    To get a more robust (but often confusing) picture, I've used https://app.glockapps.com/, which operates an array of test accounts on many services. It was disappointing to find that a completely clean message from my server with a Senderscore of 95 went to spam on all outlook.com and yahoo affiliated accounts while a message that gmail's spam filter considered "spammy" sent from a Gmail server with a Senderscore of 79 and on three RBL's went to inbox on every test account.

    Thanked by 1sanvit
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