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> Also, most of the issues will not be with obscure email servers, they will be with Outlook and Gmail. When you send email, you will never know if your email w

by wolrah 5y ago

> Also, most of the issues will not be with obscure email servers, they will be with Outlook and Gmail. When you send email, you will never know if your email will be delivered to inbox, delivered to spam folder, or blackholed entirely. In my personal experience, over five years of running my own business and personal email entirely and another decade and counting since of running PBXes that directly send voicemail messages, Gmail has only explicitly blocked me once, and that was 100% legitimate because the site the PBX was located at had an infected PC. It occasionally will filter messages to the spam folder, but that almost always means one of the users actually flagged a message. I could send an email to myself from a bogus address via raw SMTP over Telnet to port 25 and I'd be willing to bet my week's pay that Gmail delivers it. They might mark it as spam, but they deliver reliably. Microsoft on the other hand is a massive pain in my ass. They usually work, but about 4-5 times a year they seem to randomly pick one of my systems to treat as suspicious and block emails from. The process listed in their block message always works, but it's annoying to have to deal with regularly, especially with no rhyme or reason. Yahoo is the worst, they straight up block everything I do with no recourse. I have one user who insists on using his Yahoo email and I basically had to tell him we don't care that Yahoo won't accept messages.

dqv 5y ago
Do you/did you have feedback loop accounts setup for all of them? Yahoo, for example, sends a notification to sys@ (or whatever email you tell them to) when someone marks one of our emails as spam or when it thinks we're sending bulk email. They also have sender support. They did want me to set up something where we used the same connection to send email to them. I forgot My "blacklisted" email company is Zoho because they consistently greylisted and blocked our correspondence with clients and have no one to contact to resolve email issues for senders.
- ZohoMailSupport 5y ago
  Hi there! I'm contacting you from the Zoho Mail team. Please drop an email to support <AT> zohomail <DOT> com with the sending server logs & IP address. Our technical team will analyze and get back to you with a potential resolution. Thanks!
jari_mustonen 5y ago
Hi Wolrah I'm starting a new company where email connection to my user base is essential. From time to time I also need to sen all users certain notifications which looks kinda like marketing email but isn't. Could you contact me as I would like to ask your opinion on the configuration that I'm trying to set up. I would also like to discuss your experiences. If isn't too much, you can reach me by email at jari@itsellesi.fi.
- tacon 5y ago
  Rather than depend on a single person's experience about running email systems, you might check out the Mailop mail operator's list: https://www.mailop.org/ https://www.mailop.org/
- x0x0 5y ago
  I'm not sure if you know about this, but in case not -- sendgrid is dirt cheap for transactional emails. And there's tons of offerings for marketing emails; I'm partial either to sendinblue or ses depending on your use case. There really isn't much reason to roll your own, particularly with ses.
creeble 5y ago
From 23 years of running my own email (and for about a dozen other domains), this is a pretty good summary. One domain has a small mailing list of about 200 users. The @yahoo.com addresses (and related, Yahoo-handled domains like old @att and @sbcglobal domains) are often just dropped. Gmail addresses frequently go to spam, especially newly-added domains. I have found that having multiple @gmail users mark them as “not spam” tends to help, but not always. My email server has had the same IP address for over 18 yrs, fwiw.
- berkes 5y ago
  My emailserver runs at linode. It delivered fine for some 10 years, then I started getting blackholed (at Microsoft live, hotmail, 365, outlook). This IP does only mail. Server is secure, up to date and has all the DKIM/SPF nonsense. It's impossible to reach humans that can help. It's impossible to unlist. So I'm now on my third IP, my last one running mail for 4+ years, from Digital Ocean. Only now, occasionally, does an email get through. I'm almost 100% confident that Microsoft just blanket blackholes or punishes anything from Digital Ocean or Linode.
  - oarsinsync 5y ago
    I share your confidence that lots of providers blanket drop mail from IP ranges owned by cheap VPS providers. The cost of swtiching IPs within those providers is low, so spammers have already abused that, and made life worse for the rest of us as a result.
    - neop1x 5y ago
      Yes, I had a first-hand experience with this. Cheap VPS was blackholed right away at Yahoo and any attempt to unblock it was not successful. It makes sense though. Then I set up my own bare metal server and put it into a real datacenter serverhousing. I had couple of problems at the beginning and later once a few years later - problems sending to microsoft - but all those were resolved rather quickly via their forms. And I haven't had any deliverability problems since then. The serverhousing I used is very strict regarding spam reports. I once tried to use the server also for sending newsletters (no spam lists, just emails which explicitly subscribed). Someone reported it as spam once and serverhousing contacted me soon after that they don't tolerate any spam. I explained that it was not spam and that there was unsubscribe link but I decided to not use it for any kind of marketing again. I think specialized services are better for this.
kureikain 5y ago
I can totally echo this(running my email forwarding service [0]) so I deal with it at high email volume too. Outlook/Hotmail is kind of stupid in this sense: if the first time, a new domain send an email they are very likely to flagged as spam. But if the user simply reply or send to that email, the moving forward hotmail won't flagged it. In other word, hotmail rely stringly - is this domain new? - is this ip address start to send email new? - if I interact with this sender in the past Seems thing with icloud and their proofpoint spam filtering. gmail in other hand, has the best delivery rate, clear error message, great rate limiting and cool down period. gmail is very smart, if we accidently send spam(due to our failure to filter out spam), gmail won't blocklist the whole IP, but hotmail/icloud does. And the process to delist from them homail/icloud are just absurb. I'm unable to contact their team. --- [0] https://hanami.run https://hanami.run

by wolrah 5y ago

dqv 5y ago

Do you/did you have feedback loop accounts setup for all of them? Yahoo, for example, sends a notification to sys@ (or whatever email you tell them to) when someone marks one of our emails as spam or when it thinks we're sending bulk email. They also have sender support. They did want me to set up something where we used the same connection to send email to them. I forgot My "blacklisted" email company is Zoho because they consistently greylisted and blocked our correspondence with clients and have no one to contact to resolve email issues for senders.

ZohoMailSupport 5y ago
Hi there! I'm contacting you from the Zoho Mail team. Please drop an email to support <AT> zohomail <DOT> com with the sending server logs & IP address. Our technical team will analyze and get back to you with a potential resolution. Thanks!

jari_mustonen 5y ago

Hi Wolrah I'm starting a new company where email connection to my user base is essential. From time to time I also need to sen all users certain notifications which looks kinda like marketing email but isn't. Could you contact me as I would like to ask your opinion on the configuration that I'm trying to set up. I would also like to discuss your experiences. If isn't too much, you can reach me by email at jari@itsellesi.fi.

tacon 5y ago
Rather than depend on a single person's experience about running email systems, you might check out the Mailop mail operator's list: https://www.mailop.org/ https://www.mailop.org/
x0x0 5y ago
I'm not sure if you know about this, but in case not -- sendgrid is dirt cheap for transactional emails. And there's tons of offerings for marketing emails; I'm partial either to sendinblue or ses depending on your use case. There really isn't much reason to roll your own, particularly with ses.

creeble 5y ago

From 23 years of running my own email (and for about a dozen other domains), this is a pretty good summary. One domain has a small mailing list of about 200 users. The @yahoo.com addresses (and related, Yahoo-handled domains like old @att and @sbcglobal domains) are often just dropped. Gmail addresses frequently go to spam, especially newly-added domains. I have found that having multiple @gmail users mark them as “not spam” tends to help, but not always. My email server has had the same IP address for over 18 yrs, fwiw.

berkes 5y ago
My emailserver runs at linode. It delivered fine for some 10 years, then I started getting blackholed (at Microsoft live, hotmail, 365, outlook). This IP does only mail. Server is secure, up to date and has all the DKIM/SPF nonsense. It's impossible to reach humans that can help. It's impossible to unlist. So I'm now on my third IP, my last one running mail for 4+ years, from Digital Ocean. Only now, occasionally, does an email get through. I'm almost 100% confident that Microsoft just blanket blackholes or punishes anything from Digital Ocean or Linode.
- oarsinsync 5y ago
  I share your confidence that lots of providers blanket drop mail from IP ranges owned by cheap VPS providers. The cost of swtiching IPs within those providers is low, so spammers have already abused that, and made life worse for the rest of us as a result.
  - neop1x 5y ago
    Yes, I had a first-hand experience with this. Cheap VPS was blackholed right away at Yahoo and any attempt to unblock it was not successful. It makes sense though. Then I set up my own bare metal server and put it into a real datacenter serverhousing. I had couple of problems at the beginning and later once a few years later - problems sending to microsoft - but all those were resolved rather quickly via their forms. And I haven't had any deliverability problems since then. The serverhousing I used is very strict regarding spam reports. I once tried to use the server also for sending newsletters (no spam lists, just emails which explicitly subscribed). Someone reported it as spam once and serverhousing contacted me soon after that they don't tolerate any spam. I explained that it was not spam and that there was unsubscribe link but I decided to not use it for any kind of marketing again. I think specialized services are better for this.

kureikain 5y ago

I can totally echo this(running my email forwarding service [0]) so I deal with it at high email volume too. Outlook/Hotmail is kind of stupid in this sense: if the first time, a new domain send an email they are very likely to flagged as spam. But if the user simply reply or send to that email, the moving forward hotmail won't flagged it. In other word, hotmail rely stringly - is this domain new? - is this ip address start to send email new? - if I interact with this sender in the past Seems thing with icloud and their proofpoint spam filtering. gmail in other hand, has the best delivery rate, clear error message, great rate limiting and cool down period. gmail is very smart, if we accidently send spam(due to our failure to filter out spam), gmail won't blocklist the whole IP, but hotmail/icloud does. And the process to delist from them homail/icloud are just absurb. I'm unable to contact their team. --- [0] https://hanami.run https://hanami.run