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After self-hosting my email for twenty-three years I have thrown in the towel

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Re: After self-hosting my email for twenty-three years I have thrown in the towel

#71

Post by zahllos »

I'm on 12 years of self hosting email and counting. Once every so often, I do end up being blocked, usually by Outlook and once by Yahoo. I'm in their 'sender program' and they still don't actually bother to contact postmaster@, but a few emails is usually enough to unblock the block within 24h.

Agree with a sibling comment that many major providers fail to operate the SPF/DKIM/DMARC tools they insist you do.

Each to their own, but ultimately if we don't hold on to the freedom to operate our own mailservers, it will be taken away through inaction. This means doing some things right: DMARC, DKIM, SPF of course, server maintenance, good password policies and of course IP reputation. The best way I can recommend for IP reputation is to use a dedicated provider or VPS provider that disallows things like VPN endpoints, where it is less likely they'll assign an address with a poor reputation. A good provider might also ask you what you intend to host, and you might be able to discuss IP addresses with them.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#72

Post by conradev »

eikenberry wrote: post #55
jasode wrote: post #21

The sweet spot for having control over your email while simultaneously minimizing unforseen headaches is to simply own your domain name and point the MX record to whatever hosting provider you want instead of self-hosting a server at home. Same philosophy for exposing a your personal blog of html files or content like mp4 videos. The sweet spot is to focus on buying a domain name you control. Then let Amazon S3, or C…

There is also a happy medium. Host your own MX servers but use someone else's SMTP servers. You have complete control over the incoming mail but dodge the filters by using the established business for sending mail.

You can also use an MX backup service which will accept mail when your server is offline (and it will resend it when the server comes online)

You can also even keep Gmail as your MX server! Just move messages off of it as soon as they arrive. It's just a mailbox, after all

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#73

Post by tambourine_man »

secabeen wrote: post #56

The general rule of thumb for my home server is that messages to people I've contacted before, or to addressees that were in a thread that I'm also part of get delivered reliably. Messages to new people I've never emailed before often go to spam. I've learned to accept this.

The biggest challenge is in the sending.

If, for whatever reason, Gmail doesn't like your setup, even if it's 100% according to specs, it's effectively broken. And there's no one to resort to, often no previous relevant search result, because the errors are vague when not silent (you don't get to know the email was hard rejected, i.e. has not even reached the recipient's Spam box).

Your only hope is for your complain to go viral on HN or Twitter and some Googler takes pitty on you.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#75

Post by lamontcg »

gingerlime wrote: post #69

Sending email out is a royal pain. Trying to deal with a Microsoft ban on my IP even though it’s sparkling clean for several years. DKIM, DMARC, SPF etc all ser up, reverse dns, you name it. Looks like Linode is being blocked as a whole pretty much? Hate the level of centralization, particularly since there’s still a shit ton of spam still around. Sorry for the rant. https://docs.microsoft.com/en-us/answers/questions…

I have my personal e-mail on linode for probably 15 years or so and haven't had any issues with e-mail delivery (knock on wood). Had the same two static IPs there for years, and have always had things locked down so I couldn't be used as a relay for spammers.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#76

Post by tayiorrobinson »

I did training provided by a large email security firm, and one thing the presenter said was along the lines of "this spam filter defaults to block the senders domain & IP, you can set an expiration on that block butI don't see a reason why you would". One misconfigured server sending out a single email and I assume by extension someone impersonating your domain could get you perma-blocked from sending emails to that company, and I assume it'd reduce your trust rating for other orgs using that provider.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#77

Post by ShowalkKama »

>I implemented all the acronyms, secured antispam measures, verified my domain, made sure my server is neither breached nor used to relay actual spam, added new servers with supposedly clean IPs from reputable providers, tried all the silver bullets recommended by Hacker News, used kafkaesque request forms to prove legitimity, contacted the admins of some blacklists.

I cloned a repo, edited two lines in a yaml file, ran docker-compose, logged into a web ui, added my domain, added a couple of dns records (MX, spf, dkim, dmarc) and everything worked (yes, I can deliver emails to gmail and outlook).

I honestly have no idea why so many people say that self hosting emails is hard.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#78

Post by Symbiote »

rsyring wrote: post #66
dsr_ wrote: post #51

I can't send mail to mit.edu addresses. It gets rejected with a message that says I should talk to Microsoft. I frequently end up in GMail's spam folders. No idea why. I see no more than one piece of 'spam' a week; everything else is caught by a combination of a 15 minute greylist, the zen spamhaus BL, and SpamAssassin evaluating things. There are a bunch of spammers who send from accounts with valid SPF and DKIM, by…

SPF/DKIM are not intended to prevent people from sending spam. They are intended to let a domain owner tell other email providers what servers have the right to send email from that domain (and sign email). I can send email all day from joboffers@google.com. But most email providers will check SPF and see that my VPS IP is not authorized by google.com to send email, and it will go to spam. Those standards wouldn't ke…

> I can send email all day from joboffers@google.com. But most email providers will check SPF and see that my VPS IP is not authorized by google.com to send email, and it will go to spam.

Actually, it will be discarded completely.

Google's DMARC policy is for mail from unrecognized origins to be rejected:

  host -t txt _dmarc.google.com
  _dmarc.google.com descriptive text "v=DMARC1; p=reject; rua=mailto:mailauth-reports@google.com"
p=quarantine would send it to spam.

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#79

Post by lolinder »

type_Ben_struct wrote: post #16

I relate to this. I also stopped hosting my own mail server for this exact reason. However I do think it’s a case of damned if you do damned if you don’t. As a consumer of big tech email I become equally frustrated when spam makes it past the filter and I expect them to do more. If it’s easy for the average person to setup a mail sever with high reputation then it’s easy for spammers to do the same. I can’t think of…

The paradox here is the same one patio11 discussed in "The optimal amount of fraud is non-zero", on the front page yesterday [0]. The more non-tech people have an email address, the more we have to prevent fraudulent email, and the harder it becomes to run your own email address.

The original email users were much more savvy and needed less protecting against fraud. Now my grandma has an email, and if we're not careful she ends up on the phone with "Microsoft customer support" giving them full access to her computer. Spam filters aren't just a question of irritation anymore, people's life savings are at risk.

[0] https://news.ycombinator.com/item?id=32701913

Re: After self-hosting my email for twenty-three years I have thrown in the towel

#80

Post by zahllos »

gingerlime wrote: post #69

Sending email out is a royal pain. Trying to deal with a Microsoft ban on my IP even though it’s sparkling clean for several years. DKIM, DMARC, SPF etc all ser up, reverse dns, you name it. Looks like Linode is being blocked as a whole pretty much? Hate the level of centralization, particularly since there’s still a shit ton of spam still around. Sorry for the rant. https://docs.microsoft.com/en-us/answers/questions…

Wouldn't surprise me if Linode were entirely blocked. Also anything in M247 Ltd's ASN. They host a lot of VPN endpoints, including Mullvad's.

Step 1, I'd move off Linode. Find a local DC or business you can support by hosting a VPS or dedi box with them. LowEndBox might be an interesting place to search but avoid anything too famous.

Step 2, join this https://sendersupport.olc.protection.outlook.com/pm/services.... They don't actually email me when they block my IP, but at least when I contact them I can argue I'm already in their program and they didn't actually notify me of any sending issues. I've got myself unblocked relatively quickly this way.

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