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

cfenollosa.com

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

#381
post #143
post #42

Very interesting, I've self hosted my e-mail since 1999, which incidentally is 23 years ago. My current server is at Hetzner in Germany.

do you have your own asn? The entire Hetzner network has been banned by Microsoft, so you can't send to Hotmail addresses

Is that really a problem?

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

#382
post #235

Earlier quoted context omitted.

Indeed. I host my domains with dreamhost and it turns out that outgoing mail from their servers will get marked as spam by Google. The exact same mail sent through a gmail address (whether under gmail.com or a custom domain) will be delivered no problem (although after the sudden closing of legacy free email, I found that emails that I had been sending via gmail with my own domain that had been getting blocked by spa…

The problem is your outbound mail server does not have a good reputation. You also probably do not have a large enough swath of IP space to prevent bad neighbors from becoming your problem. Lots of tricks to getting your email sent reliably to most mail servers. What got me out of hosting mail was trying to send an email to a potential lead I met at a local meetup. His email was hosted at some very small and relative…

I'm guessing dreamhost has a decent chunk of IP space...

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

#383
post #243

Earlier quoted context omitted.

This indeed looks like a good direction. A decade ago Freenet (not sure if it still exists?) had a problem with spam on its equivalent of USENET. It was pretty bad, until they changed the protocol so that it's the sending node that keeps the message, which is then pulled (or not) by the recipients. It made a lot of sense to me: I'm the one sending you the message, I want you to see it, while you don't even know wheth…

Wow that's ingenious - and obvious when you think about it. I guess evolving the email standard is a much bigger obstacle though, no matter how clever the proposal.

it's ridiculously easy to create a template that is stored and when the remote client pulls the message only a few variables has to be substituted. it's how spam is generated after all :)

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

#385

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 had that issue with them once in the past, I found a form on their site, filled it out and they had it fixed in a week or so. No issues since then.

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

#386
post #168

Earlier quoted context omitted.

It could be we have different circles of acquaintances. I have managed to get non technical friends to GPG encrypt their emails. I also talked 2 lawyers into using this and the two lawyers are not only non technical but have nearly zero patience.

I guess a lawyer might know a thing or two about confidential messages.

Not all of them. I keep seeing lawyers sending photos of sensitive documents using their cellphone and Whatsapp (before encryption), and most of them don't even care about all those documents still residing on their cellphone, at the mercy of whoever steals it since all the security they have in place is that swipe thing that anyone with good eyes spots in 2 seconds straight.

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

#388

Earlier quoted context omitted.

> In every scenario, deliverability problems can be solved by smarthosting through a reputable email provider. Period. Could you provide an example of such a smarthost email provider that has the benefits you mentioned? Not challenging you, just genuinely curious.

Sure! I would never recommend, for instance, Dreamhost, but I set up a company's smarthosting with Dreamhost because the company was already using them. Dreamhost in general, though, is quite spammy. Linode and Panix come to mind. Really, though, many hosting companies won't necessarily list "smart hosting" / "smarthosting" as a service. If they offer a cheap VPS and offer outgoing SMTP, you can set up smarthosting t…

Deliverability problems sending from VPS providers like Linode are common. The article mentioned using a VPS.

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

#389
"Newsletters from my alumni organization go to spam. Medical appointments from my doctor who has a self-hosted server with a patient intranet go to spam. Important withdrawal alerts from my bank go to spam. Purchase receipts from e-commerces go to spam. Email notifications to users of my company's SaaS go to spam."

Are you talking here about incoming emails? I expected that these would be reliably delivered to you and that the problem is only with emails you send to the large providers?

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

#390
post #235

Earlier quoted context omitted.

Indeed. I host my domains with dreamhost and it turns out that outgoing mail from their servers will get marked as spam by Google. The exact same mail sent through a gmail address (whether under gmail.com or a custom domain) will be delivered no problem (although after the sudden closing of legacy free email, I found that emails that I had been sending via gmail with my own domain that had been getting blocked by spa…

The problem is your outbound mail server does not have a good reputation. You also probably do not have a large enough swath of IP space to prevent bad neighbors from becoming your problem. Lots of tricks to getting your email sent reliably to most mail servers. What got me out of hosting mail was trying to send an email to a potential lead I met at a local meetup. His email was hosted at some very small and relative…

It's more than that. I'm on a mailing list for a social organization that I've belonged to for 20 years, and has been hosted at the same place for all of that time. I have marked hundreds of the messages not spam, and still Google sends about 80% of them to spam.

Google does not care even if you have regular correspondence with an address -- if the server isn't big enough, it's going to spam. The user's wishes or ideas about what is or isn't spam are irrelevant.

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