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Floodgap may be relocating, which may mean if I can’t preserve the IP that I’d lose over a decade of accumulated good karma (I do have an SPF and have never been on any major blacklist or RBL). I run my own mail server, and have done since the late 1990s.

Although it’s attractive to consider outsourcing E-mail entirely to something like Fastmail, I’m thinking I’ll still receive E-mail and simply pay for a “recognized good relay” for sending only. Anyone done this? What service do you like?

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    I recently started running my own email server for receiving email, and sending email through Sendgrid. Sendgrid has a free plan that allows for 100 emails per day. Here’s the related Lobsters post in case you are interested: https://lobste.rs/s/s10jr0/running_my_own_email_server

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      How good a sender reputation does Sendgrid have? Have you had any instances where mail bounced or didn’t get delivered?

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        I haven’t had any problems. Sendgrid has a fairly good sender reputation as far as I know. It’s one of the larger email handling companies.

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          In my experience if you’re on free tier, you get an IP with a bad reputation. You have to pay to get a good IP.

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        I’m nervous about things like SendGrid. If I send a mail from my server to yours, then I can read it and so can anyone with access to your server. If I send through sendgrid, they’re able to see the plain text of every email that I send. I find it quite hard to believe that they’d offer this as a free service if they weren’t data mining that.

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          They’re offering a free service because it costs them very little and is useful for getting people to buy their commercial offering. Test for free is an excellent method.

          As for security:

          • if you’re sending to a mailing list, you weren’t going to encrypt

          • if you’re sending private email, you need to encrypt the payload end-to-end

          • if you’re sending really secret messages, you want to avoid traffic analysis, too, so email is not for you

          The concerning thing about SendGrid et al is that they continue to devalue individual email servers and make it easier for the NSA or agency of your choice to do mass surveillance.

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            Yes, I also consider E-mail “wide open,” so deliverability matters more to me than security, even though both are nice.

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            I just started using SendGrid, and I’m a little wary, but I think they offer the service as a loss leader, more than a source of revenue. They did send a nag email every day for a couple of weeks after I signed up, but that seems to have stopped.

            That being said, I’ve always considered email definitely not secure, and open to be read by anyone, so them being able to see the plain-text is not really a concern for me.

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          I’ve been running our own email hosting (personal) for only a decade, but haven’t run into any such deliverability related problems. If one is not sending bulk/unsolicited email, and is good on SPF/DKIM/DMARC practices, and not hosting any kind of malware, or malware operations, then that problem is mostly non-existent. The only time one may have trouble is when one end up being a participant in backscatter, which can be easily avoided by performing anti-spam checks at the time of connection, instead of delaying for later, therefore not bouncing back any email. Unless one is receiving tonnes of emails per minute that this strategy may start becoming a bottleneck. Even LKML subscriptions by couple of our users cause us no problem.

          OTOH, I would invest in a backup MX which can hold your email, if one’s primary MX is down for maintenance, but this I guess you’re already aware of.

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            Yup, invested in a small slice for a backup MX years ago. It’s paid off several times. However, I have had deliverability problems with T-Mobile and Microsoft which required some cracking heads with their support staff (they simply had banned entire netblocks), so it certainly happens.

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              I don’t think I sent as many emails to Microsoft, or T-Mobile to notice if my network block is blocked on their side. Or maybe just lucky in terms of hosting I use, which is Hetzner.

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            I’ve been using smtp2go for about five years for personal email. It supports all the major auth schemes automatically.

            (this might be my first comment on lobsters but I’m not affiliated with them by any means - just been a happy customer)

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              I’ve used mySMTP, mostly because it appears to be the only genuinely European SMTP relay operator (they are based in Denmark). I however found they were blacklisted on some blacklist that caused my e-mails to be rejected at some rare occassions (one of which was rather important and was the reason why I stopped using it).

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                I’ve run my own mailserver for about 8 years, for personal email and a few businesses that I run (about 12 people use my server daily). I’ve had surprisingly few problems sending mail directly to recipient servers without using a relay. However in the last year, some mail servers started blocking the entire IP ranges of my VPS provider (DigitalOcean). So now instead of sending all email through a relay, I just use a relay for messages destined for those servers. All others still get sent directly.

                I surveyed the following:

                • SendGrid - all emails were delivered to junk mail
                • sendinblue.com, mailjet.com - All emails got an unsubscribe header which makes it look like bulk email
                • mailgun.com - This one worked well! It is technically not free, but so far I’ve been under the threshold for them to not bother actually charging my credit card
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                  Wow, great survey. I might look into Mailgun. I don’t mind paying (in fact, I’d rather be paying).

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                  I do all my e-mail using gmail.

                  E-mail is not a decentralized protocol. It’s time we accept that. The few big players have 100% of the control and can blacklist anyone’s private server at any time for any (or no) reason, and when they do, there’s nothing you can do about it and you can’t participate in society anymore. Decentralized mail has lost.

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                    I recently renumbered an email server and it was mostly fine. Rackspace has some crazy rule about “warming up” your new IP with at least 20 but fewer than 100 emails per day for a week or some such nonsense, but other than that everything sorted itself out pretty quickly. A couple big providers deferred mails for a few, but ultimately took them. I had to update whitelists for places like outlook.com