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Here's the recipe: set up your own email server. Tweak configuration until eventually a test email from yourself to yourself lands in the inbox, then call it a

Here's the recipe: set up your own email server. Tweak configuration until eventually a test email from yourself to yourself lands in the inbox, then call it a day. Never actually measure your deliverability. Never investigate why you sometimes don't get replies to emails where you were expecting to get a reply to. In fact, just close your eyes and stick fingers in your ears. Then go on HN and talk about how easy it is to do this thing which you, totally, for real, really did do, like, for reals for reals.

horusthegame 3y ago
> Here's the recipe We read from different cookbooks and my reading comprehension is high. My sent email stats shows over 20K successfully sent emails just for my personal account, since 1999, when I started tracking it.
- baobabKoodaa 3y ago
  > My sent email stats shows over 20K successfully sent emails just for my personal account, since 1999, when I started tracking it. Ok, since you claim to have measurements, let's hear what they are: - What is the total number of emails sent? - What is the number of emails bounced? - What is the number of emails that landed in inbox (as opposed to spam)? - What is the number of emails blackholed? (recipient confirms delivery, but email doesn't show anywhere, not even in spam folder)
nulld3v 3y ago
Measuring deliverability is really not that hard. You do the following: - Setup blacklist monitoring (e.g. HetrixTools/MXToolbox) - Check if you can email Gmail - Check if you can email Hotmail - Check if you can email Office365 - Check on Microsoft SNDS that you are not blocked: https://sendersupport.olc.protection.outlook.com/snds/ https://sendersupport.olc.protection.outlook.com/snds/ Gmail, Hotmail and Office365 are the largest email providers and also the most strict ones. I have accounts on all of these providers so testing deliverability is trivial. You could argue that testing deliverability with one account is unreliable but in my experience it simply is not. Usually you send a couple emails across a week and if they all go through you are good. If you are paranoid, you can ask if any of your friends have Office365/Hotmail and email them. They probably have company or university accounts on there. My server has only been blocked once after all this, and ironically it was by another company that self-hosts their email...
- baobabKoodaa 3y ago
  > I have accounts on all of these providers so testing deliverability is trivial. You could argue that testing deliverability with one account is unreliable but in my experience it simply is not. Usually you send a couple emails across a week and if they all go through you are good. No, it's not trivial, and no, it doesn't work like that. It's fairly easy to get a test email to your own gmail/hotmail/office365 account delivered. It doesn't mean your other emails get delivered. For example, when I needed to send out a link for my wedding photographs to my wedding guests, I did exactly what you suggested: I sent a few test emails to Gmail and Hotmail test accounts that I had set up, confirmed that they delivered, and then proceeded to send the actual email which had a link and like 50 people in the BCC field. Guess what happened: all the Gmail accounts placed my email in the spam folder. So then I had to later send another email, using a different email provider, asking people to check their spam boxes for the link (this time not including the link in the body of the email with the hope that it would increase the chances of delivery). Note that this particular anecdote is not of self hosting email, it was using Migadu (I was initially not trusting that they can deliver email properly, so I ran those tests like you suggested, concluded that they seem to be delivering email, and then my actual real email was not delivered).
  - nulld3v 3y ago
    I guess I simply cannot share your pain because I've never had these problems. Actually I initially got placed in spam too in Gmail/Outlook but I always replied to my own emails and marked them as "Not Spam" and the problem just kinda disappeared? When I initially setup my server I was paranoid (as you should be) and so I had the following protocol: - Send all urgent email with Gmail - Send non-urgent email with my own server. If I don't get a reply within 24h, send again with Gmail, explaining my email troubles. Usually the other party would happily confirm whether or not my email landed in their spam without me even asking. It was never a cold-turkey migration to my self-hosted setup. It was more of a slow process over a couple months after I gained more and more trust in my server.
    - baobabKoodaa 3y ago

horusthegame 3y ago

> Here's the recipe We read from different cookbooks and my reading comprehension is high. My sent email stats shows over 20K successfully sent emails just for my personal account, since 1999, when I started tracking it.

baobabKoodaa 3y ago
> My sent email stats shows over 20K successfully sent emails just for my personal account, since 1999, when I started tracking it. Ok, since you claim to have measurements, let's hear what they are: - What is the total number of emails sent? - What is the number of emails bounced? - What is the number of emails that landed in inbox (as opposed to spam)? - What is the number of emails blackholed? (recipient confirms delivery, but email doesn't show anywhere, not even in spam folder)

nulld3v 3y ago

Measuring deliverability is really not that hard. You do the following: - Setup blacklist monitoring (e.g. HetrixTools/MXToolbox) - Check if you can email Gmail - Check if you can email Hotmail - Check if you can email Office365 - Check on Microsoft SNDS that you are not blocked: https://sendersupport.olc.protection.outlook.com/snds/ https://sendersupport.olc.protection.outlook.com/snds/ Gmail, Hotmail and Office365 are the largest email providers and also the most strict ones. I have accounts on all of these providers so testing deliverability is trivial. You could argue that testing deliverability with one account is unreliable but in my experience it simply is not. Usually you send a couple emails across a week and if they all go through you are good. If you are paranoid, you can ask if any of your friends have Office365/Hotmail and email them. They probably have company or university accounts on there. My server has only been blocked once after all this, and ironically it was by another company that self-hosts their email...

baobabKoodaa 3y ago
> I have accounts on all of these providers so testing deliverability is trivial. You could argue that testing deliverability with one account is unreliable but in my experience it simply is not. Usually you send a couple emails across a week and if they all go through you are good. No, it's not trivial, and no, it doesn't work like that. It's fairly easy to get a test email to your own gmail/hotmail/office365 account delivered. It doesn't mean your other emails get delivered. For example, when I needed to send out a link for my wedding photographs to my wedding guests, I did exactly what you suggested: I sent a few test emails to Gmail and Hotmail test accounts that I had set up, confirmed that they delivered, and then proceeded to send the actual email which had a link and like 50 people in the BCC field. Guess what happened: all the Gmail accounts placed my email in the spam folder. So then I had to later send another email, using a different email provider, asking people to check their spam boxes for the link (this time not including the link in the body of the email with the hope that it would increase the chances of delivery). Note that this particular anecdote is not of self hosting email, it was using Migadu (I was initially not trusting that they can deliver email properly, so I ran those tests like you suggested, concluded that they seem to be delivering email, and then my actual real email was not delivered).
- nulld3v 3y ago
  I guess I simply cannot share your pain because I've never had these problems. Actually I initially got placed in spam too in Gmail/Outlook but I always replied to my own emails and marked them as "Not Spam" and the problem just kinda disappeared? When I initially setup my server I was paranoid (as you should be) and so I had the following protocol: - Send all urgent email with Gmail - Send non-urgent email with my own server. If I don't get a reply within 24h, send again with Gmail, explaining my email troubles. Usually the other party would happily confirm whether or not my email landed in their spam without me even asking. It was never a cold-turkey migration to my self-hosted setup. It was more of a slow process over a couple months after I gained more and more trust in my server.
  - baobabKoodaa 3y ago