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Re:The “mail is hard” myth by ogoffart on Sunday September 01, 2019 @01:07PM (#20853325)
> I think the biggest pain in hosting your own mail server is getting your outbound mail delivered into the mailboxes of the large providers without being marked as spam

Why do you think that? The article mention exactly this could just be a myth that perpetuates because people repeat it without actually trying it.

In fact, I used to think exactly like you when I originally set up my personal mail server and opted for the hybrid setup you suggest. However, when the third party service I used to send mail shut down a couple of years ago, I quiclky set up outbound mail on my own server. None of my emails are considered as spam, and I haven't touched the mail configuration since.

Re:The “mail is hard” myth by baobabKoodaa on Sunday September 01, 2019 @03:32PM (#20854254)
> None of my emails are considered as spam, and I haven't touched the mail configuration since.

Sounds like you never actually tried to measure the delivery rates of your outgoing email. No email server is actually able to get 100% of its outgoing mail past spam filters.

I've ran my own email server for a few years and I can confirm that the article is making false claims. It's incredibly difficult to deliver email as a low volume sender. The article falsely claims that it's not difficult and that people simply haven't tried it. Well guess what, I did try it - for years - with countless hours sank into it.

I wrote a blog post documenting my numerous, unsuccessful efforts to get my email delivered. I wish people would stop spreading these baseless falsehoods.

https://www.attejuvonen.fi/dont-send-email-from-your-own-ser...

Re:The “mail is hard” myth by com2kid on Sunday September 01, 2019 @08:00PM (#20855773)
Gmail occasionally classifies the random email from YouTube as spam.

Given that, 100% delivery rate seems like a dream.

Re:The “mail is hard” myth by djsumdog on Monday September 02, 2019 @01:42AM (#20857003)
Re:The “mail is hard” myth by eikenberry on Sunday September 01, 2019 @03:13PM (#20854126)
> Why do you think that? The article mention exactly this could just be a myth that perpetuates because people repeat it without actually trying it.

Not sure about OP, but many people have tried it and it is a PITA. Even once you have everything setup right (SPF, DKIM, etc.), you still have to deal with IP issues. I ran my own mail server for years (actually, still do for incoming) and it worked fine for about 10 years until I needed to switch providers and got a new IP. Then I found I had to deal with an IP with no reputation and IP whitelist/blacklists. The deal breaker was finally dealing with blacklists that you had to pay to keep off of.

UCEPROTECT was the one at the time. They would randomly add my provider's entire IP space to one of their lists and during those times all email to a couple ISPs would bounce and the only way to get my IP whitelisted from those blanket bans was to pay $$. Switched to using an external provider for outgoing mail and haven't had a problem since as they take care of that crap.

Re:The “mail is hard” myth by al_form2000 on Sunday September 01, 2019 @03:53PM (#20854423)
UCEPROTECT was the pits and its operators were unprincipled lowlifes. Luckily they (like all the pay-to-delist BLs) never got more than minimal traction, so ignoring them and their BS mostly worked ('course you needed a /19 to be effective at doing that)
Re:The “mail is hard” myth by eikenberry on Sunday September 01, 2019 @04:02PM (#20854498)
You use past tense... why? They still exist and seem to be continuing their blacklist/blackmail BS. The ISP in question was AT&T and their subsidiaries (I mostly got hit sending to bellsouth.net), which I wouldn't consider to be that small of an ISP and was enough that I eventually gave up.
Re:The “mail is hard” myth by al_form2000 on Sunday September 01, 2019 @05:23PM (#20855008)
Past (more than 5 years ago as I reckon) is when I locked horns with them. They may have switched policies, I may have gotten smarter than them, who knows.
Re:The “mail is hard” myth by eikenberry on Sunday September 01, 2019 @06:13PM (#20855344)
Maybe your provider was taken off their lists. My last run-in was only 2 years ago, so as of then they hadn't changed.
Re:The “mail is hard” myth by al_form2000 on Sunday September 01, 2019 @07:37PM (#20855677)
I was the ISP, & they had BL'd one of my servers for delivering NDRs. They used to blacklist /16 netblocks wholesale for this kind of, "sins", and demand ransom for getting out.
Re:The “mail is hard” myth by juped on Sunday September 01, 2019 @08:54PM (#20855965)
No - the article contradicts itself. The author says it's "a myth" and "just set up spf/dkim", and then later says "This is already happening with one specifically requiring mails to be sent from another Big Mailer Corp to hit the inbox, or requiring that senders be added to the contacts for others. Any other sender will hit spambox unconditionnally for a while before being eventually upgraded to inbox."

Which is it? Those of us who have run mail servers know that you get unconditionally spammed all the time.

Re:The “mail is hard” myth by defanor on Sunday September 01, 2019 @01:24PM (#20853425)
Not GP, but it matches my experience: with reverse DNS, DKIM, SPF, being in DNSWL (and not in DNSBLs) some of my messages end up in Gmail spam folders (very recently received a reply to a message I sent 3 years ago because of that, for instance). A while ago there were strange issues with Google-hosted mailing lists as well, with some messages not being visible even to an ML administrator, while Gmail servers accepted mail just fine (maybe it still happens, I'm just not writing to those). I hear similar stories from other mail server administrators too.

I think it's more of a Gmail/BigMailerCorp issue, and still using a private mail server myself, but I don't think it's fair to say that it's all easy and works flawlessly, even with strangely behaving mail servers on the other end.

Re:The “mail is hard” myth by pw6hv on Sunday September 01, 2019 @01:41PM (#20853519)
> some of my messages end up in Gmail spam folders (very recently received a reply to a message I sent 3 years ago because of that, for instance)

How did this happen if Gmail deletes spam after some weeks?

Re:The “mail is hard” myth by RandomBacon on Sunday September 01, 2019 @02:01PM (#20853664)
I recently checked my Trash folder in Gmail. I had emails in there that were several years old, right below the text that says Gmail deletes emails in the Trash folder older than 30 days.
Re:The “mail is hard” myth by defanor on Sunday September 01, 2019 @02:00PM (#20853659)
Indeed, a quick search suggests that spam is automatically removed every 30 days there. The wording was "Google hid it from me", so either I have wrongly assumed that it's about the spam folder, or it is possible to disable autoremoval.

Edit: or, as the sibling comment suggests, it behaves strangely with respect to removal as well.

Re:The “mail is hard” myth by scarejunba on Sunday September 01, 2019 @02:22PM (#20853790)
Or user accidentally archived it. “X did Y” is often a user’s way of saying “I accidentally made X do Y” without having to accept blame. It’s the “dog ate my homework” of excuses.
Re:The “mail is hard” myth by inetknght on Sunday September 01, 2019 @02:33PM (#20853877)
Another instance of Google being user hostile?
Re:The “mail is hard” myth by toomim on Sunday September 01, 2019 @01:11PM (#20853356)
I think that because I tried it and my outgoing emails weren't being delivered.

Big mail companies have blacklisted entire C-blocks of IP addresses at VPS providers, because parts of those blocks have been used to send spam in the past, and you won't know until you actually check with people you are sending mail to, to ask if they've received them. It sucks.

Re:The “mail is hard” myth by u801e on Monday September 02, 2019 @10:48AM (#20859386)
Wouldn't the mail server log the connection attempt and the rejection reason?
Re:The “mail is hard” myth by dpifke on Sunday September 01, 2019 @03:46PM (#20854364)
New domains and new IPs are penalized heavily by most services' spam filters.

My guess is that a lot of people try it, have poor delivery rates, and abandon the effort before they have enough time to develop decent domain & IP reputations.

I've been running my own personal mail servers since 1995, on my current IP addresses since ~2016. If I add a new domain to my configuration, it takes 1-2 weeks before Gmail will reliably accept mail from it. Once I wait that out, delivery is mostly flawless.

Re:The “mail is hard” myth by rstuart4133 on Sunday September 01, 2019 @09:04PM (#20856004)
As a person who does run a number of (smallish) mail servers, some outgoing mail does get classified as SPAM and I have to fix it. It's very rare - every 3 months or so maybe, but it does happen. (Possibly the most irritating thing about this is they won't tell you what emails made them think you are sending spam, lets alone why they thing it's spam which makes root cause analysis damned near impossible.) The reverse happens too - we occasionally block non-spam emails.

But, and it's a damned big but, AFAICT, my email servers make less of those mistakes than the big email providers like Google or Microsoft, so the overall reliability of my home grow system is higher. It's got to the point that when someone complains they didn't get an email I got, my first question is "do you use gmail?".

The other big but it is it complex. It isn't just a single server - they are a network of them that distribute email across a geographically dispersed organisation. Despite being distributed it archives copies of all email that passes through it (as required by law here). There are some 2.5K of configuration lines driving it. So yes, it requires some effort to set it up. However, like your case those 2.5K lines haven't changed overly in over a decade.

The flexibility the system provides us in the way we handle email is invaluable. As a consequence of that flexibility a lot of emails are never seen by humans - they routed to a place they can be automatically processed.

Personally I wouldn't say email particularly hard, or particularly easy. It seems no more difficult than all the other things you have to do to manage a cluster of servers. The rewards for getting do it inhouse are pretty big, because just like everything else a programmer or sysadmin has control of, over time it will be scripted so heavily it will become almost invisible.

Re:The “mail is hard” myth by marticode on Sunday September 01, 2019 @09:28PM (#20856117)
I tried it a couple years ago. Delivering to large providers wasn't the problem. The problem was smaller ISP, one of them flat-out banned all IPs from my host provider (Digital Ocean), others for no reason I could find banned my specific IP. (I was not on any public block list BTW)

Getting off their block list was either impossible or involved digging some old forum posts to find an email address that you could try your luck with, usually with no result as it seems nobody was reading it anyway.

Re:The “mail is hard” myth by jojoo on Sunday September 01, 2019 @04:23PM (#20854638)
I've been running a mailserver for ~15 Years.

I found it to be very time consuming and complicated, mainly because of the trouble of outgoing mail.

Re:The “mail is hard” myth by uijdihrihr on Sunday September 01, 2019 @03:18PM (#20854157)
I work in the industry and it's no myth. Even using expensive relay servers doesn't guarantee the big email providers will deliver your or mail or care much to explain why it isn't being delivered. Big email won't even respond to their own customer complaints that they aren't receiving email.