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Then you realize the true pain of having a near-zero reputation when trying to email anything to people on Gmail, Yahoo, Live, etc, etc. Expect to go to spam ev

by dpcan 7y ago

Then you realize the true pain of having a near-zero reputation when trying to email anything to people on Gmail, Yahoo, Live, etc, etc. Expect to go to spam even if you have DKIM, SPF, and no relaying. If anyone actually knows the secret to not having your own mail-server's mail go to spam on these bigger systems, please tell, I've Googled it for years with no success.

curiousfab 7y ago
For some reason I never had problems, even after a recent change of my IP address because I moved to a new VPS. Hetzner VPS, proper reverse DNS, SPF, that's all, not even DKIM. The only big ISP that doesn't like my mails is AT&T and I couldn't care less (in Europe, rarely have to deal with people @att.net).
- xiaomai 7y ago
  I also have no issues like this (I do SPF/DMARC but not DKIM)
- jstimpfle 7y ago
  I just do reverse DNS on a cheap VPS. I believe I don't even have encryption. Almost no problems since I switched to that setup 9 years ago. Some mails to Gmail end up in spam, and just yesterday I had my first "refused due to poor reputation" problem due to an unknown problem with Cloudmark. Have been able to reset my score there by filling an HTML form. Of course, there are some mails where I don't know if they landed in spam or I just didn't get a reply.
- the_angry_angel 7y ago
  In that case you are very fortunate. I was running my own mail server for nearly 10 years on Hetzner. Prior to that on other hosts and in the distant past at home. Running mail servers is something I have done professionally and successfully. The last time I moved boxes as I had many times before. I was on clean IP range but I had no IP reputation at all. In the past this wasn’t such a problem, especially with SPF, DKIM, rDNS, DMARC, server-to-server SSL etc. Around the same time I started having to deal with organisations (legal, etc for a death in the family and later rent) rather my my own circle of friends. It became extremely apparent that my mails weren’t hitting the inbox. But they were being accepted. This was extremely problematic. I was in the group stating that running your own mail server isn’t hard. I still say that. The hard problem is convincing the big players to let your low volume domains and IPs hit the inbox. I begrudgingly gave up my MX servers last year.
  - fiddlerwoaroof 7y ago
    I wonder if there's some sort of relay setup that could be used to mitigate this: e.g. if you want to run your own mail server, sign up for some kind of "mail ring" that transparently proxies the (encrypted) traffic from all the member mailserver administrators. That way, your public IP has a higher volume and more leverage getting delivered.
    - the_angry_angel 7y ago
      Integration with SPF and would be unfun and probably even impractical (max 10 lookups iirc?). I’d also worry about the inevitable abuse which would appear to originate from your range(s). If you can mitigate those though, it sounds interesting
singron 7y ago
I had DKIM, SPF, rDNS, etc. at first and went to Gmail spam. I registered on gmail postmaster tools and got some friends and family to add me to their contact lists and send me some outbound mail. Google now sends me more mail than I send them, and now I don't go to the spam list, even for gmail accounts I haven't contacted before. This was for personal email. If you are trying to send commercial email this strategy probably won't work.
- djsumdog 7y ago
  I don't have a high enough volume for my personal e-mail to even show up on the postmaster tools.
  - singron 7y ago
    Mine doesn't show up either, but I figured the verification process might have affected the spam classification.
- hckr1292 7y ago
  I've had a similar experience. Switching IP address of my mail server lost me some reputation, but mostly just using the directions mailinabox.email has worked for me
wpietri 7y ago
Agreed! I've been running my own mail server for 20+ years, and I would not recommend that anybody do this on a lark. Deliverability to GMail is a huge problem for me and has been for years. I even asked friends at Google to find out what the story was. All I got back is that the mail group was so careful/paranoid it wouldn't talk to them either. I would long ago have switched over to a vendor, but I use qmail-style tagging for sub-addresses (that is, instead of user+sub@domain, I use user-sub@domain). Almost nobody supports that. Especially not GMail (where my friends could tell me that was tagged as WONTFIX). If anybody has solved this, please do let me know (on here, via Twitter, or the email address in my bio). It's maddening.
- mgalgs 7y ago
  Curious why you're so attached to the qmail style subaddressing. Personal preference or is there a technical advantage?
  - big_chungus 7y ago
    Possibly not getting blocked. Many sign-up fields will block foo+spam@bar.net if I try to use it.
    - 77pt77 7y ago
      That's why I use "." as the separator. Now try using an email from a domain name with more that 3 letters in the TLD. Almost no one considers that a valid address.
      - zigzaggy 7y ago
        So if I bought my “name.rocks” I’ll have trouble using that as an email? I was looking forward to “firstname@lastname.rocks” and I never even considered it would be a problem. I’m disappointed
        voltagex_ 7y ago
ryandrake 7y ago
Sample size of one but I’ve run my own mail server for years and have almost never encountered problems of this nature. Right when I started with the VPS, rejections from Comcast started showing up in my logs, and I traced it back to the IP I got being in some blacklist. Requested a new IP and it has been smooth sailing ever since.
- pbhjpbhj 7y ago
  I had problems with MS (Hotmail/Live/Outlook/whatever they're call it now) when I changed hosting provider which I traced back to the hosting provider owning an IP that had in the past been associated with spam (that for-real is what I was told) -- that seemed a bit over-zealous to me. As it wasn't possible to pre-check IP addresses (it wasn't blacklisted, and in any case the email was being served from a different IP to the one that was apparently previously an issue) for any particular hosting company - and I could only afford cheap hosting - then I decided to relent and made an Outlook online account and sent the mail from that. It seemed totally crazy to me to reject mail from a 15 year old domain that sent at most 30 emails to Outlook per month, _always_ in replay to an email; SPF/DMARC were set AFAIR and whitelisting the email address from within my own 20+yo hotmail account didn't make any difference, MS still wouldn't let _me_ receive the emails. Like if your user says the email address is fine, and sends an email to that address, .. then perhaps you should allow the user to receive that one email??
Spivak 7y ago
There is no secret, because if there was then it would be used by spammers and then cease to work. And if there was a secret to building a reputation you could make a lot more money as a brand consultant with it than running an email server.
ransom1538 7y ago
Yes. After many years, I think the algorithm is this: If the FROMs top level domain is in the top 500 websites OR is a .edu NOT SPAM, ELSE, send to "proprietary spam filter". The "proprietary spam filter" is some random crap code that is unique to each email server company. You could spend years trying to figure out how to game "proprietary spam filter" - but it is a fools errand.
- donmcronald 7y ago
  I don't think so. I see @facebookmail.com in SPAM folders way more often than you'd expect on both Office 365 and GSuite. I also see mail from Microsoft and Google filtered into SPAM on their own platforms once in a while.
  - weaksauce 7y ago
    Is that a proper email from Facebook with all that entails or is it a email from a spoofer/scammer?
    - donmcronald 7y ago
      It's completely legit. I think it's the domain Facebook uses for notifications. https://imgur.com/a/nzkMNDS https://imgur.com/a/nzkMNDS
  - peterwwillis 7y ago
    facebookmail.com is not in the alexa top 500, whereas facebook.com is. spam filters really are this dumb at big companies. usually the way we'd get around it is we'd call up $big_company and say, "hey, could you please remove our e-mails from your spam list? we would like to send your users a lot of mail right now." a few hours later, we'd be good to go. this was ~2007. it may be harder to get them on the phone now, and the value of your company may need to be higher (we only had a few hundred million, which seems like chump change these days).
deorder 7y ago
GMail even considers some emails from Google to be spam. I missed some important (billing and security notification) emails from Google this way.
- djsumdog 7y ago
  Yea I was running into problems with my gmail address to other gmail addresses, even before I split off and started running my own server. Their spam filter has a super high false-positive rate.
- XCSme 7y ago
  SkyNet is not good enough for binary classification yet, we're safe.
rhizome 7y ago
This criticism came up last time too, and I replied that I've been running my own mail server for 20 years off of a DSL line, and I have no trouble sending to anybody (that I've heard of from recipients nor MAILER-DAEMON). I have DKIM, SPF and no relaying and the only issue in recent memory was when AT&T started bouncing me for some reason. I emailed postmaster@ saying "hey wats up," and the block was removed a day or so later.
- syntheticnature 7y ago
  Do you know that your messages arrive in all cases? Not merely fail to bounce, but arrive? I help with IT for a small non-profit membership org, and the problem isn't the places that throw errors when you send, but the ones that silently accept the message without complaint and route it to /dev/null. We get through fine to Google, but the other big providers are random at best about it.
  - LIV2 7y ago
    Some mail systems can tell you if a user is valid or not during the initial connection while some forward to another mail system or delivery process and therefore cannot tell your MX during their conversation that the recipient is invalid. The downstream MX could be configured to then send an NDR email itself but this lands you on spam lists as "backscattering" will then send spam back to whoever owns the email address the spammer is spoofing so it's generally not done.
  - rhizome 7y ago
    >Do you know that your messages arrive in all cases? "I have no trouble sending to anybody (that I've heard of from recipients" might not be as artfully written as I would like, but that's what that refers to. Furthermore, blackholing emails like you suggest is generally rare. RFC 5321 (SMTP) states: "[D]ropping mail without notification of the sender is permitted in practice. However, it is extremely dangerous and violates a long tradition and community expectations that mail is either delivered or returned. If silent message-dropping is misused, it could easily undermine confidence in the reliability of the Internet's mail systems. So silent dropping of messages should be considered only in those cases where there is very high confidence that the messages are seriously fraudulent or otherwise inappropriate."
djsumdog 7y ago
Yea I ran into the same issue. I've got SPF, DKIM, DMAC, and reverse DNS for IPv4 and v6 and still get flagged as spam. I wrote about this a while back: https://battlepenguin.com/tech/how-google-and-microsoft-made-email-unreliable/ https://battlepenguin.com/tech/how-google-and-microsoft-made... It's not as bad now, so I suspect someone at Google is finally listening, but I still don't trust the reliability of e-mail. If I sent someone an e-mail I haven't e-mailed before, I'll let them know on Hangouts/SMS/Facebook that I sent them an e-mail and to check their spam folder.
deleted 7y ago
[deleted]
dvfjsdhgfv 7y ago
I run a couple of mail servers and the beginnings are always a bit rough, but then everything works (mostly) fine. I start by asking Microsoft to unban my IP (for some reasons the IP range with my favorite hosting provider are banned by default by MS servers). They lift the ban and since I'm a good netizen and use my servers strictly for the communication with the customers (and never for marketing), I never have any problems with delivering to outlook.com, hotmail.com, etc. Google is a different beast. Last time I remember I had to do strange things like disabling IPv6 support in my MTA (which is a good idea anyway as I'm not an expert in IPv6) in addition to the usual SPF setup etc. E-mail is delivered in general, but once in a while some letters go into spam for unknown reason. But this happens rarely, maybe a couple a times a year. Whenever I set up a new server, I have to start from scratch though.
johnklos 7y ago
Don't be so angry and negative. If you try, you might actually succeed. You just need some patience and perseverance.
senorjazz 7y ago
I've run our email server for the last 7 years. Don't have any trouble with gmail. Setting up was a bit of hassle, but since it was up, I don't do anything with it. Occasionally I will get the odd notification that a (usually German for some reason) email address doesn't like our domain. But the major providers, never had a problem. No idea why we haven't had a problem, I didn't know what I was doing at the time (still don't) just followed an online guide. From memory, spf, dkim which I think is all pretty basic things to setup when setting up a mail server and all guides cover it.
perlgod 7y ago
(I'm the author of TFA.) I have never had this issue. Generally the issue is either IP reputation of your server (common with VPS providers if you get a recycled IP of a previous spammer) or your domain name. Otherwise you are probably just unlucky enough to tickle the spam-prevention mechanisms in the almighty "algorithm" run by $BIGMAILER. I keep one "normie" email address at a $BIGMAILER for situations like this, but at this point in my life I mostly just shrug if some big advertising/surveillance company's email system won't deliver my mail, I just won't email that person. Be the change you want to see and all that.
- nothrabannosir 7y ago
  Honestly, you should put this quote in bold letters atop that article: > I mostly just shrug if some big advertising/surveillance company's email system won't deliver my mail, I just won't email that person. Because that changes the tone of the opening paragraphs significantly: > Luckily, running your own mail server is not as daunting as many would have you believe. Sure, if you can afford to shrug off deliverability issues to major e-mail providers. Then it is, I daresay, a walk in the park!
- zepearl 7y ago
  My IP reputation is absolutely >>pure<< and my domain name is ok. Still, usually when sending emails to Gmail & Hotmail my emails are "lost" (they don't even appear in the spam-inbox of the receivers). My usual workaround used to be to 1) login into my throwaway-account on their Gmail/Hotmail systems 2) send an email to my domain 3) reply to that email. After that usually my emails got accepted by those service providers, at least for a while. I admit that nowadays I don't even do that anymore - when I see a Gmail/Hotmail recipient I just ask for another email address at a different provider or I send the email using my provider's system.
  - shiftpgdn 7y ago
    Is your domain name a .com? I've found that domains that are not .com domain names generally get flagged by the evil algorithim even if everything else is perfect.
hcarvalhoalves 7y ago
Yes, there're a lot of tricks. I used to run a mail server in the past, and initially had problems with reverse DNS resolution not setup correctly, it's an easy oversight depending on where you host. https://mxtoolbox.com/problem/smtp/smtp-reverse-dns-resolution https://mxtoolbox.com/problem/smtp/smtp-reverse-dns-resoluti...
yellowapple 7y ago
Gmail seems to have no trouble with my mailserver. AT&T/Yahoo used to, but there was some online form I filled out at one point to get myself whitelisted (it was years ago; don't remember the details) and that stopped being an issue. The main problem right now is Craigslist (which outright refuses to deliver my server's mail, so I have to use my Gmail account or stick to SMS / phone calls). Stack: OpenBSD VM (on 1984.is) running OpenSMTPd + Dovecot + a DKIM proxy + ClamAV + spamd. The more relevant pain point is that the VM hangs every couple months and I have to hard-reboot it from the VPS web console. Also, I've been pretty lazy about staying on top of new OpenBSD releases. One of these days I'd like to go redundant (whether with both mailhosts on 1984 or putting one on a different provider), which would make it less stressful to do OS upgrades (I could keep one host running while doing an offline upgrade of the other, as opposed to hoping the online upgrade process doesn't break anything).
shirro 7y ago
The biggest problems for mail delivery across the board are probably lack of correct helo/reverse ip lookup and being on an IP blacklist such as being on an ISP dynamic address. I will bin those with my mail server as well. That is a very low bar but any naive mail server implementation on a home server is probably going to fail those instantly. DKIM and SPF are really good signals to have. I have DKIM, SPF, DANE(nobody cares), DMARC, MTA-STS, TLS (lets encrypt) which are all potentially useful in preserving reputation and repudiating emails spoofing my domain sent from other sources. I have never had issues getting throough to gmail. But for some mail systems, Microsoft in particular I think, they seem to penalise low volume mailers very heavily. You seem to need a certain volume for their systems to cache a reputation score and if you have a small vanity domain/mail server with very low mail volumes you may go straight to the spam folder.
tzs 7y ago
Gmail has never been a problem for me, even when I only had SPF, sending from my server hosted at Rackspace. But I've had my domain for 20+ years, and Gmail since 2004, so they have had plenty of time to figure out its not a spam source, so this might not have been a fair test. I just gave Yahoo a try, and that did go to spam, even though it was happy with both SPF and DKIM. I marked it as not spam, and then went and sent another. That went through fine. I also tried Live. It says my SPF and DKIM are fine, but sends it to the spam box. I marked it as not spam. Nope. Next one still went to spam. Marked that as not spam and tried again. Still spam. Marked that as not spam, but didn't try sending another one yet. I'm going to wait a while, to allow for the possibility that it takes them a while to apply feedback. I also tried comcast.net. Went through fine.
- amelius 7y ago
  Can't running your own email server be done through pulling a well-curated library on a daily basis?
  - berkes 7y ago
    Not a library, because a mailserver consists of a lot of moving parts and external configuration (DNS etc). mailinabox.email is probably close to what you want, though. It's opnionated and my tip is to follow those opinions to the letter (or use another such project).
pmlnr 7y ago
It's nearly always a badly set reverse dns vs mail server helo name difference.
jjav 7y ago
There is no one secret you can google. There is also no need to perpetuate the fear of running your own email. Decentralization of core internet services helps us all, not just the person doing it. So to anyone seriously interested and willing to learn, I highly recommend running your own email servers. If you expect 100% delivery rate, you won't necessarily get that, no matter who is running your email infrastructure. At multiple companies, I've seen email end up in spam even though it is sent from gmail-hosted company account to gmail-hosted company account. So that's the bar you want to meet or beat and beating it is not hard. From ~7 years experience now, I don't observe any problems with email delivery. I don't do anything special. I use postfix, it is well configured and everything works fine. I host several personal domains and a couple small business domains. And by doing so I avoid giving google the power to cut me off from email because some arbitrary ML gone bad.
- js4ever 7y ago
  I'm doing the same for exactly the same reason (afraid of bad ML from Google wiping my whole digital life)
- dasil003 7y ago
  I’ve seen emails marked as suspicious/phishing attempt between two GSuite domains owned by the same company.
  - davchana 7y ago
    Heck I have seen emails from Google itself, not any gmail username, but information from @google addresses landed in my Spam emails, making me double check the headers that if it is spoofed or real.
    - vzttzv2 7y ago
      I think that a good thing, since it mean they're committed to build a good algorithm, instead of just whitelist some big guy and throw everyone else to the trash.
- 7y ago
roberto 7y ago
I have the same problem. I've been running my own mail server since 2000, and last year my sister's account started being used to send spam (I assume she reused her email credentials in another site that got hacked, and spammers used the credentials to authenticate as her in my SMTP server to send spam). Google shows that my domain has a bad reputation, but I can't fix it because it doesn't have enough traffic. https://www.mail-tester.com https://www.mail-tester.com gives me a 10/10 (I have DKIM, DMARC, SPF, everything), but my email still gets flagged as spam by Google.
theqult 7y ago
You have to configure a super complicated system of SEC-DNS and connect it to Postifix. Thanks to the Spaghetti Fly Monster, this guy made all of this automatically https://mailinabox.email/ https://mailinabox.email/
- ianai 7y ago
  Gotta love dat curl pipe sudo bash!
3xblah 7y ago
However if you can get a correspondent to also set up their own mail server, then you may realise the pleasure of emailing directly from sender's server to recipient's, without using third party email "services" and third party email servers. First party to second party. No third party. Every time these posts about setting up a mail server reach the HN front page, there are usually complaints and they always center around third party email services. Perhaps it is the use of those services that is the problem, not the process of setting up a mail server. Spam is probably made easier by the fact that so many people use the same third party email providers. Spammers have less servers to target. (Not the same situation if every user had their own server.) As HN commenters oft point out, email, the protocol and software, is "decentralised". But the widespread "centralised" use of the same third parties to send and deliver mail has negated the benefits of being (theoretically) decentralised.
kazinator 7y ago
> If anyone actually knows the secret to not having your own mail-server's mail go to spam on these bigger systems, please tell, I've Googled it for years with no success. I've been running my own mail server without sending problems for almost a decade. Right from the beginning, I had a clue and knew that sending SMTP directly from a subscriber IP address was going to be a nonstarter. Such IP's have a negative reputation due to abuse. Instead, from the beginning, I used my ISP's (big ISP in Canada) SMTP forwarding host, configuring my SMTP server to log into that server with my credentials. (I had a couple of hiccups along the way with the ISP's SMTP service, and they wouldn't help me unless I reproduced the issue with a supported e-mail client. Naturally, an Exim server running on Debian isn't a supported e-mail client, because it's name doesn't sound like "Microsoft Outlook" or "Mozilla Thunderbird"). Anyway, the main advantage of running your own mail server is not the ability to send SMTP directly to someone's MX server, but rather that you have your own MX domain for receiving mail, via a machine you control. Your setup isn't "lesser" in any way just because you're sending through a more reputable SMTP forwarding host.
- linsomniac 7y ago
  So your recommendation to having your mail not go directly to spam is to run it for a decade? Got it! :-) I run a mail server for a few thousand users that has been going for ~20 years, and have regularly had to spend significant time figuring out adjustments the big mail providers make along the way. Spending a day roughly every year figuring out and implementing countermeasures isn't that bad, when you get paid for it. But I really don't have the time to do it for my personal e-mail. Your answer reminds me of something I heard a greenskeeper say about the big garden he maintains, I think in the UK: Tourists come to me all the time and ask "How can I get my lawn to look like this?" I reply: "The secret is to roll the dew off the lawn every morning." "That's it?" "Just do that for 300 years and your lawn will look like this."
  - kazinator 7y ago
    If you have to do it for your personal mail compared to a few thousand users, the problems will obviously be fewer, because you don't send to as many different destinations as a crew of a few thousand users. > "Just do that for 300 years and your lawn will look like this." My point is that I've never had problems in that decade, not that it took a decade to fix. I think on two or three occasions, mail to a gmail user mysteriously bounced, but it went away on re-try. I understood the reputation problem from the beginning instead of banging my head against it. Why I understood that is because I did some research into running mail servers before diving into it.
ekianjo 7y ago
Easy. Dont run your own SMTP server and instead use Mailgun or other reputable SMTP servers to send emails. they are used by all large newsletter/marketing systems. Free tier services are largely enough for personal users.
kikoreis 7y ago
I have run my own server for the past 20 years. I don't spend a lot of time maintaining it but managed to enable SPF, DKIM, etc as they rolled in. The most disruption I have faced has been changing connectivity providers and IP ranges. But even then I have been able to insist on being allowed to relay and removed from blacklists consistently. I think it is important some of us do it even if most people live off big provider webmail.
xelxebar 7y ago
Be sure to have a PTR record in the DNS zone of whomever owns your IP address. I have DKIM, SPF and DMARC setup, but my mails were getting sent to spam before rDNS was configured correctly. More to the point, I discovered this by reading Google's postmaster/bulk mail guidelines. All the other major email providers have similar guidelines, so definitely consult those as a first reference if you are having problems. There is no mail conspiracy. As always, the problem is DNS.
ulrikrasmussen 7y ago
I have been running my own mail server for over a decade, and still do. However, last year I had to throw in the towel and configure my server to send via an SMTP relay that my hosting provider (transip) provides. That solved all problems I had with sending to the big mail providers.
amaterasu 7y ago
Not just the big players, I had a conversation with the administrator of the Australian ISP Bigpond about why my server was being spammed. Their response was verbatim "We blocked Digital Ocean, because we get spam from there" Even with good reputation servers, admins are happy to reject legitimate mail for any reason.
baroffoos 7y ago
I must have gotten lucky because mine just works. My exact setup is mailinabox installed on a vps at vultr. Have been sending to gmail addresses mostly fine. Had 1 email go to spam in 2018 but everything else has gone through correctly. Since mailinabox configures everything for you maybe the issue is that when you set it up yourself you don't quite get it exactly right to what gmail and microsoft demand.
trekrich 7y ago
the reputation is almost like a protection scheme when it comes to emails. Its prob to make it hard for people to run their own email server. Its better for the security services if most people are doing email from a few providers.
eikenberry 7y ago
Run your own MX servers but use an external service for your SMTP server. A good service will help you with your SPF, DKIM and DMARC setup as part of the service. As you are only using the SMTP service you can optimize for that and ignore mailbox sizes, etc. when shopping around. You should be able to get multiple App Passwords so no shared credentials.
swiley 7y ago
This is not a problem I have or have had using a self hosted mail server on and off for nearly a decade now. What I have had an issue with is the network (the whole ####ing network, those guys are less than helpful) I’m on getting added to spamhause(I think?) and people setting up their (smaller) mail severs to blindly reject mails from networks like that. That’s really dumb and I’m glad for things like dkim because of it.
aleku 7y ago
I've been running my mail server off DO for the last ±5 years - Postfix with SPF no DKIM, DMARC - I get good delivery for Gmail and yahoo. Initially, I thought I would go full on spamassassin and clamav but thought I should hold off until I got spammed. Turns out in the last 5 years the only spammers I've got are 2 senders, one threatening to share video recorded of me on webcam to my contacts and another keeps telling me my domains' seo has expired blah blah. These are 1 or 2 times in 3 months, SpamAssassin would definitely be overkill. Apple Mail client junks them anyway. About 1 year ago I moved the setup into a docker container to better maximize the use of the $10 droplet.
philpem 7y ago
The trick to this is not hosting your mail server with a provider which has a bad reputation. Mine goes through a DigitalOcean droplet and my mail usually gets through (based on the assumption that if I received a reply, the other person must have received it!) By contrast a volunteer group I'm involved with was using OVH "because it's the cheapest". Suppliers and customers were routinely telling us the emails were going to spam. Moved to another provider (no idea who, the infrastructure team does that) and the complaints fell to a trickle. Good IP block reputation (check RBLs) + valid SPF + valid DKIM is usually enough to get mail through. Except occasionally to Hotmail... but that's Hotmail...
MrLabCoat 7y ago
https://support.google.com/mail/answer/6227174?hl=en https://support.google.com/mail/answer/6227174?hl=en I added my domain and have never had it marked as spam at any major email provider, only a few small, self-hosted servers and that was probably due to misconfiguration or high spam sensitivity. See if this might help you out.
pgib 7y ago
Not a perfect solution, but you _could_ relay through a provider like Sendgrid. For personal use, the cost would be very minimal if not free.
fpierfed 7y ago
I am writing this with sadness and frustration in my heart. The only issue I have found seriously limiting my ability to use my own self hosted email server is the deliberate decision of Google, Yahoo and Microsoft to make it hard for me to do so. Their decision is essentially un-appealable. I still get hotmail complaints about spam being sent from an IP I do not own anymore. For the life of me I could not find a way to solve this. Yes I did remove that address from their “responsible domain owner nonsense thingy” to no avail. Often times I would send an email to a domain owned by one of the big three and that email would just disappear. No bounce back at all. The recipient would not even see it in their spam folder. They tell you to implement various technical solution line DMARC and DKIM but in the end what really matters is the arbitrary and capricious decision of these three companies against which there is no recourse. I agree that hosting your own email server is important but this is a battle that I gave up fighting.

by dpcan 7y ago

curiousfab 7y ago

For some reason I never had problems, even after a recent change of my IP address because I moved to a new VPS. Hetzner VPS, proper reverse DNS, SPF, that's all, not even DKIM. The only big ISP that doesn't like my mails is AT&T and I couldn't care less (in Europe, rarely have to deal with people @att.net).

xiaomai 7y ago
I also have no issues like this (I do SPF/DMARC but not DKIM)
jstimpfle 7y ago
I just do reverse DNS on a cheap VPS. I believe I don't even have encryption. Almost no problems since I switched to that setup 9 years ago. Some mails to Gmail end up in spam, and just yesterday I had my first "refused due to poor reputation" problem due to an unknown problem with Cloudmark. Have been able to reset my score there by filling an HTML form. Of course, there are some mails where I don't know if they landed in spam or I just didn't get a reply.
the_angry_angel 7y ago
In that case you are very fortunate. I was running my own mail server for nearly 10 years on Hetzner. Prior to that on other hosts and in the distant past at home. Running mail servers is something I have done professionally and successfully. The last time I moved boxes as I had many times before. I was on clean IP range but I had no IP reputation at all. In the past this wasn’t such a problem, especially with SPF, DKIM, rDNS, DMARC, server-to-server SSL etc. Around the same time I started having to deal with organisations (legal, etc for a death in the family and later rent) rather my my own circle of friends. It became extremely apparent that my mails weren’t hitting the inbox. But they were being accepted. This was extremely problematic. I was in the group stating that running your own mail server isn’t hard. I still say that. The hard problem is convincing the big players to let your low volume domains and IPs hit the inbox. I begrudgingly gave up my MX servers last year.
- fiddlerwoaroof 7y ago
  I wonder if there's some sort of relay setup that could be used to mitigate this: e.g. if you want to run your own mail server, sign up for some kind of "mail ring" that transparently proxies the (encrypted) traffic from all the member mailserver administrators. That way, your public IP has a higher volume and more leverage getting delivered.
  - the_angry_angel 7y ago
    Integration with SPF and would be unfun and probably even impractical (max 10 lookups iirc?). I’d also worry about the inevitable abuse which would appear to originate from your range(s). If you can mitigate those though, it sounds interesting

singron 7y ago

I had DKIM, SPF, rDNS, etc. at first and went to Gmail spam. I registered on gmail postmaster tools and got some friends and family to add me to their contact lists and send me some outbound mail. Google now sends me more mail than I send them, and now I don't go to the spam list, even for gmail accounts I haven't contacted before. This was for personal email. If you are trying to send commercial email this strategy probably won't work.

djsumdog 7y ago
I don't have a high enough volume for my personal e-mail to even show up on the postmaster tools.
- singron 7y ago
  Mine doesn't show up either, but I figured the verification process might have affected the spam classification.
hckr1292 7y ago
I've had a similar experience. Switching IP address of my mail server lost me some reputation, but mostly just using the directions mailinabox.email has worked for me

wpietri 7y ago

Agreed! I've been running my own mail server for 20+ years, and I would not recommend that anybody do this on a lark. Deliverability to GMail is a huge problem for me and has been for years. I even asked friends at Google to find out what the story was. All I got back is that the mail group was so careful/paranoid it wouldn't talk to them either. I would long ago have switched over to a vendor, but I use qmail-style tagging for sub-addresses (that is, instead of user+sub@domain, I use user-sub@domain). Almost nobody supports that. Especially not GMail (where my friends could tell me that was tagged as WONTFIX). If anybody has solved this, please do let me know (on here, via Twitter, or the email address in my bio). It's maddening.

mgalgs 7y ago
Curious why you're so attached to the qmail style subaddressing. Personal preference or is there a technical advantage?
- big_chungus 7y ago
  Possibly not getting blocked. Many sign-up fields will block foo+spam@bar.net if I try to use it.
  - 77pt77 7y ago
    That's why I use "." as the separator. Now try using an email from a domain name with more that 3 letters in the TLD. Almost no one considers that a valid address.
    - zigzaggy 7y ago
      So if I bought my “name.rocks” I’ll have trouble using that as an email? I was looking forward to “firstname@lastname.rocks” and I never even considered it would be a problem. I’m disappointed
      - voltagex_ 7y ago

ryandrake 7y ago

Sample size of one but I’ve run my own mail server for years and have almost never encountered problems of this nature. Right when I started with the VPS, rejections from Comcast started showing up in my logs, and I traced it back to the IP I got being in some blacklist. Requested a new IP and it has been smooth sailing ever since.

pbhjpbhj 7y ago
I had problems with MS (Hotmail/Live/Outlook/whatever they're call it now) when I changed hosting provider which I traced back to the hosting provider owning an IP that had in the past been associated with spam (that for-real is what I was told) -- that seemed a bit over-zealous to me. As it wasn't possible to pre-check IP addresses (it wasn't blacklisted, and in any case the email was being served from a different IP to the one that was apparently previously an issue) for any particular hosting company - and I could only afford cheap hosting - then I decided to relent and made an Outlook online account and sent the mail from that. It seemed totally crazy to me to reject mail from a 15 year old domain that sent at most 30 emails to Outlook per month, _always_ in replay to an email; SPF/DMARC were set AFAIR and whitelisting the email address from within my own 20+yo hotmail account didn't make any difference, MS still wouldn't let _me_ receive the emails. Like if your user says the email address is fine, and sends an email to that address, .. then perhaps you should allow the user to receive that one email??

Spivak 7y ago

There is no secret, because if there was then it would be used by spammers and then cease to work. And if there was a secret to building a reputation you could make a lot more money as a brand consultant with it than running an email server.

ransom1538 7y ago

Yes. After many years, I think the algorithm is this: If the FROMs top level domain is in the top 500 websites OR is a .edu NOT SPAM, ELSE, send to "proprietary spam filter". The "proprietary spam filter" is some random crap code that is unique to each email server company. You could spend years trying to figure out how to game "proprietary spam filter" - but it is a fools errand.

donmcronald 7y ago
I don't think so. I see @facebookmail.com in SPAM folders way more often than you'd expect on both Office 365 and GSuite. I also see mail from Microsoft and Google filtered into SPAM on their own platforms once in a while.
- weaksauce 7y ago
  Is that a proper email from Facebook with all that entails or is it a email from a spoofer/scammer?
  - donmcronald 7y ago
    It's completely legit. I think it's the domain Facebook uses for notifications. https://imgur.com/a/nzkMNDS https://imgur.com/a/nzkMNDS
- peterwwillis 7y ago
  facebookmail.com is not in the alexa top 500, whereas facebook.com is. spam filters really are this dumb at big companies. usually the way we'd get around it is we'd call up $big_company and say, "hey, could you please remove our e-mails from your spam list? we would like to send your users a lot of mail right now." a few hours later, we'd be good to go. this was ~2007. it may be harder to get them on the phone now, and the value of your company may need to be higher (we only had a few hundred million, which seems like chump change these days).

deorder 7y ago

GMail even considers some emails from Google to be spam. I missed some important (billing and security notification) emails from Google this way.

djsumdog 7y ago
Yea I was running into problems with my gmail address to other gmail addresses, even before I split off and started running my own server. Their spam filter has a super high false-positive rate.
XCSme 7y ago
SkyNet is not good enough for binary classification yet, we're safe.

rhizome 7y ago

This criticism came up last time too, and I replied that I've been running my own mail server for 20 years off of a DSL line, and I have no trouble sending to anybody (that I've heard of from recipients nor MAILER-DAEMON). I have DKIM, SPF and no relaying and the only issue in recent memory was when AT&T started bouncing me for some reason. I emailed postmaster@ saying "hey wats up," and the block was removed a day or so later.

syntheticnature 7y ago
Do you know that your messages arrive in all cases? Not merely fail to bounce, but arrive? I help with IT for a small non-profit membership org, and the problem isn't the places that throw errors when you send, but the ones that silently accept the message without complaint and route it to /dev/null. We get through fine to Google, but the other big providers are random at best about it.
- LIV2 7y ago
  Some mail systems can tell you if a user is valid or not during the initial connection while some forward to another mail system or delivery process and therefore cannot tell your MX during their conversation that the recipient is invalid. The downstream MX could be configured to then send an NDR email itself but this lands you on spam lists as "backscattering" will then send spam back to whoever owns the email address the spammer is spoofing so it's generally not done.
- rhizome 7y ago
  >Do you know that your messages arrive in all cases? "I have no trouble sending to anybody (that I've heard of from recipients" might not be as artfully written as I would like, but that's what that refers to. Furthermore, blackholing emails like you suggest is generally rare. RFC 5321 (SMTP) states: "[D]ropping mail without notification of the sender is permitted in practice. However, it is extremely dangerous and violates a long tradition and community expectations that mail is either delivered or returned. If silent message-dropping is misused, it could easily undermine confidence in the reliability of the Internet's mail systems. So silent dropping of messages should be considered only in those cases where there is very high confidence that the messages are seriously fraudulent or otherwise inappropriate."

djsumdog 7y ago

Yea I ran into the same issue. I've got SPF, DKIM, DMAC, and reverse DNS for IPv4 and v6 and still get flagged as spam. I wrote about this a while back: https://battlepenguin.com/tech/how-google-and-microsoft-made-email-unreliable/ https://battlepenguin.com/tech/how-google-and-microsoft-made... It's not as bad now, so I suspect someone at Google is finally listening, but I still don't trust the reliability of e-mail. If I sent someone an e-mail I haven't e-mailed before, I'll let them know on Hangouts/SMS/Facebook that I sent them an e-mail and to check their spam folder.

deleted 7y ago

[deleted]

dvfjsdhgfv 7y ago

I run a couple of mail servers and the beginnings are always a bit rough, but then everything works (mostly) fine. I start by asking Microsoft to unban my IP (for some reasons the IP range with my favorite hosting provider are banned by default by MS servers). They lift the ban and since I'm a good netizen and use my servers strictly for the communication with the customers (and never for marketing), I never have any problems with delivering to outlook.com, hotmail.com, etc. Google is a different beast. Last time I remember I had to do strange things like disabling IPv6 support in my MTA (which is a good idea anyway as I'm not an expert in IPv6) in addition to the usual SPF setup etc. E-mail is delivered in general, but once in a while some letters go into spam for unknown reason. But this happens rarely, maybe a couple a times a year. Whenever I set up a new server, I have to start from scratch though.

johnklos 7y ago

Don't be so angry and negative. If you try, you might actually succeed. You just need some patience and perseverance.

senorjazz 7y ago

I've run our email server for the last 7 years. Don't have any trouble with gmail. Setting up was a bit of hassle, but since it was up, I don't do anything with it. Occasionally I will get the odd notification that a (usually German for some reason) email address doesn't like our domain. But the major providers, never had a problem. No idea why we haven't had a problem, I didn't know what I was doing at the time (still don't) just followed an online guide. From memory, spf, dkim which I think is all pretty basic things to setup when setting up a mail server and all guides cover it.

perlgod 7y ago

(I'm the author of TFA.) I have never had this issue. Generally the issue is either IP reputation of your server (common with VPS providers if you get a recycled IP of a previous spammer) or your domain name. Otherwise you are probably just unlucky enough to tickle the spam-prevention mechanisms in the almighty "algorithm" run by $BIGMAILER. I keep one "normie" email address at a $BIGMAILER for situations like this, but at this point in my life I mostly just shrug if some big advertising/surveillance company's email system won't deliver my mail, I just won't email that person. Be the change you want to see and all that.

nothrabannosir 7y ago
Honestly, you should put this quote in bold letters atop that article: > I mostly just shrug if some big advertising/surveillance company's email system won't deliver my mail, I just won't email that person. Because that changes the tone of the opening paragraphs significantly: > Luckily, running your own mail server is not as daunting as many would have you believe. Sure, if you can afford to shrug off deliverability issues to major e-mail providers. Then it is, I daresay, a walk in the park!
zepearl 7y ago
My IP reputation is absolutely >>pure<< and my domain name is ok. Still, usually when sending emails to Gmail & Hotmail my emails are "lost" (they don't even appear in the spam-inbox of the receivers). My usual workaround used to be to 1) login into my throwaway-account on their Gmail/Hotmail systems 2) send an email to my domain 3) reply to that email. After that usually my emails got accepted by those service providers, at least for a while. I admit that nowadays I don't even do that anymore - when I see a Gmail/Hotmail recipient I just ask for another email address at a different provider or I send the email using my provider's system.
- shiftpgdn 7y ago
  Is your domain name a .com? I've found that domains that are not .com domain names generally get flagged by the evil algorithim even if everything else is perfect.

hcarvalhoalves 7y ago

Yes, there're a lot of tricks. I used to run a mail server in the past, and initially had problems with reverse DNS resolution not setup correctly, it's an easy oversight depending on where you host. https://mxtoolbox.com/problem/smtp/smtp-reverse-dns-resolution https://mxtoolbox.com/problem/smtp/smtp-reverse-dns-resoluti...

yellowapple 7y ago

Gmail seems to have no trouble with my mailserver. AT&T/Yahoo used to, but there was some online form I filled out at one point to get myself whitelisted (it was years ago; don't remember the details) and that stopped being an issue. The main problem right now is Craigslist (which outright refuses to deliver my server's mail, so I have to use my Gmail account or stick to SMS / phone calls). Stack: OpenBSD VM (on 1984.is) running OpenSMTPd + Dovecot + a DKIM proxy + ClamAV + spamd. The more relevant pain point is that the VM hangs every couple months and I have to hard-reboot it from the VPS web console. Also, I've been pretty lazy about staying on top of new OpenBSD releases. One of these days I'd like to go redundant (whether with both mailhosts on 1984 or putting one on a different provider), which would make it less stressful to do OS upgrades (I could keep one host running while doing an offline upgrade of the other, as opposed to hoping the online upgrade process doesn't break anything).

shirro 7y ago

The biggest problems for mail delivery across the board are probably lack of correct helo/reverse ip lookup and being on an IP blacklist such as being on an ISP dynamic address. I will bin those with my mail server as well. That is a very low bar but any naive mail server implementation on a home server is probably going to fail those instantly. DKIM and SPF are really good signals to have. I have DKIM, SPF, DANE(nobody cares), DMARC, MTA-STS, TLS (lets encrypt) which are all potentially useful in preserving reputation and repudiating emails spoofing my domain sent from other sources. I have never had issues getting throough to gmail. But for some mail systems, Microsoft in particular I think, they seem to penalise low volume mailers very heavily. You seem to need a certain volume for their systems to cache a reputation score and if you have a small vanity domain/mail server with very low mail volumes you may go straight to the spam folder.

tzs 7y ago

Gmail has never been a problem for me, even when I only had SPF, sending from my server hosted at Rackspace. But I've had my domain for 20+ years, and Gmail since 2004, so they have had plenty of time to figure out its not a spam source, so this might not have been a fair test. I just gave Yahoo a try, and that did go to spam, even though it was happy with both SPF and DKIM. I marked it as not spam, and then went and sent another. That went through fine. I also tried Live. It says my SPF and DKIM are fine, but sends it to the spam box. I marked it as not spam. Nope. Next one still went to spam. Marked that as not spam and tried again. Still spam. Marked that as not spam, but didn't try sending another one yet. I'm going to wait a while, to allow for the possibility that it takes them a while to apply feedback. I also tried comcast.net. Went through fine.

amelius 7y ago
Can't running your own email server be done through pulling a well-curated library on a daily basis?
- berkes 7y ago
  Not a library, because a mailserver consists of a lot of moving parts and external configuration (DNS etc). mailinabox.email is probably close to what you want, though. It's opnionated and my tip is to follow those opinions to the letter (or use another such project).

pmlnr 7y ago

It's nearly always a badly set reverse dns vs mail server helo name difference.

jjav 7y ago

There is no one secret you can google. There is also no need to perpetuate the fear of running your own email. Decentralization of core internet services helps us all, not just the person doing it. So to anyone seriously interested and willing to learn, I highly recommend running your own email servers. If you expect 100% delivery rate, you won't necessarily get that, no matter who is running your email infrastructure. At multiple companies, I've seen email end up in spam even though it is sent from gmail-hosted company account to gmail-hosted company account. So that's the bar you want to meet or beat and beating it is not hard. From ~7 years experience now, I don't observe any problems with email delivery. I don't do anything special. I use postfix, it is well configured and everything works fine. I host several personal domains and a couple small business domains. And by doing so I avoid giving google the power to cut me off from email because some arbitrary ML gone bad.

js4ever 7y ago
I'm doing the same for exactly the same reason (afraid of bad ML from Google wiping my whole digital life)
dasil003 7y ago
I’ve seen emails marked as suspicious/phishing attempt between two GSuite domains owned by the same company.
- davchana 7y ago
  Heck I have seen emails from Google itself, not any gmail username, but information from @google addresses landed in my Spam emails, making me double check the headers that if it is spoofed or real.
  - vzttzv2 7y ago
    I think that a good thing, since it mean they're committed to build a good algorithm, instead of just whitelist some big guy and throw everyone else to the trash.
7y ago

roberto 7y ago

I have the same problem. I've been running my own mail server since 2000, and last year my sister's account started being used to send spam (I assume she reused her email credentials in another site that got hacked, and spammers used the credentials to authenticate as her in my SMTP server to send spam). Google shows that my domain has a bad reputation, but I can't fix it because it doesn't have enough traffic. https://www.mail-tester.com https://www.mail-tester.com gives me a 10/10 (I have DKIM, DMARC, SPF, everything), but my email still gets flagged as spam by Google.

theqult 7y ago

You have to configure a super complicated system of SEC-DNS and connect it to Postifix. Thanks to the Spaghetti Fly Monster, this guy made all of this automatically https://mailinabox.email/ https://mailinabox.email/

ianai 7y ago
Gotta love dat curl pipe sudo bash!

3xblah 7y ago

However if you can get a correspondent to also set up their own mail server, then you may realise the pleasure of emailing directly from sender's server to recipient's, without using third party email "services" and third party email servers. First party to second party. No third party. Every time these posts about setting up a mail server reach the HN front page, there are usually complaints and they always center around third party email services. Perhaps it is the use of those services that is the problem, not the process of setting up a mail server. Spam is probably made easier by the fact that so many people use the same third party email providers. Spammers have less servers to target. (Not the same situation if every user had their own server.) As HN commenters oft point out, email, the protocol and software, is "decentralised". But the widespread "centralised" use of the same third parties to send and deliver mail has negated the benefits of being (theoretically) decentralised.

kazinator 7y ago

> If anyone actually knows the secret to not having your own mail-server's mail go to spam on these bigger systems, please tell, I've Googled it for years with no success. I've been running my own mail server without sending problems for almost a decade. Right from the beginning, I had a clue and knew that sending SMTP directly from a subscriber IP address was going to be a nonstarter. Such IP's have a negative reputation due to abuse. Instead, from the beginning, I used my ISP's (big ISP in Canada) SMTP forwarding host, configuring my SMTP server to log into that server with my credentials. (I had a couple of hiccups along the way with the ISP's SMTP service, and they wouldn't help me unless I reproduced the issue with a supported e-mail client. Naturally, an Exim server running on Debian isn't a supported e-mail client, because it's name doesn't sound like "Microsoft Outlook" or "Mozilla Thunderbird"). Anyway, the main advantage of running your own mail server is not the ability to send SMTP directly to someone's MX server, but rather that you have your own MX domain for receiving mail, via a machine you control. Your setup isn't "lesser" in any way just because you're sending through a more reputable SMTP forwarding host.

linsomniac 7y ago
So your recommendation to having your mail not go directly to spam is to run it for a decade? Got it! :-) I run a mail server for a few thousand users that has been going for ~20 years, and have regularly had to spend significant time figuring out adjustments the big mail providers make along the way. Spending a day roughly every year figuring out and implementing countermeasures isn't that bad, when you get paid for it. But I really don't have the time to do it for my personal e-mail. Your answer reminds me of something I heard a greenskeeper say about the big garden he maintains, I think in the UK: Tourists come to me all the time and ask "How can I get my lawn to look like this?" I reply: "The secret is to roll the dew off the lawn every morning." "That's it?" "Just do that for 300 years and your lawn will look like this."
- kazinator 7y ago
  If you have to do it for your personal mail compared to a few thousand users, the problems will obviously be fewer, because you don't send to as many different destinations as a crew of a few thousand users. > "Just do that for 300 years and your lawn will look like this." My point is that I've never had problems in that decade, not that it took a decade to fix. I think on two or three occasions, mail to a gmail user mysteriously bounced, but it went away on re-try. I understood the reputation problem from the beginning instead of banging my head against it. Why I understood that is because I did some research into running mail servers before diving into it.

ekianjo 7y ago

Easy. Dont run your own SMTP server and instead use Mailgun or other reputable SMTP servers to send emails. they are used by all large newsletter/marketing systems. Free tier services are largely enough for personal users.

kikoreis 7y ago

I have run my own server for the past 20 years. I don't spend a lot of time maintaining it but managed to enable SPF, DKIM, etc as they rolled in. The most disruption I have faced has been changing connectivity providers and IP ranges. But even then I have been able to insist on being allowed to relay and removed from blacklists consistently. I think it is important some of us do it even if most people live off big provider webmail.

xelxebar 7y ago

Be sure to have a PTR record in the DNS zone of whomever owns your IP address. I have DKIM, SPF and DMARC setup, but my mails were getting sent to spam before rDNS was configured correctly. More to the point, I discovered this by reading Google's postmaster/bulk mail guidelines. All the other major email providers have similar guidelines, so definitely consult those as a first reference if you are having problems. There is no mail conspiracy. As always, the problem is DNS.

ulrikrasmussen 7y ago

I have been running my own mail server for over a decade, and still do. However, last year I had to throw in the towel and configure my server to send via an SMTP relay that my hosting provider (transip) provides. That solved all problems I had with sending to the big mail providers.

amaterasu 7y ago

Not just the big players, I had a conversation with the administrator of the Australian ISP Bigpond about why my server was being spammed. Their response was verbatim "We blocked Digital Ocean, because we get spam from there" Even with good reputation servers, admins are happy to reject legitimate mail for any reason.

baroffoos 7y ago

I must have gotten lucky because mine just works. My exact setup is mailinabox installed on a vps at vultr. Have been sending to gmail addresses mostly fine. Had 1 email go to spam in 2018 but everything else has gone through correctly. Since mailinabox configures everything for you maybe the issue is that when you set it up yourself you don't quite get it exactly right to what gmail and microsoft demand.

trekrich 7y ago

the reputation is almost like a protection scheme when it comes to emails. Its prob to make it hard for people to run their own email server. Its better for the security services if most people are doing email from a few providers.

eikenberry 7y ago

Run your own MX servers but use an external service for your SMTP server. A good service will help you with your SPF, DKIM and DMARC setup as part of the service. As you are only using the SMTP service you can optimize for that and ignore mailbox sizes, etc. when shopping around. You should be able to get multiple App Passwords so no shared credentials.

swiley 7y ago

This is not a problem I have or have had using a self hosted mail server on and off for nearly a decade now. What I have had an issue with is the network (the whole ####ing network, those guys are less than helpful) I’m on getting added to spamhause(I think?) and people setting up their (smaller) mail severs to blindly reject mails from networks like that. That’s really dumb and I’m glad for things like dkim because of it.

aleku 7y ago

I've been running my mail server off DO for the last ±5 years - Postfix with SPF no DKIM, DMARC - I get good delivery for Gmail and yahoo. Initially, I thought I would go full on spamassassin and clamav but thought I should hold off until I got spammed. Turns out in the last 5 years the only spammers I've got are 2 senders, one threatening to share video recorded of me on webcam to my contacts and another keeps telling me my domains' seo has expired blah blah. These are 1 or 2 times in 3 months, SpamAssassin would definitely be overkill. Apple Mail client junks them anyway. About 1 year ago I moved the setup into a docker container to better maximize the use of the $10 droplet.

philpem 7y ago

The trick to this is not hosting your mail server with a provider which has a bad reputation. Mine goes through a DigitalOcean droplet and my mail usually gets through (based on the assumption that if I received a reply, the other person must have received it!) By contrast a volunteer group I'm involved with was using OVH "because it's the cheapest". Suppliers and customers were routinely telling us the emails were going to spam. Moved to another provider (no idea who, the infrastructure team does that) and the complaints fell to a trickle. Good IP block reputation (check RBLs) + valid SPF + valid DKIM is usually enough to get mail through. Except occasionally to Hotmail... but that's Hotmail...

MrLabCoat 7y ago

https://support.google.com/mail/answer/6227174?hl=en https://support.google.com/mail/answer/6227174?hl=en I added my domain and have never had it marked as spam at any major email provider, only a few small, self-hosted servers and that was probably due to misconfiguration or high spam sensitivity. See if this might help you out.

pgib 7y ago

Not a perfect solution, but you _could_ relay through a provider like Sendgrid. For personal use, the cost would be very minimal if not free.

fpierfed 7y ago

I am writing this with sadness and frustration in my heart. The only issue I have found seriously limiting my ability to use my own self hosted email server is the deliberate decision of Google, Yahoo and Microsoft to make it hard for me to do so. Their decision is essentially un-appealable. I still get hotmail complaints about spam being sent from an IP I do not own anymore. For the life of me I could not find a way to solve this. Yes I did remove that address from their “responsible domain owner nonsense thingy” to no avail. Often times I would send an email to a domain owned by one of the big three and that email would just disappear. No bounce back at all. The recipient would not even see it in their spam folder. They tell you to implement various technical solution line DMARC and DKIM but in the end what really matters is the arbitrary and capricious decision of these three companies against which there is no recourse. I agree that hosting your own email server is important but this is a battle that I gave up fighting.