> I was going to set up an email server on my VPS with just SMTP that auto-forwarded everything to my gmail. But this might be simpler.
Do NOT do this. Unless you're willing to make absolutely sure that no spam gets through to gmail, you will be blacklisted by gmail when it flags spam coming from your host. And not even a lot of it.
Basically, to use gmail this way you have to be almost as good as gmail at the thing that most makes gmail worthwhile. It's not worth it. Much easier to go the other way.
> I recommend hosting an e-mail server by yourself
As someone who did this from about 2001 until three years ago, I strongly suggest most people don't bother with this route.
GMail, Outlook, etc, all throw so many arbitrary and ever-changing security conditions to accept mail, it really isn't worth the hassle - or the lost clients from mails that don't reach their walled-garden end-points.
I've used Fastmail for a few years now, and I'm 99% sure that when I respond to an email sent from GMail, they'll actually receive it (So, I'm not talking about cold-emails, which I could just about begin to understand).
do you do this personally? i've tried and found the barrier for entry is through the roof. if you don't configure everything just right you end up on gmail's spam blacklists and nobody gets your emails. and good luck getting off the blacklist once you're there.
i would love advice from anybody for self-hosting a reliable email server that the major carriers won't treat as a second-class citizen.
> Have you tried to send to Gmail addresses via your own SMTP server any time recently?
I do it all the time (from a VPS), it requires crossing all the Ts (SPF, DKM, etc), but never had any issues with Gmail, only with other self-hosted systems.
> The days of running the web server in your basement with no say-so from anyone else would come to an end.
That was never true, you had to have permission from your ISP, and many forbade it (and some outright blocked those ports).
> If you were able to somehow get your own email server to deliver email to Gmail and Outlook, great, good for you - but stop pretending that anybody can do it.
Yes, that's probably true. I've been running my own server for 20 years now, and I guess that in itself helps with getting my mail delivered (apart from t-online, but who cares about them). At some time I also hosted some mailing lists, but I quickly abandoned that because that's a surefire way to get your IP blacklisted sooner or later. If you set up a completely new mail server, there probably is a lot of luck involved, and I wouldn't recommend it to anyone, at least not for your critical business mails. I pretty much keep doing it only out of nostalgia, it doesn't really make any sense otherwise.
>I think it's unrealistic to expect everyone to host their own email servers.
It's surprisingly more difficult than it used to be. Trying to get your server reputation just right so that gmail won't flag you as spam is much tougher than it was in the past, for example.
Speaking of spam - there is so much of it that something like gmail filters out.
I still send from gmail, although I use a personally-hosted (and aggressively firewalled/ monitored) box for receiving mail for things like password resets.
>get off their butts and host their own email. It's not hard, it's not expensive and it's not a lot of work to maintain either. It can even be fun and informative.
I'd love to do this -- I ran an email server for a while and it really was informative. But my sent mail got sent straight to the spam bin every time. Ironically enough, Gmail's spam filters are usually so reliable that people don't really check for false positives with any reliable frequency, so I bailed.
>If you run your own email server and you get put onto Google's spam list - you're fucked.
It's even worse than that- I ran my own email server, and for some reason gmail delayed any emails from their system to outside of their system. That meant that people would send me an email but I wouldn't get it for 20 minutes. These delays don't exist when using big email providers (it stopped being a problem when I switched to Fastmail, for example) but if you're running a small server Google makes it a nightmare.
> I tried both Sendgrid and Mailgun and couldn't reliably get mail to Gmail through either one.
I mean, you can't reliably send email to gmail from gmail. It's not really the origin that's the issue, it is that gmail spam classification is quite bad. Good emails from known recipients you've corresponded actively for years will continue going to spam in gmail even as you mark them not-spam for the thousandth time.
So yes, sending to anyone @gmail.com has decents odds of ending up in spam for no reason. That's just how gmail is.
But no, sending it from your own email server doesn't make things worse. I run all my own email infrastructure and sending to gmail addresses works just as well from my server as it does from gmail itself.
> For non-techy home or SOHO users, they're likely using smtp.gmail.com with their gmail creds though.
That's exactly what I'm worried about. Obviously there are ways to do it safely (and gmail actually I think might even force them), but I have very low expectations of a lot of the userbase (not a dig at them: the tech isn't exactly set up to make the easy thing safe).
> I know personally several people who run mail relays and not only refuse to relay messages from and to Google email servers but even refuse to _receive_ emails addressed to their users from GMail addresses.
I don't refuse to relay messages to/from gmail addresses, but I do avoid interacting with gmail addresses as much as possible. The less I'm touching Google servers, the better.
Fortunately, most of the people I exchange email with don't use gmail.
It's not so much a security nightmare as it is a maintenance nightmare. The whole reason you pay for services is because you don't have time (or resources) to deal with it.
> security of that box is far below even the worst gmail server
If you use one time passwords and/or SSH key only access - it's probably pretty safe. Also changing SSH to some other port and blocking shodan.io bots - and you have filtered out a majority of the script kiddies. I also have an automated script that also downloads a list of known bad guys and adds them to my hosts.deny.
> Google are experts at this stuff
I wouldn't consider them experts persay - it's just that they have a seemingly infinite number of resources. I'm not saying they don't know what they are doing - but when your only job is to maintain the mail backend servers you could probably do a better job than me.
> would you not agree that your email is more secure at google (or a similar provider) than on your own server (a few experts not included)
Depends. Are you running Exchange or Dovecot? How savvy are you? Is this in the cloud or in your home? Are the drives encrypted? etc
I've purchased a lifetime license for iredadmin and it's worked pretty well. I'm currently hosting it on gandi and thought about offering email hosting.
> It's pretty common knowledge that if you need to send mission critical email, you should use a service specifically designed for that. Sending email programmatically directly from a web server has ALWAYS been a gray area.
I partially agree with this - dedicated email services have a higher deliverability rate than a random web server, especially a cloud-based server that might be using an external IP that was previously used to send spam. However, I can understand the parent poster being annoyed that their emails were being delivered one day, and not the next, without any changes on their end.
> At the VERY least you could have easily set up a gmail account and sent them from smtp. Choose the right tool for the job.
This is absolutely the wrong tool for the job. You should not be using a Gmail account to send out automated emails that you care about.
I mean gmail has the most limited frustrating filtering (lack thereof) rules of any email system I've used. Any self-hosted solution will be infinitely better.
> Gmail special like labels
How is that special?
Also, gmail spam filtering is not very good. You know how every business has that "check your spam folder" bit? Because gmail is so terrible about it. It is easy to do much better with a self-hosted solution, put an end to the false positives of gmail.
Seems that you like gmail, but in my experience it's one of the worst mainstream email implementations ever. Doing better is a trivial bar.
> Technically, I could use GMail with my own domain, but only by signing up for a business GSuite account.
Actually it is possible to use your own domain with even a regular Gmail account (although not straight-forward), and it works well -- I know because that's how I have set it up.
Requirements: own domain with MX records pointing to your server(s) running SMTP software
Receiving: SMTP server forwards to gmail account, SRS (Sender Rewriting Scheme) takes care so SPF doesn't fail, DKIM just works.
Sending: you configure Gmail to use your SMTP server for sending.
Gmail side: add email alias and verify it, the "reply" function is even smart enough to use the correct alias depending on the "TO"
Besides the bonus of "owning" your email while still using the goodies of Gmail, having "catch-all", being able to easily migrate if shit hits the fan, there were also some other things I didn't realize until doing this:
You can save a local copy of the emails on your server (nice extra backup).
You have access to email logs, if you are worried about reliability you can just check it on-the-fly, you don't have to wait for the "email delivery failed" notification.
> And if you want to run your own server, good luck getting Gmail to accept your e-mails at all.
I still can, but only because I hate myself enough to run my own email for more than 20 years, so there must be some magic field of trust somewhere in the background. I wouldn't start from scratch though.
> the barrier of entry to sending email on your own is quite a bit above zero
I can attest to this. I ran my own email server with no problem for fifteen years. Then my provider was acquired, and I decided to switch to a different provider, and so the IP address of my server changed for the first time in 15 years. I have not been able to reliably send email since, and I finally threw in the towel and signed up with Fastmail to handle my outgoing email.
The biggest problem is people banning entire blocks of IP addresses. This can give you a bad reputation even if your behavior is stellar. All it takes is for someone using the same hosting provider to be a spammer to get yourself blacklisted.
The whole situation sucks big fat honking weenies.
Do NOT do this. Unless you're willing to make absolutely sure that no spam gets through to gmail, you will be blacklisted by gmail when it flags spam coming from your host. And not even a lot of it.
Basically, to use gmail this way you have to be almost as good as gmail at the thing that most makes gmail worthwhile. It's not worth it. Much easier to go the other way.
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