Comment by jeroenhd

1 month ago

For me, as someone with their own mail server, these technologies mostly serve to inform me that Russian IP addresses are still trying to send email in the name of my domain for some stupid reason.

It makes sense that people whose business is sending email know how to set up email correctly. I'm mostly surprised at how many legitimate sysadmins struggle with getting the basics correct. Surely those dozens of DMARC emails you get that your sendgrid email has been refused because of a bad SPF signature should set in motion some kind of plan to ask if maybe marketing is using them legitimately?

Automated signatures are of limited value but I rarely see rejections based on SPF and DKIM that are a mistake. Things are probably worse for big organizations but as a small email server, technical rejections are usually the right call. The only exception is mailing lists, but the dozens of people who still use those can usually figure out how to add an exception for them.

The problems I noticed were, it doesn't matter what the SPF and DKIM look like. If Google or Microsoft refuse to relay your email based on secret internal factors then you're out of business.

  • Best, and often practically only, way to avoid this problem is to buy your email services from Google Microsoft duopoly.

    • It wouldn't shock me if an email services monopoly/duopoly would prefer email spam's only workaround to be signing up for their services, instead of fixing the root of the spam problem.

  • Microsoft seems to be the most common culprit.

    • Agree.

      I don’t understand why Microsoft are so bad at this?

      They have access to a large percentage of all email traffic to train domain reputation, and spam detection models on yet seem to be notorious for both false positives and false negatives.

      Google’s spam filters are far more accurate.

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  • This attitude is just FUD.

    The issue here generally boils down to the defining difference between a generalist Admin and a Messaging Admin. The generalist can follow instructions, and nearly all the instructions out there stop at the point where SPF/DKIM/DMARC are successfully implemented. A generalist worth their salt will then fill in the gaps if they can', and knows this isn't where you stop when you want mail deliverability. There's a higher bar.

    If you follow instructions written by non-professionals blindly you don't ever reach the point where you get to quality work.

    Google, Microsoft, and the other large ESPs don't refuse to relay your email based on secret internal factors. This is what the non-professional people say to falsely justify why they can't do something.

    Google and Microsoft publish the internal factors they use in the form of whitepapers at the industry working group. Its not ready made, and there are a lot of them, and they may not release their specific implementation details, but the metrics are there and often are based in weighted form (reputation-based systems).

    If you follow them correctly, and set up the appropriate reporting accounts, and maintain those accounts, you won't have these problems. You generally only have problems once you've violated guidelines continuously, which happens when you rely on, or are unable to discern between qualified and unqualified help.

    The factors are published at https://www.m3aawg.org/

    Every professional that specializes in email or messaging that I know of is well aware of this.

    People don't have the same vitriol when it comes to comparing Generalist Admins to DBAs, and this is the same with any specialized niche.

    If you need email and messaging to work in a complex environment, you hire a person that specializes in it.

    • MS flat out refuses to unblock our IP on their "outlook protection" racket despite many attempts through their self-service website.

      Our IP is the same for the last ... ~5 years now? Is it because we did not buy a /24? is it because we are so small they have no real reputation data? who knows!

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> Russian IP addresses are still trying to send email in the name of my domain for some stupid reason

For what it's worth, I've started seeing cybersecurity insurers requiring riders and extra payments if you don't block Russian IPs.

  • But there are big problems with mapping from IPs to countries. My IPv6 is detected as Russian, though it is London-located tunnel exit point and I'm in the Netherlands.

  • Ive got a server hosting a number of things, amd monitoring setup for a lot of stats. Got tired of seeing blips because various countries were beating on my server, not a DoS, but enough requests to notice, and sometimes generate an alert. I blocked 7 countries, in full, and the impact was fantastic. No more 2gb of logs generated every day by countries that have no business accessing my server.

    Unless you own a global business, i see no reason to even allow other countries access. The potential for attacks is too great, especially from some very specific countries.

  • Ok but you can’t block someone else using their own IPs to send email.

    If you set DMARC to report, you’ll get notices from remote email systems when they receive noncompliant emails with your domain in the Envelope From field. Those reports are where you’ll see Russian IP addresses show up when they are trying to spoof your emails.

    But there is no way to block them because neither the senders nor receivers are on your infrastructure. The best you can do is set a reject DMARC policy and hope everyone follows it.

As a non-email guy, I can tell you that if a system that boils down to having an (optionally certified?) key requires much more than just putting it into a folder with a domain name and running a service, it’s badly designed and has unnecessary complexity. Which will result into abusers having more expertise than legitimate users. The fact that you can “get” DMARC SPF DKIM wrong, while it’s basically a hard requirement for operation, is just screaming something important to the email software.

  • As a generalist admin, would you say the same about DBA operations or would you say that's just not my specialty?

    The reasoning you provide doesn't differentiate, and speaks more of frustration which naturally comes with any area you aren't steeped in, or knowledgeable about.

    • Frustration doesn't come naturally. It comes with shitty software design.

      "I don't know" is not a problem, you learn and you know, no frustration.

      The problem is "I spent N hours/days on a thing that everyone does and which is a 99.99% of use cases and boils down to just having a keyfile in a proper(?) location and this knowledge doesn't translate effing nowhere".

      would you say the same about DBA operations or would you say that's just not my specialty

      It depends on the absurdity of the complexity of setting something up, not on operations themselves. Getting some results is absurdly complex -- not naturally complex and not necessarily very complex, just much more complex than the nature of the result itself.

      For example, that's how you were supposed to install openvpn before angristan scripts: https://www.digitalocean.com/community/tutorials/how-to-set-... . To save someone a click, it's 50 pages "installation tutorial" with around 50 commands and a dozen of config files. And guess what, it uses "easyrsa" package to "set up RSA PKI easily". So it's not how openvpn meant to be installed, but an "easy" way.

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In most organizations there is no point in a sysadmin to spend the effort in understanding how to set it up correctly as Marketing has got more authority on email. Marketing will simply demand changes to the config that they do not understand and there is nothing you can do to stop it as they will have the CEO on their side.

  • > Marketing will simply demand changes to the config that they do not understand and there is nothing you can do to stop it as they will have the CEO on their side.

    Marketing should get their own (sub)domain for sending their missives, that way the primary corporate domain's reputation is not harmed.

    Unless you want to run the risk of outgoing e-mails from Finance / Accounts Receivable to be sent to other companies' Junk folder.

    • It's amusing to see this advice in this thread contrasted with the recent Troy Hunt phishing attack thread where folks are complaining about companies like Microsoft having dozens of varying domain names.

      1 reply →

    • This is email marketing 101, HN'ers are massively overstating how many domains are getting blacklisted because of "marketing".

  • Orgs like that will hire consultants like me when they can't figure out why their stuff isn't landing in the inbox. Then 3 months later their webdev will somehow delete the entire zone when adding their A record.

  • You mean like the time I had a salesperson demanding that we turn off Cloudflare across our entire domain because he'd read some random article somewhere saying we should?

    • The goal of sales isn't to block upto a 1/3 of world wide traffic. Turning off Cloudfare means more traffic and more sales are not blocked. Did you even read the article or did you dismiss it because it came from 'sales'.

      3 replies →

  • Which is another reason to strictly enforce SPF and DKIM, in my book. Let marketing break those policies, that way I don't need to bother with reading your company's spam!

  • Marketing decides on DKIM and SPF ?

    • The problem I personally ran into as a one person IT department was that the VP of marketing had more power over me, as a manager, and that meant more to my supervisor (the CEO) than me fighting to do things as correctly as possible. I was seen as a roadblock or speed bump. So, they may not decide on DKIM and SPF, but if marketing isn’t happy then their negativity could cause push back that forces changes that may technically not be good for the company.

      I’ve abandoned that role and have gone back to an IC role and I’m much happier for it.

      3 replies →

    • Indirectly, yes. Since they don't understand the details, management just "wants it to work". So too many email admins just give up and make their sending policies as permissive as they can to account for whatever new service marketing is using at the time.

    • DMARC is required for BIMI, and marketing wants that logo to show up in the Gmail app next to your mail

  • even worse when you have even less control than that, if you run some type of hosting and are trying to convince non-technical clients (or even worse, non technical clients who think they are technical) to “please just add this record exactly as it says here to your domain” and they’re somehow unable to for months and months

    • > "please just add this record exactly as it says here to your domain" and they’re somehow unable to for months and months

      I ran into this helping a friend whose biz emails to gmail recipients were getting dropped; the IT dept of the umbrella corp wouldn't respond. Same to me when I sent the correct DMARC, SPF etc.

      (My friend's biz was his own but it shared some resources with a larger corp.)

      I eventually realized that the (wrong) DMARC reporting domain wasn't even registered. I did what you'd expect and I soon had DMARC reports for subsidiaries of the umbrella corp. My friend passed that up to the CEO and suddenly IT was responsive.

      In the end, it turned out that IT was deliberately blocking his biz emails to his biz family members. After 10 years they suddenly decided that email to family+gmail was risky and that they were going to gaslight my friend about it. Because reasons.

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  • to be fair here: for a lot of companies, if the mass mailing stops, the money-flow stops then that's no good for anyone... so the CEO will probably err on the side of money, presumably.

As someone who set these up, I can tell you, the answer is rather simple:

- spammers have 1 system to set up in order to spam. They get it right.

- company admins have dozens of projects, of which this is a tiny one, with zero ROI to the bottom line (if people don't consider how critical security is). So they delay.

- companies often have dozens of systems integrated, when I set up DMARC/DKIM the first time for my company, a bunch of email tools broke, we had to do a bunch of leg work, took us a month end-to-end. The value was recognized when we almost lost 20k to a "ceo emails you" scam. But until then it wasn't a priority.

- we didn't even have a full IT, i just stepped in because I cared enough.

- my current company has a dedicated security team. These holes are plugged VERY quickly.

> that Russian IP addresses are still trying to send email in the name of my domain for some stupid reason

You can set your policy to reject, that will deter the Russians from using your domain.

  • I used to have my policy set to reject, but then I found out some part of an Enterprise Outlook mail filtering chain was rewriting the mail I sent before checking the DKIM signature. I can't fix stupid, especially for other parties, so I changed the policy to quarantine instead.

    I doubt Russian spammers will care about the difference to be honest. If they accept that their email will be delivered to spam folders, why would they care that the email gets silently dropped? In neither case anyone is going to fall for them.