8 ms·

I've been using SpamAssassin for at least 15 years and it's sadly gotten less useful as the spam arms race has moved on. We regularly see people on here post ab

by srmarm 3y ago

I've been using SpamAssassin for at least 15 years and it's sadly gotten less useful as the spam arms race has moved on. We regularly see people on here post about deliverability issues with Gmail/Outlook but the truth is that sender reputation is by far the biggest indicator of whether a message will be spam - these type of rules are just counting deckchairs on the titanic in comparison. And this plays into the strengths of the big mail networks in detection. It's a bonus to them that every time they block a smaller host there is a good chance that sender will consider a move to office365 or Google Workspace for their mail. As an aside, not sure if OP is related to them but updown.io is a nice service and I appreciate the simple PAYG pricing! For what it's worth their mails seem to get through successfully to me too. Also for those facing mail delivery issues (or just practicing good email hygiene) - I recommend www.mail-tester.com - they give you an email address to send a mail to and carry out a heap of tests - including checking against SpamAssassin + blacklists, SPF/DNS/etc testing.

andrewfromx 3y ago
there needs to be like a mozillia vs chrome thing here no? What's the best try so far for something like letsencrypt or mozilla foundation for not owned by big tech email so "will consider a move to office365 or Google Workspace for their mail" the sender has this other awesome option?
- jeffbee 3y ago
  If you wanted to operate a haven for independent email hosting, where you want to assure deliverability in the face of Gmail's sender reputation system, you would need to classify your outbound traffic, and have a death penalty for spammers. If you tolerate any activity that peers classify as spam, that would tank your reputation.
BSDobelix 3y ago
I like rspamd much more (performance and redis) than SpamAssassin, and as you mentioned: -https://www.mail-tester.com https://www.mail-tester.com -https://www.learndmarc.com https://www.learndmarc.com -https://mecsa.jrc.ec.europa.eu/en/ https://mecsa.jrc.ec.europa.eu/en/ Are exellent tool's to check your "deliverability".
- CableNinja 3y ago
  Suprised to not see https://mxtoolbox.com https://mxtoolbox.com in this list too
  - BSDobelix 3y ago
    Truetrue sorry, I forgot ;)
Retric 3y ago
Reputation works well because of those other rules. If every office365/gmail email got through and everything lose was blocked spammers would just move to those platforms. Thus email inspection is a critical component enabling reputation based filtering.
rlpb 3y ago
> It's a bonus to them that every time they block a smaller host there is a good chance that sender will consider a move to office365 or Google Workspace for their mail. The irony is that a substantial amount of the spam I receive comes from those platforms.
- nradov 3y ago
  Are you certain the spam is actually coming from IP addresses controlled by those platforms? It's common for spammers to fake the SMTP headers.
  - bombcar 3y ago
    Quite a bit is "genuine", at least with Gmail, because infinite monkeys can sign up for infinite accounts.
  - ceejayoz 3y ago
    I get plenty of spam from Gmail accounts with SPF and DKIM passing.
    - Mailtemi 3y ago
      I've got sometimes a legitimate Google or MS dev newsletter emails going into their own spam folders :) .
      - 8organicbits 3y ago
        I've seen mail from my work Google Workspace that I sent to my own personal Gmail get flagged as spam. It's me sending to me. Google to Google. Logged into both account on the same computer. If anything I'm nervous to recommend Google because they flag too many legitimate emails as spam. After years of not checking, I'm checking spam again.
        cj 3y ago
        > mail from my work Google Workspace that I sent to my own personal Gmail Does your company do outbound marketing/sales? I've seen multiple companies spin up outbound email marketing campaigns where someone compiles a list of 5000 email addresses based on certain demographics, and then send automated emails (that look not automated) over the course of a month, rinse, repeat. Google Workspace will let you do this, but if you're too aggressive with email volume it can kill the reputation, and therefore deliverability of any email from that domain. (Which is why most companies send outbound sales emails from a domain other than their primary domain to separate out the sending domain reputation)
op00to 3y ago
I switched from GMail to a personal Microsoft 365 domain when Google decided they didn't want to give me free email/domain services anymore. 365 was cheaper. I got about 10x the amount of spam to my 365 Junk folder than I did to the Junk folder in GMail. I would spend 10 minutes a day going through the junk folder to pick out false positives. I woud have inexplicable issues with missing email with 365, where the root cause was always SPF issues from a third party sender. The big issue was event tickets mailed from a third party ticket service provider using the venue's domain name rather than the ticket provider's domain. I switched back to GMail a few months ago, and not only do I see less stuff in my Junk folder (indicating Google is blocking stuff rather than identifying it) but also I have not seen a single false positive. Hopefully that means Google is more effective, but there's no way to tell if I'm missing legitimate email. So far, no complaints.
- yabones 3y ago
  Microsoft's spam filter is fundamentally broken. It's been that way for decades. There's an entire cottage industry of snakeoil salesmen that want to sell in-line antispam gateways to bolt onto 365, and the worst part is that they have a very good reason to exist...
- fer 3y ago
  Strange, while I keep my GMail address I don't use it for anything new anymore since roughly 50% of the positives are false (no false negatives, though).
JohnFen 3y ago
I've kinda given up on reputation scores to indicate spam/ham, personally, and rely more heavily on textual analysis rules. Going by "reputation" caused me far too many false positives.
alexis2b 3y ago
> As an aside, not sure if OP is related to them but updown.io is a nice service and I appreciate the simple PAYG pricing! For what it's worth their mails seem to get through successfully to me too. Not related in any way except as an happy customer. They added a blog recently and this article caught my eye because of the nightmare that is mail delivery issue for everyone. I found it particularly ironic that you now have to think like a spammer (i.e. look at spam detection engine source code to find a way to circumvent their heuristics) in order to get your totally valid email delivered (^_^). edit: typo
- adrienjarthon 3y ago
  Thank you
jmyeet 3y ago
> ... the truth is that sender reputation is by far the biggest indicator of whether a message will be spam I couldn't agree with this more. I want people to remember this whenever the topic of decentralization or federation comes up. People see this as a technical problem. it's not. It's a political and organizational problem. Even with email, which is fully decentralized (other than the ICANN TLDs) running your own node still incredibly difficult. And those reasons aren't technical at all.

by srmarm 3y ago

andrewfromx 3y ago

there needs to be like a mozillia vs chrome thing here no? What's the best try so far for something like letsencrypt or mozilla foundation for not owned by big tech email so "will consider a move to office365 or Google Workspace for their mail" the sender has this other awesome option?

jeffbee 3y ago
If you wanted to operate a haven for independent email hosting, where you want to assure deliverability in the face of Gmail's sender reputation system, you would need to classify your outbound traffic, and have a death penalty for spammers. If you tolerate any activity that peers classify as spam, that would tank your reputation.

BSDobelix 3y ago

I like rspamd much more (performance and redis) than SpamAssassin, and as you mentioned: -https://www.mail-tester.com https://www.mail-tester.com -https://www.learndmarc.com https://www.learndmarc.com -https://mecsa.jrc.ec.europa.eu/en/ https://mecsa.jrc.ec.europa.eu/en/ Are exellent tool's to check your "deliverability".

CableNinja 3y ago
Suprised to not see https://mxtoolbox.com https://mxtoolbox.com in this list too
- BSDobelix 3y ago
  Truetrue sorry, I forgot ;)

Retric 3y ago

Reputation works well because of those other rules. If every office365/gmail email got through and everything lose was blocked spammers would just move to those platforms. Thus email inspection is a critical component enabling reputation based filtering.

rlpb 3y ago

> It's a bonus to them that every time they block a smaller host there is a good chance that sender will consider a move to office365 or Google Workspace for their mail. The irony is that a substantial amount of the spam I receive comes from those platforms.

nradov 3y ago
Are you certain the spam is actually coming from IP addresses controlled by those platforms? It's common for spammers to fake the SMTP headers.
- bombcar 3y ago
  Quite a bit is "genuine", at least with Gmail, because infinite monkeys can sign up for infinite accounts.
- ceejayoz 3y ago
  I get plenty of spam from Gmail accounts with SPF and DKIM passing.
  - Mailtemi 3y ago
    I've got sometimes a legitimate Google or MS dev newsletter emails going into their own spam folders :) .
    - 8organicbits 3y ago
      I've seen mail from my work Google Workspace that I sent to my own personal Gmail get flagged as spam. It's me sending to me. Google to Google. Logged into both account on the same computer. If anything I'm nervous to recommend Google because they flag too many legitimate emails as spam. After years of not checking, I'm checking spam again.
      - cj 3y ago
        > mail from my work Google Workspace that I sent to my own personal Gmail Does your company do outbound marketing/sales? I've seen multiple companies spin up outbound email marketing campaigns where someone compiles a list of 5000 email addresses based on certain demographics, and then send automated emails (that look not automated) over the course of a month, rinse, repeat. Google Workspace will let you do this, but if you're too aggressive with email volume it can kill the reputation, and therefore deliverability of any email from that domain. (Which is why most companies send outbound sales emails from a domain other than their primary domain to separate out the sending domain reputation)

op00to 3y ago

I switched from GMail to a personal Microsoft 365 domain when Google decided they didn't want to give me free email/domain services anymore. 365 was cheaper. I got about 10x the amount of spam to my 365 Junk folder than I did to the Junk folder in GMail. I would spend 10 minutes a day going through the junk folder to pick out false positives. I woud have inexplicable issues with missing email with 365, where the root cause was always SPF issues from a third party sender. The big issue was event tickets mailed from a third party ticket service provider using the venue's domain name rather than the ticket provider's domain. I switched back to GMail a few months ago, and not only do I see less stuff in my Junk folder (indicating Google is blocking stuff rather than identifying it) but also I have not seen a single false positive. Hopefully that means Google is more effective, but there's no way to tell if I'm missing legitimate email. So far, no complaints.

yabones 3y ago
Microsoft's spam filter is fundamentally broken. It's been that way for decades. There's an entire cottage industry of snakeoil salesmen that want to sell in-line antispam gateways to bolt onto 365, and the worst part is that they have a very good reason to exist...
fer 3y ago
Strange, while I keep my GMail address I don't use it for anything new anymore since roughly 50% of the positives are false (no false negatives, though).

JohnFen 3y ago

I've kinda given up on reputation scores to indicate spam/ham, personally, and rely more heavily on textual analysis rules. Going by "reputation" caused me far too many false positives.

alexis2b 3y ago

> As an aside, not sure if OP is related to them but updown.io is a nice service and I appreciate the simple PAYG pricing! For what it's worth their mails seem to get through successfully to me too. Not related in any way except as an happy customer. They added a blog recently and this article caught my eye because of the nightmare that is mail delivery issue for everyone. I found it particularly ironic that you now have to think like a spammer (i.e. look at spam detection engine source code to find a way to circumvent their heuristics) in order to get your totally valid email delivered (^_^). edit: typo

adrienjarthon 3y ago
Thank you

jmyeet 3y ago

> ... the truth is that sender reputation is by far the biggest indicator of whether a message will be spam I couldn't agree with this more. I want people to remember this whenever the topic of decentralization or federation comes up. People see this as a technical problem. it's not. It's a political and organizational problem. Even with email, which is fully decentralized (other than the ICANN TLDs) running your own node still incredibly difficult. And those reasons aren't technical at all.