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As someone who up until recently managed the mail system and antispam for a business processing ~250k mails a das, false positives are an outlier. We had a tick

As someone who up until recently managed the mail system and antispam for a business processing ~250k mails a das, false positives are an outlier. We had a ticket because of this perhabs once a week and most of the time it was because of poorly setup Mailservers in the other end. Server side filtering works quite well, most of the spam comes from hijacked leggid accounts that are burned quite quickly.

ColinWright 5y ago
Great, I'm genuinely pleased to hear that your experience of server-side filters is a positive one. Mine is negative. The fact that you have a positive experience does not refute that mine is negative. Please: I've experimented with this for over two decades, and continue to do so. I know that lots of people say that server-side filtering is fine. My direct personal experience is that for me it is not fine, including the spam filtering provided by Google's email service. I do not deny that for other people it's fine, I'm just saying ... don't deny my experience.
- throwawayvibes 5y ago
  Never had much of a problem with Gmail's filter. An odd newsletter end up in spam once every while. How does your issue manifest?
  - goodevans 5y ago
    It's his Nigerian Prince Scam How-To newsletter, goes missing every week!
  - ColinWright 5y ago
    > How does your issue manifest? I regularly have emails to my GMail from colleagues end up in the spam folder. Perhaps as many as 5 or 10 per week, enough that I have to trawl through the spam folder every few days to make sure I've not missed something important. Similarly, reasonably often when people reply to me, often after being prompted with a second email, or even a phone call, people tell me that emails from my "other" ISP to their GMail provided mailboxes have ended up in the spam folder. It happens in waves ... it can be fine for months, and I start to think it's all good and I can trust it, and then there's a spate of emails going to spam when they really shouldn't. It's simply unreliable. So for incoming email I do my own filtering. I can do nothing about my outgoing emails ending up in someone else's GMail spam folder except to be aware that it happens, and to keep track of when I'm expecting a reply. With some colleagues I've gone to a "positive acknowledge" system to preempt what have been expensive problems in the past.
    - thraxil 5y ago
      A couple things I can think of: * What's your DKIM/SPF/DMARC setup like? That all needs to be on point to get delivery to gmail to be reliable. * Are you using a provider like Sendgrid, Mailchimp, etc. to send mail? Are you on a plan that gives you a dedicated IP address or is it part of their shared pool? The "it happens in waves" sounds a lot like a common problem with the shared pools where spammers send a bunch of mail through a service, the IP gets blacklisted, and it takes them a couple days to notice and remove it from the pool. * do you have any "noisy" alerts or similar going out to people? Not necessarily spam, but eg, sometimes users getting frequent notifications, daily summaries, etc. will sometimes just flag them as "spam" rather bother to turn them off or manage them properly. At some point, that trains Gmail's filters to increase the spam likelihood on your entire domain.
      - ColinWright 5y ago
        * I am assured by my ISP provider that the settings are as squeaky clean as they can be. * No, I'm sending email from my domain on my domain host. That has a single IP address shared among all their customers, but it's a very small ISP, and there are no spammers, and the IP address is not on any blocklists. * No, I send standard email "by hand", and I know that people are not marking them as spam. It's nice to see you go through these things because these are exactly the things I've gone through several times, so it serves to confirm that I've addressed the right things.
        thraxil 5y ago
        You should be able to look at the SPF/DKIM/DMARC related DNS entries yourself with dig and verify that they are correct. I wouldn't trust an ISP's word, especially if you are experiencing problems. I would also recommend setting up weekly DMARC digests via Postmark's free service: https://dmarc.postmarkapp.com/ https://dmarc.postmarkapp.com/ which should allow you to actually see whether emails are getting rejected and why and give you a lot more data about your actual SPF and DKIM alignment.
        5y ago

ColinWright 5y ago

Great, I'm genuinely pleased to hear that your experience of server-side filters is a positive one. Mine is negative. The fact that you have a positive experience does not refute that mine is negative. Please: I've experimented with this for over two decades, and continue to do so. I know that lots of people say that server-side filtering is fine. My direct personal experience is that for me it is not fine, including the spam filtering provided by Google's email service. I do not deny that for other people it's fine, I'm just saying ... don't deny my experience.

throwawayvibes 5y ago
Never had much of a problem with Gmail's filter. An odd newsletter end up in spam once every while. How does your issue manifest?
- goodevans 5y ago
  It's his Nigerian Prince Scam How-To newsletter, goes missing every week!
- ColinWright 5y ago
  > How does your issue manifest? I regularly have emails to my GMail from colleagues end up in the spam folder. Perhaps as many as 5 or 10 per week, enough that I have to trawl through the spam folder every few days to make sure I've not missed something important. Similarly, reasonably often when people reply to me, often after being prompted with a second email, or even a phone call, people tell me that emails from my "other" ISP to their GMail provided mailboxes have ended up in the spam folder. It happens in waves ... it can be fine for months, and I start to think it's all good and I can trust it, and then there's a spate of emails going to spam when they really shouldn't. It's simply unreliable. So for incoming email I do my own filtering. I can do nothing about my outgoing emails ending up in someone else's GMail spam folder except to be aware that it happens, and to keep track of when I'm expecting a reply. With some colleagues I've gone to a "positive acknowledge" system to preempt what have been expensive problems in the past.
  - thraxil 5y ago
    A couple things I can think of: * What's your DKIM/SPF/DMARC setup like? That all needs to be on point to get delivery to gmail to be reliable. * Are you using a provider like Sendgrid, Mailchimp, etc. to send mail? Are you on a plan that gives you a dedicated IP address or is it part of their shared pool? The "it happens in waves" sounds a lot like a common problem with the shared pools where spammers send a bunch of mail through a service, the IP gets blacklisted, and it takes them a couple days to notice and remove it from the pool. * do you have any "noisy" alerts or similar going out to people? Not necessarily spam, but eg, sometimes users getting frequent notifications, daily summaries, etc. will sometimes just flag them as "spam" rather bother to turn them off or manage them properly. At some point, that trains Gmail's filters to increase the spam likelihood on your entire domain.
    - ColinWright 5y ago
      * I am assured by my ISP provider that the settings are as squeaky clean as they can be. * No, I'm sending email from my domain on my domain host. That has a single IP address shared among all their customers, but it's a very small ISP, and there are no spammers, and the IP address is not on any blocklists. * No, I send standard email "by hand", and I know that people are not marking them as spam. It's nice to see you go through these things because these are exactly the things I've gone through several times, so it serves to confirm that I've addressed the right things.
      - thraxil 5y ago
        You should be able to look at the SPF/DKIM/DMARC related DNS entries yourself with dig and verify that they are correct. I wouldn't trust an ISP's word, especially if you are experiencing problems. I would also recommend setting up weekly DMARC digests via Postmark's free service: https://dmarc.postmarkapp.com/ https://dmarc.postmarkapp.com/ which should allow you to actually see whether emails are getting rejected and why and give you a lot more data about your actual SPF and DKIM alignment.
        5y ago