SMTP, I give up...

[Slylok]

Are the emails going out with html headers and hyperlinks? Try sending in plain text and see if they get through

[Robbie]

Are the emails going out with html headers and hyperlinks? Try sending in plain text and see if they get through

I'll have to check the settings. I'm not sure. They're all automatically generated by vbulletin. Good suggestion, but that shouldn't be what is causing my mail to be considered spam.

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[Straf]

Good call Skylok!

Anti-spam checks look at the 'rich' content like HTML, heavy image use and links.

Robbie - do you have a newsletter that you can send me? The notification emails I receive are all plain text as far as I can see, but they do have hyperlinks in them. BTW they are coming to my gmail account fine. I can at least see if they're getting through too.

[Slylok]

After rereading your OP, you're saying that the server sending the emails is marking them as spam? Are you getting an error to indicate this? Are they making it outside at all or getting stopped before?

[Robbie]

The web server is using postfix with opendkim to send the email and any isp that uses cloudmark for spam detection will deny the mail because I'm apparently on their bad list. Later tonight I can post a mail log entry to show you what I'm seeing. I've requested delisting numerous times but either they're not delisting me or I'm getting put right back on for who knows what reason.

As for the newsletter, I was wrong about the newsletter... It's on a separate system and I think it might be ok... If the system generated mails are plain text then that's good... But they will have to have links in them because they're often verification emails or password reset emails or links to subscribed thread updates.

Cloudmark supported ISPs are mostly your Internet providers. Gmail does their own verification and I seem to be good with them.

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[Slylok]

The web server is using postfix with opendkim to send the email and any isp that uses cloudmark for spam detection will deny the mail because I'm apparently on their bad list. Later tonight I can post a mail log entry to show you what I'm seeing. I've requested delisting numerous times but either they're not delisting me or I'm getting put right back on for who knows what reason.

As for the newsletter, I was wrong about the newsletter... It's on a separate system and I think it might be ok... If the system generated mails are plain text then that's good... But they will have to have links in them because they're often verification emails or password reset emails or links to subscribed thread updates.

Cloudmark supported ISPs are mostly your Internet providers. Gmail does their own verification and I seem to be good with them.

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OK I see. Yeah the blacklist thing is a pain. Hopefully, they will work with you on taking you off. It sounds like once you get them to remove you then it should work as normal.

As for the links for verification and password resets, I've recently taken to using randomly generated 8 digit passcodes that have an expiration time and sending those in the email. I did this for the specific reason of avoiding links in emails since mail apps like to flag them or disable the links.

[Robbie]

OK I see. Yeah the blacklist thing is a pain. Hopefully, they will work with you on taking you off. It sounds like once you get them to remove you then it should work as normal.

As for the links for verification and password resets, I've recently taken to using randomly generated 8 digit passcodes that have an expiration time and sending those in the email. I did this for the specific reason of avoiding links in emails since mail apps like to flag them or disable the links.

Smart. I need to see if vbulletin supports that. What software are you using?

I don't typically have any problems on the client side and it seems like cloudmark is the only one I seem to repeatedly have a problem with. It's so frustrating! Thank you all so much for posting ideas in here. Like I said after the kid goes to bed, I'll post a log entry.

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[Straf]

I don't use ISP email as I have my own domains with a hosting package. So I probably won't be much use in testing the emails. But I can PM you an email address you can try sending to.

Is the site hosted on a dedicated server/VPS, or are you hosting it from an ISP's IP pool? Some ISPs reject IP pools automatically. I know AOL used to do that when I ran one of my sites from a server beneath my desk. I was using Exim and that took some tinkering to get it to work in a satisfactory way.

[Robbie]

I don't use ISP email as I have my own domains with a hosting package. So I probably won't be much use in testing the emails. But I can PM you an email address you can try sending to.

Is the site hosted on a dedicated server/VPS, or are you hosting it from an ISP's IP pool? Some ISPs reject IP pools automatically. I know AOL used to do that when I ran one of my sites from a server beneath my desk. I was using Exim and that took some tinkering to get it to work in a satisfactory way.

It's a dedicated server running in a data center so it should be a perfectly acceptable ip address.

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[Straf]

I notice that you're using SPF and DKIM but you don't seem to have a DMARC implementation. I can't pretend to know anything about it but it seems to form a holy trinity with the other two and from the brief read I made it seems to be more about anti-phishing.