= Google Workspace is marking mail from a new VPS as spam. It's not misconfigured and the domain has no spam reputation. Are any of you are successfully hosting email services on a Digital Ocean VPS? =

More detail:
I've used this domain for 20 years for personal mail. I've old-school Linux ethos; there's never been even a hint of spam from this domain

SPF and DKIM are enabled

I've checked RBL lists. The IP is clean

There's no info in the raw message source from Google. SPF passes, hostname checks are fine

It's not just my google account that marks it as spam. Every recipient that uses google as an MX is seeing my messages get spammed

Haven't had problems with other services rejecting or misclassifying my mail as spam

The reason I suspect that Google is using Digital Ocean netblocks as a spam signal is that more or less the same postfix config has been running on various other hosting for two decades without ever a hint of trouble

I don't want to renumber everything but I'm wondering if it's worth the effort to try and use a different IP address?

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don't send email directly from the VPS. Use a transactional mail provider or SMTP relay along the lines of Amazon SES, Sendgrid, Mailchannels, etc

Digital ocean has a bad reputation when it comes to their IP range among email spam filters

Yeah, because of the ease of spinning up a VPS that seems to apply to all cloud providers. I know I've certainly had to deal with it plenty on the anti-spam admin side. The thing is, Digital Ocean does a good job in actioning abuse reports

It'sand bad administration to blindly mark whole netblocks as spam. Use it as a signal, sure, but it shouldn't be enough on its own. When everything else about the mail transaction is clean then it should not be marked as spam simply because it's a cloud provider


so must be a google thing. I've had issues in the past sending emails from privateemail.com and some recipients don't receive them at all or its marked as spam. Never could quite really solve it

I know Google's filtering. I worked for someone who had a compromise so their domain sent a buttload of spam until I cleaned it up. Google never again accepted email from their domain. It was and is rejected immediately in the SMTP transaction. It's totally reasonable to put in a temporary block but to continue to block that domain years later just because someone got compromised for a short time? Google

It sounds like your IP address doesn’t have a great history. You will need to build that up. You BSN have the best domain reputation in the world, but a bad Ip will tank everything
That much is apparent. I know that I've been guilty of blackholing IP addresses that are attacking our infrastructure and we don't have a clear policy for expiring such blocks

It makes me abut I expect better from Google with their resources. They must understand the variability and transience of IP addresses allocated to customers in cloud services

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