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I'm surprised you are having much success on Digital Ocean. I've found that their whole ASN is often marked as low reputation. For example sending to Microsoft

I'm surprised you are having much success on Digital Ocean. I've found that their whole ASN is often marked as low reputation. For example sending to Microsoft or Apple has always been unreliable for me. It does seem that it can depend somewhat on what IP you roll. I guess if you get a good one and stick to it you may be able to scrape by with just the ASN reputation holding you back. Source: I run a service that sends email on Digital Ocean and I have to use third-party services to send to many hosts. (in fact I tend to whitelist inbox providers slowly once we have built some domain reputation)

tqwhite 4y ago
For awhile I had trouble with Yahoo and a couple of others. I also had to get off a couple of spam lists. There was one big service that troubled me for years, can't remember which. But, the years went by and I guess my IP address got a better reputation. I haven't had a deliverability problem in years. Maybe it's because I got better at the SPF's, DMARC's, etc. I will say that I think it's an internet sin that these big companies make it hard for individuals to run their own servers. It seems like an attempt to make a corporate monopoly. My server has never been used for spam a single time. There is no reason I should not have been able to remedy problems instantly.