> They don't mark it as spam, they just outright block emails, so you can't even workaround it by checking the spam folder.

And there’s no reason for them to do that IMO. They should dump it into the quarantine as high confidence spam. I wonder if the drop shows up in the mail flow logs.

I deal with a lot of small businesses and more than once I’ve seen bad spam filtering or silent drops cost people money (upset customers). The spam filters I can understand. The silently dropped messages should get them a class action lawsuit.

There is a reason - DigitalOcean. A more appropriate name would be DigitalCesspool. They allow anything, so long as you pay them. I'd block email from their networks, but there are already plenty of ways that spam servers on their networks screw up (bad EHLO name, broken reverse DNS, SPF for all IP addresses), so that email is not accepted anyway.

Microsoft sucks for rejecting email without recourse, but you're on DigitalOcean, so can you really blame them?

I’m not on digital ocean and I don’t know anyone who is. I’m on the receiving end using office 365. Problems I see are for mail coming from shared hosts and isps.

IMHO there’s never a reason for Microsoft or Google to drop mail silently if it’s deliverable. Let me decide if I want to do that, but don’t force it on me.

Google is awful too. Accounts locked for “suspicious activity” stop accepting incoming mail. I’ve seen people lose a day of email over a weekend before noticing ta false positive account lock.

What it really comes down to for me is that I don’t think either of them could act that negligently in a fairer market with better competition.

Things will only change if enough paying customers complain loudly about it.

You think Microsoft blocking you is bad? They ACCEPT mail and drop it afterwards.

Pretty close! They accept the mail returning a "250 OK"ish code, but they delay it for days (or even months) not respecting the SMTP protocol. I actually recevied the emails on Outlook after many many days I have sent them :/

Gmail seems good, I never had issues with Gmail.

No, not close, it's exactly what they do.

Delays are fine by the protocol, it's not a violation, it's not IM.

My emails from my domains to my Outlook account were going straight to spam.

I tried marking them as not spam, to see if it would learn. A dozen later--no change.

I tried replying to them, to see if it could figure out that if I'm actually regularly corresponding with someone they should not be marked as spam. No change.

I tried whitelisting the domain. No change.

I have the same problem, but they fixed it. I opened a issue and a kindly guy did some checks and then removed the ban.

Was it recent? I've had no issues whitelisting my IP in the past, but all my requests in the last 6 months have been ignored.

What's Microsoft's rationale ? Has an explanation ever been given ?

I've tried reaching Microsoft by phone, email, automated tools for email administrators, and their web forms for requesting whitelisting in email deliverability. Microsoft didn't provide any rational why they are filtering email from small email providers like this, nor did they provide any opportunity to mitigate their filtering.

Probably it's more convenient for them to trust X big players rather than checking one by one. And somehow an empty spam folder looks better than a full one, as it gives the user the feeling that the service itself doesn't receive spam or does a very good job at preventing it.

That's just the thing: "doing a good job preventing spam" means throwing a lot of stuff in the spam folder. I think everyone would agree that silently dropping emails is bad, even if you're really sure it's spam.

I agree, it's just that you're not the average user. I am also surprised to see the spam folder surprisingly empty all the time, almost as if my email addresses were unknown to the world (which I am pretty sure they are not).

The average user probably sees this full spam folder as something he/she is doing bad, or the service itself is bad.

It's not just google or microsoft. I think most email providers do this, I might be wrong though.

You can create anonymous servers on DO with go-betweens like Bithost, allowing you to pay with cryptocurrency. This is a pretty easy solution for people with bad intentions (bots, scraping, black hat ...)

I run my own VPN on DO and almost always get hit by ReCaptcha. Even Google.com will put up a "we've noticed some unusual traffic from" page. Some sites like Zalando completely block me with just a plaintext error page.