Hacker News Reader

Comment by pepr | Hacker News Reader

I have tried switching to fastmail and it was incredibly painful. In a nutshell, Microsoft/Hotmail and possibly other providers started to throw my emails to people to spam. I've missed out on important things in the physical world because of this. I've invested a lot of time trying to debug the issue. To their credit, Fastmail's customer service was excellent and they really tried to resolve the issues but in the end could not.

Also, fastmail web UI was okay but not great. I do like the new GMail UI better.

View on HN

Microsoft is particularly annoying. If I send mail from my domain via my server in Rackspace's cloud to my @outlook.com address, Microsoft classifies it as spam. I tell it that the mail is not spam--and the next one still gets classified as spam. I've done this several times now, and it is still classifying them as spam. How many freaking times do you have to tell Microsoft that something is not spam before it learns?

Compare to Yahoo. The first one to my @yahoo.com address was classified as spam, but then after I told Yahoo that it was not spam, subsequent ones come through fine.

I know right? Seriously, Office 365 spam management is a joke. Not only do Microsoft's OWN HOLIDAY PROMOTION EMAILS get marked as SPAM.. but whenever I mark an item or whitelist a domain at the Exchange level it completely ignores the rules.

Has anyone ever successfully got SPAM management working using the native O365 tools?

Well, the holiday promotion emails are spam, so it is sort of working as intended in that regard

Was about to say this. The fact that MSFT even throws their own promo emails into spam just tells me that there is no special preference kind of bias towards their own stuff, which is imo a feature, not a bug.

I have a custom domain in Fastmail, and after I did all of the DKIM/SPF and other email validation stuff (took an afternoon via their helpfiles) and got a green light from a couple authentication verifier services, I haven't had a single problem with being labeled as spam.

I had this problem in the beginning (specifically and only with hotmail), but it solved itself at some point. No idea if it was something that fastmail did or that hotmail did.

I have been using fastmail for one year and had zero other problems. If we don't move away from gmail, we will lose email, which is one of the only true decentralized and free protocols still left.

I had the reverse problem, stopped accepting my mails, after decade of non issue.

I think it's time we organise ourselves as small mail provider organisation. Anybody feeling the same please ping me.

I have used fastmail for all my business accounts for years. I have never had problems with deliverability. But I did warm the accounts using best practices recommended online to start.

What do you mean by "warm" and "best practices" ?

Email spam detection is hilarious.

Basically, you have to take a set of ritual steps to "warm" various email resources (such as domains, addresses, and IPs) to be flagged as "known" and "legitimate". For example, IP addresses: you should send warming emails to a valid address that you control for a few weeks to just show up on lists without having spam marks against you.

It's insane.

Is this for your own custom domains you mean?

I found the transition to be painless, but I did discover Microsoft was spam-labeling some of my emails too. I was using a custom domain though

Reply on news.ycombinator.com