Fastmail is awesome. I'd combine DDG Email with their Masked Email in the cases where you want to strip image tracking and opaque tracking urls from your links.

(I've been a happy paying customer of Fastmail for _years_ and I didn't know about masked email. Thank you!)

Just in case you happen to be a 1Password user as well, there is an integration where they can auto-generate masked emails for you: https://support.1password.com/fastmail/ It makes it very convenient!

Auto-generated masked emails using Fastmail and 1Password has worked very well for me when I'm using Firefox, with the 1Password extension installed, on my laptop.

I can't for the life of me, however, figure out how to get 1Password to auto-gen a masked email from their iPhone app or desktop app.

Is this possible?

Would love to see a Bitwarden implementation of this

You can also use a custom domain (and/or anything else Fastmail lets you choose), this way you can put all the randomly generated emails coming to you in a single folder (as a rule).

I've heard of fastmail in years past. Your comment got me curious again about it. How's the deliverability of their service? I guess with anything "email related", the hardest part is making sure that the emails I send actually ends up where I intend to go. (Goes without saying, outbound emails are NOT spam but legitimate emails.)

I’ve never had any deliverability issues with Fastmail and am happy with their uptime. I originally used google apps (aka gsuite/workspaces these days) but had enough headaches using it for personal email that I switched and the quality of service feels the same to me.

I was a paid Fastmail user for something like 3 or 4 years, largely as a consequence of the good standing they seemed to have among the audience on HN. Deliverability (and uptime) with Fastmail is excellent.

However, during that time I filed two support tickets and neither left me feeling particularly warm and fuzzy about the faces behind the business that I was pledging my annual subscription to. The response in the latter instance in fact was so bad that it's what motivated me to look elsewhere rather than renew. I was prepared to pay more just to know that I wasn't doing business with bullies/jerks. I ended up going with a smaller provider. Without checking, my annual expenses are actually around half as much, IIRC.

Are you worried that a smaller provider may be less reliable in the long run, or you are already prepared to just switch your domain again if it becomes an issue? If you are ok sharing it, what is the provider?

I really wanted to switch to Fastmail a few years back but 1) its registration page was intermittently down for me and 2) when I caught it during uptime, it sent me to phone SMS verification which I found invasive given it is a paid service. I was ready to give it a chance anyway, but no SMS got delivered to me in the end.

"Smaller" in this case just means smaller, not newer. They've been in business for a long time, and I expect them to be around for a while. The downsides tend to be in the opposite direction: they're old, and their webmail/account management interface until recently showed its age. This was not a problem in my book; I don't use webmail. The greater concern with mail providers involves the risk that they would pull something like what Gmail did and withdraw from offering standards-based email (i.e. no more IMAP). In that respect, what the sluggishness to get with the trends really means is a lower risk rate of churn, and I'm happy with that.

Your profile doesn't list a way to contact you privately.

As of last year, it's supposed to be one of the services listed on <https://www.fsf.org/resources/webmail-systems>, but it's not. I just reached out to Greg Farough to follow up on why.

Thanks, that FSF link might be good enough. (I don't want to identify this account and don't immediately know how to set up an anonymous throwaway email)

By the way, according to my Mail's connection doctor on mac, it appears to use IMAP when talking to gmail as of now. I wasn't aware Google was phasing out proper IMAP support, my concern was more about them being known to ban accounts with little recourse.

I’m always interested in discovering paid service email providers who respect privacy. Could you please email me the provider name/URL on my temp email listed on my profile? Thanks.

could you be a bit more specific?

I've been using them for 18 months and the support has been not perfect, but 100x that of e.g. Amazon support chat

I use tutanota and the alias works. But didn't know masked emails were offered by services like fastmail!

You can also use migadu which is a lot cheaper :)

Many Fastmail customers pay them in large part for the web interface.