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There’s a single reason that I gave up on this method: having to send outbound mail to these companies. You sign up for a health plan using healthplan@example.

There’s a single reason that I gave up on this method: having to send outbound mail to these companies. You sign up for a health plan using healthplan@example.com. Great, until you need to send them a document. You send it from myrealaddress@example.com, and they write back and say hey, that’s not the account on file, etc. So now you have to set up healthplan@example.com, configure it in your mail client, etc. And now you have this long list of special addresses to remember to have to send from, depending on the situation. Email is already something I loathe. Why would I make it harder on myself?

cdubzzz 4y ago
Depends on your setup I suppose. I use FastMail for this purpose and it both automatically sets the `From` based on the `To` of the email I'm responding to and allows me to click in to the `From` email and type in whatever I want for the local part before sending.
- jen729w 4y ago
  Ah that’s cool. I don’t think it did that when I used them, and I use Mail.app anyway.
mikeiz404 4y ago
Email alias services can make this process a little easier, though certainly not painless, by letting you create reverse sending email addresses [1]. 1: https://simplelogin.io/docs/getting-started/reverse-alias/ https://simplelogin.io/docs/getting-started/reverse-alias/
Normal_gaussian 4y ago
Fastmail allows sending from any address, the client supports it easily. There is also a few self-hostable mail clients that allow it. Historically I used a more convoluted method. When I used to use migadu (dont use them) I had a little script that would check the first line of any email I sent myself for a target email and resend it from the receive address. It was janky but worked.
- josephb 4y ago
  > (dont use them) Are you able to share what made you stop using them? I've been contemplating trying them out :-)
  - Normal_gaussian 4y ago
    Here is a fullish comment thread involving me and a migadu employee on the matter. Note he still claims some kind of email was sent at the end (it wasn't). https://news.ycombinator.com/item?id=24974369 https://news.ycombinator.com/item?id=24974369 There are a few other threads on HN about them as well. Essentially they are a bargain basement supplier and expect them to treat you as accordingly. If you're happy with that then its fine!
    - jen729w 4y ago
      FWIW I use Migadu and think they're great. But I have few needs. I set mailboxes up, I IMAP to them, that works. They're great value. Job done.
wonderbore 4y ago
I had some issues with my iCloud "Hide my email" once too when trying to contact support. Either they weren't getting my emails or they were purposefully ignoring my refund requests until I contacted my card company. It is an extra step to worry about, but if your setup is good enough (e.g. use iCloud and use Mail.app), then it's probably going to be easier.

cdubzzz 4y ago

Depends on your setup I suppose. I use FastMail for this purpose and it both automatically sets the `From` based on the `To` of the email I'm responding to and allows me to click in to the `From` email and type in whatever I want for the local part before sending.

jen729w 4y ago
Ah that’s cool. I don’t think it did that when I used them, and I use Mail.app anyway.

mikeiz404 4y ago

Email alias services can make this process a little easier, though certainly not painless, by letting you create reverse sending email addresses [1]. 1: https://simplelogin.io/docs/getting-started/reverse-alias/ https://simplelogin.io/docs/getting-started/reverse-alias/

Normal_gaussian 4y ago

Fastmail allows sending from any address, the client supports it easily. There is also a few self-hostable mail clients that allow it. Historically I used a more convoluted method. When I used to use migadu (dont use them) I had a little script that would check the first line of any email I sent myself for a target email and resend it from the receive address. It was janky but worked.

josephb 4y ago
> (dont use them) Are you able to share what made you stop using them? I've been contemplating trying them out :-)
- Normal_gaussian 4y ago
  Here is a fullish comment thread involving me and a migadu employee on the matter. Note he still claims some kind of email was sent at the end (it wasn't). https://news.ycombinator.com/item?id=24974369 https://news.ycombinator.com/item?id=24974369 There are a few other threads on HN about them as well. Essentially they are a bargain basement supplier and expect them to treat you as accordingly. If you're happy with that then its fine!
  - jen729w 4y ago
    FWIW I use Migadu and think they're great. But I have few needs. I set mailboxes up, I IMAP to them, that works. They're great value. Job done.

wonderbore 4y ago

I had some issues with my iCloud "Hide my email" once too when trying to contact support. Either they weren't getting my emails or they were purposefully ignoring my refund requests until I contacted my card company. It is an extra step to worry about, but if your setup is good enough (e.g. use iCloud and use Mail.app), then it's probably going to be easier.