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I love this entire blog! I learned about it when another story—about the development of Aperature—was posted to HN a few weeks ago, and I've since read through every post. Great little peak inside of Apple.

I think my favorite, very short story might be: https://techreflect.net/2019/05/30/horsey/

Thanks, Wowfunhappy person. :) Much more to come. The long ones are too tiring.
FWIW: This is the number one thing I prefer about Apple Mail over almost any other client for handling multiple accounts.
I’ve actually considered switching away from the default mail client partially for this reason. With multiple accounts it’s gotten pretty difficult to see which account received the email, moving multiple screens to see it. And often Apple Mail will get an email to one address but when you hit respond it will try to reply with a different email address. That last one has led to a couple embarrassing moments trying to email clients in a hurry and accidentally replying from my personal account.

It certainly doesn’t work like magic.

It used to work like magic.

It also used to show exactly the email address that received the message, not just the account and certainly not just the name. The Catalina rewrite seems to have brought the oversimplification of the iOS UI to desktop along with the data loss bugs.

I think that this happens if you change the send-with account for a given account (so if account X sends via the Y server, it will have Y's return address). Other than that, I've never had the return address for a reply have anything other than the address of the account it was sent to.
Regardless of the server you set Apple mail still sends the email as from the account you hit reply on.

However some servers will rewrite the mail serverside to match the authentication user to prevent spam. The main service I know that does this is gmail (and probably any of the “big” mail providers). If you send through a more basic typical Linux server it will send as the “correct” address.

Although these days it’s mostly a bad idea to do that because you’ll hit issues with SPF, DKIM, etc.

The main actual issue you have here is if you manually hit “new message” then you need to think about which sender to choose if you’re coming from a unified inbox view instead of the specific inbox for the account you want to send from.

> Regardless of the server you set Apple mail still sends the email as from the account you hit reply on.

Unless you flip the setting to always send it from one address.

It happens quite often. It somehow decides to pick up outgoing email address based on to field. It’s annoying. There is a setting for it but it appears to reset with every update.

The only solution I found so far is to have distinct footers for each account and ALWAYS look st the footer and from.

It’s a dumb default.

This is a menu option in Thunderbird (hamburger > View > Folders > All/Unified).
Hey all, just so you know, Thunderbird can do this too. View -> Folders -> Unified :)