Prompted by a need to sign and encrypt emails, I decided to give Apple Mail a try again. The convenience offered by GPGTools was tempting.

Beed a while since I switched to Outlook for my work email and tring to set up my accounts reminded me why (kept using it for a private account). The account setup process is brain-dead - it does not allow you to specify all the options you might need but tries to auto-detect without a way to override this (let me know if there is).

So, this time around I managed to get the account settings working, not sure why. This blog post is about the other issues I had to solve.

Exchange Accounts and Aliases

After setting up my work email as an Exchange account, I ran into the problem that my username does not match my email address. Turns out I have to set the outgoing mail server to “none” and then Apple Mail allows me to edit a list of aliases (thanks to this helpful post).

Email account ordering

The order in which the email accounts appear cannot be changed either using an obvious or documented (I do not demand much, Apple!) process. So, I had to find this helpful blog post for a work-around that consists of de-activating all accounts, then re-activating them in the desired order. Hello, Apple? Too busy counting your money to design decent software?

Why not use X?

Ok, so in case you think “why does he not use email client X” - I tried Thunderbird and Outlook recently. Both suck in their own respective ways. Outlook, for example, cannot quote replied-to emails anymore. Hello, Microsoft? Did you think we would not notice?