Apple Mail Fixup Part 3: Name Your Pains and UnknownsHELLO DOG

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A good second step before we undertake to streamline Apple Mail is: what are the known pain points? What are the areas you don’t quite get? When solving any problem, especially ones with a lot of moving parts, it’s helpful to make two lists: one for what you already know you hate and one for what you already know you don’t know. The second list is more important than you might think: the mystery spots out there in the landscape might just be shadows…or they might be quicksand. It pays to put a flag beside them.

My starting list of known pain-points in Apple Mail

  • Spam has made my email a living hell
  • It can be very slow to move and delete files
  • It’s confusing that there is an “Accounts” submenu and a “Preferences/Accounts” submenu
  • My existing use of folders is more painful than helpful, more clutter than clarity
  • Rules (automated filing and deleting of email, mainly) sometimes don’t seem to work
  • Presently I have no easy way to mark an email for urgent attention
  • Important emails are always getting lost in the shuffle
  • Tedious to set up spam-fighting rules
  • Tedious to set up rules, period
  • Having some of my mail in iCloud seems to complicate and slow things down considerably
  • The app seems to randomly choose which account to use for outgoing mails
  • Setting up a new account is always a pain: the instructions provided by ISPs never line up with the screens and field names I see on my own screen
  • Sometimes searching works fast, sometimes slow, sometimes not at all
  • No progress indicator when emptying the trash
  • Deleting email takes too many steps

My starting list of unknowns in Apple Mail

  • The difference between POP and IMAP is vague, and good explanatins are hard to find
  • The difference between Junk and Trash is not clear
  • The difference between deleting and erasing is not clear
  • Should I have “Spam”, “Drafts”, “Sent” etc. folders for each account, or one set of these folders shared by all acccounts?
  • What are the pros and cons of IMAP? Of POP?
  • Is it tricky/dangerous to revert from IMAP to POP?
  • What the pros and cons of storing my mail on iCloud Drive?
  • What are the gotchas of IMAP?
  • What are the gotchas of POP?
  • What are the gotchas of storing email on iCloud Drive?
  • Should I use smart mailboxes, regular mailboxes, or a combination of both?
  • Why is my Mail folder on the hard drive sooooo large?
  • Is there a good way to export a lot of email for viewing in a separate app?
  • What is the “Archive folder all about?
  • If I delete an “account,” is it the same as deleting a mailbox for that account?
  • What does it mean to “disable” an account? Does mail get disposed of on the server if I don’t donwload it frequently?
  • Does Apple Mail have an option to only store IMAP mail on the server?
  • Exactly what does “On My Mac” mean in relation to IMAP? In relation to POP?
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Apple Mail Fixup Part 2: Name Your Goals