Configure an IMAP account in OS X Mail

The difference between POP and IMAP

POP mail is fine for most people, but if you’re more demanding there is always IMAP. IMAP has been around since 1986 and it’s features are basic but priceless. The POP mail concept is basically to only keep your email on the mail server until you mailclient downloads it. If you set the preferences to keep mail on the server for some time, you can use it with more than one mail client – for example your laptop and smart phone – without missing mail on either one, but that’s as far as it goes: You can’t see for example whether you already answered a particular mail on your smart phone when you are on your laptop, nor what you wrote.

The idea behind IMAP is to keep mail on the mailserver permanently. Not just the incoming mail, but also send mail, drafts, archived and even the thrashed email. To keep things organised, OS X Mail uses five ‘special’ mail folders:

  • Inbox for new, incoming mail
  • Send where per default a copy of all send mail is stored
  • Drafts for mail that is not send yet
  • Thrash for emails that have been deleted, that is, they will be if you empty the Thrash folder
  • Archive where you are supposed to put mail you want to get out of the way, so you can keep your Inbox mail list organised, while you still have the option to read back old mail.

Mail folders and email messages are kept synchronised between the mail server and all your mail clients. You can also create your own folders and subfolders and those will also be synchronised, as well as there content.

Configuring IMAP accounts in OS X Mail, more specifically setting up IMAP across OS X 10.9 Mavericks Mail and iOS can be confusing and frustrating. Therefore I created this walkthrough.

If you are already using the mail account and are afraid to lose mail, it’s a good idea to create a backup first, or move your mail to new mailboxes OS X Mail allows you to create. Any folders you create under the heading ‘ON MY MAC’ in the left column, will stay in place and keep their content, even if you delete or deactivate all mail accounts.

Configure an IMAP account in OS X Mail step by step

  1. First you need to set up the mail account. You can’t just change a POP account to an IMAP account in OS X Mail or iOS Mail. You need to set up a new account. Fill out the username, password and mailserver. If you already have other mail accounts configured, you might want to disable them for a moment, so it won’t be even more confusing.
  2. Quit and restart Mail, because the folder structure will be different after a restart.
  3. Create a new email and save it, but don’t send it, so Mail creates the Drafts folder.
  4. Now you have an Inbox with subfolders Drafts, Sent and Trash (then a VIPs folder) AND a second Send folder, a second Trash folder and a Spam folder. Confusing, isn’t it?
  5. (Log out if you were already logged into your mail client). If you log in a webmail client, you’ll see the Inbox and Drafts, Send and Trash subfolders, and another Drafts folder, but not the second Drafts, Send and Trash folders nor the Spam folder. Even more confusing, because IMAP was supposed to synchronise all folders, right?

What’s happening now, is that OS X Mail and the mailserver both use the Inbox folder for new, incoming mail, and but the web mail client won’t show the second Drafts folder, the second Sent folder and second Trash folder until there is email in it. You can test this by creating an email or just choosing one from the Inbox and dragging it into one of those folders. As soon as you log out and log into the webmail, it will also show those folders and mails.

Now it looks like mail is synchronised, but there are still separate Send, Drafts and Trash folders. OS X Mail will put a send message, a draft and a trashed message in one of the bottom folders, with the custom icons. The webmail client will use the Inbox Send, Drafts and Trash subdirectories that are shown in the top of the column.

Obviously, you want all mail clients to use one and the same folder for drafts, respectively send messages and trash messages.

I first tried this by adjusting the OS X Mail preferences. On the Mail preferences, Advanced tab, usually you need to fill out ‘IMAP Path Prefix:’ with ‘INBOX’ (in capitals, no quotes).

You can now delete (right click, contextual menu) the second Send and Trash mailboxes.

This didn’t solve anything, since now (after logging out and in again) the webmail client listed, as subdirectories of Inbox, not only Drafts, Send and Trash, but also two new folders: Deleted Messages and Send Messages. If you go back to OS X Mail preferences and delete the IMAP Path Prefix, these folders will disappear from OS X Mail but will still remain on the server, with the mails in them.

What you need to do to truly synchronise the Drafts, Send and Trash folders, is pointing them out to OS X Mail by hand. Select the ‘Thrash’ folder in Mail and assign it to be the Trash folder for all clients by choosing the Mailbox submenu ‘Use This Mailbox As…’ and then the ‘Thrash Mailbox’ sub submenu, the webmail interface will follow. You might have to refresh it or even login again. Also do this for the Send and Drafts folders.

The now unused leftover, second Send, Drafts and Trash folders are still in the left column of Mail (or may be shown as a subdirectory of Inbox) and on the mail server, so you won’t lose any mail message that are in them. OS X Mail will sometimes rename the leftover directory, for example ‘Sent messages’ or ‘Deleted Messages’ instead of ‘Sent’ and ‘Trash’. It’s quite confusing to still have them around. Remove any mail that is in them that you want to keep. Then you can safely delete them via the Mailbox / Delete Mailbox menu.

By the way, the OS X Mail spam folder was kept outside the synchronising, as a ON MY MAC folder.

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