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Mail.app Proper Set up on MaxOSX for IMAP

09/24/06 | by JAdP | Categories: Computers and Internet

Apple's intuitive interface is often far less than intuitive. The main reason to chose IMAP as one's email protocol is to have control of one's email, in any folder, any mailbox, from different email clients, including thick clients on more than one machine, or through webmail. This includes drafts and sent email, and even trash and junk. While Apple's Mail.app 2.x seems easy to set up to work with IMAP, there are some tricks. I've been trying to figure them out since I got my parents their iMac, and, with the help of my partner, Clarise, Mail.app is working great with IMAP on my MacBookPro.

Open the Mail application and select Mail > Preferences from the menu bar, then select the Accounts section of the Preference dialogue.

Select the "plus" sign in the lower left corner to indicate that you wish to set up a new account.

From the Account Type selection menu, chose IMAP.

In the Account Description field, provide something meaningful, not the default given; I like to use some shortened form of the email address, something like myNameDomain.

Your email address is the address to which you want folk to send email to you on that account - this may or may not be the same as your userName requested later. For example, on one account, my username consists of my initials and a bit of my last name, but my email address is my full name with dots and underlines: Joseph.A.di_Paolantonio@companyDomain.com.

Then click "continue".

The next screen will be for incoming email and you'll need to have your Incoming email server for IMAP, your username [which may or may not include the at-sign and domain.name] and your account password. Note that Mail will only allow you to set up one account for each server/userName combination.

Clicking on continue gets you to th Outgoing server information screen. Some ISPs now use email authentication methods which match the sender's email address to the mail server's domain; and other ISPs block using any other SMTP servers but theirs. This can be a problem. The firewall on your Mac or between your Mac and wild, wooly Internet, to block port 25, which is used by SMTP. Some mail hosts will allow SMTP to connect on port 587 [like dot-Mac] and others will use 2525, or still other ports. Another oddity is that Mail.app doesn't seem to handle SMTP AUTH properly, so if you were told that you need to have authentication for your SMTP server, using your userName and password, you MAY fail to connect during Mail.app's checking its ability to connect with your SMTP server. Any of these things can cause your set up to fail at this point. Now, if you have authentication checked, and know that you don't use kerboros or any other fancy authentication schemes, uncheck authentication - the fact that you just authenticated with the IMAP incoming mail server may have authenticated you on the SMTP side as well. If all goes well, you should see a screen with your account information.

Now we come to the part of how to set up the account so that Mail.app works as one would expect a well behaved MUA, or mail client, for IMAP to work. Under Mailbox Behaviors, check the options to have Draft, Sent, and maybe even Junk and Trash emails stored on the server. BUT YOU ARE NOT DONE. Mail needs to be told WHERE to put this email on your server, that is, you need to explicitly tell Mail.app what server folders match the Sent, Draft, Junk and Trash mailboxes in Mail.app. BUT... You can't do this until after you've finished setting up the account.

Next go to Advanced, and the defaults for Enable this Account [checked], Include when automatically checking for new mail [checked], Compact mailboxes automtically [checked and greyed out], the location of the account directory, and Keep Copies of Messages for Offline Viewing [drop down menu with All messages and their attachments selected] should be fine.

Here's what works for our mail servers at TeleInterActive.net [Courier IMAP] for getting those IMAP folders to sync up nicely. CHECK "Automatically synchronize changed mailboxes" and LEAVE IMAP prefix path BLANK. Port 143 is the default for IMAP, and SSL is up to your ISP or mail host or organization or whoever hosts your IMAP mail. Even if SMTP authentication was turned off, chance are you'll need Authentication here - either password or one of those fancy schemes.

And now we loop back to the need for telling Mail.app what server folders to use for Sent, etc mail. Once you have finished setting up your account [sometimes Mail.app asks if you want to save changes and sometimes not], Mail.app will subscribe to and sync with ALL the folders on your IMAP server for that account. This is great if you want all your email in this client, not so much if you don't, but I haven' seen nor conjured a way to get around this.

Once, Mail.app has your folders showing - and it can go quickly, even for me with hundreds of sent emails in that folder - you can now select the folder where your sent email is stored on the folder server, such as sent-mail or Sent, and then chose Mailbox from the menu > Use this Mailbox for > and then chose Sent, Drafts, Trash or Junk. I've seen sent-mail or Sent, Drafts, Trash or trash or Deleted, and Junk or Spam. You may have something else, but chances are you know what they are on your server. Do this for each of the four types, or 1 or 2 or 3 types if you didn't select all four to be saved on the server, and Mail.app will show those folders under the Sent, Draft, Junk and Trash mailboxes, using the account's descriptive name, and your server folder no longer are presented in Mail.app under the account. This can get confusing if you have multiple IMAP accounts, because you can click on the Sent Mailbox and see all the messages you sent from all the accounts. You can click on the account name under Sent and just see those sent messages.

I am also accustomed to having different identies for each account, matching aliases I use for different folk with whom we do business. [Helps us track who sells email addresses to spammers or to reply for "generic" accounts that are forwarded to indivudual accounts.] Mail.app only allows one account to be set up for each IMAP server/UserName pair, so we can't use the email address field to set up an account for each identity, and I don't see another way to do so. Update: There is a way. I found it by accident. I was setting up another account, and my mouse cursor was hovering over the email addresses input box when this appeared: "Enter one of more email addresses, separated by commas." More details and screenshots are in my post "Multiple Identies".

Thunderbird is still the best IMAP MUA, but sucks for syn'g with a Palm. I would love to see a Thunderbird plugin for the Palm desktop on Windows, or to continue to integrate with the iCal and Address Book apps on MacOSX.

I started looking for a solution to making Mail.app work properly with IMAP since I bought my parent's iMac some months ago. But, since they keep everything in their inbox or delete it, and only have their one account, I got around Mail.app seeming inability to save to the server's Sent folder by having Mail.app BCC them on each email they sent. I found many hundreds of forum and Apple support posts from people with the same problem, articulated in different ways. I found many, sometimes contradictory answers. What I've given above is a combination of several responses on several fourms, some of which I can't find anymore.

I hope this helps others with the same problem.

6 feedbacks »


anonymous email

Thank you Joseph, I almost trashed my Apple until I found your blog.

Helped a lot.


10/07/06 @ 00:30
Comment from: JAdP

Since it helped, I’m glad that you found it. ‘Tis nice to get a real comment rather than the many spam comments per day.

10/08/06 @ 23:27
Comment from: Jack

If you put a value in the IMAP Path Prefix field under the “Advanced” tab - it often will result in solving the problem with the app not writing to the sent items folder, and also, you will no longer be synching all of the folders on the server.
This was a good solution for me, because there were tens of thousands of emails in “public” folders that I did not want to see or synch. When adding the mail server address to the IMAP path prefix field the apps behavior changed. Give it a try.

02/07/07 @ 13:19

Thanks for this excellent walk-through! I had a really hard time setting up Mail.app to work with an IMAP server. I can get Entourage to work pretty easily, but I have a client that was reluctant to learn how to use a different email client. This write-up saved my bacon!

Thanks again!


04/19/07 @ 08:43
Comment from: JAdP


Thank you for the kind words. I’m glad that the post helped you out. I can empathize with your customer; the integration of Mail.app, Address Book, iCal, Dictionary.app, spotlight, etc is very useful.

Check out Hawk Wings, especially the plug-ins and add-ons list, for some great additions to Mail.app that your customers might also find useful.

04/19/07 @ 09:04
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I'm Joseph A. di Paolantonio and this blog has two main foci: my interest in food, and my interest in the future. This provides a look into my personal life, and is separate from my consulting work…though there will be overlap. I am an independent researcher, working as a strategic consultant and I'm an executive with over 20 years of commercial experience with a technical interest in the intersection of Internet of Things, with advanced data management and analysis methods. I view data science as a team activity, and I feel that the IoT must be viewed as a system. I am leveraging my past activities to understand the adoption and impact of the IoT; first, as a system engineer in aerospace, where I developed Bayesian risk assessment methods for systems within the Space Transportation System (including the Space Shuttle), Extreme Ultraviolet Explorer, Gravity Probe B, and many more, and second, as a enterprise data warehousing, business intelligence and analytics professional. Between my aerospace and IT careers, I indulged my hobby of cooking by starting a food company, Montara Magic, centered around my chocolate sauces. My education combined chemistry, mathematics and philosophy. I performed research into molten salt fuel cells in graduate school, and in photovoltaic materials for a short time in industry. The lure of bringing the human race into space was strong, and when I was offered the chance to combine my chemistry and mathematics skills to develop new risk assessment and system engineering methods for space launch and propulsion systems – I couldn't resist. I perform independent research and strategic consulting to bring value from the Internet of Things, Sensor Analytics Ecosystems and data science teams.I am a caregiver, a lover of science fiction and speculative fantasy, and my passion to learn has led me to a pilot's license, an assistant instructor in SCUBA, nordic and alpine skiing, sea kayaking, and reading everything I can, in as many topics as I can.

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