iCloud Mail & Windows 10 Mail App creates Duplicate Sent and Deleted Folders

Here was my problem:

It is very easy to setup Windows 10 Mail to work with iCloud.com email. It uses an iMap connection to MobileMe.

However it seems like Windows 10 Mail is somehow triggering iCloud to make duplicate Sent and Deleted Folders. I think this happens because Mail cannot access the correctly name folder when it needs it. Has anyone observed a similar behavior? I have also seen this behavior in emClient program for Windows.

Here was my Solution:

Windows 10 Mail predetermines which folders it thinks should be used as Sent and Trash and you can’t change that determination.

iCloud can use any iMap folder as its Sent and Trash. You can make a brand new Folder and Name it whatever you want and assign it as Trash and Sent. There is no real statically assigned Sent and trash Folder.

The Problem is Windows 10 Mail does not allow you to assign iMap Folders. It picks what it thinks is best.

So here is how you resolve it. What we need to do is make all our Apple Devices use the folder Windows 10 Mail Prefers.

  • Figure out which folders Windows 10 Mail thinks is your Sent and Trash. They may be named Sent Items and Deleted Items. Send and delete a few test emails until you have a good feel for which folder it is.
  • Go too icloud.com and assign these folders as Sent and Trash in Preferences.
  • Go to Mac Mail and assign these folders as Sent and Trash.
  • On your iphone Make sure these folders are being used as well by going to iCloud Settings and scrolling the end of the list to Mail and then to Advanced Settings.

Mail App on Mac


iPhone Mail App


Migrating & Copying Mail & Mailboxes between Accounts in Mac Mail

I just had some thought about best practices for moving messages between accounts using the Mac Mail App.

The Reason to Move Mail

One reason is that might want to migrate messages from an Office365 or Gmail to an iCloud Account. Outlook on Windows allows you to Import and Export PST Files at will which makes mailbox migration a cinch. However on Windows importing a PST file with a  large numbers of emails can cause iCloud to throttle or ban you especially if you have a large PST. But since we are using a Mac and iCloud lets see if we can get this done without Windows.

Things to Keep in Mind

Mac Mail is slow and queues up move jobs in the background. You can see these jobs once they are in progress by going to Mail -> Window Activity and checking win the lower right hand corner. Also the Mac Mail App is file based so the emails are stored in files in ~/Users/Library/Mail/V6.

Some Methods to Try

  • Shrink the mailbox you are copying from first. Use an App like clean.email or Mailstrom┬áto shrink your mailbox to manageable size so your are not copying Multiple Gigabytes of emails.
  • If you are using Office365 or Exchange, configure Mail to use IMAP for retrieving emails instead. You will need to set ups the account as “Other and enter your IMAP credentials.
  • Have Patience. Wait for Mail to Queue up the Job and perform it. You may also be waiting on the iMap Server.
  • Create local “On My Mac” Mailbox as a holding area for the emails you are moving to the new account. The “On My Mac” folder is like a staging area.That way only 1 imap Server is in play at a time. Move your emails from the original account to the On My Mac folder. Once that copy completes move the emails to the new account.
  • I find that dragging and dropping from Mailbox to the other works best
  • Only drag and drop several hundred emails at one time not thousands.
  • Closing Mac Mail Aborts the process and allows you start over. Closing can be helpful if the moving process gets stuck.
  • If the drag and drop does not work the first time try it again.
  • Also try splitting your mail up into sub-folders since a folder you made might accept a copy sooner than a system folder like Inbox or Sent.
  • Also try Exporting the Mail as an MBOX file and reopening it and mounting it the Mail Folder tree. From there you can copy out the emails.
  • Try AirMail and use Mailbox rules to move the messages.

I hope this helps and that the next version of Mail has better migration tools in place.