Switching from Windows Live Mail to OS X Mail

Moving a couple of thousand messages, across a handful of accounts/mailboxes, from Windows Live Mail to ‘Mail’ (Mail.app) on OS X proved an unexpected journey through several other programs, more or less as follows:

  1. On Windows, import Windows Live Mail messages (stored in .eml files, in 1 message per file) into ThunderBird using the ImportExportTools extension.

    You can find the location (otherwise known as the path) of the folder in which Windows Live Mail stores messages by going to ‘Tools’ > ‘Options’, select the ‘Advanced’ tab and then click the ‘Maintenance…’ button. In the window which opens, click the ‘Store Folder…’ button. A further window will open which will state: ‘Your personal message store is located in the following folder:’ followed by the path to the folder.

    You can copy and paste this path into a Windows Explorer window to see the contents of the folder. Each account (or mailbox, if you prefer) will have its own sub-folder, whose name will begin with the name of the corresponding account. Each such mailbox will be further organised into sub-folders, one each for Inbox, Sent Items, etc.

    Inside Thunderbird, create new folders, one each for the Inbox and Sent Items of each account under Windows Live Mail. Right click on each folder and then choose: ‘Import/Export’ > ‘Import all eml files from a directory’ > ‘just from the directory’ and then browse to the corresponding directory discovered above.

  2. Open your ThunderBird profile folder and copy the ‘Local Folders’ folder (look in the ‘Mail’ sub-folder) to OS X.

    Download and install Eudora Mailbox Cleaner* and drop the folders from ThunderBird onto the icon. This will create a corresponding folder hierarchy under ~/Library/Mail/Mailboxes.

    At this point, my expectation was that Mail.app would pick up the imported messages, but refused to do so even when told to ‘Rebuild’ the mailboxes (which it did detect, but displayed as empty). Further steps were required.

  3. Download, install and run emlx to mbox Convertor. Drag the message files – the .emlx files created in the previous step – from the imported folders under ~/Library/Mail/Mailboxes onto the main window and click the “Save mbox…” button. I created one .mbox file per folder of messages.

  4. Import each .mbox file into Mail.app, usings its in-built import function: ‘File’ > ‘Import Mailboxes…’ > ‘Files in mbox format’. Each .mbox file should be imported into its own folder in Mail.app.

There are very probably other methods, involving fewer steps, which can achieve the same end, but I found that when I took skipped any of the above, Mail.app behaved erratically: at one point, it only imported one message from each folder under each account/mailbox; at another, it appeared to import all messages, but some of them displayed as blank in the reading pane; and so on.

Your mileage may vary.

*Eudora Mailbox Cleaner requires Rosetta, which you may be prompted to install if you haven’t before.

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