Moving Mac Mail messages & folders to Exchange Server account

TidBITS Talk
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I need to move both individual email messages and whole folders from an old email address (NOPT hosted on an Exchange Server) to a new one which is hosted on an Exchange Server. I’ve run into 2 problems and I can’t seem to come up with a way around them.

  1. Messages dragged from the old account to the new Exchange account lose the original dates. They are now showing today’s date as the date of the email. I’ve tried dragging individual messages, the whole folder, and exported mailboxes. I need to consolidate the messages to one email account, but the received dates need to remain unchanged.

  2. I can’t create new folders on the Exchange account in Apple Mail and have it show up in the Exchange “InBox” alphabetically with the other folders. It shows up listed at the bottom in another “Exchange” mailbox along with a folder called “Conversation History.”

I can’t drag it to the Exchange InBox either. On the web version of Outlook, it is also after “Conversation History” but here I can move the folder into the correct place. However on Mac Mail, it is the first folder in the InBox, not alphabetical as it is online. Relaunching mail doesn’t alphabetize the folders, and synchronizing the account doesn’t fix it either. If I go to web-based Outlook I can create the folder, drag it into the right place and it shows up correctly in Mac Mail, but that shouldn’t be necessary.

Any ideas?

This is on MacOS 10.15.7 Catalina but the same behavior happened on Mojave and High Sierra.

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Interesting. When I moved from Google to Zoho and then to Fastmail, I simply setup both emails on Apple Mail and dragged the folder from one account to another. Nothing changed.

You can export email from Apple Mail to *.mbox format. Exchange/Outlook can read this export file and import it into Exchange.

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Yes, I did try exporting to .mbox and the dates still get changed.

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Sorry I have no solution.

I just option-dragged a message from a gmail account to an Exchange account. It kept its original date. Interestingly, Mail initially showed that the copied file had more than doubled in size, but then it reverted to the original size in well under a minute. I have no idea what, if anything, that means.

For comparison, I then option-dragged the same message to an icloud account. It kept its original date but also increased in size, but to a lesser extent (about 50% larger). However, the increased size persisted. This is unrelated to your issues, of course.

When I create a new folder on the Exchange server from within Mail, it also shows up at the bottom of the list. To be clear, however, I can create folders in subfolders on the Exchange server, as well as in the top level folder (which also contains “Conversation History”). In most if not all cases, if I wait a few seconds, then close and reopen the folder, the new folder will be sorted correctly.

But I had never tried to create a folder in the Inbox folder, which sounds like what you are attempting, so I just did. I hovered over the Exchange Inbox in the list of inboxes, contextually clicked, and selected New Mailbox. The default location was at the top level (with Inbox and Conversation History), but I was able to click a dropdown menu and select Inbox from it. The new folder did appear as a subfolder to Inbox.

Again, I wish I could offer a solution, but I mentioned all this to note that what you are trying to do seems to be possible on the Exchange server I use, and maybe the Exchange administrators at your site have configured something differently, intentionally or not. Good luck.

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As I have mentioned in previous threads, I recommend making a backup of email using Mail Steward or similar. This converts selected mboxes to an SQL database. It is independent of the operating system or mail app so is (hopefully) future-proof.
A few times a year I copy the database (now about 24Gb) to Bluray disk for long term backup.