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SUMMARY OF PROBLEM

I'm trying to export mail from Outlook to Mac.

I dragged an Outlook for Mac 2011 folder into a Mac folder, which created a .mbox file.

In Apple Mail, I imported this. When I clicked on the Import folder to look at the messages, the list is missing a few messages.

Can anyone tell me why?

If I click in the Search field and search for the missing messages, I can find them. But these messages won't appear on the list.

I dragged Outlook for Mac 2011 messages into a Mac folder, which created .eml files. I used this Python program (https://gist.github.com/kadin2048/c332a572a388acc22d56) to combine these .eml files into a .mbox file. Then I imported this into Apple Mail. Again, a few messages were missing from the list, but some of the missing messages were not the same as before.

Can anyone tell me why?

Again, if I searched for the missing messages, I can find them. But these messages won't appear on the list.

DETAILS

I'm using Mail 11.5 (3445.9.1), macOS High Sierra 10.13.6 and Outlook or Mac 2011 version 14.7.7 (170905).

DRAFTS

My above examples have been with the Drafts folder.

In Outlook, I have 297 messages in the Drafts folder. After exporting these and importing them into Apple Mail (File > Import Mailboxes > Files in mbox format > selected the .mbox file to create the Import folder in Apple Mail), Apple Mail’s Import folder showed 199 messages. I identified some missing messages and searched for them in Apple Mail and was able to find them. But they won’t appear in the list when not searching.

In Outlook, I copied 10 messages from the Drafts folder into a “test” folder. After exporting these and importing them into Apple Mail, Apple Mail’s Import folder showed 7 messages. I searched for the 3 missing messages in Apple Mail and was able to find them. But they won’t appear in the list when not searching.

I thought this might be caused by the blank From or To address in the draft messages. The 3 missing messages (out of 10) had blanks for From, To and Date Sent. However, there are 2 messages that appear on the list and they also had blanks for From, To and Date Sent.

When I did the 2nd method (exported from Outlook by dragging the messages onto a Mac folder, combining the .eml files into a .mbox file and importing to Apple Mail), one of the 3 missing messages was different than the 3 missing messages from the 1st method (exported by dragging the Outlook folder onto a Mac folder and importing to Apple Mail).

INBOX

In Outlook, I created a test folder and moved 351 messages from Inbox to this new folder. I used the 1st method (dragged Outlook folder to Mac and imported to Apple Mail). All 351 messages showed up on the list in Apple Mail. I opened the mbox file with TextEdit, searched for “Message-ID: “ and got 390 occurrences. When I searched for “Message-ID:” (no space after the colon) I got 826 occurrences.

SENT ITEMS

In Outlook, I created another test folder, moved 340 messages from the Sent Items folder to this new folder. I used the 1st method, but 338 messages showed up on the list in Apple Mail. I opened the mbox file with TextEdit, searched for “Message-ID: “ and got 340 occurrences.

I think I might have found the two missing messages. In Outlook, there were 3 messages, sent from the same sender, pertaining to calendar invitations. All 3 were sent on the same date. 2 were sent at the same time and the last was sent one minute later. They had different dates for the calendar events. The first two were indicating that the calendar events were “cancelled”. These 2 were missing from Apple Mail’s list, and this time, when I searched for them, I could not find them. The last of the 3 messages had “tentative” for the calendar event and this appeared in the Apple Mail list.

When importing, does Apple Mail filter out messages that are telling me that a calendar event is cancelled?

STRANGE CONVERSIONS

I noticed that there were single apostrophes in the Subject for a few messages. After importing to Apple Mail, these were changed to strange characters. Examples:

‘Truce’ Doesn’t and We’re

were changed to:

Truce¹ Doesnıt and We¹re

China’s

was changed to:

Chinašs

The following did not have an apostrophe:

This Confrontation

was changed to:

孴his Confrontation

…and much of the text in this message had a strikethrough.

FILES

Here is what my files look like:

enter image description here

Finder cannot show the contents of the .mbox files.

test-351-inbox-messages.mbox, test-340-Sent-messages.mbox and all of the .mbox files that start were "Drafts" were the result of dragging the Outlook folder to the Mac.

The rest of the .mbox files that start with "test" were created by using emlToMbox.py to combine .eml files.

If I right-click on any of the .mbox files, I get the same options as you see in the above screenshot.

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