Lost mail in OS Catalina upgrade

Thanx for this checklist, but for me and many others, I’m sure, step 8, “check that they are being displayed properly with bodies and correct dates”, it is not feasible to do this for several, if not many, thousands of messages. But still, perhaps there’s no better way.

Tripteron, Many thanks for the list you wrote, which might also help others who face that frightening Catalina upgrade.

re 2b. I would add: Make a list of all mails which are marked unread in case they lose their mark. Even better make screenshots of all mails in all mailboxes/folders (a bit time-consuming, but maybe helpful in case all get mixed up).

re 4. Of course I don't have the V7 folder yet.

re 5. How and whereto exactly? Into that IMAP account's Inbox? Why are you sure one IMAP account (I have an iCloud account I rarely use) would be enough? Wouldn't that throw all my "On My Mac" mails together – and later I would need to sort them through/out again (mission impossible!)? Or not – would the folders stay separated? If yes, why/how?

re 7. I would only have to count the messages in the Inbox (= displaying the sum of the inboxes of all my active accounts – I always empty my Sent box, because I rather keep the sent messages – Cc:ed to myself – in my Inbox) and that IMAP account (Inbox?).

re 8. In "On My Max" there should be about 32K mails. I need 1.25s to check a message, so for 50K emails it would take about 11 hours. A nuisance, but not impossible. But how can I/you be sure there are no problems in my Inbox too (around 45K additional messages)?

Re. re. 5, For IMAP accounts, the mail should still be on the mail server, right? So wouldn't the more reliable approach be to re-download from the mail server? But then, again, I'm not sure how to make that happen. Perhaps go offline, delete them all, then go back online? Don't want to delete them from the server!

Tripteron, Many thanks for the list you wrote, which might also help others who face that frightening Catalina upgrade.

re 2b. I would add: Make a list of all mails which are marked unread in case they lose their mark. Even better make screenshots of all mails in all mailboxes/folders (a bit time-consuming, but maybe helpful in case all get mixed up).

re 4. Of course I don't have the V7 folder yet.

re 5. How and whereto exactly? Into that IMAP account's Inbox? Why are you sure one IMAP account (I have an iCloud account I rarely use) would be enough? Wouldn't that throw all my "On My Mac" mails together – and later I would need to sort them through/out again (mission impossible!)? Or not – would the folders stay separated? If yes, why/how?

re 7. I would only have to count the messages in the Inbox (= displaying the sum of the inboxes of all my active accounts – I always empty my Sent box, because I rather keep the sent messages – Cc:ed to myself – in my Inbox) and that IMAP account (Inbox?).

re 8. In "On My Mac" there should be about 32K mails. I need 1.25s to check a message, so for 50K emails it would take about 11 hours*. A nuisance, but not impossible. But how can I/you be sure there are no problems in my Inbox too (around 45K additional messages)?

• * EDIT: Forgot, I would have to check the dates too, so 1.25s wouldn't be enough. BTW How should I check/compare all the dates...?

Tripteron,

Thank you again for your answer.

> All my problems occurred in mailboxes with over 1000 messages.

Good that you mention this! Then I will divide my large "On My Mac" folders into smaller ones <1000. Wanted to do that anyways...

> (5) Perhaps you’re not used to creating folders in IMAP accounts.

Indeed! Never needed it.

> ... creating new folders and mailboxes is easy. You do it just as you created your 24 folders and the mailboxes that they contain.

- Can I just alt + drag and drop local mailboxes onto the IMAP account's inbox?

- Or click on my IMAP account's inbox, add new mailbox and then copy the messages there?

> (7) You’re going to have 24 new folders in your IMAP account.

"Folders in your IMAP account" – please could you post a little screenshot how that should look like?

Thanks!

Looks like there may be some good news on the horizon for this Mail issue. Looking the comments section for this Mac Rumors article, a couple of folks look like they can no longer reproduce the "eaten mail" issue with the latest MacOS 10.15.3 beta:

https://www.macrumors.com/2020/01/24/apple-seeds-macos-catalina-10-15-3-beta-3/

Read the top comments.

If true, there were either not just a few hundred users with that problem, or we have to remember to write the three forbidden words containing c, a and l as long as Apple wont fix important bugs. ;-)

I did.

I had already repopulated my Apple Mail mailboxes from backups.

The problem that remained: a permanent miscount of unread messages in the various mailboxes.

Version 10.15.3 didn't change anything, even after mailboxes were rebuilt.

This version that said perhaps does not commit any more the irreparable (or difficult to repair) mistake of deleting emails on import, I did not try.

:-)

I did a regular upgrade from my importing my former MacBook Pro 15" (under Mojave) in a new MacBook Pro 16" (already equipped with OS Catalina). No problem with my e-mail.

Following a stupidity, a few days later, I reimported a complete backup on Time Machine (a restore) of the MBP 16" (backed up the day before) on the same MBP 16". There, the emails were deleted on import, during the inevitable rebuild that Apple Mail does when rebooting.

Thanks. Your method worked for me. It took a few iterations to get all the messages to behave correctly. I deleted all the header only emails before I transfered them back into the appropriate inboxes and sent boxes. You saved me!

As an aside, for some of the headers, the message was not showing in the preview window, but opening the message showed it was there. So it seems to be in part a viewing bug as well! Anyway, good luck to all.

In the meantime we upgraded from Sierra to 10.15.3 on two of our Macs (some POP accounts; up to 2500 messages). We checked all messages and all are still intact!

Now I'm still a bit worried before upgrading our 3rd Mac, because there are >20 Mail accounts (mostly POP, some IMAP), >50k messages with lots of attachments and many Mailboxes "On My Mac"...

Could it "help" to rebuild the mailboxes in Sierra Mail before upgrading?

(even though I don't have any problems at the moment, just as a precaution)

Or better not?

I'm waiting since 10.15.0 and actually can't wait till 10.15.4...

coxorange wrote:

In the meantime we upgraded from Sierra to 10.15.3 on two of our Macs (some POP accounts; up to 2500 messages). We checked all messages and all are still intact!

Now I'm still a bit worried before upgrading our 3rd Mac, because there are >20 Mail accounts (mostly POP, some IMAP), >50k messages with lots of attachments and many Mailboxes "On My Mac"...

Could it "help" to rebuild the mailboxes in Sierra Mail before upgrading?

(even though I don't have any problems at the moment, just as a precaution)

Or better not?

I'm waiting since 10.15.0 and actually can't wait till 10.15.4...

Upgraded from Sierra to 10.15.3. No problems at all. Everything available as before. No damage.

BTW: I did not run "Rebuild" before the upgrade, because a test with a little old mailbox

(about 20 messages) resulted in two incomplete, undeletable versions of mails,

which could only be deleted together with the correct originals!

G'day Tripteron,

Sounds like the issue may be fixed in 10.15.4 then. We won't really ever know for sure but if people stop reporting the problem on future upgrades from pre-Catalina to Catalina then I guess we can infer that its been sorted.

It is March 30. I just updated to 10.15.4 and basically lost all of my emails. Some I have been able to recover in the library but they won't import back. Generally it's a mess. I am not a computer expert and so far this has been a day's ordeal.

Given that this is apparently a known defect (as reflected by this thread) it would have been appropriate that Apple issue a warning. Something simple like: "If you are updating to Catalina, please note that there is a likelihood that your emails will be lost."

Having an update wipe out somebody's emails should not be taken lightly.

At the very least I would have expected to find clear instructions on how to retrieve what can be retrieved.

Thank you!

Thankfully I do have a backup of my most important mails. But I believe that's besides the point. I think one should be able to trust that updating to a new operating system is generally convenient and safe.