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Mac Cleanup utility "Mole" deleted my Quicken data files

MacBusinessUser

UPDATE: Original subject was: "Routine update to 9.2.0 resulted in deleting my data files"
Culprit was actually a Mac cleanup utility called "Mole" - solved by OP

___________________________

SUMMARY
Quicken Classic for Mac 9.2.0 update offered a "clean up files" step that
deleted the live data file AND the entire automatic backup history, then
displayed a misleading error blaming the user. Recovery required an
external Time Machine backup.

ENVIRONMENT
Quicken Classic Home & Business 9.2.0 (build 902.61767.100)
Upgraded from build 901.61363.100
macOS 26.5.2, Mac mini (Mac14,12 / M2 Pro, Apple Silicon)
Date: 2026-08-17, times US Eastern

WHAT HAPPENED
08:28:46 Update to 9.2.0 begins; prior app bundle moved to Trash.
~08:30 Quicken presents a dialog offering to "clean up" a list of
roughly 15-20 files. I accepted.
~08:30 Both of these directories are deleted:
~/Library/Application Support/Quicken/Documents/
- contained Latest.quicken, my LIVE data file
(175 MB, last saved 2026-07-25 15:41)
~/Library/Application Support/Quicken/Backups/
- contained ~20 .quickenbackup files, the entire
automatic backup history back to 2024-01-16,
including all "Pre-Update" backups
(Deletion time inferred from the parent directory's mtime
of 08:30:14; both subdirectories were gone by then.)
08:30-08:33 Quicken relaunches three times (PIDs 63466, 63509, 63521).
On entering my file password, Quicken displays a message to the effect
of "You should not delete files while Quicken is running," then quits.
08:38:59 Quicken exits.
On next launch, Quicken presents the new-user / setup splash screen, as
though no data file had ever existed.

EXPECTED BEHAVIOR
A cleanup routine should never propose deleting the live data file or
the automatic backup history. If it somehow does, it should refuse to
act on a data file belonging to the running application.

ACTUAL BEHAVIOR AND IMPACT
Total loss of the live data file and every automatic backup, from a
single dialog accepted during a routine update. The error message
attributes the deletion to the user, when Quicken's own cleanup
performed it.

Most deleted items did NOT go to the Trash. The Trash contained only
superseded app bundles and unrelated 2024-era leftovers, so "restore
from Trash" did not recover anything.

WHY THIS IS SEVERE
The live file and its backups were deleted in the same operation, which
removes every in-product recovery path simultaneously. Any user without
an independent, external, versioned backup would have permanently lost
their financial records. Recovery here was only possible because an
hourly Time Machine backup had run at 07:59, 29 minutes before the
update began.

ADDITIONAL NOTES
Restoring from Time Machine has its own hazard worth documenting for
support staff: Time Machine stamps files with an ACL of
"group:everyone deny write,delete,append,writeattr,writeextattr,chown".
Copying with ditto propagates that ACL and leaves the restored data
file unwritable by Quicken. Restoring with cp and then stripping ACLs
(chmod -RN) is required.

I have since relocated my data file and backups out of
~/Library/Application Support/Quicken/ entirely, on the assumption that
anything inside that directory is subject to this cleanup routine.

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Comments

MontanaKarl

Wow, that's really bad… and will be interesting to hear if others experienced this as well. I've never received any prompt to clean up or do anything during an update and 9.2 was no different. However, I keep my data file in my Documents folder… and besides Time Machine, have a backup saved to the cloud upon every exit.

Have you done a Help > Report a Problem to report this along with a link to your post here? Excellently organized/detailed report by the way.

(Unrelated… but …. you should consider updating your Mac to 26.6.1 or whatever the current update is as of when this post is read as several security issues have been patched in macOS recently.)

MacBusinessUser

Thanks for the OS update tip. I hadn't been notified in Systems Settings yet.

Just added a note in Help as well.

jacobs

@MacBusinessUser Are you sure you don't have any sort of file cleanup utility on your Mac? I am not aware of Quicken Mac having any "clean up" feature like you've described, and I've never seen any other user reference this functionality. Even when Quicken Mac deletes like an older version of the application, it typically moves them to the Trash. The only time I'm aware of that it deletes backup files is to maintain the number of backups you specify in your Quicken Mac Settings > Backup; then, it silently deletes older backups to maintain the correct number of files. I just did a test on one of my files where I reduced the number of backups to save, to see if it resulted in a dialog like you described offering to clean up files, but it did not; it just invisibly removed backup files which were over my setting for number of backups to keep. And it never deletes a complete directory of backups, as you've described.

That's why I'm suspecting you have some utility installed which provides this service, and which incorrectly determined your data file and backups were all duplicates. There are lots of such programs around — like dupeGuru, Gemini , Duplicate File Finder, Disk Drill and more — but I'm not familiar enough with them to know if one matches the dialog box you described. It would be great to capture a screen shot of the dialog that came up, but of course you can't — or wouldn't want to — reproduce it.

MacBusinessUser

Interesting - you may be right. I try to keep such things at bay, but let me try digging a bit. I used to have MacKeeper, but found it too intrusive and I think I have finally uninstalled it, but it wasn't easy!

MacBusinessUser

CORRECTION — this was not Quicken. You were right.

Thank you for pushing back. Your instinct that no such "clean up" feature
exists in Quicken Mac was correct, and it prompted me to go looking. I found
the culprit, and I want to correct the record clearly since my original post
misattributed a data-loss event to Quicken.

WHAT ACTUALLY HAPPENED

I have a Mac cleanup/uninstaller utility called Mole installed
(com.tw93.MoleApp). It keeps an operations log at:

~/Library/Logs/mole/operations.log

That log contains this entry, along with 11 more at the identical timestamp:

2026-08-17T12:29:33Z uninstall TRASHED
~/Library/Application Support/Quicken 2.96 GB

12:29:33 UTC is 08:29:33 my local time. That is Mole's application
uninstaller — its "remove all leftover files belonging to this app"
function — running against Quicken and taking the entire
Application Support/Quicken tree with it: my live data file and all 21
automatic backups, 2.96 GB in a single operation.

The corrected timeline:

08:28:46 Quicken update to 9.2.0 installs; prior app bundle → Trash
08:29:33 MOLE removes 2.96 GB across 11 Quicken paths
08:30:14 Quicken relaunches; Documents/ and Backups/ are already gone
08:38:59 Quicken exits after showing its error

So the dialog I accepted was Mole's, not Quicken's. Coming seconds after a
Quicken update dialog, I took it for part of the same process. That was my
error, not Quicken's.

QUICKEN'S ERROR MESSAGE WAS CORRECT

"You should not delete files while Quicken is running" was an accurate
description of what had just happened — another application deleted its
files mid-session. Quicken reported the truth; it simply had no way to say
which program was responsible. I criticized that message unfairly.

ONE LOOSE END

Mole logged these as TRASHED rather than DELETED, and it does distinguish
between the two — earlier entries in the same log say DELETED for cache
folders. But my Trash contained only superseded Quicken app bundles and
unrelated 2024-era files, nothing resembling the data file or backups. So
either the move to Trash did not complete as logged, or those items were
among the handful I restored before realizing what I was looking at.

RECOVERY, FOR ANYONE WHO LANDS HERE LATER

An hourly Time Machine backup had run at 07:59, 29 minutes before the
deletion, and contained the intact data file and full backup history. One
caution if you ever restore from Time Machine: TM stamps its files with an
ACL of "group:everyone deny write,delete,append,writeattr,writeextattr,chown".
Copying with ditto propagates that ACL and leaves the restored file
unwritable by Quicken. Use cp and then strip ACLs with chmod -RN.

I have since moved my data file and backups out of
~/Library/Application Support/Quicken/ entirely, on the general principle
that anything living in an app's support directory is exposed to whatever
uninstaller a user happens to run.

Apologies for the noise, and thanks again for the correction.