How I Learned To Love Quicken Deluxe and Give Up on the Past

Originally published at: How I Learned To Love Quicken Deluxe and Give Up on the Past - TidBITS

Glenn Fleishman’s 14-year relationship with Quicken 2007 finally ended this year. But it took a dead motherboard, an old Mac mini, and a conveniently timed tip for him to break with his accounting software past.


I went through a similar process when Rosetta died thus ending PowerPC emulation. I auditioned several Quicken replacements and decided that Moneydance was adequate for my needs. It was a bit week on reporting and it would not interact directly with my bank and credit card accounts, but it handled transactions in a very similar manner to Quicken and also could support investment accounts. I’ve stuck with Moneydance over the past 10 or 11 years with only a few hiccups.

I’m always somewhat mystified by a requirement to be able to live sync credit cards and bank accounts to financial software. As long as I can download a qfx file, Moneydance does a great job of importing it, even remembering the applicable account. It’s nice not to have the credit card account login information stored in the app. I’ve never attempted to sync or download bank account information as I like to enter those transactions when I initiate them, not when the exchange of funds occurs. I find it easy enough to reconcile those accounts from monthly statements.

I’ve been using Quicken since it came out. Currently use the subscription (Home and Business) for two businesses and home. I find the ability to quickly download and reconcile accounts (recently improved even more so) to be very useful for me. It makes doing taxes very easy.


If you’re virtualizing, you might consider the real (Windows) version of Quicken. I’ve been unimpressed by Intuit/Quicken Inc./H.I.G.’s commitment to Mac data conversion integrity since I tried to convert to the 2000 OSX beta, with periodic unpromising repeat attempts. (I’m still using VMware on Intel, to which I happily switched from early versions of Parallels.)

Glenn and others, can you comment on reports? I use the Income Statement in 2007 for my accountant to have a high-level overview. In my initial checking of the newer versions, I didn’t see a similar report nor a way to create it.

And the comment about APFS solves a mystery, I think, that I’ve had for almost 6 months about why someone had an issue with their 2007 data file not being backed up properly via Time Machine (and then restored). I’ll have to test their data on an HFS+ disk to see.


I highly customized all my Quicken 2007 reports, so I am not sure precisely what Income Statement did. Quicken Deluxe lets you select all the same parameters (plus more) as in Quicken 2007, so you can choose income only, pick the accounts, pick the time period, and even exclude intra-account transfers noted in the report to avoid adding $ that were just transfers among your accounts (instead of inflows).

But you cannot correctly copy the Quicken Data file from an APFS volume. (It seems to use some outdated package format that relies on HFS+.)

The idea that any application would depend on the low level format of the underlying drive is totally bizarre to me! I’m sure some ‘software architect’ thought this was A Good Idea… But I guess it’s A Good Thing Quicken has been divorced from Intuit (a company that I refuse to do business with for their business practices…)

(As a side note, every time I’ve ported software, it got better. Porting brings out latent bugs and invalid assumptions.)

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It still seems bizarre to me. It’s possible that it’s an outdated PowerPC-based package format—it’s not worth diving that deeply into it—but it was really baffling and frustrating until I found the wisdom of other people who had diagnosed it.

I don’t know the Apple API, but I’d suspect you’d have to -really try hard- to “accomplish” file-system dependent storage.

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As far as I know, the only big feature HFS+ has that APFS doesn’t is the ability to create hard-links to directories (a feature created in order to support Time Machine and not ported to APFS because APFS-based Time Machine uses snapshots to accomplish the same thing more elegantly).

I suppose Quicken might be using internal hard links to directories in the package. If they are doing that, then they must have jumped through several hoops to make it happen - normal APIs don’t allow it. It’s supposed to only be for Time Machine.

The only other HFS+ “feature” I know of is that it allows filenames with characters that are undefined UNICODE code points. APFS rejects these characters. I think the rules for normalizing UNICODE filenames is a bit different. An app’s internal data files really should not be using names where this would be an issue. If they are, I would love to know why.

As a workaround, I assume you could create an HFS+ disk image, mount it, and store the Quicken data file there.

Huh… Not supporting ‘hard links’ would break POSIX compatibility. I checked the manpage (man ln) and there’s nothing on the Big Sur manpage to indicate that hard links are not supported in APFS per the POSIX specifications.

In POSIX (traditional Unix), hard links have some useful properties, including relative atomicity in the file system. An old ‘trick’ for doing a lockfile is to create a hard-link to a file (e.g. ln file file.locked) so you can test for the existence of file.locked before you write to it. When the wright is finished, you remove (unlink) ‘file.locked’

(doing hard links on directories, as opposed to traditional files, is a whole 'nuther question. If that’s supported, it’s via a privileged operation. The problem is the chance to create infinite loops when traversing the file system.)

I came across this and thought it might interest someone. I know nothing about it, and do not use it, but it looks interesting.

All Unix systems support hard links to files, on compatible file systems. These include all the file systems commonly used by Unix platforms, including BSD’s FFS and Linux’s extfs. The most notable modern file systems that don’t support them are the various flavors of FAT.

See also: Comparison of file systems - Wikipedia

Hard links to directories is a novel feature that Apple introduced in order to support Time Machine. It is only supported on HFS+ volumes and requires special permissions. I don’t know of any other Unix-like system where they are supported in any form.

Actually, at least on BSD and DEC ULTRIX, “superuser” could do hardlinks to directories. I wrote some code that depended on that, and I had to swear on a stack of system manuals that I would NOT introduce a cycle in the file system as a result!

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Interesting article, thanks @glennf – though I have no use for Quicken myself, I find details of software migrations and system limitations interesting (which I realise is odd!). However, one thing I didn’t understand is the following… Early on, you say:

But Quicken 2007 was already behind the times in 2006! Apple had already begun its transition from PowerPC to Intel chips, and Quicken 2007 had only PowerPC code in it. Intuit never released an Intel version of its flagship software.

But then you talk about how you recently ran Quicken on MacOS 10.14 Mojave for several years. I thought that the ability to run PPC apps was removed several OS versions ago (after Snow Leopard?). So how was it possible to continue running Quicken 2007 in Mojave?

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It’s a curious story. Quicken 2007 was such a critical app for Apple to continue to have available, they allowed Intuit…to embed parts of Rosetta inside Quicken 2007 as a sort of wrapper around the app via the seemingly minor updates that appeared after Rosetta was no longer part of macOS. Truly, truly weird.

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Wow, that is wild. :exploding_head: Learn something new every day!

Intuit never released an Intel version of its flagship software.

Intuit released Quicken Mac 2007 “Lion Compatible” in 2012, which you must have been using if you’re still running Quicken 2007 on Mojave.

What’s interesting about this is first Intuit claimed that Quicken for Intel would never happen because it too many man-years of work. And then suddenly, it did happen. There are rumors of Apple proving some help but I’ve never seen definitive information on what Apple actually did. There’s nothing obvious in the Quicken 2007 package. (One rumor I heard implied that Apple provided a way for Quicken to read its priopriatary database format, that must have been problematic for the migration from Snow Leopard to Lion.)

After years of excuses, the company released an entirely new app, Quicken Essentials, that was so stripped down as to be essentially… useless.

And Quicken Financial Life for Mac was previewed in 2009, and was even more useless.

Quicken 2007 can run on a macOS system that has an HFS+ or APFS startup volume, and its data file can be stored on either kind of filesystem. But you cannot correctly copy the Quicken Data file from an APFS volume. (It seems to use some outdated package format that relies on HFS+.).

Here is where I lost you. As far as I know, Quicken 2007’s only issue with APFS is that the automatic backup doesn’t work. (The reason is that Quicken is making an incorrect assumption about file ordering on POSIX file system calls. They got away with it with HFS+ but not with APFS.)

Another limitation is that it still uses Resource forks, which are supported by macOS on APFS, however there are rumors that there are problems with resource forks in Monteray or maybe it is Big Sur.

My two cents: I’ve been using Quicken for Mac since Quicken 98, and still think there are a lot of things that Quicken 2007 does much better than the current Quicken. The key deficiencies are in ease of data entry, investment transactions, and reporting. But online transaction and stock price downloads in Quicken 2007 has been pretty much dead for some time. I had forgotten how much easier it is when Quicken auto-downloads the transactions. And the new Quicken does have some useful new features, such as being able to automatically query online statements so it knows how much your next bill is.

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I went through a lot of acrobatics in attempting different ways of copy what seemed to be a perfectly ordinary file, including using ZIP, FTP, SMB, Dropbox, etc., and all these copies failed in one way or another until I read the description of the HFS+/APFS problem. There’s a lot of discussion as to the cause.

Ultimately, my only successful path was installing Quicken Deluxe temporarily on the Intel Mac mini running Mojave and then migrating the Quicken Deluxe data file. It may or may not be worth investigating further, but it does seem tied up with HFS+. Maybe a weird artifact of its code base.

Yes, I think Quicken 2007 has some more refinement and features and ease of use than Quicken Deluxe in 2021, but Deluxe has fortunately matured to hit all the points I need. I was able to create a report a few days ago that I use for quarterly city and state filing for my two separate small businesses (one, writing; the other, publishing), and then compare it against my records from previous quarters in Numbers where I’d used Quicken 2007’s reports. I found a few discrepancies, but they were fortunately all related to report configuration. Once resolved, the reports I pulled had identical results to the Quicken 2007 reports, which was key!