My migration to modern Quicken Mac also showed that I had hundreds of linked transfers where the Quicken 2007 has lost the linkage between the two sides of the transfer.

I fairly regularly had to rebuild the transactions files indexes. (The latter is what finally got me to cut my cord with Quicken 2007.) In the 13 years I used Quicken 2007 from 2007 to 2020, I had several instances where a crash - or something I never even noticed - caused some data to be lost, and in one case, a block of transactions inexplicably shifted to dates several years off. For most people it runs flawlessly almost all the time, but the database can suffer corruption from time to time, and you can simply run out of space in some of its fixed data tables if you've been using it over a long period of years. The only other thing that scares me a bit about about remaining on Quicken 2007 indefinitely is that it's a bit, well, flakey. So while this is something to think about for the future, it isn't something you need to deal with now. You'll also run into issues where older web browsers that work on your version of macOS won't work with some websites that require newer and more secure browsers, and possibly other software will become problematic. It might run fine for another 5 years, but it's at the age where things like spinning hard drives and power supplies can, and eventually will, go south on you. 'I'm hoping to keep my current iMac going forever.' You can hope all you want, but the likelihood of that plan working is not so great. I keep that window open all the time when I have Quicken 2007 open, and I completely overlook that! It would have saved me some grief one of the times I ended up working in a backup file when I thought I was using my regular E. Anyway, this is a side issue to the matters at Thanks for the reminder about the Quicken 2007 file name appearing atop the Accounts list. When a user says they have trepidation about updating from El Capitan to High Sierra, I probably wouldn't suggest the added complexity of installing a VM. Just installing an older macOS inside the VM can be a little tricky - and then you're running an OS that is unpatched for vulnerabilities. Yeah, I'd disagree that VMs are quite that simple. Can you tell me that it will all work just fine? I've resisted upgrading from El Capitan for years because I'm terrified of losing decades' worth of minutely itemized data and categories and Repeating Transactions, etc. Will High Sierra recognize and use either of those two qdfm files seamlessly? For years Quicken opens using this data file-1514Data File 12-31-14 8-26-15.qdfm (or 111514Data File 12-31-14 8.qdfm?)-to run Quicken for Mac 2007 on El Capitan.

Upgrade from el capitan to sierra