Prompted transaction date (Q Mac)

There isn't a preference, but I wouldn't say that it is "all over the place."

New transactions in a Quicken session default to the current date. If you alter it, future transactions in that account will pre-populate the date of the last date of transaction entered.

Other accounts behave the same: Default to new date first, then altered date after that.

@drkrlow  What John describes above is all I have ever experienced: the default dates for new transactions are consistent and logical when entering multiple transactions.

But I have seen a few other users report what you describe, and I've never seen any resolution as to what could cause the date of a new transaction to be over than described above. There has to be something in your data or your Mac's configuration that it tripping up the program from behaving as expected. I don't really know what to hunt for as an answer to that question.

For starters, is your Mac's Preferences > Language & Region set to United States? And do your formats show they are set to the default values shown here:

Ideas to test to try to get a clue about what's going on…

Does it matter if the register is sorted in ascending or descending date order? (I have all my registers with the most recent on top, but some people like emulating the old Quicken 2007 with new transactions at the bottom.)

If you create a new (dummy) account, and create a few dummy transactions, then does this new register behave as you describe, or as John describes?

If you create a new (dummy) file, and create a few dummy transactions, then does this new register behave as you describe, or as John describes?

Well, this is pretty puzzling, as it seems your testing has ruled out several possible variables.

One of the unfortunate things (in my opinion) about Quicken's support infrastructure is that they will not accept a "bug" report unless it can be shown (a) how to reproduce it, and (b) that it isn't working as it was designed to work. I think (b) is satisfied here, but they put the burden of (a) on the user. The Quicken employees who are moderators of this site have the ability to enter bug reports in their internal system -- but only if they can describe a way to reliably reproduce the bug. You can report this via the Report a Problem feature on the Quicken Help menu, but if the person who receives the bug report does a test and doesn't reproduce the bug, they toss it. I find this incredibly frustrating. I know from years of software development that finding sporadic issues are often the toughest bugs to solve, and often benefits from tools that can peer inside the program as it's running to look at the intermediate state of variables in order to determine what is happening. But to my knowledge, an issue like this one can never get in front of one of the developers unless users solve the riddle of what causes the problem to show up.

Since I'm not seeing the same results as you, and other Quicken Mac users are seeing what I am and not what you are, all I can do is continue asking questions and suggesting things to test. If you grow weary of this, I understand.

There has to be something in your environment -- hardware, operating system, or data -- that is causing this. the fact that you've tried two different Macs on two different operating systems makes me thing it's not the hardware or the OS (although it could be some OS setting on both machines, this the question about Language & Region settings).

• Have you done your tests in different types of Quicken accounts. That is, are you testing in an investing account or a banking account? (There were some reports awhile back about some next-transaction-date issues in an investing account.)

• Are the tests you've done with manually-entered transactions or downloaded transactions? (If you're downloading a set of transactions to start with, I'm wondering if there's something funky in the dates coming in from the financial institution. Seems like a long shot, but when hunting bugs like this, I try not to make assumptions because the culprit always ends up being something you wouldn't have expected!)

@drkrlow, I believe you. (I kind of kept quiet on this thread after my initial post.)

When Quicken for Mac was rewritten, I did manually enter years of older investment transx, and it behaved as you explain: Cash & Credit accounts acted like 2007, but investments accounts kept defaulting to current date.

What is confusing is that I cannot reproduce it now, either in my main file (which dates back to version 1.5 started on a Mac Plus), or in newer files. (Running Big Sur.) So, I suspected the issue was resolved. (We reported it in testing back then.) I haven't heard anything about it recently, outside of this.  

I realize this isn't an answer, but do know others have seen it in the past. I thought it had been resolved.