Moving from Windows to Mac, take 2...

@Bob. Your workflow with downloaded transactions is up to your preference. There is nothing you have to do to accept the downloaded transactions; they come into your registers and require no action to "accept" them; the transactions are live transactions in your register as soon as they come in. If you review the downloaded transactions, you can clear the status icon one transaction at a time, or you can select some or all transactions and clear the icon on all of them. To do that, select a group of transactions Control-click on any one of them, and select "Set Status of Selected Transactions to > Reviewed. (You can also restore any icons you may have cleared inadvertently, or to flag transactions you want to review later, in the same way, setting the status to "Not Reviewed".) Some people ignore the status icons until they do a monthly reconciliation to a statement, and clear them then. It just depends what works best for you in reviewing your transactions.

Turning to categories, there are a number of approaches. Quicken's auto-categorization, which is done at the server level before downloading into your data file, is hard-wired to use certain categories. So the simplest thing might be to merge your old category into Quicken Mac's default category (in Window > Categories), so your old transactions will be consistent with newly downloaded ones. But perhaps you prefer to continue using your old categories. In that case, you could create QuickFill rules for the Payees where you buy gas, for instance, and set them to use your preferred category for gas. In this case, you probably don't have more than a handful of common fuel vendors, so it's not much work to set up QuickFill rules for each of them. (You may also need to create Renaming Rules, if the Payee names that come through Quicken's server-based Payee renaming aren't consistent. For instance, if you have "Exxon #1234" and "Exxon #9876", you'd create a rule to rename any Payee containing "Exxon" to be simply "Exxon"; then you'd have a QuickFill rule for the Exxon Payee to use category=Auto:Fuel.)

Another unexpected transition, but each time a new category comes in I will have to at least check it to be sure it matches what I intended. And then I will have to change my existing category to this new category. Correct me if I am wrong. Seems the best way to go. Will leave the historical categories in the list and unused I suppose.

New categories won't be created unless you create one manually.

If you have two categories which are for the same thing — e.g. one from your Quicken Windows data and one from Quicken Mac's defaults — I'd suggest merging the categories so only one remains. You just have to decide which to keep and which to jettison. When you merge two (or more) categories, all existing transactions using the category(ies) being merged into another will automatically be changed to the surviving category. So after a little cleanup, you shouldn't have old categories you no longer use: they'll either merged into a category you do use or marked as hidden.

I assume I can shift-click and then review all at once on a right click.

Correct.

I have not yet in Mac had a matched payment come in. Is there any indication it matches (or better, Quicken THINKS it matches) other than the review blue dot? Do I have control over saying it is or is not a match?

Matched transactions will have a blue pencil icon rather than a blue dot. You can see all the possible status icons on this Quicken Help page.

Yes, you can unmatch a matched transaction. Control-click a transaction and select "Reject Automatic Transaction Match" (or "Unmatch Transaction" if you manually merged them). You can re-match the transactions if you unmatched by mistake.

anyone a T-moble customer here?

I am, but I don't import bills or PDFs. My bills is on auto-pay, and when the payment downloads in my bank account, it matches my scheduled transaction when the amount is the same; when the amount changes, the transactions don't auto-match, so I match them and check why the amount has changed. I just log onto the T-Mobile website to download my bill each month. (I don't store any attachments in Quicken.)

And how does one merge? Let me look at that….OK, Isee the Merge command but not how to choose which one survives.

• In Window > Categories, select two or more categories (using Command-click to select).
• Click Merge Categories
• In the Merge window, you'll see the categories you've selected in the top portion, and the bottom "Into" dropdown menu allows you to select which one of the categories will be the one which survives:

I'll ask a question about pdf's in general in Quicken. Some seem "going away" I prefer to get them here or paper.

I'm pretty anal about bill and document retention; I just don't do it within Quicken. For many bills, I download and print statements; I have a file cabinet drawer with folders for each credit card/service provider where I file bills. For important receipts — for appliances or other things which have warranties — I capture a PDF, name and date it, and store it in a Receipts folder. And I'm inching my way to transition to saving PDFs of some of my bills in lieu of paper, but again, I don't store them in Quicken; I store them in folders by vendor/payee. (Some prefer storing documents in folders by year and then month, some prefer by payee and then year.)

Why not store them in Quicken, attached to the transaction or account they belong to? For me, a few reasons. (1) Over time, a Quicken data file can grow pretty significantly large — many GB versus a few hundred MB — if you have hundreds of PDFs stored in the file. This slows backup time when quitting and adds to the volume of other backups Time Machine, iDrive, etc.) (2) Should your Quicken data file somehow get corrupted or lock you out, or should you decide to move to different software, or should Quicken as a company go kaput, all your records are locked in the data file; I prefer having them as file accessible by the Ma operating system. (3) There's no way to search for attachments, only the transactions which may contain them. (That may not be a big deal.) (4) The biggest open for me is that there is no functionality for dealing with attachments in Quicken. You can find a transaction or account with an attachment and open it. But let's say you want to delete all your credit card bills older than 3 years: you have to find each transaction and manually delete each attachment. Or let's say you want all your bills for a certain payee: you have to find each transaction, open the attachment and export/print it, one at a time. Or let's say in five years you decide to stop using Quicken, and want to gather up all the documents you've carefully saved over time; again, you'd have to do it one transaction/document at a time. Quicken would need attachment management functionality to overcome this issue for me. Better still, if Quicken added the ability to store a link to a document stored outside Quicken in a folder on my Mac, that would be the best solution for me.

Naw, really???? If I schedule a bill to be paid via my Bank Checking Account Bill Pay, it has a transaction that will be matched when the bill is pad.

Sorry, forgot about the reminders for scheduled transactions, those will get matched just like manually entered transactions.

Still a Mac newbie, so looking for mthods and options. Particulalrly those that mirror how I work today in Windows.

As I've mentioned before, try to identify what your end goal is rather than how you're used to accomplishing it. If you're constantly trying to mirror how you've worked in Windows, it can create frustration every time things don't work the same as they worked in Windows. Doing some things differently will take patience and time to retrain your brain and fingers, but over time may be as comfortable as what you were previously used to.

I never used Quicken Windows, but I used the legacy Quicken Mac (2007 and earlier) for more than 20 years. Some changes (such as 2-line register to 1-line register) were things I pretty quickly adapted to; other things are either still missing or require an extra step or two and my brain still has the old muscle memory. Despite some shortcomings, I grew to like modern Quicken Mac more than the old Quicken Mac, but that didn't happen overnight. 🤣

The process is going to be a bit different on a Mac because in Quicken Mac you can't do much of anything with a scheduled transaction reminder other than mark it paid. Until you do that it isn't a real transaction - if I'm not mistaken you can only change the Date and Amount fields (at least none of the other fields I have displayed in my register can be changed). Once you mark it paid it becomes a real transaction and you can edit anything.

When I receive a bill that's going to be paid automatically I update the scheduled transaction as needed with the date the bill will be paid and the amount and then mark it as paid. This gives me a transaction dated in the future with a brown pencil icon, which tells me that it's a pending transaction that hasn't happened yet, and also tells me that the bill has been received & payment arranged for so I don't need to take any further action. When the transaction date has passed I start watching for the pencil to turn blue indicating the transaction has cleared.

If I receive a bill that isn't going to be paid automatically I wait until I pay it to mark the reminder as paid.

 I have a difficult time with Enter vs PAid as for me, paid is when it is really paid.

You don't have to mark it paid when you get the bill. I prefer to do it that way so I don't need to do anything further with this transaction; it's in the future, and once it's today or in the past, I know it's been processed by the credit card or utility or other company I've set to auto-pay the bill. But if you want, you can edit the amount (and date, if needed) of the upcoming transaction when you get the bill, and leave it scheduled and not paid until on or after the payment date; you just have to then click Paid.

Ok, walk me thorough Checking Account payments please.

I do not use Quicken to send payment instructions to my bank, as I prefer to do most things manually and avoid any Quicken connectivity issues, so I will leave this for someone else to answer.