Schedule B - Interest & Dividends Report on Mac

First, are the dividends in question in a brokerage account or a retirement account? Quicken Mac by default excludes retirement accounts from the tax reports, since this income is not taxable. (But you can choose to include them, or create a variation of the report just for your retirement account interest and dividends, if that's what you're looking for.)

I'm not seeing what you're describing in my Quicken Mac data file: When I run a Schedule B Tax Report, I'm seeing "Dividend Income, non-taxable" (for a tax-exempt bond fund), "Dividend Income" for individual stocks and mutual funds which have paid dividends, and "Interest Income" for interest paid on savings and brokerage cash accounts. (There is no distinction between reinvested dividend and dividends paid in cash, since these are the same for tax purposes.)

How recently did you migrate from Quicken Windows to Quicken Mac? I don't know if that's causing a problem. From your description, the transactions seem to be proper Quicken Mac Type=Dividend Income and Type=Reinvest Dividend transactions, so I wouldn't think the conversion from Quicken Windows is the culprit here.

As I wrote above, the Schedule B report is reporting correctly for me, so we need to try to figure out what's incorrect in your data that's causing it not to be reporting dividends and interest. So what follows is some suggested troubleshooting…

If you run a Schedule B report for a date range=last year, do you see any of your dividend and interest transactions or not?

I would try entering one of the dividend transactions manually — just a temporary dummy transaction — to see if it shows up in the Schedule B report.

If you generate the Schedule B Report, click Edit, click on the Account tab, click Selected Accounts, and see if the brokerage account in question is checked. 

It might be helpful if you could post a screenshot of one of your dividend transactions — in the register, and the detail of the transaction (you can obscure the amount if you wish) — to see if anyone here can identify something wrong with the transaction.

It may be that the Dividend Income and Reinvested Dividend categories are not flagged as tax related. If they aren't, then those transactions won't show up on a tax report. It's possible that got lost when importing your Windows file.

To check whether this is your problem, open the Categories window from the Window menu (or press Cmd-Shift-C). Then scroll down to the Dividend Income and Reinvest Dividend categories and see if there's a green check mark in the Tax-Related column. If there isn't you can double-click the category, check the "tax-related" box, and select the appropriate tax form and tax line.

You can use the one under Personal Income instead. That one should already be set to Schedule B → Dividend Income. But to do that you'll have to change the transaction type to Payment/Deposit.

I don't know why you're not seeing transactions with the transaction type set to Dividend Income show up on the tax report. When I entered a test transaction just now with that transaction type it showed up on my Schedule B report.

@Jon said: The screenshot only shows 3 subcategories under Investments because they were filtering on "div", so only getting the categories that started with those three letters.

D'oh! Thanks for pointing that out; I didn't look at the very top of the screenshot.

@Rafi Schwartz I'd still recommend you try the process I described above to export and import your data into a new file. If something went wrong in your migration from Quicken Windows, this process might fix the problem. It won't take too long to do the export and import to see if it makes a difference.

I wouldn't suggest changing transactions to Payment/Deposit and using a category you created. You'll have to do this for every historical transaction and continue to do it in the future. Quicken Mac is built to handle this automatically, and I think it would be better to continue to try to fix whatever underlying problem there is with your migrated data.

how do I execute a mass "Type" change from Reinvest Dividendto Payment/depositand "Category" change to 

Personal Income: Dividend Income?

You can't do a mass change on the transaction type, unfortunately; AFAIK you have to change that one transaction at a time.

You can do a mass change on the category. Just select all the transactions you want to change, right click on one of them and select Edit Transaction. In the pop-up dialog change the Category field, make sure there's a check mark next to it, then click OK.

I don't think the category in Quicken Mac should matter, because the program assigns it based on the investment transaction Type. That is, if you manually enter an investment transaction for interest or dividends, you're never specifying a category, just the Type of transaction. I assume that works the same on transactions imported from Quicken Windows, but I don't know and can't test it. (You'll note that the imported Quicken Windows category _DivInc is unused on any transactions in Quicken Mac.) And you said that if you enter a manual dividend transaction where Type=Dividend or Reinvested Dividend, that transaction does show up on the Schedule B report? If so, it clearly points at something in the way the imported transactions are being dealt with in Quicken Mac.

One thing which would help is if you go to Settings > Register and select Long Names. I'm curious where you are seeing the category Dividend Income whether it is the default one (Investments:Dividend Income) or the one you created (Personal Income:Dividend Income). It should be the former. I think it is, because your earlier screenshot of categories showed the latter was Unused. But assuming it's the former, then I'm stumped about why the transactions aren't showing up in the Schedule B report.

Out of curiosity, have you tried generating a Tax Schedule report? This is the original Quicken Mac tax report; all the other ones, like Schedule B, are just subsets of the main Tax Schedule report which were broken out last year. On the Tax Schedule report, do your dividends show up anywhere?

If we can't crack this, one possibility is simply editing all the interest and dividend transactions in 2023 to get them to show up, and just ignore that the ones in prior years don't show up in this report. After all, how likely are you to need a Schedule B report from prior years?

Well, I think getting your next downloaded dividend or interest transaction will help immensely, as it should clarify whether there's something wrong with your data file or whether the problem is limited to the transactions which were converted from Quicken Windows. (For what it's worth, I haven't seen any other Windows to Mac converters ever report this as being a problem.)

Another quick thing to test: go to one of the dividend transactions and edit it, changing the Type from Dividend to Type=Interest. Save the transaction. then edit it again and change it back to Type=Dividend Income. Does it now show up in the Schedule B report or not?

Also, in your register, temporarily edit the Columns to show the Category column. ("Category" is a separate column from "Description/Category"). I just want to verify that for a dividend transaction, the Category column is also showing "Investments:Dividend Income". Here's a Dividend transaction, manually entered, in the register:

And here's that transaction when double-clicked to edit it:

I'm still not sure what we're looking for, as I don't understand why your transactions aren't showing up in the tax reports, so I'm just poking around looking for anything which may be different in your transactions than mine.

You said above that the tax reports only show the 4 transactions that you manually changed to Type=Payment/Deposit, right. I can't remember if you've tried this before, but what happens if you manually enter a new dividend transaction, using Type=Dividend Income, like the one in my screenshot above. Does such a manually-entered transaction show up in a Schedule B or Tax Schedule report?

The problem with editing transactions to be Type=Payment/Deposit is that you'll have to do that forever. That's not the way Quicken Mac is built to handle investment returns, so although you can manually edit it to work that way, you're swimming uphill and will have to do this on all future transactions. So that's why I'm more interested in trying to figure out what's wrong with your converted transactions to see if you can get settled for 2023 and beyond.