Hi, Joe.
You've hit a sore spot!
We've often complained (and even ranted!) here about Quicken's failure to understand CDs. They CLAIM to understand, and even offer CD as one of the investment types, but trying to keep track of CDs and the interest from them - especially if the interest compounds - will convince you that they know nothing of CDs.
The best solution I've found after years of frustration is to treat a CD as a stock. When you buy one, record it as a stock purchase at $1,000 per share. When it matures, record the redemption as a sale of that CD. If you roll it over into a new CD, record it as a sale of the old and purchase of the new. If the new one is for the same amount and the same CD number, you can get by with ignoring the rollover transaction, but it probably is still best to record the sale and purchase, just so you can see the trail in your Register.
Recording interest income SHOULD BE very simple, but Quicken makes it tricky. I now have several Memorized Investment Transactions for my various CDs. For the first interest check received for each CD, I click Enter Transaction | Inc. Income (Div, Int, etc.), and choose the Transfer account (checking, cash or wherever I put the check or its proceeds). Then I Memorize the Payee so that I can use it next time.
For interest that compounds, I do much the same, but click Reinvest - Income Reinvested. Now comes a tricky part: Since Quicken insists that we treat a CD like a stock, we have to tell it how many shares we bought with our reinvested interest! I tell it that I got 0.06586 new shares at $1,000 per share for my $65.86 interest earnings this month. If I don't let it increase the shares, then Quicken will try to increase the "price per share", which is even more ridiculous than upping the number of shares. :>(
Next month (or quarter or whatever), you'll have to go through the same exercise again, probably changing the amount each time.
I've tried entering interest checks directly as deposits into my checking account, but then they never get tied back into the CDs that earned the interest. To get meaningful reports on investment results, interest must be recorded as Investment transactions, not as Cash transactions. The income then goes into _IntInc, rather than into an Interest Income\Bank of America CD #11111, where you might prefer to see it. You'll have to sort out the CDs at year-end to match your 1099s - with little help from Quicken's reporting system.
If you do record interest receipts as Cash transactions, then you can put the future scheduled income into the Calendar and be reminded each month. But there's no good way I've found to schedule and get reminded of Investment transactions. So I kind of duplicate them: I record the first interest receipt in my checking account, then schedule the future ones. Each month, when reminded to make the checking transaction, I Skip it, but go to my CDs account and record the Memorized Investment Transaction. The calendar is only a reminder; I don't enter the transaction from there.
But we can't even get this kind of reminder for interest that compounds, because we don't get a check to remind us. For one of these, I've made an Excel spreadsheet showing the monthly interest for the entire term (60 months), then pre-recorded a Reinvest transaction for each of the future months, using the future date for each one. So, each month, when I look at my Income Statement on the 10th, I see that my compound interest was recorded on the 9th. Clumsy and tedious to record that string of future compoundings, but it works. And I only had to do it once - until next December, when it matures.
Sorry, Joe, I didn't mean for this to be so long. I already deleted the long version. But I've not found a good way to explain this in a few words. It should be so simple - but Quicken doesn't handle it simply.
Now, I hope somebody else will chime in and say, "R. C., that's ridiculously excessive! Here's the simple way..."
RC