Hi, John.
As we say so often here...
First, understand what happened "in the real world".
Second, record that in Quicken.
Trying to do the second before the first will get you confused just about every time.
And reinvested dividends are actually two transactions: (1) Received a dividend. (2) Bought more shares.
The two transactions often are collapsed into one, but it's easier to follow what happened if you make two entries.
First: Record the receipt of the dividend. You didn't get cash, so it's hard to see what account to use - and it really doesn't matter because the next entry is going to wipe out whatever you enter this time, so let's just use Cash.
Second, record purchase of new shares, using the proceeds from the dividend. The important thing here is not the price per share. The two important factors are actual number of shares and actual cost to you.
If you try to record the purchase of the shares BEFORE you record the dividend, you get confused - like you have been.
For a quick example, let's make up some numbers:
You hold 100 shares and get a $0.60 per share dividend = $60.00.
Shares are worth $25 dollars today, so you get 2.4 new shares. The commission might normally be $2.40, but you don't have to pay it, so it doesn't matter. Even if the commission were $240, you only had to pay $60 for 2.4 shares, so that's what you record.
So (pardon the accountant-speak - and the formatting):
1st transaction: Debit Cash $60.00 Credit Dividend Income $60.00
2nd transaction: Debit Stock (2.4 new shares) $60.00 Credit Cash $60.00
After the two transactions, the Cash account will be back where it started. The net result: Debit Stock (2.4 new shares) $60.00 Credit Dividend Income $60.00
Since we know how it's going to end up, and since the Cash entries have no lasting effect, we can simply condense the two transactions into the last one.
To take this a step further, if you bought 100 shares for $2500 and paid a $100 commission, your total cost would be $2600. That $2600 would be your basis in the 100 shares, including the commission. Your basis is what it actually cost you, including any commission, transaction tax or other expense, to get ownership of the shares.
RC