No, that is up to the financial institution to decide how it sends it to Quicken.
As I said there isn't a preference in Quicken for this, it is what the financial institution is sending.
EDIT Provided this is Direct Connect and not Express Web Connect + you can actually see what the financial institution sent in the OFX log. Help → Contact Support → Log Files → OFX Log
Example of a reinvest (single transaction) form an old Vanguard transaction/OFX log:
<REINVEST> <INVTRAN> <FITID>488256805 <DTTRADE>20110407160000.000[-5:EST] <DTSETTLE>20110407160000.000[-5:EST] <MEMO>DIVIDEND REINVESTMENTDIVIDEND REINVESTMENT </INVTRAN> <SECID> <UNIQUEID>464288687 <UNIQUEIDTYPE>CUSIP </SECID> <INCOMETYPE>DIV <TOTAL>-109.25 <SUBACCTSEC>CASH <UNITS>2.753 <UNITPRICE>39.6839811 </REINVEST>
You can submit request for a new feature by going to the home page and selecting New Post → New Idea. That way people can vote on it to show Quicken Inc their interest in the idea. Personally I wouldn't vote for it because if Quicken I wouldn't trust Quicken to "translate" transactions without causing problems.
Splitting a ReinvDiv into a Div+Buy will cause inaccurate investing statistics because Quicken assumes the money for the Buy came out of your pocket. You can do it if you want, but be aware that some stats like Return and ROI will be wrong.
You can see dividend income in Reports > Investing > Income by security regardless of whether it was reinvested.
You can track dividend income even if the transaction is sent as a Reinvest. The dividend amount will have a Category of _DivInc or for tax free securities, _DivIncTaxFree, whether the dividend is reinvested or not.
"Splitting a ReinvDiv into a Div+Buy will cause inaccurate investing statistics because Quicken assumes the money for the Buy came out of your pocket. You can do it if you want, but be aware that some stats like Return and ROI will be wrong."
That's not the case. Quicken has to see cash crossing the boarder between Accounts to put it in the "Investments" column. A Div won't do that.
I think it is arguable as to whether the statistics are inaccurate. The ROI will be different because the Amount Invested parameter comes out differently in the two paths. That is basically the denominator the ROI calculation. The ReinvDiv action does not increase the Amount Invested; the Buy of a Div & Buy pairing will increase the Amount Invested. While I understand the intent in Quicken's different processing of the two options, I don't think either one is right or wrong, accurate or inaccurate.
My quick check indicates that the Return calculation comes out the same for both processes. That is, the cash value of the dividend gets included as part of the Return total from actual Dividend actions and from ReinvDiv actions.
I was thinking soley about the IRR calc, having never used the ROI calculation. My seat of the pants reaction is that not including the dividend in the ReinvDiv action in the ROI calculation seems wrong as Div/Bought has the same outcome as ReinvDiv action, maybe with a one day difference one way or the other.
Investors says "I put $X into this fund or $Y/week. Tell me what return rate I got on on those dollars." So Quicken tracks Amount Invested separate from Amount Reinvested. That then also leads to even broader AI issues, specifically not reducing it for sold or removed shares.
