Capital Gains, Losses and Tax Reporting

Mortimer Duke

I’m using Quicken Business & Personal / Simplifi-style QBP and trying to understand how investment transactions flow into capital gain/loss tracking and tax reporting.

I see that QBP allows investment transactions such as buying shares, selling shares, and adding shares. It appears to include fields for share quantity, price/share, commission, total amount, and, when adding shares, cost basis.

My use case involves employer stock compensation. Shares are distributed from an employer stock plan, with compensation income already reported through payroll/W-2 withholding. I would then manually enter those received shares in the brokerage account as tranches/lots, using the payroll-documented fair market value as cost basis. Later, when the shares are sold, I want QBP to track the resulting capital gain or loss, not treat the sale proceeds as ordinary income.

Can anyone confirm how QBP handles this?

Specific questions:

1. If I manually add shares with an acquisition date and cost basis, does QBP preserve that as a tax lot?
2. When those shares are later sold, does QBP calculate realized capital gain/loss using the entered basis?
3. Does QBP distinguish short-term vs. long-term gain/loss based on acquisition date and sale date?
4. Can QBP produce a capital gains report or tax report that shows proceeds, basis, holding period, and realized gain/loss?
5. Does that gain/loss flow to Schedule D or another tax-reporting section if the relevant categories/accounts are tax-mapped?
6. If brokerage transactions are downloaded from Fidelity/Schwab, does QBP preserve downloaded basis and lot information, or does it require manual adjustment?
7. For employer stock compensation, is the recommended workflow to “Add Shares” at the W-2-compensation FMV basis, then record the later sale normally?
8. Are there any known limitations with using QBP for lot-level tracking of RSUs, restricted stock, or other employer stock-plan shares?

I’m trying to avoid double-counting W-2 stock compensation as brokerage income while still correctly tracking the eventual Form 1099-B / Schedule D gain or loss.

I'd be grateful for any helpful guidance.

SRC54

I don't have an answer for you and I don't use QBP, but I am pretty sure QBP handles investments the same as QS.

Simplifi products only keep up with the overall value of the account from what it downloads. It doesn't have any investment reports other than what you find in the Investment module. It's pretty basic.

Anything you want to be able to create in a report would have to be a "payment/deposit" and in dollar amounts, and then you would have to create your own categories for what you want to keep up with.

I have managed to work around the deficiencies and keep up with my Capital Gains, Dividends, Losses, etc. by creating my own categories and including them on my Spending and Income reports. But only for realized stuff that was paid out in money amounts.

Mortimer Duke

Hugely helpful. Looks like I'll need to split out the gains and losses and manually categorize them into long/short gain/loss. Thanks again.