Entering Holdings

First, you should create an investment account.

Then add a security, and assign the security to the investment account.

Then you can enter transactions that reflect your holdings for the security.
 

If you are adding initial holdings

First, create a new category via Tools > Categories.
Create an "Income" category, named "Initial Holdings".

Then open the Investment account and select the Register view.
Enter a new transaction (the "New Transaction" button is at the top right of the register).

Change the transactions "Action" field to BuyXfr.
This allows you to purchase shares of a security using funds from another account.

Amend the Category field of the transaction to use the "Initial Holdings" category you created earlier.

This will reflect that you already possess these securities (at the creation of this account in Moneydance).
 

If you are entering a transaction that is not an initial holding

Amend the "Fee Category" field of the transaction to use a category like "transaction fee" or "commission". This will allow you to reflect applicable broker fees.
If needed, you can create a new category via Tools > Categories.
 

IMPORTANT
Moneydance will only download transactions into your investment account when you download/import transactions from your financial institution.
Therefore, unless the initial purchase of the security is included in the downloaded transactions, you will not have the complete information for your security.
In this case, you may need to manually enter transactions for the account to reflect your current holdings.
 

Entering Holdings to Track Capital Gains

The most straightforward way to enter your holdings is to manually enter all transactions.
You should enter transactions from the date of purchase to the current date into the register.
This will allow Moneydance to track capital gains.
 

Entering Holdings Without Capital Gains

If you feel you have too many historical transactions to enter manually, or if you prefer to start from your current balances, you can do so.

It is important to remember that if you start from the current balance and don't enter all the historical transactions, Moneydance will not be able to track capital gains.

Open the Investment account and select the Register view.
Enter a new transaction (the "New Transaction" button is at the top right of the register).

Change the transactions "Action" field to Buy.

Amend the number of shares to the total number of shares you currently own, using the current market value.

e.g. If you own 50 shares of XYZ stock, enter a single Buy transaction for 50 shares (even if you purchased them over time), using the current market price.
 

You may wish to enter the original basis for the stocks, and the appropriate number of shares.
This permits better tracking of your ROI.
You should repeat this for each of your securities.
 

Once you have entered your securities this way, your account will show a large negative cash balance.
To correct this, select your Investment account and choose Account > Edit Account.
In this window, enter the cash balance number as the starting amount in the Initial Balance field (without the negative sign).