Can I match one expense to 2 transactions on my linked AMEX account? If so, how do I do that? If not, I can create 2 expenses separately so that I can match them.

You can instead create two expenses and match them to the two transactions using QuickBooks Online (QBO), @smizell. I'll give more details about this.

To achieve your goal of matching transactions in QBO, I recommend creating two separate expenses for each transaction. Then, you can match each expense to its respective transaction in QBO. This way, you will be able to efficiently track and manage your expenses in the system. To match, follow the steps provided below:
 

1. From the left panel, click Bank Transactions.
2. Decide where the expense is downloaded and tap it to expand the entry.
3. To connect, tick Match.
4. From the Find Other Matches page, check the checkbox for the expense transaction.
5. After that, select Match.

On the other hand, I'll leave these resources to you if you need a guide when reconciling an account using QBO:
 

• Reconcile an account in QuickBooks Online.
• Fix issues at the end of a reconciliation in QuickBooks Online.

Once done and you still have queries about matching transactions in QBO, let me know by having a comment below. I'll circle back to assist. Take care!