Hi LaundryYard, 

I think that the issue is in the Cleared column. If you have that header,  make sure to change the N to a Y  for each transaction.  

Here are a few other tips that may help you along the way:

• Never import an IIF without backing up your data first because the process is irreversible
  • When working with IIF files, I normally work out of a copy of the company file until I get the results I want. Then I re-import to the working file after backing it up
• For large amounts of data, I prefer to use a transaction importer, or if using QuickBooks  Desktop Accountant, I use the Batch Import Transactions tool 
  • There are also similar solutions for QuickBooks Online