I can't seem to get status icons to display the way I want them to

There are two columns in the register related to transaction status.

The STATUS column (that has a dot in the column header) shows several icons depending on the status of a transaction syncing to your bank: an orange pencil for manually entered transactions that haven't matched to a downloaded transaction, a blue pencil for manually entered transactions that have been matched to a downloaded transaction, and a blue dot for downloaded transactions that didn't match to a manually entered transaction. You can mark transactions as reviewed to clear out the status icon.

The CLR column shows whether a transaction has cleared or been reconciled. A blue box with a white check is a cleared transaction, a green circle with a check is a reconciled transaction (the check might be either white or black depending on whether Light or Dark mode is active), and an empty box is neither cleared nor reconciled.

You can enable both of these columns by selecting the Columns button in the lower right corner of the register and checking the boxes next to Status and Clr.