1099B - Do you have to enter the information both in the Reporting Exception Transactions block as well as in the Quick Entry Table below? If you only enter in the Reporting Exception Transactions there is no error but form 8949 does not generate. How do you know if the transaction 'is eligible to be reported directly on Schedule D vs 8949'? Thank you.
No, not both or you will be double entering it.
From the 8949 Instructions:
Form 8949 isn't required for certain transactions. You may be able to aggregate those transactions and report them directly on either line 1a (for short-term transactions) or line 8a (for long-term transactions) of Schedule D. This option applies only to transactions (other than sales of collectibles) for which:
You received a Form 1099-B (or substitute statement) that shows basis was reported to the IRS and doesn't show any adjustments in box 1f or 1g;
The Ordinary box in box 2 isn’t checked;
You don't need to make any adjustments to the basis or type of gain or (loss) reported on Form 1099-B (or substitute statement), or to your gain or (loss); and
You aren’t electing to defer income due to an investment in a QOF and aren’t terminating deferral from an investment in a QOF.
If you choose to report these transactions directly on Schedule D, you don't need to include them on Form 8949 and don't need to attach a statement. For more information, see the Schedule D instructions.