Why isn't Lifetime Planner showing tax on tax-deferred withdrawals?

This is one reason I don't really like the Lifetime Planner for "planning" other that a ballpark plan.  It doesn't allow you to control which accounts (or account types) that it draws down at any given time.

To directly answer your question other than for RMD (and it has the wrong year for that) Quicken will in fact pull money from the Roth accounts before the tax deferred accounts.  It will also take money from your taxable accounts before your tax deferred accounts.

It is also hard even see this happening since in the details for the year they don't have a section for "tax exempt/Roth".  A withdraw from a Roth or a Traditional IRA will both be in the "You Tax-deferred" amount.  The only way you know that it is taken from Roth is that it would show up with an amount in the "Tax on Withdrawals" amount.