Retirement tax questions

You only enter the 1099R you get from the 401K.  It won't  be a new IRA contribution.  After you enter the 1099R it might ask what you did with it.  Did you get the check and deposit it into the IRA or was it a direct transfer from the 401K?  If they took withholding out of the 401K rollover the withholding will be taxable unless you replaced it with your own money when you put it in the IRA.