How do I file extension for both State MA 355S and Federal 1120S using Turbotax business 2019. Intuit has done such a bad job in guiding users to the right method.

For the Federal 1120-S Extension Form 7004, while signed in and working in TurboTax:

 

• Choose Federal Taxes
• Then Other in the far right
• You will need to go through a few screens, some may force an answer
• The Screen you are looking for is Did You File The Extension
• Answer Yes
• You will go through a couple of more screens. 
• Then you will come to a screen labeled When and Where to file your Extension.
• Click Print Extension

 

For the Mass Extension Form 335-7004:

 

• When you go into the MA return, on about the third screen it will say Need More Time To File Return.
• Click Yes
• You will pass through some more screens until you come to one like the Fed with an address and an option to print the extension