How do I set up a new GIC

There are various ways to do this - none of them particularly slick. What I do is create a unique security for each GIC, and I give it name like, "GIC - Canadian Tire Bank - 5 YR Due 2027.10.07 - 4.68%". I then purchase the security in Quicken with a share price of $1. See screenshot of the example below.

Freyr312 said:

For a TFSA, do you check the "Tax Free" box?

The Quicken documentation for the "Tax Free" check box is very brief and gives little insight into what it actually does. If I were to speculate, I would guess that it is feature from the US version because of a couple clues in Quicken's help text for that checkbox (e.g. a reference to municipal bonds being tax free, which doesn't ring a bell in the Canadian context). For the Canadian version, I don't know of any functionality that arises from that checkbox.

There are numerous artifacts from the US version that have not been aligned to Canadian laws, including tax law, and various other practices and standards in Canada.

I expect that checking the "tax free" box would do no harm, but I also speculate it would do no use as well.

Quicken Canada is the US version of Quicken with a light application of Canadian coloured lipstick; it is not a complete transformation ;-)