When you get new head from ADA, the long outer oring is usually a big loop already sized. It can be difficult to install without stretching it as you insert in the groove and at the end you have extra. If you work back the other direction each way and shimmy it back a little you can usually use up the slack. As noted above, putting some grease in the groove helps to keep it in place as you go and helps avoid it falling out or binding/pinching when installing.
For this reason and for cost savings, we just order the bulk oring stock when replacing them. That way you just install and trim to fit. It is just sealing Cooling water, not compression/combustion so the seal isnt that critical. Some super glue the ends together after sizing , some just put a dab of silicone on the joint, and some trim a fuzz long then shimmy back and just put a little grease there.