Ordering plants in winter, what shipping extras are worth it?

Fast shipping is usually worth more than any single add-on. The shorter the plant is in transit, the fewer chances for it to sit in a freezing truck or warehouse.

Ask when they ship. I prefer sellers who ship early in the week so the box is not parked somewhere over the weekend.

Heat packs can help, but they can also cook plants if packed badly or used in mild weather. A good seller knows when to use them. A checkbox on a listing does not tell you that.

I check both my weather and the seller's weather. The box has to travel through more than your front porch.

Insulation plus faster shipping is my usual combo. I skip winter ordering completely for thin-leaved or very expensive plants unless the seller has a strong track record.

Message the seller first. If they answer clearly about packing and timing, good sign. If they act annoyed before you even buy, that tells you something too.