It's mostly battery-charge that governs it which in turn relies on the state of your battery, even though there are some other factors (e.g. is the cabin temp within a percentage difference of what has been asked for etc.) but if you do a reasonable drive to work and don't have too much consuming, it should work.
In colder months, the electrical system takes more of a hammering (full lights, wipers, heated seats, high speed fan plus your usual consuming such as sound system), it will take the car longer to be in a position to enabled it.
I found my 6 year old main battery, whereby the aux had already died in the same car so the life the car has had must have meant the main battery was not the greatest, was in such a condition that stop/start struggled in colder times. After a replacement, it is enabled a lot more of the time but still less of the time than in Summer.