grammar - How to tell the difference between と as "and"/a conditional?

The particle と can mean either a fairly simple "And" or it can mean if X then Y.

1: 私は犬と猫が好きです - I like dogs and cats

2: びんを落すと壊れる - if drop the bottle, it breaks

Taken independently either of these rules is easy to remember. In fact と as "and" is probably one of the earliest things you learn in Japanese.

With these two simple example sentences it is quite easy to figure out what is going on. But, when you're reading a longer passage things might not be so clear.

Are there any rules for spotting the difference between the two　とs?

For example with example 2, how do you absolutely 100% know that it means drop it=> it breaks, rather than just drop it and break it in a unrelated actions, listy sort of way?