Js logical operators return not true or false, but truly or falsy value itself. For example in expression x && y, if x is falsy, then it will be returned, otherwise y will be returned. So the truth table for operator is correct.

In your case you could use expression customers && customers.orders && customers.orders.Length to get length value or the first falsy one.

Also you can do some magic like ((customers || {}).orders || {}).length (Personally, I don't like this syntax and possible garbage collection pressure as well)

Or even use maybe monad.

function Option(value) {
    this.value = value;
    this.hasValue = !!value;
}

Option.prototype.map = function(s) {
    return this.hasValue
        ? new Option(this.value[s])
        : this;
}

Option.prototype.valueOrNull = function() {
    return this.hasValue ? this.value : null;
}

var length = 
    new Option(customers)
        .map("orders")
        .map("length")
        .valueOrNull();

It's longer than all the previous approaches, but clearly shows your intentions without any magic behind.