Call the jail before you bring anything. That is the only advice that matters here, and it matters every single time, not just the first time.
Trustee status gives an inmate more freedom of movement and sometimes more flexibility around approved items, but what is actually permitted varies significantly from facility to facility. Some jails allow outside food and drinks for trustees under specific conditions. Others prohibit it entirely regardless of status. The rules can also change without notice based on staffing, security concerns, or incidents that happened inside that you would have no way of knowing about.
Cigarettes may have gone through fine before, but that does not mean drinks or snacks follow the same rules. Different categories of items get evaluated differently, and what worked last week is not a guarantee for this week.
The other reason to call first is to protect your person inside. If you show up with something that turns out to be prohibited, it does not just get turned away at the door. Depending on the item and the circumstances, it can create a disciplinary situation for the trustee that costs them their status. Trustee is a privileged position that most inmates work hard to earn. Losing it over an unauthorized snack drop is not a trade worth making.
One phone call to the facility before you go takes two minutes and eliminates all of the guesswork. Ask specifically what is approved for trustee drop-offs, whether food and drinks are on that list, and whether there are any packaging or quantity restrictions. Get a name if you can, so you have something to reference if there is any confusion at the door.