When Should I Upgrade my cell phone? Whether you have a beaten-up old phone like Palm Treo or a something just bought a couple of months ago, you can find great deals if you are eligible for an upgrade. OK, the typical contract cycle is 24 months or 12 months (carriers are pushing for 24 months in most cases). You eligibility depends on a lot of factors and we won’t get into details in this post. So, let’s assume that you meet all the requirements, When is the best time to upgrade my cell phone? Holiday shopping and Back to School season! Carriers offer more incentives for you to sign up another 2-year contract during back to school and holiday shopping seasons. So, act now!