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Can I Upgrade From Regular Cell Phone to Smartphone Several Months Early?

Update:10-11Source: network consolidation
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I have a Samsung Sway that I upgraded to last spring - in March. It's been a great phone, but I now have a full-time job where I need e-mail access and would like to upgrade to a Droid smartphone. Beyond that, my Sway has serious screen issues now where it frequently becomes a patchwork of lines and squiggles that I can't see anything through. I have a feeling it's dying.
I'm on a Family Plan and have been for years - my mom started the contracts 7 or 8 years ago - and I'm wondering, could I get an early upgrade to a Droid? It would require me getting a different plan for the phone since it would need data etc. versus my current 1500 minutes, unlimited texts, no data plan. Would it be possible for me to upgrade for free or for a small fee?
How do I go about upgrading even though I'm still about five or six months away from my Every Two Years upgrade? Is this even possible?

The Best Answer

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Generally, Verizon will not change your upgrade date, even if you change your plan or add high-value features like data.  Verizon allows you to reverse these changes at any time, so they are not an effective bargaining chip.
You should start by calling CS and asking if you are eligible for any early upgrade promotions.  These vary by region, so you may be lucky.
If there are no promotions, you could do an alternate upgrade using the eligibility from one of the other lines on your family plan.  Basically, they upgrade and give the phone to you, then in March, you can upgrade and get them the phone they want.
Otherwise, you will have to purchase the phone at full-price or from a non-Verizon source.
Good luck!