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Hello,

Using the Garmin WebUpdater will update the operating software.
http://www8.garmin.com/products/webupdater/howtoinstall.jsp

Map updates subscriptions are available as lifetime or onetime updates and are registered to the map that is installed on the Nuvi.
http://www.gpscity.com/garmin-numaps-north-america-lifetime-updates.html

http://www.gpscity.com/garmin-numaps-update-city-navigator-nt-2012-north-america.html

The Nuvi 255w is an older unit and is probably due to be replaced. Once the battery dies on the unit, it can not be replaced easily.

There are a number of Garmin GPSs that come with lifetime map updates.
http://www.gpscity.com/search/q=lifetime/&p=1&c=1&t=Automotive+GPS

Yes you do have to remove the North America map, I was just checking on the specs and they do not list that it supports a memory card so unfortunately due to the lack of available space on the solid state drive that comes built into this unit you will have to do the map switchover.

Maps for most GPS devices are updated several times a year. Your map is from 2010 and should be updated. You can go to the garmin site and pay to download and install upgraded maps or do a google search for map upgrades and you'll find some services offering lifetime upgrades for a few dollars more than the Garmin one time upgrade. I did this and have had no problems updating the maps on my Garmin Nuvi 250.

To update your nuvi, all you need to do is to connect your nuvi to an internet connected computer and the updates will show on the lower left of your computers screen, click on it and it will update it with the latest software version and maps.
You can also go to your nuvis website and search for latest updates. Just click on the map link and a list will pop up under the map link, select update maps if it is maps you want to update. It will ask you to choose your device from a list, after choosing your nuvi 255w then it will show you the latest maps for your gps, but you have to install its plug ins first.
That is how to update your gps.

Sorry, no free maps. I know I've tried. You either live with the old map or but the latest version.
I bought the life time maps updates and I'm glad I did.
I've updated my maps at least 6 times.
New maps are about $70.
Life time maps are about $99 (when I bought mine)
BUT FIRST make SURE you have the latest software in YOUR computer and in YOUR Garmin before you load any maps.
You can get that FREE at Garmin here:
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After installing WebUpdater once from the Garmin website, perform all future software updates from your computer. Simply connect your compatible Garmin device to your computer, then run WebUpdater from your computer's "Start Menu" by selecting "Start", "Programs", "Garmin", and finally "WebUpdater"
REMEMBER: It takes hours to do a complete a map update.
Unless you bought the Lifetime maps you may have to pay for current maps.

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Does this help? Let us know. Thanks.

Create an account at myGarmin regsiter your unit ID number this will allow you to unlock the maps that you buy. You then have two options the first requires you to have an NT 2009 or 2008 map already installed.
nüMaps Lifetime™This will cost you £99.99 and is a on off payment Remember — this map update can only be used to update the preloaded maps that came installed on your Garmin GPS device. For example, a Garmin GPS device preloaded with North America maps only cannot be updated with a nüMaps Lifetime Europe Map Update, and vice versa. Check product compatibility. nüMaps Onetime™ This will cost you £79.99 and does not rely on having a map already installed.
The City Navigator® Europe NT comes on a DVD or you can download it.

LOL

You HAVE to go through software support as this is an issue with the map. They told me it is because the map KEY is wrong, it is only for the united states, but the map is ALL of north america. The wait time is incredibly long, I have been waiting for over an hour, such bad service

FIXED:
Got a response from Garmin that didn't help much. Called Garmin today and asked to be matched with a software person for a "xml map" problem. They are aware of this problem, and will be able to remote into your computer and fixed it for you.

The problem is that the installer will install us and canada maps, when the 205 cannot support the canada maps. The old 205s didnt have as much storage space, so the installed never transferred over canada. The new 205s have twice as much storage, and the installer thinks it is helping you out. They will be working on a new installer, until then a Support rep needs to run some batch files to fix the issue.

GO TO http://www.wtorrent.com/search/?q=Garmin%20City%20Navigator%20North%20America%20NT%202009