Upgrading a major release is better done through a step-by-step process. With a minor release, you can go from 2.6.2 to 2.6.5 without a problem, but with a major upgrade it is not recommended to go straight from 2.7 from 2.3, for example.
Most people upgraded from 2.6.x to WordPress 2.7 without a problem, but just to be on the safe side, you should check to make sure that your web hosting provider is compatible. As you notice, most popular hosting providers have already supported the new release.
Although it is worth mentioning that WordPress 2.7 still supports PHP4 at the moment, it may discontinue that at some point, mostly because PHP4 is no longer being updated.
If running particular theme and plugins are compulsory, check the 2.7 Plugin Compatibility and 2.7 Theme Compatibility
Finally, once you are ready, follow the steps in the WordPress Codex, either in the standard or extended upgrade page to proceed. The latter is preferable if you have used plugins beyond the ones that come with WordPress installation.
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