You can Upgrade anything after 5.0 to latest version. Make sure to do a Confluence Update Check located at footer when you click on Manage Add-Ons Tab for plugins that might be compatible or not when you upgrade Confluence from 5.5.6 to 5.8.5.
As Phil said, refer to Release Notes and Upgrade Steps. Also, check out for known issues which were reported from here for Confluence 5.8.5https://jira.atlassian.com/issues?jql=project = Confluence AND affectedVersion in (5.8.5) ORDER BY created DESC
Hope this helps.
Good luck with Upgrade
Yes you can but make sure you read and understand all the release notes for 5.6.x, 5.7.X as well in case there are any specific extra steps to take.
Then follow the upgrade instructions at https://confluence.atlassian.com/doc/upgrading-confluence-4578.html
Hope this helps.
As the guys said above, that's possible. I also recommend to keep an eye in this bug that affects versions 5.8.x of Confluence if you are using SQL server as database: https://jira.atlassian.com/browse/CONF-38232
This bug arises when you upgrade to 5.8.x and the database contains tables with the incorrect datatypes.
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