DNN versions 4.09.00 = 4.9 = 4.9.0 and 5.05.00 = 5.5 = 5.5.0. I agree that can be confusing and prefer to always include the leading zeros in the minor and build segments of the version number.

I would suggest upgrading from 4.09.00 to 4.09.05 then to 5.05.00. Don't forget to backup BOTH the file system and database prior to each upgrade. Also, remember that DNN 5.02.00 and above requires ASP.Net 3.5 SP1 and MS SQL Server 2005 or 2008 (standard or express).

When doing a major upgrade such as this, you also need to investigate what third party or core modules are going to raise possible issues during or after the upgrade.

If you have the XML module installed, you must upgrade to XML 4.03.05 or uninstall the XML module if it is not being used on any portal before upgrading to 5.05.00. The Chat module has a similar issue but no upgrade is available. See Chat forum if you are using this module. The Events module will need to be upgraded after upgrading to DNN 5.05.00 to the latest version which is included in the 5.05.00 package. The Gallery module v 04.03.00 and 04.03.01 RC is not currently compatible with DNN 5.05.00. If you are planning to switch the ASP.Net version to 4.0, do so after you have upgraded to DNN 5.05.00. Versions of iFinity URL Master prior to the latest release will prevent modules from being added to pages and should be upgraded to the latest release.

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Bill, WESNet Designs
Team Lead - DotNetNuke Gallery Module Project
Extensions Forge Projects - UserExport, ContentDeJour, ePrayer and ImageEditorControl

you may follow my upgrade check list: http://www.deutschnetnuke.de/tabid/186/Default.aspx

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Cheers from Germany,
Sebastian Leupold