Migration from SS 2.3.7 to the 5

Silverstripe Version:
2.3.7

Question:
I would like to know what is the best possible option for upgrading from version 2.3.7 until latest or al least 4. I need to move a web application from one hosting to another. I tried copying the DB and also the whole SS directory, but for some reason it is not working - I assume because of the old version and some kind of incompatibility with the latest PHP etc.

I’d suggest the best option is to rebuild the site in CMS 5 and then manually migrate the content over. 2.3 is waaaaay out of date, so there’s not going to be any kind of direct migration.

Thank you for your suggestion! I am wondering if this would be doable for a person that has no web experience (myself) as the one who created the site back in the days is not available to assist anymore. I am wondering if it is possible to find any useful guide or information that could help the migration.

I am wondering if this would be doable for a person that has no web experience

Rebuilding the site will be way easier than trying to upgrade at this point. If you’re not able to rebuild it yourself you definitely won’t be able to upgrade it.

Your best bet is to hire a developer if you don’t have the necessary skillset to rebuild the site yourself.