On more annotation regarding going from 4.9.5 to 5.2.3 and then to 5.4.4, which is not the recommended upgrade path. In our case, we got some other weird problem because of that, causing an error if editing any module's settings. The problems we encountered during 4.9.5 to 5.2.3 were actually the same we got while going from 4.9.5 to 5.4.4. So now 4.9.5 to 5.4.4 works, after applying the same solution (corrupted data in a table), all is green and OK and editing module settings also works! Maybe there is other issues, requiring to add 5.2.3 into the mix.
After upgrading our 5.4.4 to 5.6.8 we got the same problem again editing module settings, producing a ModuleLoadException originating in get_ActionRoot during page load. Anything else worked 100%. The culprit for this were differences in the system.codedom node of the web.config. I copied over the original node, from the install package's web.config and it worked. So most likely our previous upgrade path with the additional 5.2.3 step would have worked as well if we applied the web.config change. However, for us the recommended upgrade path worked so far. The next upgrades will all work error free up to 9.1.1, but beginning with 6.x our skin breaks as it seems. The pages still work but they are displayed using the default skin. I will open another thread for this one. We also had to update the JQuery URL in Host Settings to get the page settings displayed correctly. Our installed version was quite old causing the checkboxes for permissions to be all unchecked, also checking anything and updating seems to not have worked before. Since JQuery is updated this works as well.
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