Alexander, the core in TW5 is fundamentally different from TW2 so when you 
say;

I thought I might be able to do an automatic upgrade. When I press the 
> upgrade button in backstage
>

...it seems you're trying something from within TW2. This is not possible.

Instead you must go to

https://tiddlywiki.com/upgrade

and drop your TW2 file onto that area and follow the instructions 
thereafter.

Do understand that basically all code you may have (plugins etc etc) from 
TW2 will fail to work in TW5.

You may want to consider a softer route all together: Start with an empty 
TW5 and build it from scratch and take theopportunity to "correct the 
flaws" in your original TWs structure. Then, manually import only *content* 
tiddlers on a per-need basis. I found this "route" better for my cases 
because my old TW2s had grown very complex over the years so it was 
impossible to retro fit it into TW5.

<:-)

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