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I created a content type using a WSP feature and deployed it to my site with a list using this content type.

Later, I had to make changes to the list, feature, columns etc.

I made those changes, deployed the feature again, disabled and re-enabled it through powershell.

The list seems to have updated, but not the content type?

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It seems like you are running into the issue of not being able to change content type while it's being used but not sure.

Normally when I built WSP with content types I would just update the content type using code if I needed to make changes. IAW, once the WSP was created and deployed, I would no longer "visually" touch the content type but instead, modify/add the feature updated event to push all the changes from there in code. If the list is inheriting properly it should reflect those changes just fine.

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