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Its not a good practice to redirect old -> new -> newer urls. It is referred as sneaky redirects and it will lower the SERPs. Good option will a. old -> newer b. new -> newer Decide any of the two options from above depending the number of backlinks to old and   new urls. Also put a custom 404 error pages to handle the 404 errors occured from other urls.

Exactly, it would mean that you're minimizing the risk of having the site penalised as well. Let me know how it goes!