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Migrating from Wordpress "Danger, Danger"

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I have a large wordpress site that I am migrating to squarespace.

My marketing manager is begging (pleading) with me not to do it:

Because putting 301 directs on all our blog posts will hurt our traffic, and make Google have to re-search over 1,000 pages.

(website.com/blog/nut-farming  v. website.com/nut-farming)

Question: if I move to an enterprise squarespace membership, am I able to get my developer to hard code this change, instead of using 301 directs?

It would seem an impediment for established blogs to move over to what is in most other factors a great CMS.

Many thanks for your thoughts and replies,

Nut Farmer.

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