This is an illustrative composite scenario. It does not describe any single real organization; it generalizes patterns we see repeatedly across small-business replatforming projects. Figures are typical ranges, not one company’s exact numbers.
Context
Picture a growing brand that started on Squarespace — a beautiful, template-driven site that got them to market fast. As the business matured they hit the ceiling: they wanted full control over SEO, custom functionality Squarespace could not offer, a plugin ecosystem, and true ownership of their platform. WordPress was the move.
Squarespace to WordPress sounds like a simple export-import, and that expectation is the problem. Squarespace is a closed, all-in-one system; its export is partial by design, and everything that made the old site look and work the way it did lives in template features that do not come with the content.
What broke
The export leaves things behind
Squarespace’s export produces a WordPress-flavored file for basic pages and blog posts, but it is incomplete: certain block types, galleries, product/commerce data, some page types, and audio/event content do not come across. The team that assumed “export, then import, done” discovered gaps only after cutover. The realistic plan treats the export as a starting point and budgets for re-creating what it misses.
Design does not port
Squarespace templates are part of the closed platform — they cannot be exported to WordPress. The visual design had to be rebuilt with a WordPress theme (block-based, in this case). This is expected once you know it, and a disaster when you do not, because stakeholders often assume the site will “look the same” automatically.
URLs change — and Squarespace had its own scheme
Squarespace uses specific URL patterns (for example, dated or collection-prefixed blog paths). WordPress permalinks differ, so the slugs and paths change on migration. Without a 301 map from the old Squarespace URLs to the new WordPress permalinks, the site loses the search rankings and inbound links it had built.
Forms, commerce, and images
Squarespace forms and any commerce functionality do not transfer — they are rebuilt with WordPress plugins (and a commerce plugin if selling). Images are re-hosted, so their URLs change and in-body references need rewriting. SEO titles and descriptions set in Squarespace also need to be carried across deliberately.
What worked
The migration succeeded because the team scoped it honestly. They inventoried the Squarespace site page by page and marked exactly what the export would and would not carry, then planned manual or scripted re-entry for the gaps. They rebuilt the design in a maintainable WordPress theme rather than trying to clone the template pixel-for-pixel. They crawled the live Squarespace site to capture every URL and built a complete redirect map before launch. And they rebuilt forms and any store functionality with well-supported plugins, tested end to end before cutover.
Lessons
- The export is partial. Treat Squarespace’s export as a starting point; inventory what it omits and plan to re-create it.
- Design is a rebuild. Templates do not port — budget for a fresh WordPress theme and set stakeholder expectations early.
- Map the old URLs. Crawl the Squarespace site and 301 every path to its new permalink to hold rankings.
- Rebuild forms and commerce. These do not transfer; plan the plugins and test real submissions and checkouts.
- Carry SEO metadata and rewrite media links. Migrate titles and descriptions; fix in-body image and file references to the new host.
Before you make this move
- Inventory every page, post, gallery, form, and product, and mark what the export will and will not carry.
- Crawl the live site for all URLs and build the redirect map before launch.
- Plan the WordPress theme and the plugins that replace Squarespace’s built-in features.
- Export SEO titles and descriptions and migrate them explicitly.
- Test forms, commerce, and image links on staging before flipping DNS.
A pre-migration scan makes the gaps visible before they become launch-day surprises. Replatform Radar inventories your pages, URLs, forms, and SEO signals so a move off Squarespace keeps the traffic and functionality you already have.