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Moving from Squarespace to WordPress

Squarespace vs. WordPress.


Seems to be a heated debate these days among professional creatives and business owners! I am firmly of the opinion that each platform has the great capacity to make a stunning website – it all depends on your needs and what you are trying to accomplish. If you want a plug and play solution, Squarespace is going to be your best friend. Their well designed templates make it super easy to launch a beautiful site in no time. However, and this is a big however, you will eventually come to realize that you crave more functionality and freedom, especially considering such high monthly fees.


WordPress is the king of all website builders. At the time of writing, it powers 28.9% of the internet. Although you may pay for some design and development upfront, the software is completely free. You own your site and all its content, you are in complete control. There are also tons of free resources, plugins and courses for you to learn the back-end yourself.



Opinions aside…

I will curb this debate for now, perhaps in a later post I will go deeper into why we use WordPress almost exclusively here at Brave New Creative. For now, suffice it to say that it all comes down to your needs as a website owner. For Young Space, an independent curatorial platform for emerging artists, Squarespace had become too restrictive and limiting for an exponentially growing blog and online gallery shop. They came to us with a blog of over 800 pages and posts, a huge dedicated monthly readership, and a desire to level up the site’s functionality, SEO, and look and feel.


Moving from Squarespace to WordPress…The struggle was REAL. This was my first time migrating a live site to the greener grasses of WordPress.

I hope that by sharing some of the roadblocks I encountered here, I can help someone else who is struggling to find information on how to properly migrate.

This is not a start to finish guide, it is a summary of the most challenging parts I experienced. Some great resources I consulted prior to the migration can be found at the end of the post.

Reasons for the move

First off, Young Space was moving from Squarespace for a few reasons:

  1. The site was primarily a blog – WordPress is a native blogging platform and simply can’t be beat. Squarespace is much better suited to small businesses or portfolio sites that don’t post new content every day. Their blogging platform lacks the customization of WordPress.
  2. Greater control of SEO and Analytics – Squarespace has basic analytics tools built in for business sites, and even integrated with Google Analytics. However, fine tuning SEO is much more efficiently done through plugins like Yoast SEO available in WordPress
  3. A growing site with a need for refined content management – Young Space’s content has many sections and categories. Because of the large amount of articles, throwing all posts into broad tags and categories was not doing users any favours. Custom post types in WordPress allow the categories to be organized neatly into more broad groupings of posts, making it easier for users to find what they’re looking for. Squarespace does not support custom post types, only categories and tags.


It was not quick and painless

I assumed this from the start!

Any time you’re moving from one platform to another, you’re going to hit some snags – It’s just inevitable.

The problem

The first roadblock was exporting the site’s content from Squarespace. I followed along with this guide on the export process, seemingly a breeze, click the Export button and you have a fully compatible WordPress file! Great! I hit the button. Preparing Export….. Preparing Export…. No problem, it’s a big site, this takes time. I leave the computer to do its thing for an hour, come back and it’s still stuck on the loading screen and it appears nothing has downloaded!

The Solution

For anyone else who is experiencing this, don’t panic! If you have waited an hour and still see no progress, exit the page, clear your browsing cache, and revisit the ‘Export’ menu. There, thankfully, was a big grey download button along with the full confirmation that the export had in fact been completed. For some reason, Squarespace support told me that with large sites it may not show any progress while preparing the export in the background.


Some content will not export

This was only a minor inconvenience for me because the bulk of the information I needed was posts, but it’s good to keep in mind that Squarespace won’t export:

  • Product Pages
  • Folders
  • Index Pages
  • Event Pages
  • Album Pages
  • Cover Pages
  • More than one Blog Page
  • Audio Blocks
  • Video Blocks
  • Product Blocks
  • Drafts
  • Style changes
  • Custom CSS

For the full list of what Squarespace will and won’t export, click here.


No Images were Imported

The next challenge I faced was formatting the posts once in WordPress. For starters, everything was wrapped in old html from Squarespace. Random <div>s with multiple cluttered classes and <img>s that linked directly back to Squarespace hosted images. None of the images had been imported into the new media library!

This can happen frequently, I learned from many others experiencing the same problem. Luckily, there are a few plugins that came to the rescue.


Plugins to the rescue!

To import the images, this plugin was the only one that did the job. It can only process 50 images at a time, so you’ll have to keep an eye on it and reload the page once you hit 50. Also, it wasn’t perfect. There were about 70 images that did not import and showed error messages. These images were hosted on Flickr, so bear in mind that if you have image content hosted elsewhere you may have to manually re-upload those to the WordPress Media Library. All in all, the Import External Images plugin was a godsend.


Post-Migration Check

It was imperative to triple check all the permalinks and post content to make sure nothing was broken, and all the content was indeed there on the new site. I combed through each individual post to be sure. It’s also helpful to use a plugin to check broken links, or do this through Google Search Console. I set the new permalink structure to mimic the old one almost exactly. Then, before setting up all the 301 redirects, I made a master list of all the new URLs and which new URL they will point to. This was most easily done by accessing the sitemap of both sites, running it through a URL extractor like this one from Rob Hammond, then pasting the resulting URL list into my text editor.

Pro-tip for Atom/Sublime

I use Atom, and there is a SUPER handy function you can use to append 301 to all your lines (I’m pretty sure this works in Sublime Text as well!):

Select all the lines you want to add to, then press

Cmd + Shift + L

Voila! You can use your right arrow key to append to all the selected lines at once. Since the 301 redirect structure must include ‘301’ at the end of each line, this is a HUGE timesaver for large sites.


Final Thoughts

These were just a few of the challenges I faced when migrating a large Squarespace site to WordPress. Luckily, as Squarespace has grown in popularity, there is quite a bit of information out there if you hit any other snags not mentioned here. The WordPress community was extremely helpful in helping to solve many of these issues. When in doubt, post on a WP forum and see if someone else had experienced the same issue! Waiting for the Squarespace support team was far too time consuming for me… Most of the time I had already hacked my way around an issue before hearing from a customer service rep who was not trained in development or migration at all.


If you’d like a more step by step guide on proper practices for migrating, check out these great resources here and here.


Till next time,


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