How do I see changes made by or via Squared.io in My Change History?

The user email in your change history will be the one that authorised Squared.io to access the account (you can see who's email authorised Squared.io here). You could create a unique Google Ads account with a Squared.io email address (e.g. squaredchanges@example.com) and use that email address to authorise the application - this way you would be able to filter for changes made by this user.
You can also see the changes made by automation in your Google Ads change history by filtering for ‘Tool: Google Ads API’.