Tip: We always recommend doing the upgrade either "before" or "after" switching servers, just to help rule out "the server config" as a cause of any issues that arise.
That said, sometimes it's impossible to do this if PHP versions aren't compatible between servers ... such as the very large version-jump you're doing in this case.
I'm just mentioning it for future reference.
By "successfully connected" I'm assuming you mean a "token has been exchanged". This is good, insomuch as it confirms that the Zen Cart store is successfully listening to Square's webhook.
Uninstalling/reinstalling are probably not going to add much value, but good to have tested that at least once.
However, it would be good to ensure the module's files are all up-to-date with the latest release of the Square module compatible with your PHP and Zen Cart versions.
What's the output of running the site's `/extras/curltester.php` script?
You can get the latest version of it from:
https://github.com/zencart/zencart/b...curltester.php
(It's a standalone file, independent of Zen Cart or PHP versions. It tests connectivity to common modules, including Square. It's intended for Hosting companies to use for quick troubleshooting.)
Where's the server located? ie: I wonder if Square's endpoints are easily reachable from your IP location without long lag times?
The Square endpoint is https :// connect.squareup.com (The curltester script above tries to connect to it.)
You could uncomment the setDebug line highlighted here, to have it log connection/communication attempts, to see whether the endpoint is providing any useful troubleshooting information:
https://github.com/zencart/square_pa....php#L468-L476
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