I deleted my exiting EE4 4.4.3 plugin.
I downloaded the new 4.4.4 from the web site.
I upload the Zip, and I get the following message
Installing Plugin from uploaded file: event-espresso-core-reg.zip
Unpacking the package…
Could not copy file. caffeinated/core/libraries/messages/message_type/cancelled_registration/templates/admin/cancelled-registration-message-type-admin-main-content.template.php
Return to Plugins page
Extract Zip, and upload via FTP, and the files transfer fine, and the Plugin Activates.
I tested this out with a fresh copy of Event Espresso 4.4.4 on several WordPress sites but was not able to duplicate this issue. I grabbed this quick video from one of them:
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