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Note that different paid extensions can depend on different versions of the licensing application, and not always the latest version. So if you install a paid app that depends on an older version of the licensing application, and the licensing application is not already installed then it's normal to not get an automatic trial license.
In you case the Ideas application you installed depends on an older version of the licensing application which doesn't support automatic trial license generation. Still, when you installed the Calendar 2.9.4 the licensing application should have been upgraded to 1.17.1 which has support for automatic trial license generation. So this is something to investigate @oanalavinia . Maybe it's expected: the licensing application is upgraded, the install listener is registered but the extension might be already installed? This would explain why it works for the next installed paid extension.
Steps to reproduce:
Expected results: As per issue 92 the license is automatically generated for the other installed apps.
Actual results: No trial license is generated for the Calendar.
Environment: Windows 10, XWiki 13.4 with MySQL 8.0 and IE 11
NOTE: After installing Calendar I've also installed Office 365 which worked as expected - the trial was added automatically.
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