The Apache access.log always (with and without the AliasMatch) shows
192.168.56.1 - - [09/Apr/2019:23:15:38 +0100] "GET 
/ajc/static/_0.0.0/css/web2py-bootstrap4.css HTTP/1.1" 200 8372
192.168.56.1 - - [09/Apr/2019:23:15:38 +0100] "GET 
/ajc/static/_0.0.0/css/bootstrap.min.css HTTP/1.1" 200 144877
192.168.56.1 - - [09/Apr/2019:23:15:38 +0100] "GET 
/ajc/static/_0.0.0/js/web2py-bootstrap4.js HTTP/1.1" 200 3029
192.168.56.1 - - [09/Apr/2019:23:15:38 +0100] "GET 
/ajc/static/_0.0.0/js/modernizr-2.8.3.min.js HTTP/1.1" 200 15514
192.168.56.1 - - [09/Apr/2019:23:15:38 +0100] "GET 
/ajc/static/_0.0.0/js/bootstrap.bundle.min.js HTTP/1.1" 200 67742
which means that web2py is doing what is supposed to be doing.

Is AliasMatch doing anything?

How can I check that the files are indeed being cached?

-- 
Resources:
- http://web2py.com
- http://web2py.com/book (Documentation)
- http://github.com/web2py/web2py (Source code)
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