This is correct: 

grant codeBase "file:${catalina.home}/webapps/my_app/WEB-INF/-" {
     permission java.io.FilePermission "${catalina.home}/webapps/my_app/file1.txt",
                                       "read,write,delete";
};

This is correct: 

grant codeBase "file:${catalina.home}/webapps/my_app/WEB-INF/-" {
     permission java.io.FilePermission "${catalina.home}\\webapps\\my_app\\file1.txt",
                                       "read,write,delete";
};

This is NOT correct: 

grant codeBase "file:${catalina.home}/webapps/my_app/WEB-INF/-" {
     permission java.io.FilePermission "${catalina.home}/webapps/my_app/-",
                                       "read,write,delete";
};

This is NOT correct: 

grant codeBase "file:${catalina.home}/webapps/my_app/WEB-INF/-" {
     permission java.io.FilePermission "${catalina.home}\\webapps\\my_app\\-",
                                       "read,write,delete";
};

This is *correct*: 

grant codeBase "file:${catalina.home}/webapps/my_app/WEB-INF/-" {
     permission java.io.FilePermission "${catalina.home}${/}webapps${/}my_app${/}-",
                                       "read,write,delete";
};

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