Well there is a workaround using expect or pexpect or similar perl
module but I agree this should be a feature of the core code.

This should be relatively easy. A patch to roundup/admin.py in the
do_initialize function should make this work. I suggest using:

  initialize -f filename

for this case and checking for args > 1 and args[1] cto be -f
then opening the filename and reading the first line for the 
password. The code change needs to occur near:

         # password
        if len(args) > 1:
            adminpw = args[1]
        else:

It should keep it backwards compatible when used with a
single password argument. (Also is the code above a bug?
initialise shouldn't allow > 1 argument currently as the
additional args are ignored.)