If you want to authinticate someone through apache, there is a mod_pam
module that lets apache go to a PAM sorce for authintication. (You will have
to chage existing .htaccess files not to go to PAM, see documentation)

If you only have 95/98 clients, using the latest samba as a domain
controller should be fin. NT4 should be ok too, but won't do everything. (9x
doesn't fully suport every feature of domain, samba caters to this right
now)

There are two PAM modules you could use. pam-smb-auth and pam-ntdom. For
your situation, I'd go with pam-smb-auth. 

You might want to consider squid instead of apache. 

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