When the students go to gmail.com, the authentication pop-up just keeps occurring. The student can cancel out of it and get logged in, but it still keeps doing it and will never accept the password. They just have to keep cancelling out of it. I authenticate with my ldap server. Here are the lines in my squid that are causing this. acl bpsblocked dstdomain "/home/bloomfield/blocked/domains" http_access deny bpsblocked !teacher_group http_access deny banned_users http_access allow ldap_username http_access allow localnet http_access allow localhost The bpsblocked !teacher_group is what is causing it. Those are a list of blocked sites that are blocked for students, but are not for teachers. Nothing pertaining to gmail or google is in that list. I can remark the statement out and then the students are fine and it does not keep popping up. Here is the list of sites that is in that file in case someone sees something that I don't. .xxx .2dplay.com .access-any-website.com .alot.com .andkon.com .bing.com .bored.com .boxhead2player.net .chickipedia.com .cmtv.com .cowboylyrics.com .dailyunblocker.com .dtunnel .facebook.com .fastgames.com .file.mubbit.com .filestube.com .funcorder.com .grooveshark.com .hotornot.com .ilike.com .iviewtube.com .jerryspringertv.com .leetgaming.org .metacafe.com .mosports.com .mosports.rivals.com .mtv.com .music.com .myspace.com .netflix.com .notdoppler.com .nuip.net .omegle.com .pandora.com .pinktube.com .pinktube.net .pinterest.com .plazmaburst2.com .prehackshub.com .realraptalk.com .rottentomatoes.com .runescape.com .scumlabs.com .sex.com .slack-time.com .thegamehomepage.com .tr3s.com .videolife.tk .wattpad.com .youtube.com .vtunnel -- Scott Mayo