>This is with Squid 2.5.STABLE3 and Samba 2.2.8a. NTLM authentication is 
>working for the most part, but every so often a user is prompted with a 
>basic password for some reason.

Hi,

I had the same behaviour.
I solved it with the following patch:


------------------- CUT HERE -------------------
--- squid-2.5.STABLE2-20030401/src/auth/ntlm/auth_ntlm.c        2003-02-05 
00:17:26.000000000 +0100
+++ squid-2.5.STABLE2-20030401-ntmulti/src/auth/ntlm/auth_ntlm.c 
2003-05-16 14:56:17.000000000 +0200
@@ -719,15 +719,7 @@
         */
        server = helperStatefulDefer(ntlmauthenticators);
        helperstate = server ? helperStatefulServerGetData(server) : NULL;
-       while ((server != NULL) && 
authenticateNTLMChangeChallenge_p(helperstate)) {
-           /* flag this helper for challenge changing */
-           helperstate->starve = 1;
-           /* and release the deferred request */
-           helperStatefulReleaseServer(server);
-           /* Get another deferrable server */
-           server = helperStatefulDefer(ntlmauthenticators);
-           helperstate = server ? helperStatefulServerGetData(server) : 
NULL;
-       }
+       if (helperstate) helperstate->starve = 1;
        if (server == NULL)
            debug(29, 9) ("unable to get a deferred ntlm helper... all 
helpers are refreshing challenges. Queuing as a placeholder request.\n");
------------------- CUT HERE -------------------

BE CAREFUL: 
1) I applied the patch to suid-2.5.STABLE2 and not to STABLE3.
2) I'm not a squid guru.

You can test it with only 1 helper started (auth_param ntlm children 1) to increase 
the probability of popup windows.

If you can confirm correct behaviour of this patch, a squid developper can 
review and approve/reject it (please ...).

ciao
Michele

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