diff --git a/headers/os/net/HttpRequest.h b/headers/os/net/HttpRequest.h
index 2c4248cac2..d18222a1b0 100644
--- a/headers/os/net/HttpRequest.h
+++ b/headers/os/net/HttpRequest.h
@@ -9,7 +9,6 @@
 #include <deque>
 
 
-#include <HttpAuthentication.h>
 #include <HttpForm.h>
 #include <HttpHeaders.h>
 #include <HttpResult.h>
@@ -93,7 +92,6 @@ private:
 			BNetBuffer			fInputBuffer;
 
 			BHttpHeaders		fHeaders;
-			BHttpAuthentication	fAuthentication;
 
 	// Request status
 
diff --git a/headers/os/net/UrlContext.h b/headers/os/net/UrlContext.h
index 414a371106..6a4541f073 100644
--- a/headers/os/net/UrlContext.h
+++ b/headers/os/net/UrlContext.h
@@ -6,22 +6,36 @@
 #define _B_URL_CONTEXT_H_
 
 
+#include <HttpAuthentication.h>
 #include <NetworkCookieJar.h>
 
 
+namespace BPrivate {
+	template <class key, class value> class HashMap;
+	class HashString;
+}
+
+
 class BUrlContext {
 public:
 								BUrlContext();
+								~BUrlContext();
 
 	// Context modifiers
 			void				SetCookieJar(
 									const BNetworkCookieJar& cookieJar);
+			void				AddAuthentication(const BUrl& url,
+									BHttpAuthentication* const authentication);
 											
 	// Context accessors
 			BNetworkCookieJar&	GetCookieJar();
+			BHttpAuthentication& GetAuthentication(const BUrl& url);
 
 private:
 			BNetworkCookieJar	fCookieJar;
+			typedef BPrivate::HashMap<BPrivate::HashString,
+				BHttpAuthentication*> BHttpAuthenticationMap;
+			BHttpAuthenticationMap* fAuthenticationMap;
 };
 
 #endif // _B_URL_CONTEXT_H_
diff --git a/src/kits/network/libnetapi/HttpRequest.cpp b/src/kits/network/libnetapi/HttpRequest.cpp
index 7b19990f85..6330a3025c 100644
--- a/src/kits/network/libnetapi/HttpRequest.cpp
+++ b/src/kits/network/libnetapi/HttpRequest.cpp
@@ -344,22 +344,35 @@ BHttpRequest::_ProtocolLoop()
 				break;
 
 			case B_HTTP_STATUS_CLASS_CLIENT_ERROR:
-				switch (fResult.StatusCode()) {
-					case B_HTTP_STATUS_UNAUTHORIZED:
-						if (fAuthentication.Method() != B_HTTP_AUTHENTICATION_NONE) {
-							newRequest = false;
-							break;
-						}
+				if(fResult.StatusCode() == B_HTTP_STATUS_UNAUTHORIZED) {
+					BHttpAuthentication* authentication
+						= &fContext->GetAuthentication(fUrl);
+					status_t status = B_OK;
 
-						newRequest = false;
-						if (fOptUsername.Length() > 0
-							&& fAuthentication.Initialize(fHeaders["WWW-Authenticate"])
-								== B_OK) {
-							fAuthentication.SetUserName(fOptUsername);
-							fAuthentication.SetPassword(fOptPassword);
-							newRequest = true;
-						}
-						break;
+					if (authentication->Method() == B_HTTP_AUTHENTICATION_NONE)
+					{
+						// There is no authentication context for this
+						// url yet, so let's create one.
+						authentication = new BHttpAuthentication();
+						status = authentication->Initialize(
+							fHeaders["WWW-Authenticate"]);
+						fContext->AddAuthentication(fUrl, authentication);
+					}
+
+					newRequest = false;
+					if (fOptUsername.Length() > 0 && status == B_OK) {
+						// If we received an username and password, add them
+						// to the request. This will either change the
+						// credentials for an existing request, or set them
+						// for a new one we created just above.
+						//
+						// If this request handles HTTP redirections, it will
+						// also automatically retry connecting and send the
+						// login information.
+						authentication->SetUserName(fOptUsername);
+						authentication->SetPassword(fOptPassword);
+						newRequest = true;
+					}
 				}
 				break;
 
@@ -811,11 +824,16 @@ BHttpRequest::_AddHeaders()
 		fOutputHeaders.AddHeader("Referer", fOptReferer.String());
 
 	// Authentication
-	if (fAuthentication.Method() != B_HTTP_AUTHENTICATION_NONE) {
-		BString request(fRequestMethod);
+	BHttpAuthentication& authentication = fContext->GetAuthentication(fUrl);
+	if (authentication.Method() != B_HTTP_AUTHENTICATION_NONE) {
+		if (fOptUsername.Length() > 0) {
+			authentication.SetUserName(fOptUsername);
+			authentication.SetPassword(fOptPassword);
+		}
 
+		BString request(fRequestMethod);
 		fOutputHeaders.AddHeader("Authorization",
-			fAuthentication.Authorization(fUrl, request));
+			authentication.Authorization(fUrl, request));
 	}
 
 	// Required headers for POST data
diff --git a/src/kits/network/libnetapi/UrlContext.cpp b/src/kits/network/libnetapi/UrlContext.cpp
index a8693043c2..429eb5918d 100644
--- a/src/kits/network/libnetapi/UrlContext.cpp
+++ b/src/kits/network/libnetapi/UrlContext.cpp
@@ -9,11 +9,35 @@
 
 #include <UrlContext.h>
 
+#include <stdio.h>
+
+#include <HashMap.h>
+#include <HashString.h>
+
 
 BUrlContext::BUrlContext()
 	: 
-	fCookieJar()
+	fCookieJar(),
+	fAuthenticationMap(NULL)
 {
+	fAuthenticationMap = new(std::nothrow) BHttpAuthenticationMap();
+	if(!fAuthenticationMap)
+		return;
+	// This is the default authentication, used when nothing else is found.
+	// The empty string used as a key will match all the domain strings, once
+	// we have removed all components.
+	fAuthenticationMap->Put(HashString("", 0), new BHttpAuthentication());
+}
+
+
+BUrlContext::~BUrlContext()
+{
+	BHttpAuthenticationMap::Iterator iterator =
+		fAuthenticationMap->GetIterator();
+	while(iterator.HasNext())
+		delete iterator.Remove().value;
+
+	delete fAuthenticationMap;
 }
 
 
@@ -27,6 +51,21 @@ BUrlContext::SetCookieJar(const BNetworkCookieJar& cookieJar)
 }
 
 
+void
+BUrlContext::AddAuthentication(const BUrl& url,
+	BHttpAuthentication* const authentication)
+{
+	BString domain = url.Host();
+	domain += url.Path();
+	BPrivate::HashString hostHash(domain.String(), domain.Length());
+
+	delete fAuthenticationMap->Get(hostHash);
+		// Make sure we don't leak memory by overriding a previous
+		// authentication for the same domain.
+	fAuthenticationMap->Put(hostHash, authentication);
+}
+
+
 // #pragma mark Context accessors
 
 
@@ -35,3 +74,23 @@ BUrlContext::GetCookieJar()
 {
 	return fCookieJar;
 }
+
+
+BHttpAuthentication&
+BUrlContext::GetAuthentication(const BUrl& url)
+{
+	BString domain = url.Host();
+	domain += url.Path();
+
+	BHttpAuthentication* authentication = NULL;
+
+	do {
+		authentication = fAuthenticationMap->Get( HashString(domain.String(),
+			domain.Length()));
+
+		domain.Truncate(domain.FindLast('/'));
+
+	} while(authentication == NULL);
+
+	return *authentication;
+}