diff --git a/org.eclipse.jgit.http.test/tst/org/eclipse/jgit/http/test/SmartClientSmartServerTest.java b/org.eclipse.jgit.http.test/tst/org/eclipse/jgit/http/test/SmartClientSmartServerTest.java
index 51a7a8ddc..8d1870a87 100644
--- a/org.eclipse.jgit.http.test/tst/org/eclipse/jgit/http/test/SmartClientSmartServerTest.java
+++ b/org.eclipse.jgit.http.test/tst/org/eclipse/jgit/http/test/SmartClientSmartServerTest.java
@@ -112,6 +112,10 @@ public class SmartClientSmartServerTest extends AllFactoriesHttpTestCase {
 
 	private URIish authOnPostURI;
 
+	private URIish slowURI;
+
+	private URIish slowAuthURI;
+
 	private RevBlob A_txt;
 
 	private RevCommit A, B, unreachableCommit;
@@ -152,6 +156,10 @@ public class SmartClientSmartServerTest extends AllFactoriesHttpTestCase {
 
 		ServletContextHandler authOnPost = addAuthContext(gs, "pauth", "POST");
 
+		ServletContextHandler slow = addSlowContext(gs, "slow", false);
+
+		ServletContextHandler slowAuth = addSlowContext(gs, "slowAuth", true);
+
 		server.setUp();
 
 		remoteRepository = src.getRepository();
@@ -160,6 +168,8 @@ public class SmartClientSmartServerTest extends AllFactoriesHttpTestCase {
 		redirectURI = toURIish(redirect, srcName);
 		authURI = toURIish(auth, srcName);
 		authOnPostURI = toURIish(authOnPost, srcName);
+		slowURI = toURIish(slow, srcName);
+		slowAuthURI = toURIish(slowAuth, srcName);
 
 		A_txt = src.blob("A");
 		A = src.commit().add("A_txt", A_txt).create();
@@ -372,6 +382,43 @@ public class SmartClientSmartServerTest extends AllFactoriesHttpTestCase {
 		return redirect;
 	}
 
+	private ServletContextHandler addSlowContext(GitServlet gs, String path,
+			boolean auth) {
+		ServletContextHandler slow = server.addContext('/' + path);
+		slow.addFilter(new FilterHolder(new Filter() {
+
+			@Override
+			public void init(FilterConfig filterConfig)
+					throws ServletException {
+				// empty
+			}
+
+			// Simply delays the servlet for two seconds. Used for timeout
+			// tests, which use a one-second timeout.
+			@Override
+			public void doFilter(ServletRequest request,
+					ServletResponse response, FilterChain chain)
+					throws IOException, ServletException {
+				try {
+					Thread.sleep(2000);
+				} catch (InterruptedException e) {
+					throw new IOException(e);
+				}
+				chain.doFilter(request, response);
+			}
+
+			@Override
+			public void destroy() {
+				// empty
+			}
+		}), "/*", EnumSet.of(DispatcherType.REQUEST));
+		slow.addServlet(new ServletHolder(gs), "/*");
+		if (auth) {
+			return server.authBasic(slow);
+		}
+		return slow;
+	}
+
 	@Test
 	public void testListRemote() throws IOException {
 		assertEquals("http", remoteURI.getScheme());
@@ -488,6 +535,35 @@ public class SmartClientSmartServerTest extends AllFactoriesHttpTestCase {
 		}
 	}
 
+	@Test
+	public void testTimeoutExpired() throws Exception {
+		try (Repository dst = createBareRepository();
+				Transport t = Transport.open(dst, slowURI)) {
+			t.setTimeout(1);
+			TransportException expected = assertThrows(TransportException.class,
+					() -> t.fetch(NullProgressMonitor.INSTANCE,
+							mirror(master)));
+			assertTrue("Unexpected exception message: " + expected.toString(),
+					expected.getMessage().contains("time"));
+		}
+	}
+
+	@Test
+	public void testTimeoutExpiredWithAuth() throws Exception {
+		try (Repository dst = createBareRepository();
+				Transport t = Transport.open(dst, slowAuthURI)) {
+			t.setTimeout(1);
+			t.setCredentialsProvider(testCredentials);
+			TransportException expected = assertThrows(TransportException.class,
+					() -> t.fetch(NullProgressMonitor.INSTANCE,
+							mirror(master)));
+			assertTrue("Unexpected exception message: " + expected.toString(),
+					expected.getMessage().contains("time"));
+			assertFalse("Unexpected exception message: " + expected.toString(),
+					expected.getMessage().contains("auth"));
+		}
+	}
+
 	@Test
 	public void testInitialClone_Small() throws Exception {
 		try (Repository dst = createBareRepository();
diff --git a/org.eclipse.jgit/src/org/eclipse/jgit/transport/TransportHttp.java b/org.eclipse.jgit/src/org/eclipse/jgit/transport/TransportHttp.java
index c3c1f2a40..16169f028 100644
--- a/org.eclipse.jgit/src/org/eclipse/jgit/transport/TransportHttp.java
+++ b/org.eclipse.jgit/src/org/eclipse/jgit/transport/TransportHttp.java
@@ -39,11 +39,13 @@ import java.io.FileNotFoundException;
 import java.io.IOException;
 import java.io.InputStream;
 import java.io.InputStreamReader;
+import java.io.InterruptedIOException;
 import java.io.OutputStream;
 import java.net.HttpCookie;
 import java.net.MalformedURLException;
 import java.net.Proxy;
 import java.net.ProxySelector;
+import java.net.SocketException;
 import java.net.URI;
 import java.net.URISyntaxException;
 import java.net.URL;
@@ -573,6 +575,14 @@ public class TransportHttp extends HttpTransport implements WalkTransport,
 				}
 			} catch (NotSupportedException | TransportException e) {
 				throw e;
+			} catch (InterruptedIOException e) {
+				// Timeout!? Don't try other authentication methods.
+				throw new TransportException(uri, MessageFormat.format(
+						JGitText.get().connectionTimeOut, u.getHost()), e);
+			} catch (SocketException e) {
+				// Nothing on other end, timeout, connection reset, ...
+				throw new TransportException(uri,
+						JGitText.get().connectionFailed, e);
 			} catch (SSLHandshakeException e) {
 				handleSslFailure(e);
 				continue; // Re-try
@@ -1501,6 +1511,10 @@ public class TransportHttp extends HttpTransport implements WalkTransport,
 				} catch (SSLHandshakeException e) {
 					handleSslFailure(e);
 					continue; // Re-try
+				} catch (SocketException | InterruptedIOException e) {
+					// Timeout!? Must propagate; don't try other authentication
+					// methods.
+					throw e;
 				} catch (IOException e) {
 					if (authenticator == null || authMethod
 							.getType() != HttpAuthMethod.Type.NONE) {