diff --git a/core/src/main/java/org/springframework/security/remoting/httpinvoker/AuthenticationSimpleHttpInvokerRequestExecutor.java b/core/src/main/java/org/springframework/security/remoting/httpinvoker/AuthenticationSimpleHttpInvokerRequestExecutor.java
index 6bde4a9742..d294773bd8 100644
--- a/core/src/main/java/org/springframework/security/remoting/httpinvoker/AuthenticationSimpleHttpInvokerRequestExecutor.java
+++ b/core/src/main/java/org/springframework/security/remoting/httpinvoker/AuthenticationSimpleHttpInvokerRequestExecutor.java
@@ -21,6 +21,8 @@ import java.net.HttpURLConnection;
 import org.apache.commons.logging.Log;
 import org.apache.commons.logging.LogFactory;
 import org.springframework.remoting.httpinvoker.SimpleHttpInvokerRequestExecutor;
+import org.springframework.security.authentication.AuthenticationTrustResolver;
+import org.springframework.security.authentication.AuthenticationTrustResolverImpl;
 import org.springframework.security.core.Authentication;
 import org.springframework.security.core.codec.Base64;
 import org.springframework.security.core.context.SecurityContextHolder;
@@ -30,12 +32,17 @@ import org.springframework.security.core.context.SecurityContextHolder;
  * Adds BASIC authentication support to <code>SimpleHttpInvokerRequestExecutor</code>.
  *
  * @author Ben Alex
+ * @author Rob Winch
  */
 public class AuthenticationSimpleHttpInvokerRequestExecutor extends SimpleHttpInvokerRequestExecutor {
     //~ Static fields/initializers =====================================================================================
 
     private static final Log logger = LogFactory.getLog(AuthenticationSimpleHttpInvokerRequestExecutor.class);
 
+    //~ Instance fields ================================================================================================
+
+    private AuthenticationTrustResolver trustResolver = new AuthenticationTrustResolverImpl();
+
     //~ Methods ========================================================================================================
 
     /**
@@ -65,7 +72,7 @@ public class AuthenticationSimpleHttpInvokerRequestExecutor extends SimpleHttpIn
 
         Authentication auth = SecurityContextHolder.getContext().getAuthentication();
 
-        if ((auth != null) && (auth.getName() != null) && (auth.getCredentials() != null)) {
+        if ((auth != null) && (auth.getName() != null) && (auth.getCredentials() != null) && !trustResolver.isAnonymous(auth)) {
             String base64 = auth.getName() + ":" + auth.getCredentials().toString();
             con.setRequestProperty("Authorization", "Basic " + new String(Base64.encode(base64.getBytes())));
 
diff --git a/core/src/test/java/org/springframework/security/remoting/httpinvoker/AuthenticationSimpleHttpInvokerRequestExecutorTests.java b/core/src/test/java/org/springframework/security/remoting/httpinvoker/AuthenticationSimpleHttpInvokerRequestExecutorTests.java
index d32d1665d5..0990a2bccb 100644
--- a/core/src/test/java/org/springframework/security/remoting/httpinvoker/AuthenticationSimpleHttpInvokerRequestExecutorTests.java
+++ b/core/src/test/java/org/springframework/security/remoting/httpinvoker/AuthenticationSimpleHttpInvokerRequestExecutorTests.java
@@ -18,8 +18,10 @@ package org.springframework.security.remoting.httpinvoker;
 import junit.framework.TestCase;
 
 
+import org.springframework.security.authentication.AnonymousAuthenticationToken;
 import org.springframework.security.authentication.UsernamePasswordAuthenticationToken;
 import org.springframework.security.core.Authentication;
+import org.springframework.security.core.authority.AuthorityUtils;
 import org.springframework.security.core.context.SecurityContextHolder;
 
 import org.springframework.security.remoting.httpinvoker.AuthenticationSimpleHttpInvokerRequestExecutor;
@@ -37,6 +39,7 @@ import java.util.Map;
  * Tests {@link AuthenticationSimpleHttpInvokerRequestExecutor}.
  *
  * @author Ben Alex
+ * @author Rob Winch
  */
 public class AuthenticationSimpleHttpInvokerRequestExecutorTests extends TestCase {
 
@@ -77,6 +80,22 @@ public class AuthenticationSimpleHttpInvokerRequestExecutorTests extends TestCas
         assertNull(conn.getRequestProperty("Authorization"));
     }
 
+    // SEC-1975
+    public void testNullContextHolderWhenAnonymous() throws Exception {
+        AnonymousAuthenticationToken anonymous = new AnonymousAuthenticationToken("key", "principal",
+                AuthorityUtils.createAuthorityList("ROLE_ANONYMOUS"));
+        SecurityContextHolder.getContext().setAuthentication(anonymous);
+
+        // Create a connection and ensure our executor sets its
+        // properties correctly
+        AuthenticationSimpleHttpInvokerRequestExecutor executor = new AuthenticationSimpleHttpInvokerRequestExecutor();
+        HttpURLConnection conn = new MockHttpURLConnection(new URL("http://localhost/"));
+        executor.prepareConnection(conn, 10);
+
+        // Check connection properties (shouldn't be an Authorization header)
+        assertNull(conn.getRequestProperty("Authorization"));
+    }
+
     //~ Inner Classes ==================================================================================================
 
     private class MockHttpURLConnection extends HttpURLConnection {