diff --git a/connectors/apache-connector/src/test/java/org/glassfish/jersey/apache/connector/AuthTest.java b/connectors/apache-connector/src/test/java/org/glassfish/jersey/apache/connector/AuthTest.java
index 3da55c1ade..8f628706b3 100644
--- a/connectors/apache-connector/src/test/java/org/glassfish/jersey/apache/connector/AuthTest.java
+++ b/connectors/apache-connector/src/test/java/org/glassfish/jersey/apache/connector/AuthTest.java
@@ -64,6 +64,7 @@
 import org.apache.http.auth.AuthScope;
 import org.apache.http.auth.UsernamePasswordCredentials;
 import org.apache.http.client.CredentialsProvider;
+import org.apache.http.impl.conn.PoolingHttpClientConnectionManager;
 import org.junit.Ignore;
 import org.junit.Test;
 import static org.junit.Assert.assertEquals;
@@ -168,6 +169,19 @@ public String getFilter(@Context HttpHeaders h) {
             return "GET";
         }
 
+        @GET
+        @Path("digest")
+        public String getDigest(@Context HttpHeaders h) {
+            String value = h.getRequestHeaders().getFirst("Authorization");
+            if (value == null) {
+                throw new WebApplicationException(
+                        Response.status(401).header("WWW-Authenticate", "Digest realm=\"WallyWorld\"")
+                            .entity("Forbidden").build());
+            }
+
+            return "GET";
+        }
+
         @POST
         public String post(@Context HttpHeaders h, String e) {
             requestCount++;
@@ -278,6 +292,24 @@ public void testAuthGetWithClientFilter() {
         assertEquals("GET", r.request().get(String.class));
     }
 
+    @Test
+    public void testAuthGetWithDigestFilter() {
+        ClientConfig cc = new ClientConfig();
+        PoolingHttpClientConnectionManager cm = new PoolingHttpClientConnectionManager();
+        cc.connectorProvider(new ApacheConnectorProvider());
+        cc.property(ApacheClientProperties.CONNECTION_MANAGER, cm);
+        Client client = ClientBuilder.newClient(cc);
+        client.register(HttpAuthenticationFeature.universal("name", "password"));
+        WebTarget r = client.target(getBaseUri()).path("test/digest");
+
+        assertEquals("GET", r.request().get(String.class));
+
+        // Verify the connection that was used for the request is available for reuse
+        // and no connections are leased
+        assertEquals(cm.getTotalStats().getAvailable(), 1);
+        assertEquals(cm.getTotalStats().getLeased(), 0);
+    }
+
     @Test
     @Ignore("JERSEY-1750: Cannot retry request with a non-repeatable request entity. How to buffer the entity?"
             + " Allow repeatable write in jersey?")
diff --git a/core-client/src/main/java/org/glassfish/jersey/client/authentication/HttpAuthenticationFilter.java b/core-client/src/main/java/org/glassfish/jersey/client/authentication/HttpAuthenticationFilter.java
index 3b085f5333..5ca47a30c7 100644
--- a/core-client/src/main/java/org/glassfish/jersey/client/authentication/HttpAuthenticationFilter.java
+++ b/core-client/src/main/java/org/glassfish/jersey/client/authentication/HttpAuthenticationFilter.java
@@ -49,9 +49,9 @@
 import java.util.List;
 import java.util.Map;
 
+import javax.annotation.Priority;
 import javax.ws.rs.Priorities;
 import javax.ws.rs.client.Client;
-import javax.ws.rs.client.ClientBuilder;
 import javax.ws.rs.client.ClientRequestContext;
 import javax.ws.rs.client.ClientRequestFilter;
 import javax.ws.rs.client.ClientResponseContext;
@@ -66,8 +66,6 @@
 import javax.ws.rs.core.MultivaluedMap;
 import javax.ws.rs.core.Response;
 
-import javax.annotation.Priority;
-
 import org.glassfish.jersey.client.ClientProperties;
 import org.glassfish.jersey.client.internal.LocalizationMessages;
 
@@ -294,8 +292,16 @@ private void updateCache(ClientRequestContext request, boolean success, Type ope
      * {@code false} otherwise).
      */
     static boolean repeatRequest(ClientRequestContext request, ClientResponseContext response, String newAuthorizationHeader) {
-        Client client = request.getClient();
+        // If the failed response has an entity stream, close it. We must do this to avoid leaking a connection
+        // when we replace the entity stream of the failed response with that of the repeated response (see below).
+        // Notice that by closing the entity stream before sending the repeated request we allow the connection allocated
+        // to the failed request to be reused, if possible, for the repeated request.
+        if (response.hasEntity()) {
+            discardInputAndClose(response.getEntityStream());
+            response.setEntityStream(null);
+        }
 
+        Client client = request.getClient();
         String method = request.getMethod();
         MediaType mediaType = request.getMediaType();
         URI lUri = request.getUri();
@@ -318,6 +324,12 @@ static boolean repeatRequest(ClientRequestContext request, ClientResponseContext
 
         builder.property(REQUEST_PROPERTY_FILTER_REUSED, "true");
 
+        // Copy other properties, if any, from the original request
+        for (String propertyName : request.getPropertyNames()) {
+            Object propertyValue = request.getProperty(propertyName);
+            builder.property(propertyName, propertyValue);
+        }
+
         Invocation invocation;
         if (request.getEntity() == null) {
             invocation = builder.build(method);
@@ -443,4 +455,23 @@ static Credentials getCredentials(ClientRequestContext request, Credentials defa
             return specificCredentials != null ? specificCredentials : defaultCredentials;
         }
     }
+
+    private static void discardInputAndClose(InputStream is) {
+        byte[] buf = new byte[4096];
+        try {
+            while (true) {
+                if (is.read(buf) <= 0) {
+                    break;
+                }
+            }
+        } catch (IOException ex) {
+            // ignore
+        } finally {
+            try {
+                is.close();
+            } catch (IOException ex) {
+                // ignore
+            }
+        }
+    }
 }