diff --git a/test/core/end2end/fixtures/http_proxy_fixture.cc b/test/core/end2end/fixtures/http_proxy_fixture.cc
index ac0c953a79f49..1cac0e98de55b 100644
--- a/test/core/end2end/fixtures/http_proxy_fixture.cc
+++ b/test/core/end2end/fixtures/http_proxy_fixture.cc
@@ -68,6 +68,15 @@ struct grpc_end2end_http_proxy {
 // Connection handling
 //
 
+#define SERVER_EP_READ_FAIL 1
+#define SERVER_EP_WRITE_FAIL 2
+#define CLIENT_EP_READ_FAIL 4
+#define CLIENT_EP_WRITE_FAIL 8
+
+#define SERVER_EP_FAIL (SERVER_EP_READ_FAIL | SERVER_EP_WRITE_FAIL)
+#define CLIENT_EP_FAIL (CLIENT_EP_READ_FAIL | CLIENT_EP_WRITE_FAIL)
+#define EP_FAIL (SERVER_EP_FAIL | CLIENT_EP_FAIL)
+
 typedef struct proxy_connection {
   grpc_end2end_http_proxy* proxy;
 
@@ -76,6 +85,13 @@ typedef struct proxy_connection {
 
   gpr_refcount refcount;
 
+  // The lower four bits store the endpoint failure information
+  //   bit-0 Server endpoint read failure
+  //   bit-1 Server endpoint write failure
+  //   bit-2 Client endpoint read failure
+  //   bit-3 Client endpoint write failure
+  gpr_atm ep_state;
+
   grpc_pollset_set* pollset_set;
 
   grpc_closure on_read_request_done;
@@ -132,17 +148,50 @@ static void proxy_connection_unref(grpc_exec_ctx* exec_ctx,
 // Helper function to shut down the proxy connection.
 // Does NOT take ownership of a reference to error.
 static void proxy_connection_failed(grpc_exec_ctx* exec_ctx,
-                                    proxy_connection* conn, bool is_client,
+                                    proxy_connection* conn, int failure_type,
                                     const char* prefix, grpc_error* error) {
   const char* msg = grpc_error_string(error);
   gpr_log(GPR_INFO, "%s: %s", prefix, msg);
 
-  grpc_endpoint_shutdown(exec_ctx, conn->client_endpoint,
-                         GRPC_ERROR_REF(error));
-  if (conn->server_endpoint != nullptr) {
-    grpc_endpoint_shutdown(exec_ctx, conn->server_endpoint,
-                           GRPC_ERROR_REF(error));
+  gpr_atm ep_state;
+  gpr_atm new_ep_state;
+  while (true) {
+    ep_state = gpr_atm_no_barrier_load(&conn->ep_state);
+    new_ep_state = ep_state | failure_type;
+
+    if (ep_state == new_ep_state) {
+      break;
+    }
+
+    if (!gpr_atm_no_barrier_cas(&conn->ep_state, ep_state, new_ep_state)) {
+      continue;
+    }
+
+    // failure_type is successfully set and new_ep_state != ep_state at this
+    // point
+
+    // Shutdown the endpoint (client and/or server) if both read and write
+    // failures are observed after setting the failure_type.
+    // To prevent calling endpoint shutdown multiple times, It is important to
+    // ensure that ep_state i.e the old state, did not already have both
+    // failures set.
+    if (((ep_state & SERVER_EP_FAIL) != SERVER_EP_FAIL) &&
+        ((new_ep_state & SERVER_EP_FAIL) == SERVER_EP_FAIL)) {
+      if (conn->server_endpoint != nullptr) {
+        grpc_endpoint_shutdown(exec_ctx, conn->server_endpoint,
+                               GRPC_ERROR_REF(error));
+      }
+    }
+
+    if (((ep_state & CLIENT_EP_FAIL) != CLIENT_EP_FAIL) &&
+        ((new_ep_state & CLIENT_EP_FAIL) == CLIENT_EP_FAIL)) {
+      grpc_endpoint_shutdown(exec_ctx, conn->client_endpoint,
+                             GRPC_ERROR_REF(error));
+    }
+
+    break;
   }
+
   proxy_connection_unref(exec_ctx, conn, "conn_failed");
 }
 
@@ -152,7 +201,7 @@ static void on_client_write_done(grpc_exec_ctx* exec_ctx, void* arg,
   proxy_connection* conn = (proxy_connection*)arg;
   conn->client_is_writing = false;
   if (error != GRPC_ERROR_NONE) {
-    proxy_connection_failed(exec_ctx, conn, true /* is_client */,
+    proxy_connection_failed(exec_ctx, conn, CLIENT_EP_WRITE_FAIL,
                             "HTTP proxy client write", error);
     return;
   }
@@ -179,7 +228,7 @@ static void on_server_write_done(grpc_exec_ctx* exec_ctx, void* arg,
   proxy_connection* conn = (proxy_connection*)arg;
   conn->server_is_writing = false;
   if (error != GRPC_ERROR_NONE) {
-    proxy_connection_failed(exec_ctx, conn, false /* is_client */,
+    proxy_connection_failed(exec_ctx, conn, SERVER_EP_WRITE_FAIL,
                             "HTTP proxy server write", error);
     return;
   }
@@ -206,7 +255,7 @@ static void on_client_read_done(grpc_exec_ctx* exec_ctx, void* arg,
                                 grpc_error* error) {
   proxy_connection* conn = (proxy_connection*)arg;
   if (error != GRPC_ERROR_NONE) {
-    proxy_connection_failed(exec_ctx, conn, true /* is_client */,
+    proxy_connection_failed(exec_ctx, conn, CLIENT_EP_READ_FAIL,
                             "HTTP proxy client read", error);
     return;
   }
@@ -239,7 +288,7 @@ static void on_server_read_done(grpc_exec_ctx* exec_ctx, void* arg,
                                 grpc_error* error) {
   proxy_connection* conn = (proxy_connection*)arg;
   if (error != GRPC_ERROR_NONE) {
-    proxy_connection_failed(exec_ctx, conn, false /* is_client */,
+    proxy_connection_failed(exec_ctx, conn, SERVER_EP_READ_FAIL,
                             "HTTP proxy server read", error);
     return;
   }
@@ -272,7 +321,7 @@ static void on_write_response_done(grpc_exec_ctx* exec_ctx, void* arg,
   proxy_connection* conn = (proxy_connection*)arg;
   conn->client_is_writing = false;
   if (error != GRPC_ERROR_NONE) {
-    proxy_connection_failed(exec_ctx, conn, true /* is_client */,
+    proxy_connection_failed(exec_ctx, conn, EP_FAIL,
                             "HTTP proxy write response", error);
     return;
   }
@@ -301,7 +350,7 @@ static void on_server_connect_done(grpc_exec_ctx* exec_ctx, void* arg,
     // connection failed.  However, for the purposes of this test code,
     // it's fine to pretend this is a client-side error, which will
     // cause the client connection to be dropped.
-    proxy_connection_failed(exec_ctx, conn, true /* is_client */,
+    proxy_connection_failed(exec_ctx, conn, EP_FAIL,
                             "HTTP proxy server connect", error);
     return;
   }
@@ -351,8 +400,8 @@ static void on_read_request_done(grpc_exec_ctx* exec_ctx, void* arg,
   gpr_log(GPR_DEBUG, "on_read_request_done: %p %s", conn,
           grpc_error_string(error));
   if (error != GRPC_ERROR_NONE) {
-    proxy_connection_failed(exec_ctx, conn, true /* is_client */,
-                            "HTTP proxy read request", error);
+    proxy_connection_failed(exec_ctx, conn, EP_FAIL, "HTTP proxy read request",
+                            error);
     return;
   }
   // Read request and feed it to the parser.
@@ -361,7 +410,7 @@ static void on_read_request_done(grpc_exec_ctx* exec_ctx, void* arg,
       error = grpc_http_parser_parse(
           &conn->http_parser, conn->client_read_buffer.slices[i], nullptr);
       if (error != GRPC_ERROR_NONE) {
-        proxy_connection_failed(exec_ctx, conn, true /* is_client */,
+        proxy_connection_failed(exec_ctx, conn, EP_FAIL,
                                 "HTTP proxy request parse", error);
         GRPC_ERROR_UNREF(error);
         return;
@@ -382,8 +431,8 @@ static void on_read_request_done(grpc_exec_ctx* exec_ctx, void* arg,
                  conn->http_request.method);
     error = GRPC_ERROR_CREATE_FROM_COPIED_STRING(msg);
     gpr_free(msg);
-    proxy_connection_failed(exec_ctx, conn, true /* is_client */,
-                            "HTTP proxy read request", error);
+    proxy_connection_failed(exec_ctx, conn, EP_FAIL, "HTTP proxy read request",
+                            error);
     GRPC_ERROR_UNREF(error);
     return;
   }
@@ -403,7 +452,7 @@ static void on_read_request_done(grpc_exec_ctx* exec_ctx, void* arg,
     if (!client_authenticated) {
       const char* msg = "HTTP Connect could not verify authentication";
       error = GRPC_ERROR_CREATE_FROM_STATIC_STRING(msg);
-      proxy_connection_failed(exec_ctx, conn, true /* is_client */,
+      proxy_connection_failed(exec_ctx, conn, EP_FAIL,
                               "HTTP proxy read request", error);
       GRPC_ERROR_UNREF(error);
       return;
@@ -414,8 +463,8 @@ static void on_read_request_done(grpc_exec_ctx* exec_ctx, void* arg,
   error = grpc_blocking_resolve_address(conn->http_request.path, "80",
                                         &resolved_addresses);
   if (error != GRPC_ERROR_NONE) {
-    proxy_connection_failed(exec_ctx, conn, true /* is_client */,
-                            "HTTP proxy DNS lookup", error);
+    proxy_connection_failed(exec_ctx, conn, EP_FAIL, "HTTP proxy DNS lookup",
+                            error);
     GRPC_ERROR_UNREF(error);
     return;
   }
@@ -441,6 +490,7 @@ static void on_accept(grpc_exec_ctx* exec_ctx, void* arg,
   conn->client_endpoint = endpoint;
   conn->proxy = proxy;
   gpr_ref_init(&conn->refcount, 1);
+  gpr_atm_no_barrier_store(&conn->ep_state, 0);
   conn->pollset_set = grpc_pollset_set_create();
   grpc_pollset_set_add_pollset(exec_ctx, conn->pollset_set, proxy->pollset);
   grpc_endpoint_add_to_pollset_set(exec_ctx, endpoint, conn->pollset_set);