diff --git a/src/core/ext/client_channel/http_connect_handshaker.c b/src/core/ext/client_channel/http_connect_handshaker.c
index c9861a5aed246705cb3a6eceb36d554705e4f1de..48990f9dacc54319c65e4ef3ad362a00ae2b90fd 100644
--- a/src/core/ext/client_channel/http_connect_handshaker.c
+++ b/src/core/ext/client_channel/http_connect_handshaker.c
@@ -41,6 +41,7 @@
 #include <grpc/support/string_util.h>
 
 #include "src/core/ext/client_channel/uri_parser.h"
+#include "src/core/lib/channel/channel_args.h"
 #include "src/core/lib/http/format_request.h"
 #include "src/core/lib/http/parser.h"
 #include "src/core/lib/support/env.h"
@@ -55,9 +56,12 @@ typedef struct http_connect_handshaker {
   gpr_refcount refcount;
   gpr_mu mu;
 
+  bool shutdown;
+  // Endpoint and read buffer to destroy after a shutdown.
+  grpc_endpoint* endpoint_to_destroy;
+  grpc_slice_buffer* read_buffer_to_destroy;
+
   // State saved while performing the handshake.
-  // args will be NULL when either there is no handshake in progress or
-  // when the handshaker is shutting down.
   grpc_handshaker_args* args;
   grpc_closure* on_handshake_done;
 
@@ -70,9 +74,17 @@ typedef struct http_connect_handshaker {
 } http_connect_handshaker;
 
 // Unref and clean up handshaker.
-static void http_connect_handshaker_unref(http_connect_handshaker* handshaker) {
+static void http_connect_handshaker_unref(grpc_exec_ctx* exec_ctx,
+                                          http_connect_handshaker* handshaker) {
   if (gpr_unref(&handshaker->refcount)) {
     gpr_mu_destroy(&handshaker->mu);
+    if (handshaker->endpoint_to_destroy != NULL) {
+      grpc_endpoint_destroy(exec_ctx, handshaker->endpoint_to_destroy);
+    }
+    if (handshaker->read_buffer_to_destroy != NULL) {
+      grpc_slice_buffer_destroy(handshaker->read_buffer_to_destroy);
+      gpr_free(handshaker->read_buffer_to_destroy);
+    }
     gpr_free(handshaker->proxy_server);
     gpr_free(handshaker->server_name);
     grpc_slice_buffer_destroy(&handshaker->write_buffer);
@@ -82,18 +94,42 @@ static void http_connect_handshaker_unref(http_connect_handshaker* handshaker) {
   }
 }
 
+// Set args fields to NULL, saving the endpoint and read buffer for
+// later destruction.
+static void cleanup_args_for_failure_locked(
+    http_connect_handshaker* handshaker) {
+  handshaker->endpoint_to_destroy = handshaker->args->endpoint;
+  handshaker->args->endpoint = NULL;
+  handshaker->read_buffer_to_destroy = handshaker->args->read_buffer;
+  handshaker->args->read_buffer = NULL;
+  grpc_channel_args_destroy(handshaker->args->args);
+  handshaker->args->args = NULL;
+}
+
 // Callback invoked when finished writing HTTP CONNECT request.
 static void on_write_done(grpc_exec_ctx* exec_ctx, void* arg,
                           grpc_error* error) {
   http_connect_handshaker* handshaker = arg;
   gpr_mu_lock(&handshaker->mu);
-  if (error != GRPC_ERROR_NONE || handshaker->args == NULL) {
-    // If the write failed, invoke the callback immediately with the error.
-    grpc_exec_ctx_sched(exec_ctx, handshaker->on_handshake_done,
-                        GRPC_ERROR_REF(error), NULL);
-    handshaker->args = NULL;
+  if (error != GRPC_ERROR_NONE || handshaker->shutdown) {
+    // If the write failed or we're shutting down, clean up and invoke the
+    // callback with the error.
+    if (error == GRPC_ERROR_NONE) {
+      // If we were shut down after the write succeeded but before this
+      // callback was invoked, we need to generate our own error.
+      error = GRPC_ERROR_CREATE("Handshaker shutdown");
+    } else {
+      GRPC_ERROR_REF(error);  // Take ref for the handshake-done callback.
+    }
+    if (!handshaker->shutdown) {
+      // Not shutting down, so the write failed.  Clean up before
+      // invoking the callback.
+      cleanup_args_for_failure_locked(handshaker);
+    }
+    // Invoke callback.
+    grpc_exec_ctx_sched(exec_ctx, handshaker->on_handshake_done, error, NULL);
     gpr_mu_unlock(&handshaker->mu);
-    http_connect_handshaker_unref(handshaker);
+    http_connect_handshaker_unref(exec_ctx, handshaker);
   } else {
     // Otherwise, read the response.
     // The read callback inherits our ref to the handshaker.
@@ -109,8 +145,21 @@ static void on_read_done(grpc_exec_ctx* exec_ctx, void* arg,
                          grpc_error* error) {
   http_connect_handshaker* handshaker = arg;
   gpr_mu_lock(&handshaker->mu);
-  if (error != GRPC_ERROR_NONE || handshaker->args == NULL) {
-    GRPC_ERROR_REF(error);  // Take ref to pass to the handshake-done callback.
+  if (error != GRPC_ERROR_NONE || handshaker->shutdown) {
+    // If the write failed or we're shutting down, clean up and invoke the
+    // callback with the error.
+    if (error == GRPC_ERROR_NONE) {
+      // If we were shut down after the write succeeded but before this
+      // callback was invoked, we need to generate our own error.
+      error = GRPC_ERROR_CREATE("Handshaker shutdown");
+    } else {
+      GRPC_ERROR_REF(error);  // Take ref for the handshake-done callback.
+    }
+    if (!handshaker->shutdown) {
+      // Not shutting down, so the write failed.  Clean up before
+      // invoking the callback.
+      cleanup_args_for_failure_locked(handshaker);
+    }
     goto done;
   }
   // Add buffer to parser.
@@ -172,10 +221,9 @@ static void on_read_done(grpc_exec_ctx* exec_ctx, void* arg,
   }
 done:
   // Invoke handshake-done callback.
-  handshaker->args = NULL;
   grpc_exec_ctx_sched(exec_ctx, handshaker->on_handshake_done, error, NULL);
   gpr_mu_unlock(&handshaker->mu);
-  http_connect_handshaker_unref(handshaker);
+  http_connect_handshaker_unref(exec_ctx, handshaker);
 }
 
 //
@@ -185,16 +233,17 @@ done:
 static void http_connect_handshaker_destroy(grpc_exec_ctx* exec_ctx,
                                             grpc_handshaker* handshaker_in) {
   http_connect_handshaker* handshaker = (http_connect_handshaker*)handshaker_in;
-  http_connect_handshaker_unref(handshaker);
+  http_connect_handshaker_unref(exec_ctx, handshaker);
 }
 
 static void http_connect_handshaker_shutdown(grpc_exec_ctx* exec_ctx,
                                              grpc_handshaker* handshaker_in) {
   http_connect_handshaker* handshaker = (http_connect_handshaker*)handshaker_in;
   gpr_mu_lock(&handshaker->mu);
-  if (handshaker->args != NULL) {
+  if (!handshaker->shutdown) {
+    handshaker->shutdown = true;
     grpc_endpoint_shutdown(exec_ctx, handshaker->args->endpoint);
-    handshaker->args = NULL;
+    cleanup_args_for_failure_locked(handshaker);
   }
   gpr_mu_unlock(&handshaker->mu);
 }
diff --git a/src/core/ext/transport/chttp2/client/insecure/channel_create.c b/src/core/ext/transport/chttp2/client/insecure/channel_create.c
index e0bce57fc28bfb99ed6d4a75b9ed4b145849a7fe..00b272de2706bb6530776a835755e672043c8f48 100644
--- a/src/core/ext/transport/chttp2/client/insecure/channel_create.c
+++ b/src/core/ext/transport/chttp2/client/insecure/channel_create.c
@@ -96,11 +96,7 @@ static void on_handshake_done(grpc_exec_ctx *exec_ctx, void *arg,
                               grpc_error *error) {
   grpc_handshaker_args *args = arg;
   connector *c = args->user_data;
-  if (error != GRPC_ERROR_NONE) {
-    grpc_endpoint_destroy(exec_ctx, args->endpoint);
-    grpc_channel_args_destroy(args->args);
-    gpr_free(args->read_buffer);
-  } else {
+  if (error == GRPC_ERROR_NONE) {
     c->result->transport =
         grpc_create_chttp2_transport(exec_ctx, args->args, args->endpoint, 1);
     GPR_ASSERT(c->result->transport);
diff --git a/src/core/ext/transport/chttp2/client/secure/secure_channel_create.c b/src/core/ext/transport/chttp2/client/secure/secure_channel_create.c
index 4182aa730fbf3a01aeb125ad7b42eb417383a31e..b4a30f94fc8cfd7c0365e6d262d162efaac4a059 100644
--- a/src/core/ext/transport/chttp2/client/secure/secure_channel_create.c
+++ b/src/core/ext/transport/chttp2/client/secure/secure_channel_create.c
@@ -135,8 +135,6 @@ static void on_handshake_done(grpc_exec_ctx *exec_ctx, void *arg,
   connector *c = args->user_data;
   c->tmp_args = args->args;
   if (error != GRPC_ERROR_NONE) {
-    grpc_endpoint_destroy(exec_ctx, args->endpoint);
-    gpr_free(args->read_buffer);
     grpc_closure *notify = c->notify;
     c->notify = NULL;
     grpc_exec_ctx_sched(exec_ctx, notify, GRPC_ERROR_REF(error), NULL);
diff --git a/src/core/ext/transport/chttp2/server/insecure/server_chttp2.c b/src/core/ext/transport/chttp2/server/insecure/server_chttp2.c
index 5a9d4f89280872ecd28fce25d4a70cd649ce1a73..1b38d4decdcebaa7795f8d1397acd117fbf0ace0 100644
--- a/src/core/ext/transport/chttp2/server/insecure/server_chttp2.c
+++ b/src/core/ext/transport/chttp2/server/insecure/server_chttp2.c
@@ -62,8 +62,6 @@ static void on_handshake_done(grpc_exec_ctx *exec_ctx, void *arg,
     const char *error_str = grpc_error_string(error);
     gpr_log(GPR_ERROR, "Handshaking failed: %s", error_str);
     grpc_error_free_string(error_str);
-    grpc_endpoint_destroy(exec_ctx, args->endpoint);
-    gpr_free(args->read_buffer);
   } else {
     // Beware that the call to grpc_create_chttp2_transport() has to happen
     // before grpc_tcp_server_destroy(). This is fine here, but similar code
@@ -76,9 +74,9 @@ static void on_handshake_done(grpc_exec_ctx *exec_ctx, void *arg,
                                 state->accepting_pollset,
                                 grpc_server_get_channel_args(state->server));
     grpc_chttp2_transport_start_reading(exec_ctx, transport, args->read_buffer);
+    grpc_channel_args_destroy(args->args);
   }
   // Clean up.
-  grpc_channel_args_destroy(args->args);
   grpc_handshake_manager_destroy(exec_ctx, state->handshake_mgr);
   gpr_free(state);
 }
diff --git a/src/core/ext/transport/chttp2/server/secure/server_secure_chttp2.c b/src/core/ext/transport/chttp2/server/secure/server_secure_chttp2.c
index 1d1973be8bfb602f035284744b29a861dbd2e81d..22af94199f2e8d8738b76789abd8dda4bc0b4746 100644
--- a/src/core/ext/transport/chttp2/server/secure/server_secure_chttp2.c
+++ b/src/core/ext/transport/chttp2/server/secure/server_secure_chttp2.c
@@ -123,9 +123,6 @@ static void on_handshake_done(grpc_exec_ctx *exec_ctx, void *arg,
     const char *error_str = grpc_error_string(error);
     gpr_log(GPR_ERROR, "Handshaking failed: %s", error_str);
     grpc_error_free_string(error_str);
-    grpc_endpoint_destroy(exec_ctx, args->endpoint);
-    grpc_channel_args_destroy(args->args);
-    gpr_free(args->read_buffer);
     grpc_handshake_manager_destroy(exec_ctx, connection_state->handshake_mgr);
     grpc_tcp_server_unref(exec_ctx, connection_state->server_state->tcp);
     gpr_free(connection_state);
diff --git a/src/core/lib/channel/handshaker.c b/src/core/lib/channel/handshaker.c
index 3c125a22f37b6d3034e0d7971f3c1f3bd2a298be..f3bd91284ee1edcf65893bfd259c35f57e3a7c60 100644
--- a/src/core/lib/channel/handshaker.c
+++ b/src/core/lib/channel/handshaker.c
@@ -141,25 +141,20 @@ void grpc_handshake_manager_destroy(grpc_exec_ctx* exec_ctx,
 void grpc_handshake_manager_shutdown(grpc_exec_ctx* exec_ctx,
                                      grpc_handshake_manager* mgr) {
   gpr_mu_lock(&mgr->mu);
-  for (size_t i = 0; i < mgr->count; ++i) {
-    grpc_handshaker_shutdown(exec_ctx, mgr->handshakers[i]);
+  if (mgr->index > 0) {
+    grpc_handshaker_shutdown(exec_ctx, mgr->handshakers[mgr->index - 1]);
   }
   gpr_mu_unlock(&mgr->mu);
 }
 
-static void call_next_handshaker(grpc_exec_ctx* exec_ctx, void* arg,
-                                 grpc_error* error);
-
 // Helper function to call either the next handshaker or the
 // on_handshake_done callback.
 static void call_next_handshaker_locked(grpc_exec_ctx* exec_ctx,
                                         grpc_handshake_manager* mgr,
                                         grpc_error* error) {
   GPR_ASSERT(mgr->index <= mgr->count);
-  // If we got an error, skip all remaining handshakers and invoke the
-  // caller-supplied callback immediately.
-  // Otherwise, if this is the last handshaker, then call the on_handshake_done
-  // callback instead of chaining back to this function again.
+  // If we got an error or we've finished the last handshaker, invoke
+  // the on_handshake_done callback.  Otherwise, call the next handshaker.
   if (error != GRPC_ERROR_NONE || mgr->index == mgr->count) {
     // Cancel deadline timer, since we're invoking the on_handshake_done
     // callback now.
@@ -202,6 +197,8 @@ void grpc_handshake_manager_do_handshake(
     grpc_endpoint* endpoint, const grpc_channel_args* channel_args,
     gpr_timespec deadline, grpc_tcp_server_acceptor* acceptor,
     grpc_iomgr_cb_func on_handshake_done, void* user_data) {
+  gpr_mu_lock(&mgr->mu);
+  GPR_ASSERT(mgr->index == 0);
   // Construct handshaker args.  These will be passed through all
   // handshakers and eventually be freed by the on_handshake_done callback.
   mgr->args.endpoint = endpoint;
@@ -210,8 +207,6 @@ void grpc_handshake_manager_do_handshake(
   mgr->args.read_buffer = gpr_malloc(sizeof(*mgr->args.read_buffer));
   grpc_slice_buffer_init(mgr->args.read_buffer);
   // Initialize state needed for calling handshakers.
-  gpr_mu_lock(&mgr->mu);
-  GPR_ASSERT(mgr->index == 0);
   mgr->acceptor = acceptor;
   grpc_closure_init(&mgr->call_next_handshaker, call_next_handshaker, mgr);
   grpc_closure_init(&mgr->on_handshake_done, on_handshake_done, &mgr->args);
diff --git a/src/core/lib/channel/handshaker.h b/src/core/lib/channel/handshaker.h
index f0614c354b9972fa6c5b9c768dbfd289ae3499b9..2e1f5435121dbaa67602fa0a2d3dba7410256f51 100644
--- a/src/core/lib/channel/handshaker.h
+++ b/src/core/lib/channel/handshaker.h
@@ -57,17 +57,24 @@ typedef struct grpc_handshaker grpc_handshaker;
 /// Arguments passed through handshakers and to the on_handshake_done callback.
 ///
 /// For handshakers, all members are input/output parameters; for
-/// example, a handshaker may read from \a endpoint and then later
-/// replace it with a wrapped endpoint.  Similarly, a handshaker may
-/// modify \a args.
+/// example, a handshaker may read from or write to \a endpoint and
+/// then later replace it with a wrapped endpoint.  Similarly, a
+/// handshaker may modify \a args.
+///
+/// A handshaker takes ownership of the members while a handshake is in
+/// progress.  Upon failure or shutdown of an in-progress handshaker,
+/// the handshaker is responsible for destroying the members and setting
+/// them to NULL before invoking the on_handshake_done callback.
 ///
 /// For the on_handshake_done callback, all members are input arguments,
 /// which the callback takes ownership of.
 typedef struct {
   grpc_endpoint* endpoint;
   grpc_channel_args* args;
-  void* user_data;
   grpc_slice_buffer* read_buffer;
+  // User data passed through the handshake manager.  Not used by
+  // individual handshakers.
+  void* user_data;
 } grpc_handshaker_args;
 
 typedef struct {
@@ -132,9 +139,9 @@ void grpc_handshake_manager_shutdown(grpc_exec_ctx* exec_ctx,
 ///
 /// When done, invokes \a on_handshake_done with a grpc_handshaker_args
 /// object as its argument.  If the callback is invoked with error !=
-/// GRPC_ERROR_NONE, then handshaking failed and the resulting endpoint
-/// will have already been shut down (although the caller will still be
-/// responsible for destroying it).
+/// GRPC_ERROR_NONE, then handshaking failed and the handshaker has done
+/// the necessary clean-up.  Otherwise, the callback takes ownership of
+/// the arguments.
 void grpc_handshake_manager_do_handshake(
     grpc_exec_ctx* exec_ctx, grpc_handshake_manager* mgr,
     grpc_endpoint* endpoint, const grpc_channel_args* channel_args,