Drop buffers in idle SSLClientSockets (and SSLServerSockets).

net/socket/socket_bio_adapter_unittest.cc

+// Copyright 2016 The Chromium Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style license that can be
+// found in the LICENSE file.
+
+#include "net/socket/socket_bio_adapter.h"
+
+#include <openssl/bio.h>
+#include <openssl/err.h>
+#include <openssl/ssl.h>
+#include <string.h>
+
+#include <memory>
+
+#include "base/location.h"
+#include "base/logging.h"
+#include "base/macros.h"
+#include "base/memory/ptr_util.h"
+#include "base/run_loop.h"
+#include "crypto/openssl_util.h"
+#include "net/base/address_list.h"
+#include "net/base/net_errors.h"
+#include "net/log/net_log_source.h"
+#include "net/socket/socket_test_util.h"
+#include "net/socket/stream_socket.h"
+#include "net/ssl/openssl_ssl_util.h"
+#include "testing/gtest/include/gtest/gtest.h"
+
+namespace net {
+
+class SocketBIOAdapterTest : public testing::Test,
+                             public SocketBIOAdapter::Delegate {
+ protected:
+  std::unique_ptr<StreamSocket> MakeTestSocket(SocketDataProvider* data) {
+    data->set_connect_data(MockConnect(SYNCHRONOUS, OK));
+    factory_.AddSocketDataProvider(data);
+    std::unique_ptr<StreamSocket> socket = factory_.CreateTransportClientSocket(
+        AddressList(), nullptr, nullptr, NetLogSource());
+    CHECK_EQ(OK, socket->Connect(net::CompletionCallback()));
+    return socket;
+  }
+
+  void set_reset_on_write_ready(
+      std::unique_ptr<SocketBIOAdapter>* reset_on_write_ready) {
+    reset_on_write_ready_ = reset_on_write_ready;
+  }
+
+  void ExpectReadError(BIO* bio,
+                       int error,
+                       const crypto::OpenSSLErrStackTracer& tracer) {
+    // BIO_read should fail.
+    char buf;
+    EXPECT_EQ(-1, BIO_read(bio, &buf, 1));
+    EXPECT_EQ(error, MapOpenSSLError(SSL_ERROR_SSL, tracer));
+    EXPECT_FALSE(BIO_should_read(bio));
+
+    // Repeating the operation should replay the error.
+    EXPECT_EQ(-1, BIO_read(bio, &buf, 1));
+    EXPECT_EQ(error, MapOpenSSLError(SSL_ERROR_SSL, tracer));
+    EXPECT_FALSE(BIO_should_read(bio));
+  }
+
+  void ExpectBlockingRead(BIO* bio, void* buf, int len) {
+    // BIO_read should return a retryable error.
+    EXPECT_EQ(-1, BIO_read(bio, buf, len));
+    EXPECT_TRUE(BIO_should_read(bio));
+    EXPECT_EQ(0u, ERR_peek_error());
+
+    // Repeating the operation has the same result.
+    EXPECT_EQ(-1, BIO_read(bio, buf, len));
+    EXPECT_TRUE(BIO_should_read(bio));
+    EXPECT_EQ(0u, ERR_peek_error());
+  }
+
+  void ExpectWriteError(BIO* bio,
+                        int error,
+                        const crypto::OpenSSLErrStackTracer& tracer) {
+    // BIO_write should fail.
+    char buf = '?';
+    EXPECT_EQ(-1, BIO_write(bio, &buf, 1));
+    EXPECT_EQ(error, MapOpenSSLError(SSL_ERROR_SSL, tracer));
+    EXPECT_FALSE(BIO_should_write(bio));
+
+    // Repeating the operation should replay the error.
+    EXPECT_EQ(-1, BIO_write(bio, &buf, 1));
+    EXPECT_EQ(error, MapOpenSSLError(SSL_ERROR_SSL, tracer));
+    EXPECT_FALSE(BIO_should_write(bio));
+  }
+
+  void ExpectBlockingWrite(BIO* bio, const void* buf, int len) {
+    // BIO_write should return a retryable error.
+    EXPECT_EQ(-1, BIO_write(bio, buf, len));
+    EXPECT_TRUE(BIO_should_write(bio));
+    EXPECT_EQ(0u, ERR_peek_error());
+
+    // Repeating the operation has the same result.
+    EXPECT_EQ(-1, BIO_write(bio, buf, len));
+    EXPECT_TRUE(BIO_should_write(bio));
+    EXPECT_EQ(0u, ERR_peek_error());
+  }
+
+  void WaitForReadReady() {
+    expect_read_ready_ = true;
+    base::RunLoop().RunUntilIdle();
+    EXPECT_FALSE(expect_read_ready_);
+  }
+
+  void WaitForWriteReady(SequencedSocketData* to_resume) {
+    expect_write_ready_ = true;
+    if (to_resume) {
+      to_resume->Resume();
+    }
+    base::RunLoop().RunUntilIdle();
+    EXPECT_FALSE(expect_write_ready_);
+    CHECK(!expect_write_ready_);
+  }
+
+  void WaitForBothReady() {
+    expect_read_ready_ = true;
+    expect_write_ready_ = true;
+    base::RunLoop().RunUntilIdle();
+    EXPECT_FALSE(expect_read_ready_);
+    EXPECT_FALSE(expect_write_ready_);
+  }
+
+  // SocketBIOAdapter::Delegate implementation:
+  void OnReadReady() override {
+    EXPECT_TRUE(expect_read_ready_);
+    expect_read_ready_ = false;
+  }
+
+  void OnWriteReady() override {
+    EXPECT_TRUE(expect_write_ready_);
+    expect_write_ready_ = false;
+    if (reset_on_write_ready_)
+      reset_on_write_ready_->reset();
+  }
+
+ private:
+  bool expect_read_ready_ = false;
+  bool expect_write_ready_ = false;
+  MockClientSocketFactory factory_;
+  std::unique_ptr<SocketBIOAdapter>* reset_on_write_ready_ = nullptr;
+};
+
+// Test that data can be read synchronously.
+TEST_F(SocketBIOAdapterTest, ReadSync) {
+  crypto::OpenSSLErrStackTracer tracer(FROM_HERE);
+
+  MockRead reads[] = {
+      MockRead(SYNCHRONOUS, 0, "hello"), MockRead(SYNCHRONOUS, 1, "world"),
+      MockRead(SYNCHRONOUS, ERR_CONNECTION_RESET, 2),
+  };
+
+  SequencedSocketData data(reads, arraysize(reads), nullptr, 0);
+  std::unique_ptr<StreamSocket> socket = MakeTestSocket(&data);
+  std::unique_ptr<SocketBIOAdapter> adapter =
+      base::MakeUnique<SocketBIOAdapter>(socket.get(), 100, 100, this);
+  BIO* bio = adapter->bio();
+  EXPECT_FALSE(adapter->HasPendingReadData());
+
+  // Read the data synchronously. Although the buffer has room for both,
+  // BIO_read only reports one socket-level Read.
+  char buf[10];
+  EXPECT_EQ(5, BIO_read(bio, buf, sizeof(buf)));
+  EXPECT_EQ(0, memcmp("hello", buf, 5));
+  EXPECT_FALSE(adapter->HasPendingReadData());
+
+  // Consume the next portion one byte at a time.
+  EXPECT_EQ(1, BIO_read(bio, buf, 1));
+  EXPECT_EQ('w', buf[0]);
+  EXPECT_TRUE(adapter->HasPendingReadData());
+
+  EXPECT_EQ(1, BIO_read(bio, buf, 1));
+  EXPECT_EQ('o', buf[0]);
+  EXPECT_TRUE(adapter->HasPendingReadData());
+
+  // The remainder may be consumed in a single BIO_read.
+  EXPECT_EQ(3, BIO_read(bio, buf, sizeof(buf)));
+  EXPECT_EQ(0, memcmp("rld", buf, 3));
+  EXPECT_FALSE(adapter->HasPendingReadData());
+
+  // The error is available synchoronously.
+  ExpectReadError(bio, ERR_CONNECTION_RESET, tracer);
+}
+
+// Test that data can be read asynchronously.
+TEST_F(SocketBIOAdapterTest, ReadAsync) {
+  crypto::OpenSSLErrStackTracer tracer(FROM_HERE);
+
+  MockRead reads[] = {
+      MockRead(ASYNC, 0, "hello"), MockRead(ASYNC, 1, "world"),
+      MockRead(ASYNC, ERR_CONNECTION_RESET, 2),
+  };
+
+  SequencedSocketData data(reads, arraysize(reads), nullptr, 0);
+  std::unique_ptr<StreamSocket> socket = MakeTestSocket(&data);
+  std::unique_ptr<SocketBIOAdapter> adapter =
+      base::MakeUnique<SocketBIOAdapter>(socket.get(), 100, 100, this);
+  BIO* bio = adapter->bio();
+  EXPECT_FALSE(adapter->HasPendingReadData());
+
+  // Attempt to read data. It will fail but schedule a Read.
+  char buf[10];
+  ExpectBlockingRead(bio, buf, sizeof(buf));
+  EXPECT_FALSE(adapter->HasPendingReadData());
+
+  // After waiting, the data is available.
+  WaitForReadReady();
+  EXPECT_TRUE(adapter->HasPendingReadData());
+
+  // The first read is now available synchronously.
+  EXPECT_EQ(5, BIO_read(bio, buf, sizeof(buf)));
+  EXPECT_EQ(0, memcmp("hello", buf, 5));
+  EXPECT_FALSE(adapter->HasPendingReadData());
+
+  // The adapter does not schedule another Read until BIO_read is next called.
+  base::RunLoop().RunUntilIdle();
+  EXPECT_FALSE(adapter->HasPendingReadData());
+
+  // This time, under-request the data. The adapter should still read the full
+  // amount.
+  ExpectBlockingRead(bio, buf, 1);
+  EXPECT_FALSE(adapter->HasPendingReadData());
+  WaitForReadReady();
+  EXPECT_TRUE(adapter->HasPendingReadData());
+
+  // The next read is now available synchronously.
+  EXPECT_EQ(5, BIO_read(bio, buf, sizeof(buf)));
+  EXPECT_EQ(0, memcmp("world", buf, 5));
+  EXPECT_FALSE(adapter->HasPendingReadData());
+
+  // The error is not yet available.
+  ExpectBlockingRead(bio, buf, sizeof(buf));
+  WaitForReadReady();
+
+  // The error is now available synchoronously.
+  ExpectReadError(bio, ERR_CONNECTION_RESET, tracer);
+}
+
+// Test that synchronous EOF is mapped to ERR_CONNECTION_CLOSED.
+TEST_F(SocketBIOAdapterTest, ReadEOFSync) {
+  crypto::OpenSSLErrStackTracer tracer(FROM_HERE);
+
+  MockRead reads[] = {
+      MockRead(SYNCHRONOUS, 0, 0),
+  };
+
+  SequencedSocketData data(reads, arraysize(reads), nullptr, 0);
+  std::unique_ptr<StreamSocket> socket = MakeTestSocket(&data);
+  std::unique_ptr<SocketBIOAdapter> adapter =
+      base::MakeUnique<SocketBIOAdapter>(socket.get(), 100, 100, this);
+
+  ExpectReadError(adapter->bio(), ERR_CONNECTION_CLOSED, tracer);
+}
+
+// Test that asynchronous EOF is mapped to ERR_CONNECTION_CLOSED.
+TEST_F(SocketBIOAdapterTest, ReadEOFAsync) {
+  crypto::OpenSSLErrStackTracer tracer(FROM_HERE);
+
+  MockRead reads[] = {
+      MockRead(ASYNC, 0, 0),
+  };
+
+  SequencedSocketData data(reads, arraysize(reads), nullptr, 0);
+  std::unique_ptr<StreamSocket> socket = MakeTestSocket(&data);
+  std::unique_ptr<SocketBIOAdapter> adapter =
+      base::MakeUnique<SocketBIOAdapter>(socket.get(), 100, 100, this);
+
+  char buf;
+  ExpectBlockingRead(adapter->bio(), &buf, 1);
+  WaitForReadReady();
+  ExpectReadError(adapter->bio(), ERR_CONNECTION_CLOSED, tracer);
+}
+
+// Test that data can be written synchronously.
+TEST_F(SocketBIOAdapterTest, WriteSync) {
+  crypto::OpenSSLErrStackTracer tracer(FROM_HERE);
+
+  MockWrite writes[] = {
+      MockWrite(SYNCHRONOUS, 0, "hello"),
+      MockWrite(SYNCHRONOUS, 1, "wor"),
+      MockWrite(SYNCHRONOUS, 2, "ld"),
+      MockWrite(SYNCHRONOUS, 3, "helloworld"),
+      MockWrite(SYNCHRONOUS, ERR_CONNECTION_RESET, 4),
+  };
+
+  SequencedSocketData data(nullptr, 0, writes, arraysize(writes));
+  std::unique_ptr<StreamSocket> socket = MakeTestSocket(&data);
+  std::unique_ptr<SocketBIOAdapter> adapter =
+      base::MakeUnique<SocketBIOAdapter>(socket.get(), 10, 10, this);
+  BIO* bio = adapter->bio();
+
+  // Test data entering and leaving the buffer synchronously. The second write
+  // takes multiple iterations (events 0 to 2).
+  EXPECT_EQ(5, BIO_write(bio, "hello", 5));
+  EXPECT_EQ(5, BIO_write(bio, "world", 5));
+
+  // If writing larger than the buffer size, only part of the data is written
+  // (event 3).
+  EXPECT_EQ(10, BIO_write(bio, "helloworldhelloworld", 20));
+
+  // Writing "aaaaa" fails (event 4), but there is a write buffer, so errors
+  // are delayed.
+  EXPECT_EQ(5, BIO_write(bio, "aaaaa", 5));
+
+  // However once the error is registered, subsequent writes fail.
+  ExpectWriteError(bio, ERR_CONNECTION_RESET, tracer);
+}
+
+// Test that data can be written asynchronously.
+TEST_F(SocketBIOAdapterTest, WriteAsync) {
+  crypto::OpenSSLErrStackTracer tracer(FROM_HERE);
+
+  MockWrite writes[] = {
+      MockWrite(ASYNC, 0, "aaa"),
+      MockWrite(ASYNC, ERR_IO_PENDING, 1),  // pause
+      MockWrite(ASYNC, 2, "aabbbbb"),
+      MockWrite(ASYNC, 3, "ccc"),
+      MockWrite(ASYNC, 4, "ddd"),
+      MockWrite(ASYNC, ERR_IO_PENDING, 5),  // pause
+      MockWrite(ASYNC, 6, "dd"),
+      MockWrite(SYNCHRONOUS, 7, "e"),
+      MockWrite(SYNCHRONOUS, 8, "e"),
+      MockWrite(ASYNC, 9, "e"),
+      MockWrite(ASYNC, 10, "ee"),
+      MockWrite(ASYNC, ERR_IO_PENDING, 11),  // pause
+      MockWrite(ASYNC, 12, "eff"),
+      MockWrite(ASYNC, 13, "ggggggg"),
+      MockWrite(ASYNC, ERR_CONNECTION_RESET, 14),
+  };
+
+  SequencedSocketData data(nullptr, 0, writes, arraysize(writes));
+  std::unique_ptr<StreamSocket> socket = MakeTestSocket(&data);
+  std::unique_ptr<SocketBIOAdapter> adapter =
+      base::MakeUnique<SocketBIOAdapter>(socket.get(), 10, 10, this);
+  BIO* bio = adapter->bio();
+
+  // Data which fits in the buffer is returned synchronously, even if not
+  // flushed synchronously.
+  EXPECT_EQ(5, BIO_write(bio, "aaaaa", 5));
+  EXPECT_EQ(5, BIO_write(bio, "bbbbb", 5));
+
+  // The buffer contains:
+  //
+  //   [aaaaabbbbb]
+  //    ^
+
+  // The buffer is full now, so the next write will block.
+  ExpectBlockingWrite(bio, "zzzzz", 5);
+
+  // Let the first socket write complete (event 0) and pause (event 1).
+  WaitForWriteReady(nullptr);
+  EXPECT_TRUE(data.IsPaused());
+
+  // The buffer contains:
+  //
+  //   [...aabbbbb]
+  //       ^
+
+  // The ring buffer now has 3 bytes of space with "aabbbbb" still to be
+  // written. Attempting to write 3 bytes means 3 succeed.
+  EXPECT_EQ(3, BIO_write(bio, "cccccccccc", 10));
+
+  // The buffer contains:
+  //
+  //   [cccaabbbbb]
+  //       ^
+
+  // Drain the buffer (events 2 and 3).
+  WaitForWriteReady(&data);
+
+  // The buffer is now empty.
+
+  // Now test something similar but arrange for a BIO_write (the 'e's below) to
+  // wrap around the buffer.  Write five bytes into the buffer, flush the first
+  // three (event 4), and pause (event 5). OnWriteReady is not signaled because
+  // the buffer was not full.
+  EXPECT_EQ(5, BIO_write(bio, "ddddd", 5));
+  base::RunLoop().RunUntilIdle();
+  EXPECT_TRUE(data.IsPaused());
+
+  // The buffer contains:
+  //
+  //   [...dd.....]
+  //       ^
+
+  // The adapter maintains a ring buffer, so 6 bytes fit.
+  EXPECT_EQ(6, BIO_write(bio, "eeeeee", 6));
+
+  // The buffer contains:
+  //
+  //   [e..ddeeeee]
+  //       ^
+
+  // The remaining space may be filled in.
+  EXPECT_EQ(2, BIO_write(bio, "ffffffffff", 10));
+
+  // The buffer contains:
+  //
+  //   [effddeeeee]
+  //       ^
+
+  // Drain to the end of the ring buffer, so it wraps around (events 6 to 10)
+  // and pause (event 11). Test that synchronous and asynchronous writes both
+  // drain. The start of the buffer has now wrapped around.
+  WaitForWriteReady(&data);
+  EXPECT_TRUE(data.IsPaused());
+
+  // The buffer contains:
+  //
+  //   [eff.......]
+  //    ^
+
+  // Test wrapping around works correctly and the buffer may be appended to.
+  EXPECT_EQ(7, BIO_write(bio, "gggggggggg", 10));
+
+  // The buffer contains:
+  //
+  //   [effggggggg]
+  //    ^
+
+  // The buffer is full now, so the next write will block.
+  ExpectBlockingWrite(bio, "zzzzz", 5);
+
+  // Drain the buffer to confirm the ring buffer's contents are as expected
+  // (events 12 and 13).
+  WaitForWriteReady(&data);
+
+  // Write again so the write error may be discovered.
+  EXPECT_EQ(5, BIO_write(bio, "hhhhh", 5));
+
+  // Release the write error (event 14). At this point future BIO_write calls
+  // fail. The buffer was not full, so OnWriteReady is not signalled.
+  base::RunLoop().RunUntilIdle();
+  ExpectWriteError(bio, ERR_CONNECTION_RESET, tracer);
+}
+
+// Test that a failed socket write is reported through BIO_read and prevents it
+// from scheduling a socket read. See https://crbug.com/249848.
+TEST_F(SocketBIOAdapterTest, WriteStopsRead) {
+  crypto::OpenSSLErrStackTracer tracer(FROM_HERE);
+
+  MockWrite writes[] = {
+      MockWrite(SYNCHRONOUS, ERR_CONNECTION_RESET, 0),
+  };
+
+  SequencedSocketData data(nullptr, 0, writes, arraysize(writes));
+  std::unique_ptr<StreamSocket> socket = MakeTestSocket(&data);
+  std::unique_ptr<SocketBIOAdapter> adapter =
+      base::MakeUnique<SocketBIOAdapter>(socket.get(), 100, 100, this);
+  BIO* bio = adapter->bio();
+
+  // The write fails, but there is a write buffer, so errors are delayed.
+  EXPECT_EQ(5, BIO_write(bio, "aaaaa", 5));
+
+  // The write error is surfaced out of BIO_read. There are no MockReads, so
+  // this also tests that no socket reads are attempted.
+  ExpectReadError(bio, ERR_CONNECTION_RESET, tracer);
+}
+
+// Test that a synchronous failed socket write interrupts a blocked
+// BIO_read. See https://crbug.com/249848.
+TEST_F(SocketBIOAdapterTest, SyncWriteInterruptsRead) {
+  crypto::OpenSSLErrStackTracer tracer(FROM_HERE);
+
+  MockRead reads[] = {
+      MockRead(SYNCHRONOUS, ERR_IO_PENDING, 0),
+  };
+
+  MockWrite writes[] = {
+      MockWrite(SYNCHRONOUS, ERR_CONNECTION_RESET, 1),
+  };
+
+  SequencedSocketData data(reads, arraysize(reads), writes, arraysize(writes));
+  std::unique_ptr<StreamSocket> socket = MakeTestSocket(&data);
+  std::unique_ptr<SocketBIOAdapter> adapter =
+      base::MakeUnique<SocketBIOAdapter>(socket.get(), 100, 100, this);
+  BIO* bio = adapter->bio();
+
+  // Attempt to read from the transport. It will block indefinitely.
+  char buf;
+  ExpectBlockingRead(adapter->bio(), &buf, 1);
+
+  // Schedule a socket write.
+  EXPECT_EQ(5, BIO_write(bio, "aaaaa", 5));
+
+  // The write error triggers OnReadReady.
+  WaitForReadReady();
+
+  // The write error is surfaced out of BIO_read.
+  ExpectReadError(bio, ERR_CONNECTION_RESET, tracer);
+}
+
+// Test that an asynchronous failed socket write interrupts a blocked
+// BIO_read. See https://crbug.com/249848.
+TEST_F(SocketBIOAdapterTest, AsyncWriteInterruptsRead) {
+  crypto::OpenSSLErrStackTracer tracer(FROM_HERE);
+
+  MockRead reads[] = {
+      MockRead(SYNCHRONOUS, ERR_IO_PENDING, 0),
+  };
+
+  MockWrite writes[] = {
+      MockWrite(ASYNC, ERR_CONNECTION_RESET, 1),
+  };
+
+  SequencedSocketData data(reads, arraysize(reads), writes, arraysize(writes));
+  std::unique_ptr<StreamSocket> socket = MakeTestSocket(&data);
+  std::unique_ptr<SocketBIOAdapter> adapter =
+      base::MakeUnique<SocketBIOAdapter>(socket.get(), 100, 100, this);
+  BIO* bio = adapter->bio();
+
+  // Attempt to read from the transport. It will block indefinitely.
+  char buf;
+  ExpectBlockingRead(adapter->bio(), &buf, 1);
+
+  // Schedule a socket write.
+  EXPECT_EQ(5, BIO_write(bio, "aaaaa", 5));
+
+  // The write error is signaled asynchronously and interrupts BIO_read, so
+  // OnReadReady is signaled. The write buffer was not full, so OnWriteReady is
+  // not signaled.
+  WaitForReadReady();
+
+  // The write error is surfaced out of BIO_read.
+  ExpectReadError(bio, ERR_CONNECTION_RESET, tracer);
+}
+
+// Test that an asynchronous failed socket write interrupts a blocked BIO_read,
+// signaling both if the buffer was full. See https://crbug.com/249848.
+TEST_F(SocketBIOAdapterTest, AsyncWriteInterruptsBoth) {
+  crypto::OpenSSLErrStackTracer tracer(FROM_HERE);
+
+  MockRead reads[] = {
+      MockRead(SYNCHRONOUS, ERR_IO_PENDING, 0),
+  };
+
+  MockWrite writes[] = {
+      MockWrite(ASYNC, ERR_CONNECTION_RESET, 1),
+  };
+
+  SequencedSocketData data(reads, arraysize(reads), writes, arraysize(writes));
+  std::unique_ptr<StreamSocket> socket = MakeTestSocket(&data);
+  std::unique_ptr<SocketBIOAdapter> adapter =
+      base::MakeUnique<SocketBIOAdapter>(socket.get(), 5, 5, this);
+  BIO* bio = adapter->bio();
+
+  // Attempt to read from the transport. It will block indefinitely.
+  char buf;
+  ExpectBlockingRead(adapter->bio(), &buf, 1);
+
+  // Schedule a socket write.
+  EXPECT_EQ(5, BIO_write(bio, "aaaaa", 5));
+
+  // The write error is signaled asynchronously and interrupts BIO_read, so
+  // OnReadReady is signaled. The write buffer was full, so both OnWriteReady is
+  // also signaled.
+  WaitForBothReady();
+
+  // The write error is surfaced out of BIO_read.
+  ExpectReadError(bio, ERR_CONNECTION_RESET, tracer);
+}
+
+// Test that SocketBIOAdapter handles OnWriteReady deleting itself when both
+// need to be signaled.
+TEST_F(SocketBIOAdapterTest, DeleteOnWriteReady) {
+  crypto::OpenSSLErrStackTracer tracer(FROM_HERE);
+
+  MockRead reads[] = {
+      MockRead(SYNCHRONOUS, ERR_IO_PENDING, 0),
+  };
+
+  MockWrite writes[] = {
+      MockWrite(ASYNC, ERR_CONNECTION_RESET, 1),
+  };
+
+  SequencedSocketData data(reads, arraysize(reads), writes, arraysize(writes));
+  std::unique_ptr<StreamSocket> socket = MakeTestSocket(&data);
+  std::unique_ptr<SocketBIOAdapter> adapter =
+      base::MakeUnique<SocketBIOAdapter>(socket.get(), 5, 5, this);
+  BIO* bio = adapter->bio();
+
+  // Arrange for OnReadReady and OnWriteReady to both be signaled due to write
+  // error propagation (see the AsyncWriteInterruptsBoth test).
+  char buf;
+  ExpectBlockingRead(adapter->bio(), &buf, 1);
+  EXPECT_EQ(5, BIO_write(bio, "aaaaa", 5));
+
+  // Both OnWriteReady and OnReadReady would be signaled, but OnWriteReady
+  // deletes the adapter first.
+  set_reset_on_write_ready(&adapter);
+  WaitForWriteReady(nullptr);
+
+  EXPECT_FALSE(adapter);
+}
+
+// Test that using a BIO after the underlying adapter is destroyed fails
+// gracefully.
+TEST_F(SocketBIOAdapterTest, Detached) {
+  crypto::OpenSSLErrStackTracer tracer(FROM_HERE);
+
+  SequencedSocketData data(nullptr, 0, nullptr, 0);
+  std::unique_ptr<StreamSocket> socket = MakeTestSocket(&data);
+  std::unique_ptr<SocketBIOAdapter> adapter =
+      base::MakeUnique<SocketBIOAdapter>(socket.get(), 100, 100, this);
+
+  // Retain an additional reference to the BIO.
+  bssl::UniquePtr<BIO> bio(adapter->bio());
+  BIO_up_ref(bio.get());
+
+  // Release the adapter.
+  adapter.reset();
+
+  ExpectReadError(bio.get(), ERR_UNEXPECTED, tracer);
+  ExpectWriteError(bio.get(), ERR_UNEXPECTED, tracer);
+}
+
+}  // namespace net