diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3c62bf55dc1..c583667e3a6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,10 @@
 ## 1.19.0
 
+### Core library changes
+
+* `dart:io`
+  * Report a better error when a bind fails because of a bad source address.
+
 ### Tool Changes
 
 * `dartfmt` - upgraded to v0.2.9
diff --git a/runtime/bin/io_natives.cc b/runtime/bin/io_natives.cc
index 609bbef264f..8c9c8c8fd5e 100644
--- a/runtime/bin/io_natives.cc
+++ b/runtime/bin/io_natives.cc
@@ -121,6 +121,7 @@ namespace bin {
   V(Socket_CreateConnect, 3)                                                   \
   V(Socket_CreateBindConnect, 4)                                               \
   V(Socket_CreateBindDatagram, 4)                                              \
+  V(Socket_IsBindError, 2)                                                     \
   V(Socket_Available, 1)                                                       \
   V(Socket_Read, 2)                                                            \
   V(Socket_RecvFrom, 1)                                                        \
diff --git a/runtime/bin/socket.cc b/runtime/bin/socket.cc
index 7b6f95ae27b..745306d0e53 100644
--- a/runtime/bin/socket.cc
+++ b/runtime/bin/socket.cc
@@ -234,6 +234,12 @@ void FUNCTION_NAME(Socket_CreateBindConnect)(Dart_NativeArguments args) {
   }
 }
 
+void FUNCTION_NAME(Socket_IsBindError)(Dart_NativeArguments args) {
+  intptr_t error_number =
+      DartUtils::GetIntptrValue(Dart_GetNativeArgument(args, 1));
+  bool is_bind_error = Socket::IsBindError(error_number);
+  Dart_SetReturnValue(args, is_bind_error ? Dart_True() : Dart_False());
+}
 
 void FUNCTION_NAME(Socket_CreateBindDatagram)(Dart_NativeArguments args) {
   RawAddr addr;
diff --git a/runtime/bin/socket.h b/runtime/bin/socket.h
index 0b17706446b..6a50d796da6 100644
--- a/runtime/bin/socket.h
+++ b/runtime/bin/socket.h
@@ -278,6 +278,9 @@ class Socket {
   // specified as the port component of the passed RawAddr structure.
   static intptr_t CreateBindConnect(const RawAddr& addr,
                                     const RawAddr& source_addr);
+  // Returns true if the given error-number is because the system was not able
+  // to bind the socket to a specific IP.
+  static bool IsBindError(intptr_t error_number);
   // Creates a datagram socket which is bound. The port to bind
   // to is specified as the port component of the RawAddr structure.
   static intptr_t CreateBindDatagram(const RawAddr& addr, bool reuseAddress);
diff --git a/runtime/bin/socket_android.cc b/runtime/bin/socket_android.cc
index b3e3fc4cb10..caddb3a0de1 100644
--- a/runtime/bin/socket_android.cc
+++ b/runtime/bin/socket_android.cc
@@ -101,6 +101,12 @@ intptr_t Socket::CreateBindConnect(const RawAddr& addr,
 }
 
 
+bool Socket::IsBindError(intptr_t error_number) {
+  return error_number == EADDRINUSE || error_number == EADDRNOTAVAIL ||
+      error_number == EINVAL;
+}
+
+
 intptr_t Socket::Available(intptr_t fd) {
   return FDUtils::AvailableBytes(fd);
 }
diff --git a/runtime/bin/socket_fuchsia.cc b/runtime/bin/socket_fuchsia.cc
index 78b5071dff4..b79d1c0956b 100644
--- a/runtime/bin/socket_fuchsia.cc
+++ b/runtime/bin/socket_fuchsia.cc
@@ -45,6 +45,12 @@ intptr_t Socket::CreateBindConnect(const RawAddr& addr,
 }
 
 
+bool Socket::IsBindError(intptr_t error_number) {
+  UNIMPLEMENTED();
+  return false;
+}
+
+
 intptr_t Socket::Available(intptr_t fd) {
   UNIMPLEMENTED();
   return -1;
diff --git a/runtime/bin/socket_linux.cc b/runtime/bin/socket_linux.cc
index 63935676fab..fc0f1e413c3 100644
--- a/runtime/bin/socket_linux.cc
+++ b/runtime/bin/socket_linux.cc
@@ -101,6 +101,12 @@ intptr_t Socket::CreateBindConnect(const RawAddr& addr,
 }
 
 
+bool Socket::IsBindError(intptr_t error_number) {
+  return error_number == EADDRINUSE || error_number == EADDRNOTAVAIL ||
+      error_number == EINVAL;
+}
+
+
 intptr_t Socket::Available(intptr_t fd) {
   return FDUtils::AvailableBytes(fd);
 }
diff --git a/runtime/bin/socket_macos.cc b/runtime/bin/socket_macos.cc
index 708cd3cdea9..2e336a20037 100644
--- a/runtime/bin/socket_macos.cc
+++ b/runtime/bin/socket_macos.cc
@@ -103,6 +103,12 @@ intptr_t Socket::CreateBindConnect(const RawAddr& addr,
 }
 
 
+bool Socket::IsBindError(intptr_t error_number) {
+  return error_number == EADDRINUSE || error_number == EADDRNOTAVAIL ||
+      error_number == EINVAL;
+}
+
+
 intptr_t Socket::Available(intptr_t fd) {
   return FDUtils::AvailableBytes(fd);
 }
diff --git a/runtime/bin/socket_patch.dart b/runtime/bin/socket_patch.dart
index 2d3ba73b3f7..a8b60c3e063 100644
--- a/runtime/bin/socket_patch.dart
+++ b/runtime/bin/socket_patch.dart
@@ -431,7 +431,13 @@ class _NativeSocket extends _NativeSocketNativeWrapper with _ServiceObject {
             if (result is OSError) {
               // Keep first error, if present.
               if (error == null) {
-                error = createError(result, "Connection failed", address, port);
+                int errorCode = result.errorCode;
+                if (errorCode != null && socket.isBindError(errorCode)) {
+                  error = createError(result, "Bind failed", sourceAddress);
+                } else {
+                  error =
+                      createError(result, "Connection failed", address, port);
+                }
               }
               connectNext();
             } else {
@@ -1075,6 +1081,7 @@ class _NativeSocket extends _NativeSocketNativeWrapper with _ServiceObject {
   nativeCreateBindConnect(
       List<int> addr, int port, List<int> sourceAddr)
       native "Socket_CreateBindConnect";
+  bool isBindError(int errorNumber) native "Socket_IsBindError";
   nativeCreateBindListen(List<int> addr, int port, int backlog, bool v6Only,
                          bool shared)
       native "ServerSocket_CreateBindListen";
diff --git a/runtime/bin/socket_unsupported.cc b/runtime/bin/socket_unsupported.cc
index 0ea27f1aee0..089e48e8967 100644
--- a/runtime/bin/socket_unsupported.cc
+++ b/runtime/bin/socket_unsupported.cc
@@ -35,6 +35,12 @@ void FUNCTION_NAME(Socket_CreateBindConnect)(Dart_NativeArguments args) {
 }
 
 
+void FUNCTION_NAME(Socket_IsBindError)(Dart_NativeArguments args) {
+  Dart_ThrowException(DartUtils::NewDartArgumentError(
+      "Sockets unsupported on this platform"));
+}
+
+
 void FUNCTION_NAME(Socket_CreateBindDatagram)(Dart_NativeArguments args) {
   Dart_ThrowException(DartUtils::NewDartArgumentError(
       "Sockets unsupported on this platform"));
diff --git a/runtime/bin/socket_win.cc b/runtime/bin/socket_win.cc
index e3d366da53b..f76f764c7c4 100644
--- a/runtime/bin/socket_win.cc
+++ b/runtime/bin/socket_win.cc
@@ -250,6 +250,12 @@ intptr_t Socket::CreateBindConnect(const RawAddr& addr,
 }
 
 
+bool Socket::IsBindError(intptr_t error_number) {
+  return error_number == WSAEADDRINUSE || error_number == WSAEADDRNOTAVAIL ||
+      error_number == WSAEINVAL;
+}
+
+
 void Socket::GetError(intptr_t fd, OSError* os_error) {
   Handle* handle = reinterpret_cast<Handle*>(fd);
   os_error->SetCodeAndMessage(OSError::kSystem, handle->last_error());
diff --git a/tests/standalone/io/socket_source_address_test.dart b/tests/standalone/io/socket_source_address_test.dart
index 4b95433e2bc..64dc490bde9 100644
--- a/tests/standalone/io/socket_source_address_test.dart
+++ b/tests/standalone/io/socket_source_address_test.dart
@@ -43,7 +43,8 @@ Future testArguments(connectFunction) async {
     await throws(() => connectFunction('127.0.0.1',
                                        server.port,
                                        sourceAddress: sourceAddress),
-                 (e) => e is SocketException);
+                 (e) => e is SocketException &&
+                     e.address == new InternetAddress('8.8.8.8'));
   }
   // Address family mismatch.
   for (sourceAddress in ['::1', InternetAddress.LOOPBACK_IP_V6]) {