diff --git a/CHANGELOG.md b/CHANGELOG.md
index 594e4298..eaad58bd 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,7 @@
 
 * Improve handling of network related timeouts
 * Fix error reporting when preceded by info message
+* Raise error if client is unable to execute statement
 
 ## 2.1.3
 
diff --git a/ext/tiny_tds/client.c b/ext/tiny_tds/client.c
index a65208df..0756cd03 100644
--- a/ext/tiny_tds/client.c
+++ b/ext/tiny_tds/client.c
@@ -296,8 +296,8 @@ static VALUE rb_tinytds_execute(VALUE self, VALUE sql) {
   REQUIRE_OPEN_CLIENT(cwrap);
   dbcmd(cwrap->client, StringValueCStr(sql));
   if (dbsqlsend(cwrap->client) == FAIL) {
-    rb_warn("TinyTds: dbsqlsend() returned FAIL.\n");
-    return Qfalse;
+    rb_raise(cTinyTdsError, "failed to execute statement");
+    return self;
   }
   cwrap->userdata->dbsql_sent = 1;
   result = rb_tinytds_new_result_obj(cwrap);
diff --git a/test/client_test.rb b/test/client_test.rb
index 15a0421e..88ab5b23 100644
--- a/test/client_test.rb
+++ b/test/client_test.rb
@@ -132,6 +132,25 @@ class ClientTest < TinyTds::TestCase
       end
     end
 
+    it 'raises TinyTds exception when tcp socket is down' do
+      skip if ENV['CI'] && ENV['APPVEYOR_BUILD_FOLDER'] # only CI using docker
+      begin
+        client = new_connection timeout: 2, port: 1234
+        assert_client_works(client)
+        action = lambda { client.execute("waitfor delay '00:00:01'").do }
+
+        # Use toxiproxy to close the TCP socket immediately.
+        # We want TinyTds to fail to execute the statement and raise an error immediately.
+        Toxiproxy[:sqlserver_test].down do
+          assert_raise_tinytds_error(action) do |e|
+            assert_match %r{failed to execute statement}i, e.message, 'ignore if non-english test run'
+          end
+        end
+      ensure
+        assert_new_connections_work
+      end
+    end
+
     it 'raises TinyTds exception with tcp socket network failure' do
       skip if ENV['CI'] && ENV['APPVEYOR_BUILD_FOLDER'] # only CI using docker
       begin