diff --git a/poetry/installation/executor.py b/poetry/installation/executor.py
index c7d02df520b..4fdffdeba13 100644
--- a/poetry/installation/executor.py
+++ b/poetry/installation/executor.py
@@ -134,32 +134,29 @@ def _write(self, operation, line):
             return
 
         if self._io.is_debug():
-            self._lock.acquire()
-            section = self._sections[id(operation)]
-            section.write_line(line)
-            self._lock.release()
+            with self._lock:
+                section = self._sections[id(operation)]
+                section.write_line(line)
 
             return
 
-        self._lock.acquire()
-        section = self._sections[id(operation)]
-        section.output.clear()
-        section.write(line)
-        self._lock.release()
+        with self._lock:
+            section = self._sections[id(operation)]
+            section.output.clear()
+            section.write(line)
 
     def _execute_operation(self, operation):
         try:
             if self.supports_fancy_output():
                 if id(operation) not in self._sections:
                     if self._should_write_operation(operation):
-                        self._lock.acquire()
-                        self._sections[id(operation)] = self._io.section()
-                        self._sections[id(operation)].write_line(
-                            "  <fg=blue;options=bold>•</> {message}: <fg=blue>Pending...</>".format(
-                                message=self.get_operation_message(operation),
-                            ),
-                        )
-                        self._lock.release()
+                        with self._lock:
+                            self._sections[id(operation)] = self._io.section()
+                            self._sections[id(operation)].write_line(
+                                "  <fg=blue;options=bold>•</> {message}: <fg=blue>Pending...</>".format(
+                                    message=self.get_operation_message(operation),
+                                ),
+                            )
             else:
                 if self._should_write_operation(operation):
                     if not operation.skipped:
@@ -193,37 +190,37 @@ def _execute_operation(self, operation):
             if result == -2:
                 raise KeyboardInterrupt
         except Exception as e:
-            from clikit.ui.components.exception_trace import ExceptionTrace
-
-            if not self.supports_fancy_output():
-                io = self._io
-            else:
-                message = "  <error>•</error> {message}: <error>Failed</error>".format(
-                    message=self.get_operation_message(operation, error=True),
-                )
-                self._write(operation, message)
-                io = self._sections.get(id(operation), self._io)
-
-            self._lock.acquire()
-
-            trace = ExceptionTrace(e)
-            trace.render(io)
-            io.write_line("")
+            try:
+                from clikit.ui.components.exception_trace import ExceptionTrace
 
-            self._shutdown = True
-            self._lock.release()
+                if not self.supports_fancy_output():
+                    io = self._io
+                else:
+                    message = "  <error>•</error> {message}: <error>Failed</error>".format(
+                        message=self.get_operation_message(operation, error=True),
+                    )
+                    self._write(operation, message)
+                    io = self._sections.get(id(operation), self._io)
+
+                with self._lock:
+                    trace = ExceptionTrace(e)
+                    trace.render(io)
+                    io.write_line("")
+            finally:
+                with self._lock:
+                    self._shutdown = True
         except KeyboardInterrupt:
-            message = "  <warning>•</warning> {message}: <warning>Cancelled</warning>".format(
-                message=self.get_operation_message(operation, warning=True),
-            )
-            if not self.supports_fancy_output():
-                self._io.write_line(message)
-            else:
-                self._write(operation, message)
-
-            self._lock.acquire()
-            self._shutdown = True
-            self._lock.release()
+            try:
+                message = "  <warning>•</warning> {message}: <warning>Cancelled</warning>".format(
+                    message=self.get_operation_message(operation, warning=True),
+                )
+                if not self.supports_fancy_output():
+                    self._io.write_line(message)
+                else:
+                    self._write(operation, message)
+            finally:
+                with self._lock:
+                    self._shutdown = True
 
     def _do_execute_operation(self, operation):
         method = operation.job_type
@@ -269,14 +266,12 @@ def _do_execute_operation(self, operation):
         return result
 
     def _increment_operations_count(self, operation, executed):
-        self._lock.acquire()
-        if executed:
-            self._executed_operations += 1
-            self._executed[operation.job_type] += 1
-        else:
-            self._skipped[operation.job_type] += 1
-
-        self._lock.release()
+        with self._lock:
+            if executed:
+                self._executed_operations += 1
+                self._executed[operation.job_type] += 1
+            else:
+                self._skipped[operation.job_type] += 1
 
     def run_pip(self, *args, **kwargs):  # type: (...) -> int
         try:
@@ -625,9 +620,8 @@ def _download_archive(self, operation, link):  # type: (Operation, Link) -> Path
                 progress.set_format(message + " <b>%percent%%</b>")
 
         if progress:
-            self._lock.acquire()
-            progress.start()
-            self._lock.release()
+            with self._lock:
+                progress.start()
 
         done = 0
         archive = self._chef.get_cache_directory_for_link(link) / link.filename
@@ -640,16 +634,14 @@ def _download_archive(self, operation, link):  # type: (Operation, Link) -> Path
                 done += len(chunk)
 
                 if progress:
-                    self._lock.acquire()
-                    progress.set_progress(done)
-                    self._lock.release()
+                    with self._lock:
+                        progress.set_progress(done)
 
                 f.write(chunk)
 
         if progress:
-            self._lock.acquire()
-            progress.finish()
-            self._lock.release()
+            with self._lock:
+                progress.finish()
 
         return archive
 
diff --git a/tests/installation/test_executor.py b/tests/installation/test_executor.py
index a9dea0d136a..278f4a2a138 100644
--- a/tests/installation/test_executor.py
+++ b/tests/installation/test_executor.py
@@ -182,6 +182,32 @@ def test_execute_should_show_operation_as_cancelled_on_subprocess_keyboard_inter
     assert expected == io.fetch_output()
 
 
+def test_execute_should_gracefully_handle_io_error(config, mocker, io):
+    env = MockEnv()
+    executor = Executor(env, pool, config, io)
+    executor.verbose()
+
+    original_write_line = executor._io.write_line
+
+    def write_line(string, flags=None):
+        # Simulate UnicodeEncodeError
+        string.encode("ascii")
+        original_write_line(string, flags)
+
+    mocker.patch.object(io, "write_line", side_effect=write_line)
+
+    assert 1 == executor.execute([Install(Package("clikit", "0.2.3"))])
+
+    expected = r"""
+Package operations: 1 install, 0 updates, 0 removals
+
+
+\s*Unicode\w+Error
+"""
+
+    assert re.match(expected, io.fetch_output())
+
+
 def test_executor_should_delete_incomplete_downloads(
     config, io, tmp_dir, mocker, pool, mock_file_downloads
 ):