diff --git a/src/ptvsd/adapter/servers.py b/src/ptvsd/adapter/servers.py
index 0a2789b4..cf29a34c 100644
--- a/src/ptvsd/adapter/servers.py
+++ b/src/ptvsd/adapter/servers.py
@@ -86,16 +86,12 @@ if 'ptvsd' not in sys.modules:
             inject_ptvsd = fmt(inject_ptvsd, ptvsd_dir=ptvsd_dir)
 
             try:
-                self.channel.request(
-                    "evaluate", {"expression": inject_ptvsd}
-                )
+                self.channel.request("evaluate", {"expression": inject_ptvsd})
             except messaging.MessageHandlingError:
                 # Failure to inject is not a fatal error - such a subprocess can
                 # still be debugged, it just won't support "import ptvsd" in user
                 # code - so don't terminate the session.
-                log.exception(
-                    "Failed to inject ptvsd into {0}:", self, level="warning"
-                )
+                log.exception("Failed to inject ptvsd into {0}:", self, level="warning")
 
             with _lock:
                 if any(conn.pid == self.pid for conn in _connections):
@@ -343,7 +339,7 @@ def wait_for_connection(pid=any, timeout=None):
     wait_for_timeout.timed_out = timeout == 0
     if timeout:
         thread = threading.Thread(
-            target=wait_for_timeout, name="server.wait_for_connection() timeout"
+            target=wait_for_timeout, name="servers.wait_for_connection() timeout"
         )
         thread.daemon = True
         thread.start()
@@ -404,15 +400,32 @@ def inject(pid, ptvsd_args):
 
     log.info("Spawning attach-to-PID debugger injector: {0!r}", cmdline)
     try:
-        subprocess.Popen(
+        injector = subprocess.Popen(
             cmdline,
             bufsize=0,
             stdin=subprocess.PIPE,
             stdout=subprocess.PIPE,
-            stderr=subprocess.PIPE,
+            stderr=subprocess.STDOUT,
         )
     except Exception as exc:
         log.exception("Failed to inject debug server into process with PID={0}", pid)
         raise messaging.MessageHandlingError(
             "Failed to inject debug server into process with PID={0}: {1}", pid, exc
         )
+
+    # We need to capture the output of the injector - otherwise it can get blocked
+    # on a write() syscall when it tries to print something.
+
+    def capture_output():
+        while True:
+            line = injector.stdout.readline()
+            if not line:
+                break
+            log.info("Injector[PID={0}] output:\n{1}", pid, line.rstrip())
+        log.info("Injector[PID={0}] exited.", pid)
+
+    thread = threading.Thread(
+        target=capture_output, name=fmt("Injector[PID={0}] output", pid)
+    )
+    thread.daemon = True
+    thread.start()
diff --git a/src/ptvsd/server/cli.py b/src/ptvsd/server/cli.py
index 38708038..33982062 100644
--- a/src/ptvsd/server/cli.py
+++ b/src/ptvsd/server/cli.py
@@ -267,7 +267,7 @@ def run_code():
 
 
 def attach_to_pid():
-    log.info("Attaching to process with ID {0}", options.target)
+    log.info("Attaching to process with PID={0}", options.target)
 
     pid = options.target
     host = options.host
@@ -324,7 +324,7 @@ attach_pid_injected.attach(port={port}, host=host, client={client}, log_dir=log_
         import add_code_to_python_process  # noqa
 
         show_debug_info_on_target_process = 0  # hard-coded (1 to debug)
-        log.info("Code injector begin")
+        log.info("Injecting code into process with PID={0} ...", pid)
         add_code_to_python_process.run_python_code(
             pid,
             python_code,
@@ -332,8 +332,8 @@ attach_pid_injected.attach(port={port}, host=host, client={client}, log_dir=log_
             show_debug_info=show_debug_info_on_target_process,
         )
     except Exception:
-        raise log.exception()
-    log.info("Code injector exiting")
+        raise log.exception("Code injection into PID={0} failed:", pid)
+    log.info("Code injection into PID={0} completed.", pid)
 
 
 def main():
diff --git a/tests/debug/comms.py b/tests/debug/comms.py
index 24b28427..89eea8a7 100644
--- a/tests/debug/comms.py
+++ b/tests/debug/comms.py
@@ -46,6 +46,11 @@ class BackChannel(object):
                 sock, _ = server_socket.accept()
             except socket.timeout:
                 raise log.exception("Timed out waiting for {0} to connect", self)
+            except Exception:
+                if self._server_socket is None:
+                    return
+                else:
+                    raise
 
             sock.setsockopt(socket.IPPROTO_TCP, socket.TCP_NODELAY, 1)
             log.info("Incoming connection from {0} accepted.", self)
diff --git a/tests/debug/runners.py b/tests/debug/runners.py
index 89d02a0b..4787f967 100644
--- a/tests/debug/runners.py
+++ b/tests/debug/runners.py
@@ -152,9 +152,7 @@ def _attach_common_config(session, target, cwd):
 
 @_runner
 def attach_by_pid(session, target, cwd=None, wait=True):
-    if platform.system() != "Windows":
-        pytest.skip("https://github.com/microsoft/ptvsd/issues/1810")
-    if sys.version_info < (3,):
+    if sys.version_info < (3,) and platform.system() == "Windows":
         pytest.skip("https://github.com/microsoft/ptvsd/issues/1811")
 
     log.info("Attaching {0} to {1} by PID.", session, target)
@@ -172,9 +170,16 @@ def attach_by_pid(session, target, cwd=None, wait=True):
         if wait:
             debug_me = """
 import sys
-while not "ptvsd" in sys.modules: pass
+import threading
+import time
+
+while not "ptvsd" in sys.modules:
+    time.sleep(0.1)
+
 import ptvsd
-while not ptvsd.is_attached(): pass
+
+while not ptvsd.is_attached():
+    time.sleep(0.1)
     """
         else:
             debug_me = None