diff --git a/pex/commands/command.py b/pex/commands/command.py
index 22d61931f..962bbc8ec 100644
--- a/pex/commands/command.py
+++ b/pex/commands/command.py
@@ -19,7 +19,7 @@
 from pex.cache import access as cache_access
 from pex.common import environment_as, safe_mkdtemp, safe_open
 from pex.compatibility import shlex_quote
-from pex.os import LINUX
+from pex.os import MAC, WINDOWS
 from pex.result import Error, Ok, Result
 from pex.subprocess import subprocess_daemon_kwargs
 from pex.typing import TYPE_CHECKING, Generic, cast
@@ -52,7 +52,7 @@
 def try_run_program(
     program,  # type: str
     args,  # type: Iterable[str]
-    url=None,  # type: Optional[str]
+    program_info_url=None,  # type: Optional[str]
     error=None,  # type: Optional[str]
     disown=False,  # type: bool
     **kwargs  # type: Any
@@ -76,35 +76,39 @@ def try_run_program(
     except OSError as e:
         msg = [error] if error else []
         msg.append("Do you have `{}` installed on the $PATH?: {}".format(program, e))
-        if url:
+        if program_info_url:
             msg.append(
-                "Find more information on `{program}` at {url}.".format(program=program, url=url)
+                "Find more information on `{program}` at {url}.".format(
+                    program=program, url=program_info_url
+                )
             )
         return Error("\n".join(msg))
 
 
-def try_open_file(
-    path,  # type: str
+def try_open(
+    path_or_url,  # type: str
     open_program=None,  # type: Optional[str]
     error=None,  # type: Optional[str]
     suppress_stderr=False,  # type: bool
 ):
     # type: (...) -> Result
 
-    url = None  # type: Optional[str]
+    program_info_url = None  # type: Optional[str]
     if open_program:
         opener = open_program
-    elif LINUX:
-        opener = "xdg-open"
-        url = "https://www.freedesktop.org/wiki/Software/xdg-utils/"
-    else:
+    elif WINDOWS:
+        opener = "explorer"
+    elif MAC:
         opener = "open"
+    else:
+        opener = "xdg-open"
+        program_info_url = "https://www.freedesktop.org/wiki/Software/xdg-utils/"
 
     with open(os.devnull, "wb") as devnull:
         return try_run_program(
             opener,
-            [path],
-            url=url,
+            [path_or_url],
+            program_info_url=program_info_url,
             error=error,
             disown=True,
             stdout=devnull,
diff --git a/pex/docs/command.py b/pex/docs/command.py
index 9a7609edb..42d85e643 100644
--- a/pex/docs/command.py
+++ b/pex/docs/command.py
@@ -8,7 +8,7 @@
 from textwrap import dedent
 
 from pex import docs
-from pex.commands.command import try_open_file
+from pex.commands.command import try_open
 from pex.docs.server import SERVER_NAME, LaunchError, LaunchResult
 from pex.docs.server import launch as launch_docs_server
 from pex.result import Error, try_
@@ -91,8 +91,6 @@ def serve_html_docs(
             return Error("Failed to launch {server}.".format(server=SERVER_NAME))
 
     if open_browser:
-        try_(
-            try_open_file(result.server_info.url, open_program=config.browser, suppress_stderr=True)
-        )
+        try_(try_open(result.server_info.url, open_program=config.browser, suppress_stderr=True))
 
     return result
diff --git a/pex/docs/server.py b/pex/docs/server.py
index 47ff14766..af266b32c 100644
--- a/pex/docs/server.py
+++ b/pex/docs/server.py
@@ -1,7 +1,6 @@
 # Copyright 2024 Pex project contributors.
 # Licensed under the Apache License, Version 2.0 (see LICENSE).
 
-import errno
 import json
 import logging
 import os
@@ -13,7 +12,7 @@
 
 from pex.cache.dirs import CacheDir
 from pex.common import safe_open
-from pex.os import kill
+from pex.os import is_alive, kill
 from pex.subprocess import launch_python_daemon
 from pex.typing import TYPE_CHECKING
 from pex.version import __version__
@@ -79,7 +78,7 @@ def _read_url(
             with open(server_log) as fp:
                 for line in fp:
                     if line.endswith(("\r", "\n")):
-                        match = re.search(r"Serving HTTP on 0\.0\.0\.0 port (?P<port>\d+)", line)
+                        match = re.search(r"Serving HTTP on \S+ port (?P<port>\d+)", line)
                         if match:
                             port = match.group("port")
                             return "http://localhost:{port}".format(port=port)
@@ -106,13 +105,7 @@ def record(
     def alive(self):
         # type: () -> bool
         # TODO(John Sirois): Handle pid rollover
-        try:
-            os.kill(self.server_info.pid, 0)
-            return True
-        except OSError as e:
-            if e.errno == errno.ESRCH:  # No such process.
-                return False
-            raise
+        return is_alive(self.server_info.pid)
 
     def kill(self):
         # type: () -> None
diff --git a/pex/os.py b/pex/os.py
index a18651592..43b6af317 100644
--- a/pex/os.py
+++ b/pex/os.py
@@ -120,6 +120,49 @@ def is_exe(path):
 
 if WINDOWS:
 
+    def is_alive(pid):
+        # type: (int) -> bool
+
+        # TODO(John Sirois): This is extremely hacky, consider adding a psutil dependency for
+        #  Windows. See: https://github.com/pex-tool/pex/issues/2699
+
+        import csv
+        import subprocess
+
+        args = ["tasklist", "/FI", "PID eq {pid}".format(pid=pid), "/FO", "CSV"]
+        process = subprocess.Popen(args=args, stdout=subprocess.PIPE, stderr=subprocess.PIPE)
+        stdout, stderr = process.communicate()
+        if process.returncode != 0:
+            raise RuntimeError(
+                "Failed to query status of process with pid {pid}.\n"
+                "Execution of `{args}` returned exit code {returncode}.\n"
+                "{stderr}".format(
+                    pid=pid,
+                    args=" ".join(args),
+                    returncode=process.returncode,
+                    stderr=stderr.decode("utf-8"),
+                )
+            )
+
+        output = stdout.decode("utf-8")
+        if "No tasks are running" in output:
+            return False
+
+        lines = output.splitlines()
+        if len(lines) != 2:
+            return False
+
+        csv_reader = csv.DictReader(lines)
+        for row in csv_reader:
+            pid_value = row.get("PID", -1)
+            if pid_value == -1:
+                return False
+            try:
+                return pid == int(pid_value)
+            except (ValueError, TypeError):
+                return False
+        return False
+
     # https://learn.microsoft.com/en-us/windows/win32/procthread/process-security-and-access-rights
     _PROCESS_TERMINATE = 0x1  # Required to terminate a process using TerminateProcess.
 
@@ -170,6 +213,19 @@ def kill(pid):
 
 else:
 
+    def is_alive(pid):
+        # type: (int) -> bool
+
+        import errno
+
+        try:
+            os.kill(pid, 0)
+            return True
+        except OSError as e:
+            if e.errno == errno.ESRCH:  # No such process.
+                return False
+            raise
+
     def kill(pid):
         # type: (int) -> None
 
diff --git a/pex/tools/commands/graph.py b/pex/tools/commands/graph.py
index 2fd7b8242..27244d025 100644
--- a/pex/tools/commands/graph.py
+++ b/pex/tools/commands/graph.py
@@ -10,7 +10,7 @@
 from argparse import ArgumentParser
 from contextlib import contextmanager
 
-from pex.commands.command import OutputMixin, try_open_file, try_run_program
+from pex.commands.command import OutputMixin, try_open, try_run_program
 from pex.common import safe_mkdir
 from pex.dist_metadata import requires_dists
 from pex.interpreter_constraints import InterpreterConstraint
@@ -124,7 +124,7 @@ def emit():
         try:
             return try_run_program(
                 "dot",
-                url="https://graphviz.org/",
+                program_info_url="https://graphviz.org/",
                 error="Failed to render dependency graph for {}.".format(graph.name),
                 args=["-T", self.options.format],
                 stdin=read_fd,
@@ -168,7 +168,7 @@ def run(self, pex):
             if result.is_error:
                 return result
 
-        return try_open_file(
+        return try_open(
             open_path,
             error="Failed to open dependency graph of {} rendered in {} for viewing.".format(
                 pex.path(), open_path