diff --git a/src/octoprint/plugins/softwareupdate/__init__.py b/src/octoprint/plugins/softwareupdate/__init__.py
index 779c6af0..1efdb064 100644
--- a/src/octoprint/plugins/softwareupdate/__init__.py
+++ b/src/octoprint/plugins/softwareupdate/__init__.py
@@ -122,6 +122,7 @@ class SoftwareUpdatePlugin(octoprint.plugin.BlueprintPlugin,
 
 			"octoprint_restart_command": None,
 			"environment_restart_command": None,
+			"pip_command": None,
 
 			"cache_ttl": 24 * 60,
 		}
@@ -571,6 +572,8 @@ class SoftwareUpdatePlugin(octoprint.plugin.BlueprintPlugin,
 		if "update_script" in check:
 			return updaters.update_script
 		elif "pip" in check:
+			if not "pip_command" in check and self._settings.get(["pip_command"]) is not None:
+				check["pip_command"] = self._settings.get(["pip_command"])
 			return updaters.pip
 		elif "python_updater" in check:
 			return updaters.python_updater
diff --git a/src/octoprint/plugins/softwareupdate/updaters/pip.py b/src/octoprint/plugins/softwareupdate/updaters/pip.py
index 3b1eeac4..c6f8e590 100644
--- a/src/octoprint/plugins/softwareupdate/updaters/pip.py
+++ b/src/octoprint/plugins/softwareupdate/updaters/pip.py
@@ -7,19 +7,19 @@ __copyright__ = "Copyright (C) 2014 The OctoPrint Project - Released under terms
 
 
 import logging
+import sarge
+import sys
 
-try:
-	import pip as _pip
-except:
-	_pip = None
-
+logger = logging.getLogger("octoprint.plugins.softwareupdate.updaters.pip")
+console_logger = logging.getLogger("octoprint.plugins.softwareupdate.updaters.pip.console")
 
 def can_perform_update(target, check):
-	return "pip" in check and _pip is not None
-
+	return "pip" in check
 
 def perform_update(target, check, target_version):
-	logger = logging.getLogger("octoprint.plugins.softwareupdate.updaters.pip")
+	pip_command = None
+	if "pip_command" in check:
+		pip_command = check["pip_command"]
 
 	install_arg = check["pip"].format(target_version=target_version)
 
@@ -27,15 +27,94 @@ def perform_update(target, check, target_version):
 	pip_args = ["install", check["pip"].format(target_version=target_version, target=target_version)]
 
 	if "dependency_links" in check and check["dependency_links"]:
-		pip_args += "--process-dependency-links"
+		pip_args += ["--process-dependency-links"]
 
-	_pip.main(pip_args)
+	_call_pip(pip_args, pip_command=pip_command)
 
-	if "force_reinstall" in check and check["force_reinstall"]:
-		# if force_reinstall is true, we need to install the package a second time, this time forcing its reinstall
-		# without forcing its dependencies too
-		logger.debug("Target. %s, executing pip install %s --ignore-reinstalled --force-reinstall --no-deps" % (target, install_arg))
-		pip_args += ["--ignore-installed", "--force-reinstall", "--no-deps"]
-		_pip.main(pip_args)
+	logger.debug("Target. %s, executing pip install %s --ignore-reinstalled --force-reinstall --no-deps" % (target, install_arg))
+	pip_args += ["--ignore-installed", "--force-reinstall", "--no-deps"]
+	_call_pip(pip_args, pip_command=pip_command)
 
 	return "ok"
+
+def _call_pip(args, pip_command=None):
+	if pip_command is None:
+		import os
+		python_command = sys.executable
+		binary_dir = os.path.dirname(python_command)
+
+		pip_command = os.path.join(binary_dir, "pip")
+		if sys.platform == "win32":
+			# Windows is a bit special... first of all the file will be called pip.exe, not just pip, and secondly
+			# for a non-virtualenv install (e.g. global install) the pip binary will not be located in the
+			# same folder as python.exe, but in a subfolder Scripts, e.g.
+			#
+			# C:\Python2.7\
+			#  |- python.exe
+			#  `- Scripts
+			#      `- pip.exe
+
+			# virtual env?
+			pip_command = os.path.join(binary_dir, "pip.exe")
+
+			if not os.path.isfile(pip_command):
+				# nope, let's try the Scripts folder then
+				scripts_dir = os.path.join(binary_dir, "Scripts")
+				if os.path.isdir(scripts_dir):
+					pip_command = os.path.join(scripts_dir, "pip.exe")
+
+		if not os.path.isfile(pip_command) or not os.access(pip_command, os.X_OK):
+			raise RuntimeError(u"No pip path configured and {pip_command} does not exist or is not executable, can't install".format(**locals()))
+
+	command = [pip_command] + args
+
+	logger.debug(u"Calling: {}".format(" ".join(command)))
+
+	p = sarge.run(" ".join(command), shell=True, async=True, stdout=sarge.Capture(), stderr=sarge.Capture())
+	p.wait_events()
+
+	all_stdout = []
+	all_stderr = []
+	try:
+		while p.returncode is None:
+			line = p.stderr.readline(timeout=0.5)
+			if line:
+				_log_stderr(line)
+				all_stderr.append(line)
+
+			line = p.stdout.readline(timeout=0.5)
+			if line:
+				_log_stdout(line)
+				all_stdout.append(line)
+
+			p.commands[0].poll()
+
+	finally:
+		p.close()
+
+	stderr = p.stderr.text
+	if stderr:
+		split_lines = stderr.split("\n")
+		_log_stderr(*split_lines)
+		all_stderr += split_lines
+
+	stdout = p.stdout.text
+	if stdout:
+		split_lines = stdout.split("\n")
+		_log_stdout(*split_lines)
+		all_stdout += split_lines
+
+	return p.returncode, all_stdout, all_stderr
+
+def _log_stdout(*lines):
+	_log(lines, prefix=">", stream="stdout")
+
+def _log_stderr(*lines):
+	_log(lines, prefix="!", stream="stderr")
+
+def _log(lines, prefix=None, stream=None, strip=True):
+	if strip:
+		lines = map(lambda x: x.strip(), lines)
+	for line in lines:
+		console_logger.debug(u"{prefix} {line}".format(**locals()))
+