diff --git a/platformio/commands/upgrade.py b/platformio/commands/upgrade.py
index 44e3b8ea..4f1f9b8e 100644
--- a/platformio/commands/upgrade.py
+++ b/platformio/commands/upgrade.py
@@ -1,4 +1,4 @@
-# Copyright 2014-2016 Ivan Kravets <me@ikravets.com>
+# Copyright 2014-present Ivan Kravets <me@ikravets.com>
 #
 # Licensed under the Apache License, Version 2.0 (the "License");
 # you may not use this file except in compliance with the License.
@@ -13,19 +13,20 @@
 # limitations under the License.
 
 import os
+import re
 import sys
 
 import click
 import requests
 
-from platformio import __version__, exception, util
+from platformio import VERSION, __version__, exception, util
 
 
 @click.command("upgrade",
                short_help="Upgrade PlatformIO to the latest version")
 def cli():
-    last = get_latest_version()
-    if __version__ == last:
+    latest = get_latest_version()
+    if __version__ == latest:
         return click.secho(
             "You're up-to-date!\nPlatformIO %s is currently the "
             "newest version available." % __version__, fg="green"
@@ -34,13 +35,7 @@ def cli():
         click.secho("Please wait while upgrading PlatformIO ...",
                     fg="yellow")
 
-        to_develop = False
-        try:
-            from pkg_resources import parse_version
-            to_develop = parse_version(last) < parse_version(__version__)
-        except ImportError:
-            pass
-
+        to_develop = not all([c.isdigit() for c in latest if c != "."])
         cmds = (
             ["pip", "install", "--upgrade",
              "https://github.com/platformio/platformio/archive/develop.zip"
@@ -100,10 +95,43 @@ WARNING! Don't use `sudo` for the rest PlatformIO commands.
 
 def get_latest_version():
     try:
-        pkgdata = requests.get(
-            "https://pypi.python.org/pypi/platformio/json",
-            headers=util.get_request_defheaders()
-        ).json()
-        return pkgdata['info']['version']
+        if not isinstance(VERSION[2], int):
+            try:
+                return get_develop_latest_version()
+            except:  # pylint: disable=bare-except
+                pass
+        return get_pypi_latest_version()
     except:
         raise exception.GetLatestVersionError()
+
+
+def get_develop_latest_version():
+    version = None
+    r = requests.get(
+        "https://raw.githubusercontent.com/platformio/platformio"
+        "/develop/platformio/__init__.py",
+        headers=util.get_request_defheaders()
+    )
+    r.raise_for_status()
+    for line in r.text.split("\n"):
+        line = line.strip()
+        if not line.startswith("VERSION"):
+            continue
+        match = re.match(r"VERSION\s*=\s*\(([^\)]+)\)", line)
+        if not match:
+            continue
+        version = match.group(1)
+        for c in (" ", "'", '"'):
+            version = version.replace(c, "")
+        version = ".".join(version.split(","))
+    assert version
+    return version
+
+
+def get_pypi_latest_version():
+    r = requests.get(
+        "https://pypi.python.org/pypi/platformio/json",
+        headers=util.get_request_defheaders()
+    )
+    r.raise_for_status()
+    return r.json()['info']['version']
diff --git a/platformio/maintenance.py b/platformio/maintenance.py
index ad190080..5bc31f2c 100644
--- a/platformio/maintenance.py
+++ b/platformio/maintenance.py
@@ -67,8 +67,10 @@ def on_platformio_exception(e):
 class Upgrader(object):
 
     def __init__(self, from_version, to_version):
-        self.from_version = semantic_version.Version.coerce(from_version)
-        self.to_version = semantic_version.Version.coerce(to_version)
+        self.from_version = semantic_version.Version.coerce(
+            util.pepver_to_semver(from_version))
+        self.to_version = semantic_version.Version.coerce(
+            util.pepver_to_semver(to_version))
 
         self._upgraders = [
             (semantic_version.Version("3.0.0"), self._upgrade_to_3_0_0)
@@ -180,8 +182,9 @@ def check_platformio_upgrade():
     app.set_state_item("last_check", last_check)
 
     latest_version = get_latest_version()
-    if (semantic_version.Version.coerce(latest_version) <=
-            semantic_version.Version.coerce(__version__)):
+    if semantic_version.Version.coerce(util.pepver_to_semver(
+            latest_version)) <= semantic_version.Version.coerce(
+                util.pepver_to_semver(__version__)):
         return
 
     terminal_width, _ = click.get_terminal_size()
diff --git a/platformio/util.py b/platformio/util.py
index 2eeaec55..d3ac1980 100644
--- a/platformio/util.py
+++ b/platformio/util.py
@@ -461,3 +461,7 @@ def where_is_program(program, envpath=None):
             return join(bin_dir, "%s.exe" % program)
 
     return program
+
+
+def pepver_to_semver(pepver):
+    return re.sub(r"(\.\d+)\.?(dev|a|b|rc|post)", r"\1-\2", pepver, 1)