diff --git a/plugin/wakatime.vim b/plugin/wakatime.vim
index 601885d..81e7427 100644
--- a/plugin/wakatime.vim
+++ b/plugin/wakatime.vim
@@ -126,13 +126,13 @@ let s:VERSION = '9.0.1'
                 let path = path . '.exe'
             endif
 
-            " Check for wakatime-cli installed via Homebrew
-            if !filereadable(path) && filereadable('/usr/local/bin/wakatime-cli')
-                let s:wakatime_cli = '/usr/local/bin/wakatime-cli'
+            " Check for wakatime-cli
+            if !filereadable(path) && executable('wakatime-cli')
+                let s:wakatime_cli = 'wakatime-cli'
 
-            " Check for wakatime binary in /usr/bin
-            elseif !filereadable(path) && filereadable('/usr/bin/wakatime')
-                let s:wakatime_cli = '/usr/bin/wakatime'
+            " Check for wakatime
+            elseif !filereadable(path) && executable('wakatime')
+                let s:wakatime_cli = 'wakatime'
 
             " Default to ~/.wakatime/wakatime-cli-<os>-<arch>
             else
@@ -144,17 +144,17 @@ let s:VERSION = '9.0.1'
     endfunction
 
     function! s:InstallCLI(use_external_python)
-        if !s:autoupdate_cli && filereadable(s:wakatime_cli)
+        if !s:autoupdate_cli && executable(s:wakatime_cli)
             return
         endif
 
-        let python_bin = s:false
+        let python_bin = ''
         if a:use_external_python
             let python_bin = s:GetPythonBinary()
         endif
 
         " First try install wakatime-cli in background, then using Vim's Python
-        if !empty(python_bin) && python_bin != s:false
+        if !empty(python_bin)
             let install_script = s:plugin_root_folder . '/scripts/install_cli.py'
             let cmd = [python_bin, '-W', 'ignore', install_script, s:home]
             if s:has_async
@@ -371,36 +371,35 @@ EOF
         if has('g:wakatime_PythonBinary')
             let python_bin = g:wakatime_PythonBinary
         endif
-        if !empty(python_bin) && !filereadable(python_bin) && !executable(python_bin)
+        if empty(python_bin) || !filereadable(python_bin) || !executable(python_bin)
             if executable('python3')
                 let python_bin = 'python3'
             elseif executable('python')
                 let python_bin = 'python'
-            endif
-        endif
-        if !empty(python_bin) && !filereadable(python_bin) && !executable(python_bin)
-            let paths = ['python3']
-            if s:IsWindows()
-                let pyver = 39
-                while pyver >= 27
-                    let paths = paths + [printf('/Python%d/pythonw', pyver), printf('/python%d/pythonw', pyver), printf('/Python%d/python', pyver), printf('/python%d/python', pyver)]
-                    let pyver = pyver - 1
-                endwhile
             else
-                let paths = paths + ['/usr/bin/python3', '/usr/local/bin/python3', '/usr/bin/python3.6', '/usr/local/bin/python3.6', '/usr/bin/python', '/usr/local/bin/python', '/usr/bin/python2', '/usr/local/bin/python2']
-            endif
-            let paths = paths + ['python']
-            let index = 0
-            let limit = len(paths)
-            while index < limit
-                if filereadable(paths[index])
-                    let python_bin = paths[index]
-                    let index = limit
+                let paths = ['python3']
+                if s:IsWindows()
+                    let pyver = 39
+                    while pyver >= 27
+                        let paths = paths + [printf('/Python%d/pythonw', pyver), printf('/python%d/pythonw', pyver), printf('/Python%d/python', pyver), printf('/python%d/python', pyver)]
+                        let pyver = pyver - 1
+                    endwhile
+                else
+                    let paths = paths + ['/usr/bin/python3', '/usr/local/bin/python3', '/usr/bin/python3.6', '/usr/local/bin/python3.6', '/usr/bin/python', '/usr/local/bin/python', '/usr/bin/python2', '/usr/local/bin/python2']
                 endif
-                let index = index + 1
-            endwhile
+                let paths = paths + ['python']
+                let index = 0
+                let limit = len(paths)
+                while index < limit
+                    if filereadable(paths[index])
+                        let python_bin = paths[index]
+                        let index = limit
+                    endif
+                    let index = index + 1
+                endwhile
+            endif
         endif
-        if s:IsWindows() && !empty(python_bin) && (filereadable(printf('%sw', python_bin)) || executable(printf('%sw', python_bin)))
+        if !empty(python_bin) && s:IsWindows() && (filereadable(printf('%sw', python_bin)) || executable(printf('%sw', python_bin)))
             let python_bin = printf('%sw', python_bin)
         endif
         return python_bin
diff --git a/scripts/install_cli.py b/scripts/install_cli.py
index 2f4adcf..6de0228 100644
--- a/scripts/install_cli.py
+++ b/scripts/install_cli.py
@@ -26,13 +26,20 @@
     from urllib.error import HTTPError
 
 
+def getOsName():
+    os = platform.system().lower()
+    if os.startswith('cygwin') or os.startswith('mingw') or os.startswith('msys'):
+        return 'windows'
+    return os
+
+
 GITHUB_RELEASES_STABLE_URL = 'https://api.github.com/repos/wakatime/wakatime-cli/releases/latest'
 GITHUB_DOWNLOAD_PREFIX = 'https://github.com/wakatime/wakatime-cli/releases/download'
 PLUGIN = 'vim'
 
 is_py2 = (sys.version_info[0] == 2)
 is_py3 = (sys.version_info[0] == 3)
-is_win = platform.system() == 'Windows'
+is_win = getOsName() == 'windows'
 
 HOME_FOLDER = None
 CONFIGS = None
@@ -49,10 +56,13 @@ def main(home=None):
     if not isCliLatest():
         downloadCLI()
 
-    try:
-        os.symlink(getCliLocation(), os.path.join(getResourcesFolder(), 'wakatime-cli'))
-    except:
-        pass
+    cli = os.path.join(getResourcesFolder(), 'wakatime-cli')
+    if not os.path.exists(cli):
+        try:
+            os.symlink(getCliLocation(), cli)
+        except:
+            # May not have permission on Windows
+            pass
 
 
 if is_py2:
@@ -223,7 +233,7 @@ def getCliLocation():
 
     if not WAKATIME_CLI_LOCATION:
         binary = 'wakatime-cli-{osname}-{arch}{ext}'.format(
-            osname=platform.system().lower(),
+            osname=getOsName(),
             arch=architecture(),
             ext='.exe' if is_win else '',
         )
@@ -337,7 +347,7 @@ def extractVersion(text):
 
 
 def cliDownloadUrl():
-    osname = platform.system().lower()
+    osname = getOsName()
     arch = architecture()
 
     validCombinations = [