diff --git a/lib/docker.js b/lib/docker.js
index f4d7bdbb..e247b286 100644
--- a/lib/docker.js
+++ b/lib/docker.js
@@ -18,7 +18,7 @@ function dockerCommand(options) {
     throw new Error(ps.stderr);
   }
   return ps;
-}
+};
 
 /**
  * Build the custom Docker image
@@ -34,34 +34,67 @@ function buildImage(dockerFile) {
   return imageName;
 };
 
+/**
+ * Test bind path to make sure it's working
+ * @param {string} bindPath
+ * @return {boolean}
+ */
+function tryBindPath(bindPath) {
+  const options = ['run', '--rm', '-v', `${bindPath}:/test`,
+    'alpine', 'ls', '/test/serverless.yml'];
+  try {
+    const ps = dockerCommand(options);
+    return ps.stdout.trim() === '/test/serverless.yml';
+  } catch (err) {
+    return false;
+  }
+};
+
 /**
  * Get bind path depending on os platform
  * @param {string} servicePath
  * @return {string} The bind path.
  */
 function getBindPath(servicePath) {
-  // Determine os platform of docker CLI from 'docker version'
-  const options = ['version', '--format', '{{with .Client}}{{.Os}}{{end}}'];
-  const ps = dockerCommand(options);
-  const cliPlatform = ps.stdout.trim();
-
   // Determine bind path
-  let bindPath;
-  if (process.platform === 'win32') {
-    bindPath = servicePath.replace(/\\([^\s])/g, '/$1');
-    if (cliPlatform === 'windows') {
-      bindPath = bindPath.replace(/^\/(\w)\//i, '$1:/');
-    }
-  } else if (isWsl) {
-    bindPath = servicePath.replace(/^\/mnt\//, '/');
-    if (cliPlatform === 'windows') {
-      bindPath = bindPath.replace(/^\/(\w)\//i, '$1:/');
-    }
+  if (process.platform !== 'win32' && !isWsl) {
+    return servicePath;
+  }
+
+  let bindPaths = [];
+  let baseBindPath = servicePath.replace(/\\([^\s])/g, '/$1');
+  let drive;
+  let path;
+
+  bindPaths.push(baseBindPath);
+  if (baseBindPath.startsWith('/mnt/')) { // cygwin "/mnt/C/users/..."
+    baseBindPath = baseBindPath.replace(/^\/mnt\//, '/');
+  }
+  if (baseBindPath[1] == ':') { // normal windows "c:/users/..."
+    drive = baseBindPath[0];
+    path = baseBindPath.substring(3);
+  } else if (baseBindPath[0] == '/' && baseBindPath[2] == '/') { // gitbash "/c/users/..."
+    drive = baseBindPath[1];
+    path = baseBindPath.substring(3);
   } else {
-    bindPath = servicePath;
+    throw new Error(`Unknown path format ${baseBindPath.substr(10)}...`);
+  }
+
+  bindPaths.push(`/${drive.toLowerCase()}/${path}`);
+  bindPaths.push(`/${drive.toUpperCase()}/${path}`);
+  bindPaths.push(`/mnt/${drive.toLowerCase()}/${path}`);
+  bindPaths.push(`/mnt/${drive.toUpperCase()}/${path}`);
+  bindPaths.push(`${drive.toLowerCase()}:/${path}`);
+  bindPaths.push(`${drive.toUpperCase()}:/${path}`);
+
+  for (let i = 0; i < bindPaths.length; i++) {
+    const bindPath = bindPaths[i];
+    if (tryBindPath(bindPath)) {
+      return bindPath;
+    }
   }
 
-  return bindPath;
+  throw new Error('Unable to find good bind path format');
 };
 
 module.exports = {buildImage, getBindPath};