diff --git a/pkg/apis/core/types.go b/pkg/apis/core/types.go
index f861925cc74..e74469d9bb8 100644
--- a/pkg/apis/core/types.go
+++ b/pkg/apis/core/types.go
@@ -1530,7 +1530,9 @@ type VolumeMount struct {
 	// Optional: Defaults to false (read-write).
 	// +optional
 	ReadOnly bool
-	// Required. Must not contain ':'.
+	// Required. If the path is not an absolute path (e.g. some/path) it
+	// will be prepended with the appropriate root prefix for the operating
+	// system.  On Linux this is '/', on Windows this is 'C:\'.
 	MountPath string
 	// Path within the volume from which the container's volume should be mounted.
 	// Defaults to "" (volume's root).
diff --git a/pkg/apis/core/validation/validation.go b/pkg/apis/core/validation/validation.go
index 8fe283ddfeb..1dd944f10e7 100644
--- a/pkg/apis/core/validation/validation.go
+++ b/pkg/apis/core/validation/validation.go
@@ -1965,13 +1965,6 @@ func ValidateVolumeMounts(mounts []core.VolumeMount, volumes sets.String, contai
 		if mountpoints.Has(mnt.MountPath) {
 			allErrs = append(allErrs, field.Invalid(idxPath.Child("mountPath"), mnt.MountPath, "must be unique"))
 		}
-		if !path.IsAbs(mnt.MountPath) {
-			// also allow windows absolute path
-			p := mnt.MountPath
-			if len(p) < 2 || ((p[0] < 'A' || p[0] > 'Z') && (p[0] < 'a' || p[0] > 'z')) || p[1] != ':' {
-				allErrs = append(allErrs, field.Invalid(idxPath.Child("mountPath"), mnt.MountPath, "must be an absolute path"))
-			}
-		}
 		mountpoints.Insert(mnt.MountPath)
 		if len(mnt.SubPath) > 0 {
 			allErrs = append(allErrs, validateLocalDescendingPath(mnt.SubPath, fldPath.Child("subPath"))...)
diff --git a/pkg/apis/core/validation/validation_test.go b/pkg/apis/core/validation/validation_test.go
index 3a6121715ce..43cdd8a3ead 100644
--- a/pkg/apis/core/validation/validation_test.go
+++ b/pkg/apis/core/validation/validation_test.go
@@ -3849,10 +3849,8 @@ func TestValidateVolumeMounts(t *testing.T) {
 		"empty name":                             {{Name: "", MountPath: "/foo"}},
 		"name not found":                         {{Name: "", MountPath: "/foo"}},
 		"empty mountpath":                        {{Name: "abc", MountPath: ""}},
-		"relative mountpath":                     {{Name: "abc", MountPath: "bar"}},
 		"mountpath collision":                    {{Name: "foo", MountPath: "/path/a"}, {Name: "bar", MountPath: "/path/a"}},
 		"absolute subpath":                       {{Name: "abc", MountPath: "/bar", SubPath: "/baz"}},
-		"windows absolute subpath":               {{Name: "abc", MountPath: "D", SubPath: ""}},
 		"subpath in ..":                          {{Name: "abc", MountPath: "/bar", SubPath: "../baz"}},
 		"subpath contains ..":                    {{Name: "abc", MountPath: "/bar", SubPath: "baz/../bat"}},
 		"subpath ends in ..":                     {{Name: "abc", MountPath: "/bar", SubPath: "./.."}},
diff --git a/pkg/kubelet/kubelet_pods.go b/pkg/kubelet/kubelet_pods.go
index bf2dede98a9..8a180747423 100644
--- a/pkg/kubelet/kubelet_pods.go
+++ b/pkg/kubelet/kubelet_pods.go
@@ -111,6 +111,23 @@ func (kl *Kubelet) makeDevices(pod *v1.Pod, container *v1.Container) ([]kubecont
 	return devices, nil
 }
 
+func makeAbsolutePath(goos, path string) string {
+	if goos != "windows" {
+		return "/" + path
+	}
+	// These are all for windows
+	// If there is a colon, give up.
+	if strings.Contains(path, ":") {
+		return path
+	}
+	// If there is a slash, but no drive, add 'c:'
+	if strings.HasPrefix(path, "/") || strings.HasPrefix(path, "\\") {
+		return "c:" + path
+	}
+	// Otherwise, add 'c:\'
+	return "c:\\" + path
+}
+
 // makeMounts determines the mount points for the given container.
 func makeMounts(pod *v1.Pod, podDir string, container *v1.Container, hostName, hostDomain, podIP string, podVolumes kubecontainer.VolumeMap) ([]kubecontainer.Mount, error) {
 	// Kubernetes only mounts on /etc/hosts if:
@@ -187,9 +204,9 @@ func makeMounts(pod *v1.Pod, podDir string, container *v1.Container, hostName, h
 			if (strings.HasPrefix(hostPath, "/") || strings.HasPrefix(hostPath, "\\")) && !strings.Contains(hostPath, ":") {
 				hostPath = "c:" + hostPath
 			}
-			if (strings.HasPrefix(containerPath, "/") || strings.HasPrefix(containerPath, "\\")) && !strings.Contains(containerPath, ":") {
-				containerPath = "c:" + containerPath
-			}
+		}
+		if !filepath.IsAbs(containerPath) {
+			containerPath = makeAbsolutePath(runtime.GOOS, containerPath)
 		}
 
 		propagation, err := translateMountPropagation(mount.MountPropagation)
diff --git a/pkg/kubelet/kubelet_pods_test.go b/pkg/kubelet/kubelet_pods_test.go
index 5b759d5d1a5..79e1f15361a 100644
--- a/pkg/kubelet/kubelet_pods_test.go
+++ b/pkg/kubelet/kubelet_pods_test.go
@@ -49,6 +49,52 @@ import (
 	"k8s.io/kubernetes/pkg/kubelet/server/remotecommand"
 )
 
+func TestMakeAbsolutePath(t *testing.T) {
+	tests := []struct {
+		goos         string
+		path         string
+		expectedPath string
+		name         string
+	}{
+		{
+			goos:         "linux",
+			path:         "non-absolute/path",
+			expectedPath: "/non-absolute/path",
+			name:         "basic linux",
+		},
+		{
+			goos:         "windows",
+			path:         "some\\path",
+			expectedPath: "c:\\some\\path",
+			name:         "basic windows",
+		},
+		{
+			goos:         "windows",
+			path:         "/some/path",
+			expectedPath: "c:/some/path",
+			name:         "linux path on windows",
+		},
+		{
+			goos:         "windows",
+			path:         "\\some\\path",
+			expectedPath: "c:\\some\\path",
+			name:         "windows path no drive",
+		},
+		{
+			goos:         "windows",
+			path:         "\\:\\some\\path",
+			expectedPath: "\\:\\some\\path",
+			name:         "windows path with colon",
+		},
+	}
+	for _, test := range tests {
+		path := makeAbsolutePath(test.goos, test.path)
+		if path != test.expectedPath {
+			t.Errorf("[%s] Expected %s saw %s", test.name, test.expectedPath, path)
+		}
+	}
+}
+
 func TestMakeMounts(t *testing.T) {
 	bTrue := true
 	propagationHostToContainer := v1.MountPropagationHostToContainer