diff --git a/runtime/v2/shim/util.go b/runtime/v2/shim/util.go
index 77afaa1f3..75878fb3f 100644
--- a/runtime/v2/shim/util.go
+++ b/runtime/v2/shim/util.go
@@ -31,8 +31,6 @@ import (
 	"github.com/pkg/errors"
 )
 
-const shimBinaryFormat = "containerd-shim-%s-%s"
-
 var runtimePaths sync.Map
 
 // Command returns the shim command with the provided args and configuration
@@ -65,7 +63,19 @@ func Command(ctx context.Context, runtime, containerdAddress, path string, cmdAr
 		if cmdPath, lerr = exec.LookPath(name); lerr != nil {
 			if eerr, ok := lerr.(*exec.Error); ok {
 				if eerr.Err == exec.ErrNotFound {
-					return nil, errors.Wrapf(os.ErrNotExist, "runtime %q binary not installed %q", runtime, name)
+					// LookPath only finds current directory matches based on
+					// the callers current directory but the caller is not
+					// likely in the same directory as the containerd
+					// executables. Instead match the calling binaries path
+					// (containerd) and see if they are side by side. If so
+					// execute the shim found there.
+					testPath := filepath.Join(filepath.Dir(self), name)
+					if _, serr := os.Stat(testPath); serr == nil {
+						path = testPath
+					}
+					if path == "" {
+						return nil, errors.Wrapf(os.ErrNotExist, "runtime %q binary not installed %q", runtime, name)
+					}
 				}
 			}
 		}
diff --git a/runtime/v2/shim/util_unix.go b/runtime/v2/shim/util_unix.go
index 262fe2b36..b86f8624a 100644
--- a/runtime/v2/shim/util_unix.go
+++ b/runtime/v2/shim/util_unix.go
@@ -31,6 +31,8 @@ import (
 	"github.com/pkg/errors"
 )
 
+const shimBinaryFormat = "containerd-shim-%s-%s"
+
 func getSysProcAttr() *syscall.SysProcAttr {
 	return &syscall.SysProcAttr{
 		Setpgid: true,
diff --git a/runtime/v2/shim/util_windows.go b/runtime/v2/shim/util_windows.go
index 594a0f75b..ef26ebe22 100644
--- a/runtime/v2/shim/util_windows.go
+++ b/runtime/v2/shim/util_windows.go
@@ -29,6 +29,8 @@ import (
 	"github.com/pkg/errors"
 )
 
+const shimBinaryFormat = "containerd-shim-%s-%s.exe"
+
 func getSysProcAttr() *syscall.SysProcAttr {
 	return nil
 }
diff --git a/vendor.conf b/vendor.conf
index 5eeaa4f3a..5abbc57b5 100644
--- a/vendor.conf
+++ b/vendor.conf
@@ -33,7 +33,7 @@ golang.org/x/sync 450f422ab23cf9881c94e2db30cac0eb1b7cf80c
 github.com/BurntSushi/toml a368813c5e648fee92e5f6c30e3944ff9d5e8895
 github.com/grpc-ecosystem/go-grpc-prometheus 6b7015e65d366bf3f19b2b2a000a831940f0f7e0
 github.com/Microsoft/go-winio v0.4.11
-github.com/Microsoft/hcsshim v0.8.4
+github.com/Microsoft/hcsshim v0.8.5
 google.golang.org/genproto d80a6e20e776b0b17a324d0ba1ab50a39c8e8944
 golang.org/x/text 19e51611da83d6be54ddafce4a4af510cb3e9ea4
 github.com/containerd/ttrpc f02858b1457c5ca3aaec3a0803eb0d59f96e41d6
diff --git a/vendor/github.com/Microsoft/hcsshim/pkg/go-runhcs/runhcs.go b/vendor/github.com/Microsoft/hcsshim/pkg/go-runhcs/runhcs.go
index 5d5205abd..64491a70c 100644
--- a/vendor/github.com/Microsoft/hcsshim/pkg/go-runhcs/runhcs.go
+++ b/vendor/github.com/Microsoft/hcsshim/pkg/go-runhcs/runhcs.go
@@ -35,9 +35,22 @@ func getCommandPath() string {
 	if pathi == nil {
 		path, err := exec.LookPath(command)
 		if err != nil {
-			// Failed to look up command just use it directly and let the
-			// Windows loader find it.
-			path = command
+			// LookPath only finds current directory matches based on the
+			// callers current directory but the caller is not likely in the
+			// same directory as the containerd executables. Instead match the
+			// calling binaries path (a containerd shim usually) and see if they
+			// are side by side. If so execute the runhcs.exe found there.
+			if self, serr := os.Executable(); serr == nil {
+				testPath := filepath.Join(filepath.Dir(self), command)
+				if _, serr := os.Stat(testPath); serr == nil {
+					path = testPath
+				}
+			}
+			if path == "" {
+				// Failed to look up command just use it directly and let the
+				// Windows loader find it.
+				path = command
+			}
 			runhcsPath.Store(path)
 			return path
 		}