diff --git a/appveyor.yml b/appveyor.yml
index 576c6f80c78f..18906d917be2 100644
--- a/appveyor.yml
+++ b/appveyor.yml
@@ -46,6 +46,7 @@ test_script:
       gotestsum --junitfile results.xml
            github.com/hashicorp/nomad/drivers/docker
            github.com/hashicorp/nomad/client/lib/fifo
+           github.com/hashicorp/nomad/client/logmon
 # on_finish:
 #   - ps: |
 #       Push-AppveyorArtifact (Resolve-Path .\results.xml)
diff --git a/client/lib/fifo/fifo_windows.go b/client/lib/fifo/fifo_windows.go
index 4feaa63da1d0..9963570bb78f 100644
--- a/client/lib/fifo/fifo_windows.go
+++ b/client/lib/fifo/fifo_windows.go
@@ -1,6 +1,7 @@
 package fifo
 
 import (
+	"fmt"
 	"io"
 	"net"
 	"os"
@@ -75,7 +76,7 @@ func CreateAndRead(path string) (func() (io.ReadCloser, error), error) {
 		OutputBufferSize: PipeBufferSize,
 	})
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("failed to create fifo: %v", err)
 	}
 
 	return func() (io.ReadCloser, error) {
@@ -88,7 +89,7 @@ func CreateAndRead(path string) (func() (io.ReadCloser, error), error) {
 func OpenReader(path string) (io.ReadCloser, error) {
 	l, err := winio.ListenOnlyPipe(path, nil)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("failed to open fifo listener: %v", err)
 	}
 
 	return &winFIFO{listener: l}, nil
diff --git a/client/logmon/logmon_test.go b/client/logmon/logmon_test.go
index 609b3db6eaf7..5821658e0a96 100644
--- a/client/logmon/logmon_test.go
+++ b/client/logmon/logmon_test.go
@@ -6,6 +6,7 @@ import (
 	"io/ioutil"
 	"os"
 	"path/filepath"
+	"runtime"
 	"testing"
 
 	"github.com/hashicorp/nomad/client/lib/fifo"
@@ -16,13 +17,23 @@ import (
 
 func TestLogmon_Start_rotate(t *testing.T) {
 	require := require.New(t)
+
+	stdoutLog := "stdout"
+	stderrLog := "stderr"
+
+	var stdoutFifoPath, stderrFifoPath string
+
 	dir, err := ioutil.TempDir("", "nomadtest")
 	require.NoError(err)
 	defer os.RemoveAll(dir)
-	stdoutLog := "stdout"
-	stdoutFifoPath := filepath.Join(dir, "stdout.fifo")
-	stderrLog := "stderr"
-	stderrFifoPath := filepath.Join(dir, "stderr.fifo")
+
+	if runtime.GOOS == "windows" {
+		stdoutFifoPath = "//./pipe/test-rotate.stdout"
+		stderrFifoPath = "//./pipe/test-rotate.stderr"
+	} else {
+		stdoutFifoPath = filepath.Join(dir, "stdout.fifo")
+		stderrFifoPath = filepath.Join(dir, "stderr.fifo")
+	}
 
 	cfg := &LogConfig{
 		LogDir:        dir,
@@ -69,13 +80,23 @@ func TestLogmon_Start_rotate(t *testing.T) {
 // asserts that calling Start twice restarts the log rotator
 func TestLogmon_Start_restart(t *testing.T) {
 	require := require.New(t)
+
+	stdoutLog := "stdout"
+	stderrLog := "stderr"
+
+	var stdoutFifoPath, stderrFifoPath string
+
 	dir, err := ioutil.TempDir("", "nomadtest")
 	require.NoError(err)
 	defer os.RemoveAll(dir)
-	stdoutLog := "stdout"
-	stdoutFifoPath := filepath.Join(dir, "stdout.fifo")
-	stderrLog := "stderr"
-	stderrFifoPath := filepath.Join(dir, "stderr.fifo")
+
+	if runtime.GOOS == "windows" {
+		stdoutFifoPath = "//./pipe/test-restart.stdout"
+		stderrFifoPath = "//./pipe/test-restart.stderr"
+	} else {
+		stdoutFifoPath = filepath.Join(dir, "stdout.fifo")
+		stderrFifoPath = filepath.Join(dir, "stderr.fifo")
+	}
 
 	cfg := &LogConfig{
 		LogDir:        dir,
@@ -122,6 +143,9 @@ func TestLogmon_Start_restart(t *testing.T) {
 		require.NoError(err)
 	})
 
+	// Start logmon again and assert that it appended to the file
+	require.NoError(lm.Start(cfg))
+
 	stdout, err = fifo.OpenWriter(stdoutFifoPath)
 	require.NoError(err)
 	stderr, err = fifo.OpenWriter(stderrFifoPath)
@@ -140,14 +164,6 @@ func TestLogmon_Start_restart(t *testing.T) {
 		require.NoError(err)
 	})
 
-	// Start logmon again and assert that it appended to the file
-	require.NoError(lm.Start(cfg))
-
-	stdout, err = fifo.OpenWriter(stdoutFifoPath)
-	require.NoError(err)
-	stderr, err = fifo.OpenWriter(stderrFifoPath)
-	require.NoError(err)
-
 	_, err = stdout.Write([]byte("st\n"))
 	require.NoError(err)
 	testutil.WaitForResult(func() (bool, error) {