diff --git a/integration_tests/context/arr[0].txt b/integration_tests/context/arr[0].txt
new file mode 100644
index 0000000000..b6fc4c620b
--- /dev/null
+++ b/integration_tests/context/arr[0].txt
@@ -0,0 +1 @@
+hello
\ No newline at end of file
diff --git a/integration_tests/context/empty/.gitignore b/integration_tests/context/empty/.gitignore
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/integration_tests/dockerfiles/Dockerfile_test_copy b/integration_tests/dockerfiles/Dockerfile_test_copy
index 517f655a29..44e49e82ff 100644
--- a/integration_tests/dockerfiles/Dockerfile_test_copy
+++ b/integration_tests/dockerfiles/Dockerfile_test_copy
@@ -10,3 +10,5 @@ COPY . newdir
 COPY context/bar /baz/
 COPY ["context/foo", "/tmp/foo" ]
 COPY context/b* /baz/
+COPY context/foo context/bar/ba? /test/
+COPY context/arr[[]0].txt /mydir/
\ No newline at end of file
diff --git a/pkg/commands/copy.go b/pkg/commands/copy.go
index 9b0ffaf56b..afacf57ebe 100644
--- a/pkg/commands/copy.go
+++ b/pkg/commands/copy.go
@@ -41,7 +41,7 @@ func (c *CopyCommand) ExecuteCommand(config *manifest.Schema2Config) error {
 	logrus.Infof("dest: %s", dest)
 
 	// Get a map of [src]:[files rooted at src]
-	srcMap, err := util.ResolveSources(c.cmd.SourcesAndDest, c.buildcontext, config.WorkingDir)
+	srcMap, err := util.ResolveSources(c.cmd.SourcesAndDest, c.buildcontext)
 	if err != nil {
 		return err
 	}
@@ -88,7 +88,7 @@ func (c *CopyCommand) FilesToSnapshot() []string {
 	return c.snapshotFiles
 }
 
-// Author returns some information about the command for the image config
+// CreatedBy returns some information about the command for the image config
 func (c *CopyCommand) CreatedBy() string {
 	return strings.Join(c.cmd.SourcesAndDest, " ")
 }
diff --git a/pkg/util/command_util.go b/pkg/util/command_util.go
index 86321c5bdf..0b92e133fd 100644
--- a/pkg/util/command_util.go
+++ b/pkg/util/command_util.go
@@ -19,6 +19,7 @@ package util
 import (
 	"github.com/docker/docker/builder/dockerfile/instructions"
 	"github.com/pkg/errors"
+	"github.com/sirupsen/logrus"
 	"os"
 	"path/filepath"
 	"strings"
@@ -38,21 +39,22 @@ func ContainsWildcards(paths []string) bool {
 	return false
 }
 
-// ResolveSources resolves the given sources if the sources contains wildcard
+// ResolveSources resolves the given sources if the sources contains wildcards
 // It returns a map of [src]:[files rooted at src]
-func ResolveSources(srcsAndDest instructions.SourcesAndDest, root, cwd string) (map[string][]string, error) {
+func ResolveSources(srcsAndDest instructions.SourcesAndDest, root string) (map[string][]string, error) {
 	srcs := srcsAndDest[:len(srcsAndDest)-1]
 	// If sources contain wildcards, we first need to resolve them to actual paths
-	wildcard := ContainsWildcards(srcs)
-	if wildcard {
-		files, err := Files("", root)
+	if ContainsWildcards(srcs) {
+		logrus.Debugf("Resolving srcs %v...", srcs)
+		files, err := RelativeFiles("", root)
 		if err != nil {
 			return nil, err
 		}
-		srcs, err = matchSources(srcs, files, cwd)
+		srcs, err = matchSources(srcs, files)
 		if err != nil {
 			return nil, err
 		}
+		logrus.Debugf("Resolved sources to %v", srcs)
 	}
 	// Now, get a map of [src]:[files rooted at src]
 	srcMap, err := SourcesToFilesMap(srcs, root)
@@ -63,8 +65,8 @@ func ResolveSources(srcsAndDest instructions.SourcesAndDest, root, cwd string) (
 	return srcMap, IsSrcsValid(srcsAndDest, srcMap)
 }
 
-// matchSources returns a map of [src]:[matching filepaths], used to resolve wildcards
-func matchSources(srcs, files []string, cwd string) ([]string, error) {
+// matchSources returns a list of sources that match wildcards
+func matchSources(srcs, files []string) ([]string, error) {
 	var matchedSources []string
 	for _, src := range srcs {
 		src = filepath.Clean(src)
@@ -73,12 +75,7 @@ func matchSources(srcs, files []string, cwd string) ([]string, error) {
 			if err != nil {
 				return nil, err
 			}
-			// Check cwd
-			matchedRoot, err := filepath.Match(filepath.Join(cwd, src), file)
-			if err != nil {
-				return nil, err
-			}
-			if !(matched || matchedRoot) {
+			if !matched {
 				continue
 			}
 			matchedSources = append(matchedSources, file)
@@ -91,13 +88,17 @@ func IsDestDir(path string) bool {
 	return strings.HasSuffix(path, "/")
 }
 
-// RelativeFilepath returns the relative filepath
-// If source is a file:
-//	If dest is a dir, copy it to /cwd/dest/relpath
-// 	If dest is a file, copy directly to /cwd/dest
+func IsAbsoluteFilepath(path string) bool {
+	return strings.HasPrefix(path, "/")
+}
 
+// RelativeFilepath returns the relative filepath from the build context to the image filesystem
+// If source is a file:
+//	If dest is a dir, copy it to /dest/relpath
+// 	If dest is a file, copy directly to dest
 // If source is a dir:
-//	Assume dest is also a dir, and copy to /cwd/dest/relpath
+//	Assume dest is also a dir, and copy to dest/relpath
+// If dest is not an absolute filepath, add /cwd to the beginning
 func RelativeFilepath(filename, srcName, dest, cwd, buildcontext string) (string, error) {
 	fi, err := os.Stat(filepath.Join(buildcontext, filename))
 	if err != nil {
@@ -115,9 +116,15 @@ func RelativeFilepath(filename, srcName, dest, cwd, buildcontext string) (string
 		if relPath == "." && !fi.IsDir() {
 			relPath = filepath.Base(filename)
 		}
-		destPath := filepath.Join(cwd, dest, relPath)
+		destPath := filepath.Join(dest, relPath)
+		if !IsAbsoluteFilepath(dest) {
+			destPath = filepath.Join(cwd, destPath)
+		}
 		return destPath, nil
 	}
+	if IsAbsoluteFilepath(dest) {
+		return dest, nil
+	}
 	return filepath.Join(cwd, dest), nil
 }
 
@@ -126,7 +133,7 @@ func SourcesToFilesMap(srcs []string, root string) (map[string][]string, error)
 	srcMap := make(map[string][]string)
 	for _, src := range srcs {
 		src = filepath.Clean(src)
-		files, err := Files(src, root)
+		files, err := RelativeFiles(src, root)
 		if err != nil {
 			return nil, err
 		}
diff --git a/pkg/util/command_util_test.go b/pkg/util/command_util_test.go
index ed89d182f0..4585ef8c9e 100644
--- a/pkg/util/command_util_test.go
+++ b/pkg/util/command_util_test.go
@@ -79,7 +79,7 @@ var relativeFilepathTests = []struct {
 		filename:         "context/empty",
 		cwd:              "/dir",
 		dest:             "/empty",
-		expectedFilepath: "/dir/empty",
+		expectedFilepath: "/empty",
 	},
 	{
 		srcName:          "./",
@@ -121,7 +121,6 @@ func Test_RelativeFilepath(t *testing.T) {
 var matchSourcesTests = []struct {
 	srcs          []string
 	files         []string
-	cwd           string
 	expectedFiles []string
 }{
 	{
@@ -135,18 +134,16 @@ var matchSourcesTests = []struct {
 			"pkg/b/d/",
 			"dir/",
 		},
-		cwd: "/",
 		expectedFiles: []string{
 			"pkg/a",
 			"pkg/b",
-			"/pkg/d",
 		},
 	},
 }
 
 func Test_MatchSources(t *testing.T) {
 	for _, test := range matchSourcesTests {
-		actualFiles, err := matchSources(test.srcs, test.files, test.cwd)
+		actualFiles, err := matchSources(test.srcs, test.files)
 		sort.Strings(actualFiles)
 		sort.Strings(test.expectedFiles)
 		testutil.CheckErrorAndDeepEqual(t, false, err, test.expectedFiles, actualFiles)
@@ -253,7 +250,6 @@ func Test_IsSrcsValid(t *testing.T) {
 
 var testResolveSources = []struct {
 	srcsAndDest []string
-	cwd         string
 	expectedMap map[string][]string
 }{
 	{
@@ -262,7 +258,6 @@ var testResolveSources = []struct {
 			"context/b*",
 			"dest/",
 		},
-		cwd: "/",
 		expectedMap: map[string][]string{
 			"context/foo": {
 				"context/foo",
@@ -280,7 +275,7 @@ var testResolveSources = []struct {
 
 func Test_ResolveSources(t *testing.T) {
 	for _, test := range testResolveSources {
-		actualMap, err := ResolveSources(test.srcsAndDest, buildContextPath, test.cwd)
+		actualMap, err := ResolveSources(test.srcsAndDest, buildContextPath)
 		testutil.CheckErrorAndDeepEqual(t, false, err, test.expectedMap, actualMap)
 	}
 }
diff --git a/pkg/util/fs_util.go b/pkg/util/fs_util.go
index 3b56c6cce7..995e7c0035 100644
--- a/pkg/util/fs_util.go
+++ b/pkg/util/fs_util.go
@@ -98,8 +98,8 @@ func fileSystemWhitelist(path string) ([]string, error) {
 	return whitelist, nil
 }
 
-// Files returns a list of all files at the filepath relative to root
-func Files(fp string, root string) ([]string, error) {
+// RelativeFiles returns a list of all files at the filepath relative to root
+func RelativeFiles(fp string, root string) ([]string, error) {
 	var files []string
 	fullPath := filepath.Join(root, fp)
 	logrus.Debugf("Getting files and contents at root %s", fullPath)
@@ -112,7 +112,7 @@ func Files(fp string, root string) ([]string, error) {
 			return err
 		}
 		files = append(files, relPath)
-		return err
+		return nil
 	})
 	return files, err
 }
diff --git a/pkg/util/fs_util_test.go b/pkg/util/fs_util_test.go
index f21c6f788e..c8ebc88cf3 100644
--- a/pkg/util/fs_util_test.go
+++ b/pkg/util/fs_util_test.go
@@ -114,7 +114,7 @@ var tests = []struct {
 	},
 }
 
-func Test_Files(t *testing.T) {
+func Test_RelativeFiles(t *testing.T) {
 	for _, test := range tests {
 		testDir, err := ioutil.TempDir("", "")
 		if err != nil {
@@ -124,7 +124,7 @@ func Test_Files(t *testing.T) {
 		if err := testutil.SetupFiles(testDir, test.files); err != nil {
 			t.Fatalf("err setting up files: %v", err)
 		}
-		actualFiles, err := Files(test.directory, testDir)
+		actualFiles, err := RelativeFiles(test.directory, testDir)
 		sort.Strings(actualFiles)
 		sort.Strings(test.expectedFiles)
 		testutil.CheckErrorAndDeepEqual(t, false, err, test.expectedFiles, actualFiles)