diff --git a/internal/fs/fs.go b/internal/fs/fs.go
index 84f0346856..90d6f87908 100644
--- a/internal/fs/fs.go
+++ b/internal/fs/fs.go
@@ -318,6 +318,13 @@ func copyFile(src, dst string) (err error) {
 		return
 	}
 
+	// Temporary fix for Go < 1.9
+	//
+	// See: https://github.com/golang/dep/issues/774
+	// and https://github.com/golang/go/issues/20829
+	if runtime.GOOS == "windows" {
+		dst = fixLongPath(dst)
+	}
 	err = os.Chmod(dst, si.Mode())
 
 	return
@@ -400,3 +407,133 @@ func IsSymlink(path string) (bool, error) {
 
 	return l.Mode()&os.ModeSymlink == os.ModeSymlink, nil
 }
+
+// fixLongPath returns the extended-length (\\?\-prefixed) form of
+// path when needed, in order to avoid the default 260 character file
+// path limit imposed by Windows. If path is not easily converted to
+// the extended-length form (for example, if path is a relative path
+// or contains .. elements), or is short enough, fixLongPath returns
+// path unmodified.
+//
+// See https://msdn.microsoft.com/en-us/library/windows/desktop/aa365247(v=vs.85).aspx#maxpath
+func fixLongPath(path string) string {
+	// Do nothing (and don't allocate) if the path is "short".
+	// Empirically (at least on the Windows Server 2013 builder),
+	// the kernel is arbitrarily okay with < 248 bytes. That
+	// matches what the docs above say:
+	// "When using an API to create a directory, the specified
+	// path cannot be so long that you cannot append an 8.3 file
+	// name (that is, the directory name cannot exceed MAX_PATH
+	// minus 12)." Since MAX_PATH is 260, 260 - 12 = 248.
+	//
+	// The MSDN docs appear to say that a normal path that is 248 bytes long
+	// will work; empirically the path must be less then 248 bytes long.
+	if len(path) < 248 {
+		// Don't fix. (This is how Go 1.7 and earlier worked,
+		// not automatically generating the \\?\ form)
+		return path
+	}
+
+	// The extended form begins with \\?\, as in
+	// \\?\c:\windows\foo.txt or \\?\UNC\server\share\foo.txt.
+	// The extended form disables evaluation of . and .. path
+	// elements and disables the interpretation of / as equivalent
+	// to \. The conversion here rewrites / to \ and elides
+	// . elements as well as trailing or duplicate separators. For
+	// simplicity it avoids the conversion entirely for relative
+	// paths or paths containing .. elements. For now,
+	// \\server\share paths are not converted to
+	// \\?\UNC\server\share paths because the rules for doing so
+	// are less well-specified.
+	if len(path) >= 2 && path[:2] == `\\` {
+		// Don't canonicalize UNC paths.
+		return path
+	}
+	if !isAbs(path) {
+		// Relative path
+		return path
+	}
+
+	const prefix = `\\?`
+
+	pathbuf := make([]byte, len(prefix)+len(path)+len(`\`))
+	copy(pathbuf, prefix)
+	n := len(path)
+	r, w := 0, len(prefix)
+	for r < n {
+		switch {
+		case os.IsPathSeparator(path[r]):
+			// empty block
+			r++
+		case path[r] == '.' && (r+1 == n || os.IsPathSeparator(path[r+1])):
+			// /./
+			r++
+		case r+1 < n && path[r] == '.' && path[r+1] == '.' && (r+2 == n || os.IsPathSeparator(path[r+2])):
+			// /../ is currently unhandled
+			return path
+		default:
+			pathbuf[w] = '\\'
+			w++
+			for ; r < n && !os.IsPathSeparator(path[r]); r++ {
+				pathbuf[w] = path[r]
+				w++
+			}
+		}
+	}
+	// A drive's root directory needs a trailing \
+	if w == len(`\\?\c:`) {
+		pathbuf[w] = '\\'
+		w++
+	}
+	return string(pathbuf[:w])
+}
+
+func isAbs(path string) (b bool) {
+	v := volumeName(path)
+	if v == "" {
+		return false
+	}
+	path = path[len(v):]
+	if path == "" {
+		return false
+	}
+	return os.IsPathSeparator(path[0])
+}
+
+func volumeName(path string) (v string) {
+	if len(path) < 2 {
+		return ""
+	}
+	// with drive letter
+	c := path[0]
+	if path[1] == ':' &&
+		('0' <= c && c <= '9' || 'a' <= c && c <= 'z' ||
+			'A' <= c && c <= 'Z') {
+		return path[:2]
+	}
+	// is it UNC
+	if l := len(path); l >= 5 && os.IsPathSeparator(path[0]) && os.IsPathSeparator(path[1]) &&
+		!os.IsPathSeparator(path[2]) && path[2] != '.' {
+		// first, leading `\\` and next shouldn't be `\`. its server name.
+		for n := 3; n < l-1; n++ {
+			// second, next '\' shouldn't be repeated.
+			if os.IsPathSeparator(path[n]) {
+				n++
+				// third, following something characters. its share name.
+				if !os.IsPathSeparator(path[n]) {
+					if path[n] == '.' {
+						break
+					}
+					for ; n < l; n++ {
+						if os.IsPathSeparator(path[n]) {
+							break
+						}
+					}
+					return path[:n]
+				}
+				break
+			}
+		}
+	}
+	return ""
+}
diff --git a/internal/fs/fs_test.go b/internal/fs/fs_test.go
index 163b26e647..41aab2d537 100644
--- a/internal/fs/fs_test.go
+++ b/internal/fs/fs_test.go
@@ -547,6 +547,34 @@ func TestCopyFileSymlink(t *testing.T) {
 	}
 }
 
+func TestCopyFileLongFilePath(t *testing.T) {
+	if runtime.GOOS != "windows" {
+		// We want to ensure the temporary fix actually fixes the issue with
+		// os.Chmod and long file paths. This is only applicable on Windows.
+		t.Skip("skipping on non-windows")
+	}
+
+	h := test.NewHelper(t)
+	h.TempDir(".")
+
+	baseDir := h.Path(".")
+	dir := ""
+
+	// Create a directory with a long-enough path name to cause the bug in #774.
+	for len(baseDir)+len(dir) <= 300 {
+		dir += string(os.PathSeparator) + "dir4567890"
+	}
+	h.TempDir(dir)
+
+	tmpPath := h.Path(dir) + string(os.PathSeparator)
+
+	h.TempFile(tmpPath+"src", "")
+
+	if err := copyFile(tmpPath+"src", tmpPath+"dst"); err != nil {
+		t.Fatalf("unexpected error while copying file: %v", err)
+	}
+}
+
 func TestCopyFileFail(t *testing.T) {
 	if runtime.GOOS == "windows" {
 		// XXX: setting permissions works differently in