diff --git a/gapi/helpers.go b/gapi/helpers.go
index 804631e8..51f25bcc 100644
--- a/gapi/helpers.go
+++ b/gapi/helpers.go
@@ -89,3 +89,9 @@ func CopyDirToFsForceAll(fs engine.Fs, src, dst string) error {
 func CopyDirContentsToFs(fs engine.Fs, src, dst string) error {
 	return util.CopyDiskContentsToFs(fs, src, dst, false)
 }
+
+// MkdirAllOnFs writes a dir to a dst path on fs. It makes the parent dirs if
+// they don't exist.
+func MkdirAllOnFs(fs engine.WriteableFS, dst string, perm os.FileMode) error {
+	return fs.MkdirAll(dst, perm)
+}
diff --git a/lang/gapi/gapi.go b/lang/gapi/gapi.go
index 1013f140..3d2fb6e9 100644
--- a/lang/gapi/gapi.go
+++ b/lang/gapi/gapi.go
@@ -463,6 +463,11 @@ func (obj *GAPI) Cli(info *gapi.Info) (*gapi.Deploy, error) {
 			continue
 		}
 		// it's a regular file path
+
+		// Occasionally, we need the dir to exist first or we'll error.
+		if err := gapi.MkdirAllOnFs(writeableFS, util.Dirname(dst), 0700); err != nil {
+			return nil, errwrap.Wrapf(err, "can't mkdir at `%s`", dst)
+		}
 		if err := gapi.CopyFileToFs(writeableFS, src, dst); err != nil {
 			return nil, errwrap.Wrapf(err, "can't copy file from `%s` to `%s`", src, dst)
 		}