diff --git a/cmd/moby/build.go b/cmd/moby/build.go
index f550cba01..4ea263300 100644
--- a/cmd/moby/build.go
+++ b/cmd/moby/build.go
@@ -574,6 +574,14 @@ func filesystem(m Moby, tw *tar.Writer) error {
 			if len(f.Source) > 2 && f.Source[:2] == "~/" {
 				f.Source = homeDir() + f.Source[1:]
 			}
+			if f.Optional {
+				_, err := os.Stat(f.Source)
+				if err != nil {
+					// skip if not found or readable
+					log.Debugf("Skipping file [%s] as not readable and marked optional", f.Source)
+					continue
+				}
+			}
 			contents, err := ioutil.ReadFile(f.Source)
 			if err != nil {
 				return err
diff --git a/cmd/moby/config.go b/cmd/moby/config.go
index 4f100e9b7..2650b610b 100644
--- a/cmd/moby/config.go
+++ b/cmd/moby/config.go
@@ -32,6 +32,7 @@ type Moby struct {
 		Symlink   string
 		Contents  string
 		Source    string
+		Optional  bool
 		Mode      string
 	}
 }
diff --git a/cmd/moby/schema.go b/cmd/moby/schema.go
index ddfed0d45..5444cf47d 100644
--- a/cmd/moby/schema.go
+++ b/cmd/moby/schema.go
@@ -23,6 +23,7 @@ var schema = string(`
           "symlink": {"type": "string"},
           "contents": {"type": "string"},
           "source": {"type": "string"},
+          "optional": {"type": "boolean"},
           "mode": {"type": "string"}
         }
     },
diff --git a/docs/yaml.md b/docs/yaml.md
index 7ac729747..af23567a8 100644
--- a/docs/yaml.md
+++ b/docs/yaml.md
@@ -58,12 +58,17 @@ files:
     source: "/some/path/on/local/filesystem"
     mode: "0666"
   - path: dir/name2
+    source: "/some/path/that/it/is/ok/to/omit"
+    optional: true
+    mode: "0666"
+  - path: dir/name3
     contents: "orange"
     mode: "0644"
 ```
 
 Specifying the `mode` is optional, and will default to `0600`. Leading directories will be
-created if not specified.
+created if not specified. You can use `~/path` in `source` to specify a path in the build
+user's home directory.
 
 ## `trust`