diff --git a/sdk/src/androidTest/java/com/bugsnag/android/JsonStreamTest.java b/sdk/src/androidTest/java/com/bugsnag/android/JsonStreamTest.java
index f0053644d6..ba68cb5d8e 100644
--- a/sdk/src/androidTest/java/com/bugsnag/android/JsonStreamTest.java
+++ b/sdk/src/androidTest/java/com/bugsnag/android/JsonStreamTest.java
@@ -1,17 +1,22 @@
 package com.bugsnag.android;
 
 import static org.junit.Assert.assertEquals;
+import static org.junit.Assert.assertNotNull;
 import static org.junit.Assert.assertTrue;
 
+import android.support.test.InstrumentationRegistry;
 import android.support.test.filters.SmallTest;
 import android.support.test.runner.AndroidJUnit4;
 
+import org.json.JSONArray;
 import org.json.JSONException;
 import org.json.JSONObject;
 import org.junit.Before;
 import org.junit.Test;
 import org.junit.runner.RunWith;
 
+import java.io.File;
+import java.io.FileWriter;
 import java.io.IOException;
 import java.io.StringWriter;
 
@@ -21,11 +26,20 @@ public class JsonStreamTest {
 
     private StringWriter writer;
     private JsonStream stream;
+    private File file;
 
+    /**
+     * Deletes a file in the cache directory if it already exists from previous test cases
+     *
+     * @throws Exception if setup failed
+     */
     @Before
     public void setUp() throws Exception {
         writer = new StringWriter();
         stream = new JsonStream(writer);
+        File cacheDir = InstrumentationRegistry.getContext().getCacheDir();
+        file = new File(cacheDir, "whoops");
+        file.delete();
     }
 
     @Test
@@ -61,4 +75,36 @@ public void testSaneValues() throws JSONException, IOException {
         assertEquals(123, json.getInt("int"));
         assertEquals(123L, json.getLong("long"));
     }
+
+    @Test
+    public void testEmptyFileValue() throws Throwable {
+        file.createNewFile();
+        stream.beginArray();
+        stream.value(file);
+        stream.value(file);
+        stream.endArray();
+        assertEquals("[]", writer.toString());
+    }
+
+    @Test
+    public void testNullFileValue() throws Throwable {
+        File file = null;
+        stream.beginArray();
+        stream.value(file);
+        stream.value(file);
+        stream.endArray();
+        assertEquals("[]", writer.toString());
+    }
+
+    @Test
+    public void testDeletedFile() throws Throwable {
+        file.createNewFile();
+        file.delete();
+        stream.beginArray();
+        stream.value(file);
+        stream.value(file);
+        stream.endArray();
+        assertEquals("[]", writer.toString());
+    }
+
 }
diff --git a/sdk/src/main/java/com/bugsnag/android/JsonStream.java b/sdk/src/main/java/com/bugsnag/android/JsonStream.java
index d440f939c1..21147a9c1d 100644
--- a/sdk/src/main/java/com/bugsnag/android/JsonStream.java
+++ b/sdk/src/main/java/com/bugsnag/android/JsonStream.java
@@ -49,6 +49,10 @@ public void value(@Nullable Streamable streamable) throws IOException {
      * Writes a File (its content) into the stream
      */
     public void value(@NonNull File file) throws IOException {
+        if (file == null || file.length() <= 0) {
+            return;
+        }
+
         super.flush();
         beforeValue(false); // add comma if in array