diff --git a/doc/files.md b/doc/files.md
index 566dcfdcb..746ae52b5 100644
--- a/doc/files.md
+++ b/doc/files.md
@@ -144,6 +144,23 @@ BoxFile.Info newFileInfo = rootFolder.uploadFile(stream, "My File.txt");
 stream.close();
 ```
 
+Note that using `FileInputStream` allows you to read the content of the file only once. 
+If the first upload attempt fails, the stream will become exhausted,
+and request retry with no content might be performed. To retry an upload, you would have to 
+create a new `FileInputStream` and call `uploadFile()` method again.
+
+If you want the SDK to automatically retry the upload in case of any error, you need to provide an 
+`InputStream` class that supports the `reset()` operation. For example, you can read all bytes from your file into
+a `ByteArrayInputStream` and then use it for the upload method. Be aware that this approach will load the whole file
+into memory, so it is not recommended for large files, as it can exhaust easily your memory.
+
+```java
+BoxFolder rootFolder = BoxFolder.getRootFolder(api);
+InputStream stream = new ByteArrayInputStream(Files.readAllBytes(new File(path).toPath()));
+BoxFile.Info newFileInfo = rootFolder.uploadFile(stream, "My File.txt");
+stream.close();
+```
+
 Upload progress can be tracked by providing the size of the file and a
 [`ProgressListener`][progress] to
 [`uploadFile(InputStream fileContents, String fileName, long fileSize, ProgressListener progress)`][upload2].
diff --git a/src/test/java/com/box/sdk/BoxFolderTest.java b/src/test/java/com/box/sdk/BoxFolderTest.java
index 5d820635a..5c1d0e780 100644
--- a/src/test/java/com/box/sdk/BoxFolderTest.java
+++ b/src/test/java/com/box/sdk/BoxFolderTest.java
@@ -8,6 +8,7 @@
 import static com.box.sdk.http.ContentType.APPLICATION_JSON_PATCH;
 import static com.box.sdk.http.ContentType.APPLICATION_OCTET_STREAM;
 import static com.github.tomakehurst.wiremock.core.WireMockConfiguration.wireMockConfig;
+import static com.github.tomakehurst.wiremock.stubbing.Scenario.STARTED;
 import static java.lang.String.format;
 import static org.hamcrest.MatcherAssert.assertThat;
 import static org.hamcrest.Matchers.is;
@@ -1255,6 +1256,40 @@ public void testUploadFileWithDescriptionSucceeds() {
         assertEquals(fileDescription, file.getDescription());
     }
 
+    @Test
+    public void testUploadFileSucceedsAfter500InTheFirstAttempt() throws IOException {
+        final String folderID = "12345";
+        final String fileURL = "/2.0/files/content";
+        final String fileContent = "Test file";
+        final String fileName = "Test File.txt";
+        InputStream stream = new ByteArrayInputStream(fileContent.getBytes(StandardCharsets.UTF_8));
+
+        String result = TestUtils.getFixture("BoxFile/CreateFileWithDescription201");
+
+        wireMockRule.stubFor(WireMock.post(WireMock.urlPathEqualTo(fileURL))
+                .inScenario("Retry Scenario")
+                .whenScenarioStateIs(STARTED)
+                .willReturn(WireMock.aResponse()
+                    .withStatus(500))
+                .willSetStateTo("Retry"));
+
+        wireMockRule.stubFor(WireMock.post(WireMock.urlPathEqualTo(fileURL))
+                .inScenario("Retry Scenario")
+                .whenScenarioStateIs("Retry")
+                .willReturn(WireMock.aResponse()
+                        .withHeader("Content-Type", APPLICATION_JSON_PATCH)
+                        .withBody(result)
+                        .withStatus(201))
+                .willSetStateTo("Success"));
+
+        BoxFolder folder = new BoxFolder(this.api, folderID);
+        BoxFile.Info file = folder.uploadFile(stream, fileName);
+
+        WireMock.verify(2, WireMock.postRequestedFor(WireMock.urlEqualTo("/2.0/files/content")));
+
+        assertEquals(fileName, file.getName());
+    }
+
     @Test
     public void testGetFolderItemsWithSortAndOffset() {
         final String folderID = "12345";