diff --git a/nifi-nar-bundles/nifi-standard-bundle/nifi-standard-processors/src/main/java/org/apache/nifi/processors/standard/PostHTTP.java b/nifi-nar-bundles/nifi-standard-bundle/nifi-standard-processors/src/main/java/org/apache/nifi/processors/standard/PostHTTP.java
index 2aaf8008de..760c069a2c 100644
--- a/nifi-nar-bundles/nifi-standard-bundle/nifi-standard-processors/src/main/java/org/apache/nifi/processors/standard/PostHTTP.java
+++ b/nifi-nar-bundles/nifi-standard-bundle/nifi-standard-processors/src/main/java/org/apache/nifi/processors/standard/PostHTTP.java
@@ -227,10 +227,9 @@ public class PostHTTP extends AbstractProcessor {
             .build();
     public static final PropertyDescriptor CHUNKED_ENCODING = new PropertyDescriptor.Builder()
             .name("Use Chunked Encoding")
-            .description("Specifies whether or not to use Chunked Encoding to send the data. If false, the entire content of the FlowFile will be buffered into memory.")
-            .required(true)
+            .description("Specifies whether or not to use Chunked Encoding to send the data. This property is ignored in the event the contents are compressed "
+                    + "or sent as FlowFiles.")
             .allowableValues("true", "false")
-            .defaultValue("true")
             .build();
     public static final PropertyDescriptor SSL_CONTEXT_SERVICE = new PropertyDescriptor.Builder()
             .name("SSL Context Service")
@@ -331,6 +330,15 @@ public class PostHTTP extends AbstractProcessor {
                     .build());
         }
 
+        boolean sendAsFlowFile = context.getProperty(SEND_AS_FLOWFILE).asBoolean();
+        int compressionLevel = context.getProperty(COMPRESSION_LEVEL).asInteger();
+        boolean chunkedSet = context.getProperty(CHUNKED_ENCODING).isSet();
+
+        if(compressionLevel == 0 && !sendAsFlowFile && !chunkedSet) {
+            results.add(new ValidationResult.Builder().valid(false).subject(CHUNKED_ENCODING.getName())
+                    .explanation("if compression level is 0 and not sending as a FlowFile, then the \'"+CHUNKED_ENCODING.getName()+"\' property must be set").build());
+        }
+
         return results;
     }
 
@@ -625,9 +633,21 @@ public class PostHTTP extends AbstractProcessor {
                     out.flush();
                 }
             }
-        });
+        }) {
 
-        entity.setChunked(context.getProperty(CHUNKED_ENCODING).asBoolean());
+            @Override
+            public long getContentLength() {
+                if(compressionLevel == 0 && !sendAsFlowFile && !context.getProperty(CHUNKED_ENCODING).asBoolean() ) {
+                    return toSend.get(0).getSize();
+                } else {
+                    return -1;
+                }
+            }
+        };
+
+        if(context.getProperty(CHUNKED_ENCODING).isSet()) {
+            entity.setChunked(context.getProperty(CHUNKED_ENCODING).asBoolean());
+        }
         post.setEntity(entity);
         post.setConfig(requestConfig);
 
diff --git a/nifi-nar-bundles/nifi-standard-bundle/nifi-standard-processors/src/test/java/org/apache/nifi/processors/standard/TestPostHTTP.java b/nifi-nar-bundles/nifi-standard-bundle/nifi-standard-processors/src/test/java/org/apache/nifi/processors/standard/TestPostHTTP.java
index 67bd82c731..52629648c1 100644
--- a/nifi-nar-bundles/nifi-standard-bundle/nifi-standard-processors/src/test/java/org/apache/nifi/processors/standard/TestPostHTTP.java
+++ b/nifi-nar-bundles/nifi-standard-bundle/nifi-standard-processors/src/test/java/org/apache/nifi/processors/standard/TestPostHTTP.java
@@ -82,6 +82,7 @@ public class TestPostHTTP {
 
         runner.setProperty(PostHTTP.URL, server.getSecureUrl());
         runner.setProperty(PostHTTP.SSL_CONTEXT_SERVICE, "ssl-context");
+        runner.setProperty(PostHTTP.CHUNKED_ENCODING, "false");
 
         runner.enqueue("Hello world".getBytes());
         runner.run();
@@ -113,6 +114,7 @@ public class TestPostHTTP {
 
         runner.setProperty(PostHTTP.URL, server.getSecureUrl());
         runner.setProperty(PostHTTP.SSL_CONTEXT_SERVICE, "ssl-context");
+        runner.setProperty(PostHTTP.CHUNKED_ENCODING, "false");
 
         runner.enqueue("Hello world".getBytes());
         runner.run();
@@ -141,6 +143,7 @@ public class TestPostHTTP {
 
         runner.setProperty(PostHTTP.URL, server.getSecureUrl());
         runner.setProperty(PostHTTP.SSL_CONTEXT_SERVICE, "ssl-context");
+        runner.setProperty(PostHTTP.CHUNKED_ENCODING, "false");
 
         runner.enqueue("Hello world".getBytes());
         runner.run();
@@ -186,6 +189,7 @@ public class TestPostHTTP {
         assertEquals("World", new String(contentReceived));
         assertEquals("abc", receivedAttrs.get("abc"));
         assertEquals("xyz.txt", receivedAttrs.get("filename"));
+        Assert.assertNull(receivedAttrs.get("Content-Length"));
     }
 
     @Test
@@ -258,18 +262,21 @@ public class TestPostHTTP {
         final String suppliedMimeType = "text/plain";
         attrs.put(CoreAttributes.MIME_TYPE.key(), suppliedMimeType);
         runner.enqueue("Camping is in tents.".getBytes(), attrs);
+        runner.setProperty(PostHTTP.CHUNKED_ENCODING, "false");
 
         runner.run(1);
         runner.assertAllFlowFilesTransferred(PostHTTP.REL_SUCCESS);
 
         Map<String, String> lastPostHeaders = servlet.getLastPostHeaders();
         Assert.assertEquals(suppliedMimeType, lastPostHeaders.get(PostHTTP.CONTENT_TYPE_HEADER));
+        Assert.assertEquals("20",lastPostHeaders.get("Content-Length"));
     }
 
     @Test
     public void testSendWithEmptyELExpression() throws Exception {
         setup(null);
         runner.setProperty(PostHTTP.URL, server.getUrl());
+        runner.setProperty(PostHTTP.CHUNKED_ENCODING, "false");
 
         final Map<String, String> attrs = new HashMap<>();
         attrs.put(CoreAttributes.MIME_TYPE.key(), "");
@@ -289,6 +296,7 @@ public class TestPostHTTP {
         final String suppliedMimeType = "text/plain";
         runner.setProperty(PostHTTP.URL, server.getUrl());
         runner.setProperty(PostHTTP.CONTENT_TYPE, suppliedMimeType);
+        runner.setProperty(PostHTTP.CHUNKED_ENCODING, "false");
 
         final Map<String, String> attrs = new HashMap<>();
         attrs.put(CoreAttributes.MIME_TYPE.key(), "text/csv");
@@ -322,6 +330,7 @@ public class TestPostHTTP {
         Assert.assertEquals(suppliedMimeType, lastPostHeaders.get(PostHTTP.CONTENT_TYPE_HEADER));
         // Ensure that a 'Content-Encoding' header was set with a 'gzip' value
         Assert.assertEquals(PostHTTP.CONTENT_ENCODING_GZIP_VALUE, lastPostHeaders.get(PostHTTP.CONTENT_ENCODING_HEADER));
+        Assert.assertNull(lastPostHeaders.get("Content-Length"));
     }
 
     @Test
@@ -332,6 +341,7 @@ public class TestPostHTTP {
         runner.setProperty(PostHTTP.URL, server.getUrl());
         runner.setProperty(PostHTTP.CONTENT_TYPE, suppliedMimeType);
         runner.setProperty(PostHTTP.COMPRESSION_LEVEL, "0");
+        runner.setProperty(PostHTTP.CHUNKED_ENCODING, "false");
 
         final Map<String, String> attrs = new HashMap<>();
         attrs.put(CoreAttributes.MIME_TYPE.key(), "text/plain");
@@ -345,6 +355,7 @@ public class TestPostHTTP {
         Assert.assertEquals(suppliedMimeType, lastPostHeaders.get(PostHTTP.CONTENT_TYPE_HEADER));
         // Ensure that the request was not sent with a 'Content-Encoding' header
         Assert.assertNull(lastPostHeaders.get(PostHTTP.CONTENT_ENCODING_HEADER));
+        Assert.assertEquals("6200",lastPostHeaders.get("Content-Length"));
     }
 
     @Test
@@ -370,4 +381,30 @@ public class TestPostHTTP {
         // Ensure that the request was not sent with a 'Content-Encoding' header
         Assert.assertNull(lastPostHeaders.get(PostHTTP.CONTENT_ENCODING_HEADER));
     }
+
+    @Test
+    public void testSendChunked() throws Exception {
+        setup(null);
+
+        final String suppliedMimeType = "text/plain";
+        runner.setProperty(PostHTTP.URL, server.getUrl());
+        runner.setProperty(PostHTTP.CONTENT_TYPE, suppliedMimeType);
+        runner.setProperty(PostHTTP.CHUNKED_ENCODING, "true");
+
+        final Map<String, String> attrs = new HashMap<>();
+        attrs.put(CoreAttributes.MIME_TYPE.key(), "text/plain");
+
+        runner.enqueue(StringUtils.repeat("This is the song that never ends. It goes on and on my friend.", 100).getBytes(), attrs);
+
+        runner.run(1);
+        runner.assertAllFlowFilesTransferred(PostHTTP.REL_SUCCESS);
+
+        byte[] postValue = servlet.getLastPost();
+        Assert.assertArrayEquals(StringUtils.repeat("This is the song that never ends. It goes on and on my friend.", 100).getBytes(),postValue);
+
+        Map<String, String> lastPostHeaders = servlet.getLastPostHeaders();
+        Assert.assertEquals(suppliedMimeType, lastPostHeaders.get(PostHTTP.CONTENT_TYPE_HEADER));
+        Assert.assertNull(lastPostHeaders.get("Content-Length"));
+        Assert.assertEquals("chunked",lastPostHeaders.get("Transfer-Encoding"));
+    }
 }