diff --git a/core/core-awt/src/main/java/org/icepdf/core/util/redaction/Redactor.java b/core/core-awt/src/main/java/org/icepdf/core/util/redaction/Redactor.java
index 2d4758320..00160b734 100644
--- a/core/core-awt/src/main/java/org/icepdf/core/util/redaction/Redactor.java
+++ b/core/core-awt/src/main/java/org/icepdf/core/util/redaction/Redactor.java
@@ -4,6 +4,7 @@
 import org.icepdf.core.pobjects.PObject;
 import org.icepdf.core.pobjects.Page;
 import org.icepdf.core.pobjects.StateManager;
+import org.icepdf.core.pobjects.annotations.Annotation;
 import org.icepdf.core.pobjects.annotations.RedactionAnnotation;
 
 import java.io.IOException;
@@ -40,13 +41,11 @@ public static void burnRedactions(Document document) throws InterruptedException
     private static void convertRedactionToSquareAnnotation(StateManager stateManager,
                                                            List<RedactionAnnotation> redactionAnnotations) {
         for (RedactionAnnotation redactionAnnotation : redactionAnnotations) {
-            // todo clean up popup as square isn't markup
-//            redactionAnnotation.setSubtype(Annotation.SUBTYPE_SQUARE);
-//            redactionAnnotation.setFlag(Annotation.FLAG_LOCKED, true);
-//            redactionAnnotation.setFlag(Annotation.FLAG_READ_ONLY, true);
-//            redactionAnnotation.setFlag(Annotation.FLAG_LOCKED_CONTENTS, true);
-//            stateManager.addChange(new PObject(redactionAnnotation, redactionAnnotation.getPObjectReference()));
-            stateManager.addDeletion(new PObject(redactionAnnotation, redactionAnnotation.getPObjectReference()));
+            redactionAnnotation.setSubtype(Annotation.SUBTYPE_SQUARE);
+            redactionAnnotation.setFlag(Annotation.FLAG_LOCKED, true);
+            redactionAnnotation.setFlag(Annotation.FLAG_READ_ONLY, true);
+            redactionAnnotation.setFlag(Annotation.FLAG_LOCKED_CONTENTS, true);
+            stateManager.addChange(new PObject(redactionAnnotation, redactionAnnotation.getPObjectReference()));
         }
     }
 }
diff --git a/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/BaseWriter.java b/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/BaseWriter.java
index 96c09ce21..17881dee6 100644
--- a/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/BaseWriter.java
+++ b/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/BaseWriter.java
@@ -248,7 +248,7 @@ protected void writeByteString(String str, CountingOutputStream output) throws I
         }
     }
 
-    protected byte[] encryptStream(Stream stream) throws IOException {
+    protected byte[] encryptStream(Stream stream, byte[] outputData) throws IOException {
         // check if we need to encrypt the stream
         if (securityManager != null) {
             DictionaryEntries decodeParams;
@@ -264,7 +264,7 @@ protected byte[] encryptStream(Stream stream) throws IOException {
                     stream.getPObjectReference(),
                     securityManager.getDecryptionKey(),
                     decodeParams,
-                    new ByteArrayInputStream(stream.getRawBytes()), true);
+                    new ByteArrayInputStream(outputData), true);
             ByteArrayOutputStream out = new ByteArrayOutputStream();
             int nRead;
             byte[] data = new byte[16384];
diff --git a/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/HexStringObjectWriter.java b/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/HexStringObjectWriter.java
index 41c3f0f88..ce0557364 100644
--- a/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/HexStringObjectWriter.java
+++ b/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/HexStringObjectWriter.java
@@ -13,6 +13,9 @@ public class HexStringObjectWriter extends BaseWriter {
     private static final byte[] BEGIN_HEX_STRING = "<".getBytes();
     private static final byte[] END_HEX_STRING = ">".getBytes();
 
+    private static final String HEX_REGEX = "(?=[<>\\\\])";
+    private static final String HEX_REPLACEMENT = "\\\\";
+
     public HexStringObjectWriter(SecurityManager securityManager) {
         this.securityManager = securityManager;
     }
@@ -20,20 +23,20 @@ public HexStringObjectWriter(SecurityManager securityManager) {
     public void write(PObject pObject, CountingOutputStream output) throws IOException {
         HexStringObject writeable = (HexStringObject) pObject.getObject();
         if (pObject.isDoNotEncrypt()) {
-            writeRaw(writeable.getHexString(), output);
+            writeRaw(writeable.getHexString().replaceAll(HEX_REGEX, HEX_REPLACEMENT), output);
         } else if (securityManager != null) {
             if (writeable.isModified()) {
                 // encryption will take care of any escape issue.
                 String writeableString = writeable.encryption(writeable.getHexString(), pObject.getReference(),
                         securityManager);
-                writeRaw(writeableString, output);
+                writeRaw(writeableString.replaceAll(HEX_REGEX, HEX_REPLACEMENT), output);
             } else {
                 // just need to write the string data as is, string data will already be in the correct state
                 writeRaw(writeable.toString(), output);
             }
         } else {
             // plain string make sure it's properly escaped.
-            writeRaw(writeable.getHexString(), output);
+            writeRaw(writeable.getHexString().replaceAll(HEX_REGEX, HEX_REPLACEMENT), output);
         }
     }
 
diff --git a/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/ImageStreamWriter.java b/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/ImageStreamWriter.java
index 367a3e761..62427a27f 100644
--- a/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/ImageStreamWriter.java
+++ b/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/ImageStreamWriter.java
@@ -22,7 +22,7 @@ public ImageStreamWriter(SecurityManager securityManager) {
 
     public void write(ImageStream imageStream, SecurityManager securityManager, CountingOutputStream output) throws IOException {
         byte[] outputData;
-        // decoded image is only set if the image was touch via a redaction burn.
+        // decoded image is only set if the image was touch via a redaction burn and will always be unencrypted
         if (imageStream.getDecodedImage() != null) {
             ImageEncoder imageEncoder = ImageEncoderFactory.createEncodedImage(imageStream);
             imageStream = imageEncoder.encode();
@@ -30,7 +30,7 @@ public void write(ImageStream imageStream, SecurityManager securityManager, Coun
 
             // check if we need to encrypt the stream
             if (securityManager != null) {
-                outputData = encryptStream(imageStream);
+                outputData = encryptStream(imageStream, outputData);
             }
         } else {
             // no modification, just write out the image unaltered.
diff --git a/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/LiteralStringWriter.java b/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/LiteralStringWriter.java
index 59045dfd6..e5fdec2d6 100644
--- a/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/LiteralStringWriter.java
+++ b/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/LiteralStringWriter.java
@@ -29,10 +29,10 @@ public void write(PObject pObject, CountingOutputStream output) throws IOExcepti
                 // encryption will take care of any escape issue.
                 String writeableString = writeable.encryption(writeable.getLiteralString(), pObject.getReference(),
                         securityManager);
-                writeRaw(writeableString, output);
+                writeRaw(writeableString.replaceAll(LITERAL_REGEX, LITERAL_REPLACEMENT), output);
             } else {
                 // just need to write the string data as is, string data will already be in the correct state
-                writeRaw(writeable.getLiteralString(), output);
+                writeRaw(writeable.getLiteralString().replaceAll(LITERAL_REGEX, LITERAL_REPLACEMENT), output);
             }
         } else {
             // plain string make sure it's properly escaped.
diff --git a/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/StreamWriter.java b/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/StreamWriter.java
index c8033ada2..5e53c4042 100644
--- a/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/StreamWriter.java
+++ b/core/core-awt/src/main/java/org/icepdf/core/util/updater/writeables/StreamWriter.java
@@ -42,7 +42,7 @@ public void write(Stream stream, SecurityManager securityManager, CountingOutput
 
             // check if we need to encrypt the stream
             if (securityManager != null) {
-                outputData = encryptStream(stream);
+                outputData = encryptStream(stream, outputData);
             }
         } else {
             outputData = stream.getRawBytes();