diff --git a/CHANGELOG.md b/CHANGELOG.md
index 42bece984..88ef26a6a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,3 +1,11 @@
+v2.4.8 (FUTURE)
+
+## Bug Fixes
+
+* [#2473](https://github.com/digitalocean/netbox/issues/2473) - Fix encoding of long (>127 character) secrets
+
+---
+
 v2.4.7 (2018-11-06)
 
 ## Enhancements
diff --git a/netbox/secrets/models.py b/netbox/secrets/models.py
index 8bbf3d14d..6beb86c9e 100644
--- a/netbox/secrets/models.py
+++ b/netbox/secrets/models.py
@@ -1,6 +1,7 @@
 from __future__ import unicode_literals
 
 import os
+import sys
 
 from Crypto.Cipher import AES, PKCS1_OAEP
 from Crypto.PublicKey import RSA
@@ -392,6 +393,7 @@ class Secret(ChangeLoggedModel, CustomFieldModel):
         s = s.encode('utf8')
         if len(s) > 65535:
             raise ValueError("Maximum plaintext size is 65535 bytes.")
+
         # Minimum ciphertext size is 64 bytes to conceal the length of short secrets.
         if len(s) <= 62:
             pad_length = 62 - len(s)
@@ -399,12 +401,14 @@ class Secret(ChangeLoggedModel, CustomFieldModel):
             pad_length = 16 - ((len(s) + 2) % 16)
         else:
             pad_length = 0
-        return (
-            chr(len(s) >> 8).encode() +
-            chr(len(s) % 256).encode() +
-            s +
-            os.urandom(pad_length)
-        )
+
+        # Python 2 compatibility
+        if sys.version_info[0] < 3:
+            header = chr(len(s) >> 8) + chr(len(s) % 256)
+        else:
+            header = bytes([len(s) >> 8]) + bytes([len(s) % 256])
+
+        return header + s + os.urandom(pad_length)
 
     def _unpad(self, s):
         """
diff --git a/netbox/secrets/tests/test_models.py b/netbox/secrets/tests/test_models.py
index 887c048bf..2fb7c3781 100644
--- a/netbox/secrets/tests/test_models.py
+++ b/netbox/secrets/tests/test_models.py
@@ -1,4 +1,5 @@
 from __future__ import unicode_literals
+import string
 
 from Crypto.PublicKey import RSA
 from django.conf import settings
@@ -88,7 +89,7 @@ class SecretTestCase(TestCase):
         """
         Test basic encryption and decryption functionality using a random master key.
         """
-        plaintext = "FooBar123"
+        plaintext = string.printable * 2
         secret_key = generate_random_key()
         s = Secret(plaintext=plaintext)
         s.encrypt(secret_key)