diff --git a/changelogs/fragments/callback_fixes.yml b/changelogs/fragments/callback_fixes.yml
new file mode 100644
index 00000000000..5acc8e4ff6a
--- /dev/null
+++ b/changelogs/fragments/callback_fixes.yml
@@ -0,0 +1,2 @@
+bugfixes:
+    - Update callbacks to use Ansible's JSON encoder to avoid known serialization issues
diff --git a/lib/ansible/plugins/callback/json.py b/lib/ansible/plugins/callback/json.py
index 3961a78aab9..e1f511cc464 100644
--- a/lib/ansible/plugins/callback/json.py
+++ b/lib/ansible/plugins/callback/json.py
@@ -35,7 +35,7 @@ import json
 from functools import partial
 
 from ansible.inventory.host import Host
-
+from ansible.parsing.ajson import AnsibleJSONEncoder
 from ansible.plugins.callback import CallbackBase
 
 
@@ -111,7 +111,7 @@ class CallbackModule(CallbackBase):
             'custom_stats': custom_stats,
         }
 
-        self._display.display(json.dumps(output, indent=4, sort_keys=True))
+        self._display.display(json.dumps(output, cls=AnsibleJSONEncoder, indent=4, sort_keys=True))
 
     def _record_task_result(self, on_info, result, **kwargs):
         """This function is used as a partial to add failed/skipped info in a single method"""
diff --git a/lib/ansible/plugins/callback/log_plays.py b/lib/ansible/plugins/callback/log_plays.py
index 146165fa3a0..f6986208cd1 100644
--- a/lib/ansible/plugins/callback/log_plays.py
+++ b/lib/ansible/plugins/callback/log_plays.py
@@ -24,6 +24,7 @@ import json
 from collections import MutableMapping
 
 from ansible.module_utils._text import to_bytes
+from ansible.parsing.ajson import AnsibleJSONEncoder
 from ansible.plugins.callback import CallbackBase
 
 
@@ -61,7 +62,7 @@ class CallbackModule(CallbackBase):
             else:
                 data = data.copy()
                 invocation = data.pop('invocation', None)
-                data = json.dumps(data)
+                data = json.dumps(data, cls=AnsibleJSONEncoder)
                 if invocation is not None:
                     data = json.dumps(invocation) + " => %s " % data
 
diff --git a/lib/ansible/plugins/callback/mail.py b/lib/ansible/plugins/callback/mail.py
index 18f6fca7ff6..98c36ff651f 100644
--- a/lib/ansible/plugins/callback/mail.py
+++ b/lib/ansible/plugins/callback/mail.py
@@ -70,6 +70,7 @@ import smtplib
 
 from ansible.module_utils.six import string_types
 from ansible.module_utils._text import to_bytes
+from ansible.parsing.ajson import AnsibleJSONEncoder
 from ansible.plugins.callback import CallbackBase
 
 
@@ -207,7 +208,7 @@ class CallbackModule(CallbackBase):
                 body += self.body_blob(result._result['deprecations'][i], 'exception %d' % (i + 1))
 
         body += 'and a complete dump of the error:\n\n'
-        body += self.indent('%s: %s' % (failtype, json.dumps(result._result, indent=4)))
+        body += self.indent('%s: %s' % (failtype, json.dumps(result._result, cls=AnsibleJSONEncoder, indent=4)))
 
         self.mail(subject=subject, body=body)
 
@@ -230,4 +231,4 @@ class CallbackModule(CallbackBase):
     def v2_runner_item_on_failed(self, result):
         # Pass item information to task failure
         self.itemsubject = result._result['msg']
-        self.itembody += self.body_blob(json.dumps(result._result, indent=4), "failed item dump '%(item)s'" % result._result)
+        self.itembody += self.body_blob(json.dumps(result._result, cls=AnsibleJSONEncoder, indent=4), "failed item dump '%(item)s'" % result._result)
diff --git a/lib/ansible/plugins/callback/sumologic.py b/lib/ansible/plugins/callback/sumologic.py
index 69b457f33fe..4a2bd0b5bb0 100644
--- a/lib/ansible/plugins/callback/sumologic.py
+++ b/lib/ansible/plugins/callback/sumologic.py
@@ -61,8 +61,9 @@ import getpass
 from datetime import datetime
 from os.path import basename
 
-from ansible.plugins.callback import CallbackBase
 from ansible.module_utils.urls import open_url
+from ansible.parsing.ajson import AnsibleJSONEncoder
+from ansible.plugins.callback import CallbackBase
 
 
 class SumologicHTTPCollectorSource(object):
@@ -108,7 +109,7 @@ class SumologicHTTPCollectorSource(object):
 
         open_url(
             url,
-            data=json.dumps(data, sort_keys=True),
+            data=json.dumps(data, cls=AnsibleJSONEncoder, sort_keys=True),
             headers={
                 'Content-type': 'application/json',
                 'X-Sumo-Host': data['ansible_host']
diff --git a/lib/ansible/plugins/callback/yaml.py b/lib/ansible/plugins/callback/yaml.py
index 50d334a5a9e..756fb79bf22 100644
--- a/lib/ansible/plugins/callback/yaml.py
+++ b/lib/ansible/plugins/callback/yaml.py
@@ -24,11 +24,12 @@ import json
 import re
 import string
 import sys
-from ansible.plugins.callback import CallbackBase, strip_internal_keys
-from ansible.plugins.callback.default import CallbackModule as Default
-from ansible.module_utils.six import string_types
+
 from ansible.module_utils._text import to_bytes, to_text
+from ansible.module_utils.six import string_types
 from ansible.parsing.yaml.dumper import AnsibleDumper
+from ansible.plugins.callback import CallbackBase, strip_internal_keys
+from ansible.plugins.callback.default import CallbackModule as Default
 
 
 # from http://stackoverflow.com/a/15423007/115478
@@ -81,7 +82,7 @@ class CallbackModule(Default):
 
     def _dump_results(self, result, indent=None, sort_keys=True, keep_invocation=False):
         if result.get('_ansible_no_log', False):
-            return json.dumps(dict(censored="the output has been hidden due to the fact that 'no_log: true' was specified for this result"))
+            return json.dumps(dict(censored="The output has been hidden due to the fact that 'no_log: true' was specified for this result"))
 
         # All result keys stating with _ansible_ are internal, so remove them from the result before we output anything.
         abridged_result = strip_internal_keys(result)