diff --git a/newrelic/admin/license_key.py b/newrelic/admin/license_key.py
index 35aaed1f4..e1eaaa39b 100644
--- a/newrelic/admin/license_key.py
+++ b/newrelic/admin/license_key.py
@@ -15,18 +15,22 @@
 from __future__ import print_function
 
 from newrelic.admin import command, usage
+from newrelic.common.encoding_utils import obfuscate_license_key
 
 
-@command('license-key', 'config_file [log_file]',
-"""Prints out the account license key after having loaded the settings
-from <config_file>.""")
+@command(
+    "license-key",
+    "config_file [log_file]",
+    """Prints out an obfuscated account license key after having loaded the settings
+from <config_file>.""",
+)
 def license_key(args):
+    import logging
     import os
     import sys
-    import logging
 
     if len(args) == 0:
-        usage('license-key')
+        usage("license-key")
         sys.exit(1)
 
     from newrelic.config import initialize
@@ -35,7 +39,7 @@ def license_key(args):
     if len(args) >= 2:
         log_file = args[1]
     else:
-        log_file = '/tmp/python-agent-test.log'
+        log_file = "/tmp/python-agent-test.log"
 
     log_level = logging.DEBUG
 
@@ -45,14 +49,13 @@ def license_key(args):
         pass
 
     config_file = args[0]
-    environment = os.environ.get('NEW_RELIC_ENVIRONMENT')
+    environment = os.environ.get("NEW_RELIC_ENVIRONMENT")
 
-    if config_file == '-':
-        config_file = os.environ.get('NEW_RELIC_CONFIG_FILE')
+    if config_file == "-":
+        config_file = os.environ.get("NEW_RELIC_CONFIG_FILE")
 
-    initialize(config_file, environment, ignore_errors=False,
-            log_file=log_file, log_level=log_level)
+    initialize(config_file, environment, ignore_errors=False, log_file=log_file, log_level=log_level)
 
     _settings = global_settings()
 
-    print('license_key = %r' % _settings.license_key)
+    print("license_key = %r" % obfuscate_license_key(_settings.license_key))
diff --git a/newrelic/admin/validate_config.py b/newrelic/admin/validate_config.py
index ac25b715e..64645b0c6 100644
--- a/newrelic/admin/validate_config.py
+++ b/newrelic/admin/validate_config.py
@@ -149,6 +149,7 @@ def validate_config(args):
         sys.exit(1)
 
     from newrelic.api.application import register_application
+    from newrelic.common.encoding_utils import obfuscate_license_key
     from newrelic.config import initialize
     from newrelic.core.config import global_settings
 
@@ -200,7 +201,7 @@ def validate_config(args):
     _logger.debug("Proxy port is %r.", _settings.proxy_port)
     _logger.debug("Proxy user is %r.", _settings.proxy_user)
 
-    _logger.debug("License key is %r.", _settings.license_key)
+    _logger.debug("License key is %r.", obfuscate_license_key(_settings.license_key))
 
     _timeout = 30.0
 
diff --git a/newrelic/common/agent_http.py b/newrelic/common/agent_http.py
index 89876a60c..0e1fa682b 100644
--- a/newrelic/common/agent_http.py
+++ b/newrelic/common/agent_http.py
@@ -23,7 +23,11 @@
 import newrelic.packages.urllib3 as urllib3
 from newrelic import version
 from newrelic.common import certs
-from newrelic.common.encoding_utils import json_decode, json_encode
+from newrelic.common.encoding_utils import (
+    json_decode,
+    json_encode,
+    obfuscate_license_key,
+)
 from newrelic.common.object_names import callable_name
 from newrelic.common.object_wrapper import patch_function_wrapper
 from newrelic.core.internal_metrics import internal_count_metric, internal_metric
@@ -41,6 +45,9 @@ def get_default_verify_paths():
         return _DEFAULT_CERT_PATH
 
 
+HEADER_AUDIT_LOGGING_DENYLIST = frozenset(("x-api-key", "api-key"))
+
+
 # User agent string that must be used in all requests. The data collector
 # does not rely on this, but is used to target specific agents if there
 # is a problem with data collector handling requests.
@@ -119,6 +126,14 @@ def log_request(cls, fp, method, url, params, payload, headers, body=None, compr
         if not fp:
             return
 
+        # Obfuscate license key from headers and URL params
+        if headers:
+            headers = {k: obfuscate_license_key(v) if k.lower() in HEADER_AUDIT_LOGGING_DENYLIST else v for k, v in headers.items()}
+
+        if params and "license_key" in params:
+            params = params.copy()
+            params["license_key"] = obfuscate_license_key(params["license_key"])
+
         # Maintain a global AUDIT_LOG_ID attached to all class instances
         # NOTE: this is not thread safe so this class cannot be used
         # across threads when audit logging is on
diff --git a/newrelic/common/encoding_utils.py b/newrelic/common/encoding_utils.py
index 3b7a519a2..41ffb1dfa 100644
--- a/newrelic/common/encoding_utils.py
+++ b/newrelic/common/encoding_utils.py
@@ -613,3 +613,20 @@ def snake_case(string):
         return string  # Don't touch strings that are already snake cased
 
     return "_".join([s for s in _snake_case_re.split(string) if s]).lower()
+
+
+_obfuscate_license_key_ending = "*" * 32
+
+
+def obfuscate_license_key(license_key):
+    """Obfuscate license key to allow it to be printed out."""
+
+    if not isinstance(license_key, six.string_types):
+        # For non-string values passed in such as None, return the original.
+        return license_key
+    elif len(license_key) == 40:
+        #  For valid license keys of length 40, show the first 8 characters and then replace the remainder with ****
+        return license_key[:8] + _obfuscate_license_key_ending
+    else:
+        # For invalid lengths of license key, it's unclear how much is acceptable to show, so fully redact with ****
+        return "*" * len(license_key)