diff --git a/AzureMonitorAgent/agent.py b/AzureMonitorAgent/agent.py
index 73b50008c..81c246cad 100644
--- a/AzureMonitorAgent/agent.py
+++ b/AzureMonitorAgent/agent.py
@@ -2714,19 +2714,32 @@ def get_settings():
                                             '{0}.prv'.format(
                                                       settings_thumbprint))
             decoded_settings = base64.standard_b64decode(encoded_settings)
-            decrypt_cmd = 'openssl smime -inform DER -decrypt -recip {0} ' \
-                          '-inkey {1}'.format(encoded_cert_path,
-                                              encoded_key_path)
 
-            try:
-                session = subprocess.Popen([decrypt_cmd], shell = True,
-                                           stdin = subprocess.PIPE,
-                                           stderr = subprocess.STDOUT,
-                                           stdout = subprocess.PIPE)
-                output = session.communicate(decoded_settings)
-            except OSError:
-                pass
-            protected_settings_str = output[0]
+
+             # FIPS 140-3: use 'openssl cms' (supports AES256 & DES_EDE3_CBC) with fallback to legacy 'openssl smime'
+            cms_cmd = 'openssl cms -inform DER -decrypt -recip {0} -inkey {1}'.format(encoded_cert_path, encoded_key_path)
+            smime_cmd = 'openssl smime -inform DER -decrypt -recip {0} -inkey {1}'.format(encoded_cert_path, encoded_key_path)
+
+            protected_settings_str = None
+            for decrypt_cmd in [cms_cmd, smime_cmd]:
+                try:
+                    session = subprocess.Popen([decrypt_cmd], shell=True,
+                                               stdin=subprocess.PIPE,
+                                               stderr=subprocess.STDOUT,
+                                               stdout=subprocess.PIPE)
+                    output = session.communicate(decoded_settings)
+                    # success only if return code is 0 and we have output
+                    if session.returncode == 0 and output[0]:
+                        protected_settings_str = output[0]
+                        if decrypt_cmd == cms_cmd:
+                            hutil_log_info('Decrypted protectedSettings using openssl cms.')
+                        else:
+                            hutil_log_info('Decrypted protectedSettings using openssl smime fallback.')
+                        break
+                    else:
+                        hutil_log_info('Attempt to decrypt protectedSettings with "{0}" failed (rc={1}).'.format(decrypt_cmd, session.returncode))
+                except OSError:
+                    pass
 
             if protected_settings_str is None:
                 log_and_exit('Enable', GenericErrorCode, 'Failed decrypting protectedSettings')
diff --git a/Utils/HandlerUtil.py b/Utils/HandlerUtil.py
index ef2e1a419..30f961921 100755
--- a/Utils/HandlerUtil.py
+++ b/Utils/HandlerUtil.py
@@ -58,6 +58,7 @@
 import json
 import time
 import re
+import subprocess
 # imp was deprecated in python 3.12
 if sys.version_info >= (3, 12):
     import importlib
@@ -195,16 +196,37 @@ def _parse_config(self, ctxt):
                 cert = waagent.LibDir + '/' + thumb + '.crt'
                 pkey = waagent.LibDir + '/' + thumb + '.prv'
                 unencodedSettings = base64.standard_b64decode(protectedSettings)
-                openSSLcmd = "openssl smime -inform DER -decrypt -recip {0} -inkey {1}"
-                cleartxt = waagent.RunSendStdin(openSSLcmd.format(cert, pkey), unencodedSettings)[1]
-                if cleartxt is None:
-                    self.error("OpenSSL decode error using  thumbprint " + thumb)
-                    self.do_exit(1, "Enable", 'error', '1', 'Failed to decrypt protectedSettings')
+
+                # FIPS 140-3: use 'openssl cms' (supports AES256 & DES_EDE3_CBC) with fallback to legacy 'openssl smime'
+                cms_cmd = 'openssl cms -inform DER -decrypt -recip {0} -inkey {1}'.format(cert,pkey)
+                smime_cmd = 'openssl smime -inform DER -decrypt -recip {0} -inkey {1}'.format(cert,pkey)
+
+                protected_settings_str = None
+                for decrypt_cmd in [cms_cmd, smime_cmd]:
+                    try:
+                        session = subprocess.Popen([decrypt_cmd], shell=True,
+                                                stdin=subprocess.PIPE,
+                                                stderr=subprocess.STDOUT,
+                                                stdout=subprocess.PIPE)
+                        output = session.communicate(unencodedSettings)
+                        # success only if return code is 0 and we have output
+                        if session.returncode == 0 and output[0]:
+                            protected_settings_str = output[0]
+                            if decrypt_cmd == cms_cmd:
+                                self.log('Decrypted protectedSettings using openssl cms.')
+                            else:
+                                self.log('Decrypted protectedSettings using openssl smime fallback.')
+                            break
+                        else:
+                            self.log('Attempt to decrypt protectedSettings with "{0}" failed (rc={1}).'.format(decrypt_cmd, session.returncode))
+                    except OSError:
+                        pass
+
                 jctxt = ''
                 try:
-                    jctxt = json.loads(cleartxt)
+                    jctxt = json.loads(protected_settings_str)
                 except:
-                    self.error('JSON exception decoding ' + HandlerUtility.redact_protected_settings(cleartxt))
+                    self.error('JSON exception decoding ' + HandlerUtility.redact_protected_settings(protected_settings_str))
                 handlerSettings['protectedSettings']=jctxt
                 self.log('Config decoded correctly.')
         return config