diff --git a/Source/common/santa.proto b/Source/common/santa.proto
index e09c6df72..fc7da670c 100644
--- a/Source/common/santa.proto
+++ b/Source/common/santa.proto
@@ -214,8 +214,8 @@ message CertificateInfo {
 }
 
 message Entitlement {
-	string key = 1;
-	string value = 2;
+  string key = 1;
+  string value = 2;
 }
 
 // Information about a process execution event
diff --git a/Source/santad/Logs/EndpointSecurity/Serializers/Protobuf.mm b/Source/santad/Logs/EndpointSecurity/Serializers/Protobuf.mm
index 0d0808c8b..1db360d7c 100644
--- a/Source/santad/Logs/EndpointSecurity/Serializers/Protobuf.mm
+++ b/Source/santad/Logs/EndpointSecurity/Serializers/Protobuf.mm
@@ -72,6 +72,7 @@
 namespace santa::santad::logs::endpoint_security::serializers {
 
 static constexpr NSUInteger kMaxEncodeObjectEntries = 64;
+static constexpr NSUInteger kMaxEncodeObjectLevels = 5;
 
 std::shared_ptr<Protobuf> Protobuf::Create(std::shared_ptr<EndpointSecurityAPI> esapi,
                                            SNTDecisionCache *decision_cache, bool json) {
@@ -451,11 +452,49 @@ static inline void EncodeCertificateInfo(::pbv1::CertificateInfo *pb_cert_info,
   return FinalizeProto(santa_msg);
 }
 
+id StandardizedNestedObjects(id obj, int level) {
+  if (level-- == 0) {
+    return [obj description];
+  }
+
+  if ([obj isKindOfClass:[NSNumber class]] || [obj isKindOfClass:[NSString class]]) {
+    return obj;
+  } else if ([obj isKindOfClass:[NSArray class]]) {
+    NSMutableArray *arr = [NSMutableArray array];
+    for (id item in obj) {
+      [arr addObject:StandardizedNestedObjects(item, level)];
+    }
+    return arr;
+  } else if ([obj isKindOfClass:[NSDictionary class]]) {
+    NSMutableDictionary *dict = [NSMutableDictionary dictionary];
+    for (id key in obj) {
+      [dict setObject:StandardizedNestedObjects(obj[key], level) forKey:key];
+    }
+    return dict;
+  } else if ([obj isKindOfClass:[NSData class]]) {
+    return [obj base64EncodedStringWithOptions:0];
+  } else if ([obj isKindOfClass:[NSDate class]]) {
+    return [NSISO8601DateFormatter stringFromDate:obj
+                                         timeZone:[NSTimeZone timeZoneWithAbbreviation:@"UTC"]
+                                    formatOptions:NSISO8601DateFormatWithFractionalSeconds | NSISO8601DateFormatWithInternetDateTime];
+
+  } else {
+    NSLog(@"Got unknown... %d", level);
+    LOGW(@"Unexpected object encountered: %@", obj);
+    return [obj description];
+  }
+}
+
 void EncodeEntitlements(::pbv1::Execution *pb_exec, NSDictionary *entitlements) {
   if (!entitlements) {
     return;
   }
 
+  // Since nested objects with varying types is hard for the API to serialize to
+  // JSON, first go through and standardize types to ensure better serialization
+  // as well as a consitent view of data.
+  entitlements = StandardizedNestedObjects(entitlements, kMaxEncodeObjectLevels);
+
   __block int numObjectsToEncode = (int)std::min(kMaxEncodeObjectEntries, entitlements.count);
 
   pb_exec->mutable_entitlements()->Reserve(numObjectsToEncode);
@@ -474,19 +513,7 @@ void EncodeEntitlements(::pbv1::Execution *pb_exec, NSDictionary *entitlements)
     NSError *err;
     NSData *jsonData;
     @try {
-      id val = obj;
-
-      // Fixup some types with data that can be better represented in JSON
-      if ([obj isKindOfClass:[NSDate class]]) {
-        // Example format output: "November 6, 2023 at 10:25:20 AM EST"
-        val = [NSDateFormatter localizedStringFromDate:obj
-                                             dateStyle:NSDateFormatterLongStyle
-                                             timeStyle:NSDateFormatterLongStyle];
-      } else if ([obj isKindOfClass:[NSData class]]) {
-        val = [obj base64EncodedStringWithOptions:0];
-      }
-
-      jsonData = [NSJSONSerialization dataWithJSONObject:val
+      jsonData = [NSJSONSerialization dataWithJSONObject:obj
                                                  options:NSJSONWritingFragmentsAllowed
                                                    error:&err];
     } @catch (NSException *e) {
diff --git a/Source/santad/Logs/EndpointSecurity/Serializers/ProtobufTest.mm b/Source/santad/Logs/EndpointSecurity/Serializers/ProtobufTest.mm
index afd9d78dd..d98925d11 100644
--- a/Source/santad/Logs/EndpointSecurity/Serializers/ProtobufTest.mm
+++ b/Source/santad/Logs/EndpointSecurity/Serializers/ProtobufTest.mm
@@ -276,7 +276,10 @@ void SerializeAndCheck(es_event_type_t eventType,
                  options:NSJSONReadingMutableContainers
                    error:&jsonError];
     XCTAssertNil(jsonError, @"failed to parse got data as JSON");
+
     XCTAssertNil(FindDelta(wantJSONDict, gotJSONDict));
+    // Note: Uncomment this line to help create testfile JSON when the assert above fails
+    // XCTAssertEqualObjects([NSString stringWithUTF8String:gotData.c_str()], wantData);
   }
 
   XCTBubbleMockVerifyAndClearExpectations(mockESApi.get());
diff --git a/Source/santad/testdata/protobuf/v1/exec.json b/Source/santad/testdata/protobuf/v1/exec.json
index bec33b2f9..72f1760cb 100644
--- a/Source/santad/testdata/protobuf/v1/exec.json
+++ b/Source/santad/testdata/protobuf/v1/exec.json
@@ -123,16 +123,16 @@
  "quarantine_url": "google.com",
  "entitlements": [
   {
-   "key": "key_with_arr_val",
-   "value": "[\"v1\",\"v2\",\"v3\"]"
+   "key": "key_with_arr_val_multitype",
+   "value": "[\"v1\",\"v2\",\"v3\",123,\"2023-11-07T17:00:02.000Z\"]"
   },
   {
    "key": "key_with_data_val",
    "value": "\"SGVsbG8gV29ybGQ=\""
   },
   {
-   "key": "key_with_arr_val_multitype",
-   "value": "\"(\\n    v1,\\n    v2,\\n    v3,\\n    123,\\n    \\\"2023-11-07 17:00:02 +0000\\\"\\n)\""
+   "key": "key_with_str_val",
+   "value": "\"bar\""
   },
   {
    "key": "key_with_arr_val_nested",
@@ -140,23 +140,23 @@
   },
   {
    "key": "key_with_dict_val",
-   "value": "{\"k1\":\"v1\",\"k2\":\"v2\"}"
+   "value": "{\"k2\":\"v2\",\"k1\":\"v1\"}"
   },
   {
    "key": "key_with_date_val",
-   "value": "\"November 7, 2023 at 5:00:02 PM GMT\""
+   "value": "\"2023-11-07T17:00:02.000Z\""
   },
   {
    "key": "key_with_dict_val_nested",
-   "value": "\"{\\n    k1 = v1;\\n    k2 = v2;\\n    k3 =     {\\n        nk1 = nv1;\\n        nk2 = \\\"2023-11-07 17:00:02 +0000\\\";\\n    };\\n}\""
+   "value": "{\"k3\":{\"nk1\":\"nv1\",\"nk2\":\"2023-11-07T17:00:02.000Z\"},\"k2\":\"v2\",\"k1\":\"v1\"}"
   },
   {
    "key": "key_with_num_val",
    "value": "1234"
   },
   {
-   "key": "key_with_str_val",
-   "value": "\"bar\""
+   "key": "key_with_arr_val",
+   "value": "[\"v1\",\"v2\",\"v3\"]"
   }
  ]
 }
diff --git a/Source/santad/testdata/protobuf/v2/exec.json b/Source/santad/testdata/protobuf/v2/exec.json
index 4340a488e..95f2d81ac 100644
--- a/Source/santad/testdata/protobuf/v2/exec.json
+++ b/Source/santad/testdata/protobuf/v2/exec.json
@@ -151,16 +151,16 @@
  "quarantine_url": "google.com",
  "entitlements": [
   {
-   "key": "key_with_arr_val",
-   "value": "[\"v1\",\"v2\",\"v3\"]"
+   "key": "key_with_arr_val_multitype",
+   "value": "[\"v1\",\"v2\",\"v3\",123,\"2023-11-07T17:00:02.000Z\"]"
   },
   {
    "key": "key_with_data_val",
    "value": "\"SGVsbG8gV29ybGQ=\""
   },
   {
-   "key": "key_with_arr_val_multitype",
-   "value": "\"(\\n    v1,\\n    v2,\\n    v3,\\n    123,\\n    \\\"2023-11-07 17:00:02 +0000\\\"\\n)\""
+   "key": "key_with_str_val",
+   "value": "\"bar\""
   },
   {
    "key": "key_with_arr_val_nested",
@@ -168,23 +168,23 @@
   },
   {
    "key": "key_with_dict_val",
-   "value": "{\"k1\":\"v1\",\"k2\":\"v2\"}"
+   "value": "{\"k2\":\"v2\",\"k1\":\"v1\"}"
   },
   {
    "key": "key_with_date_val",
-   "value": "\"November 7, 2023 at 5:00:02 PM GMT\""
+   "value": "\"2023-11-07T17:00:02.000Z\""
   },
   {
    "key": "key_with_dict_val_nested",
-   "value": "\"{\\n    k1 = v1;\\n    k2 = v2;\\n    k3 =     {\\n        nk1 = nv1;\\n        nk2 = \\\"2023-11-07 17:00:02 +0000\\\";\\n    };\\n}\""
+   "value": "{\"k3\":{\"nk1\":\"nv1\",\"nk2\":\"2023-11-07T17:00:02.000Z\"},\"k2\":\"v2\",\"k1\":\"v1\"}"
   },
   {
    "key": "key_with_num_val",
    "value": "1234"
   },
   {
-   "key": "key_with_str_val",
-   "value": "\"bar\""
+   "key": "key_with_arr_val",
+   "value": "[\"v1\",\"v2\",\"v3\"]"
   }
  ]
 }
diff --git a/Source/santad/testdata/protobuf/v4/exec.json b/Source/santad/testdata/protobuf/v4/exec.json
index c55d46e86..4781ef27b 100644
--- a/Source/santad/testdata/protobuf/v4/exec.json
+++ b/Source/santad/testdata/protobuf/v4/exec.json
@@ -200,16 +200,16 @@
  "quarantine_url": "google.com",
  "entitlements": [
   {
-   "key": "key_with_arr_val",
-   "value": "[\"v1\",\"v2\",\"v3\"]"
+   "key": "key_with_arr_val_multitype",
+   "value": "[\"v1\",\"v2\",\"v3\",123,\"2023-11-07T17:00:02.000Z\"]"
   },
   {
    "key": "key_with_data_val",
    "value": "\"SGVsbG8gV29ybGQ=\""
   },
   {
-   "key": "key_with_arr_val_multitype",
-   "value": "\"(\\n    v1,\\n    v2,\\n    v3,\\n    123,\\n    \\\"2023-11-07 17:00:02 +0000\\\"\\n)\""
+   "key": "key_with_str_val",
+   "value": "\"bar\""
   },
   {
    "key": "key_with_arr_val_nested",
@@ -217,23 +217,23 @@
   },
   {
    "key": "key_with_dict_val",
-   "value": "{\"k1\":\"v1\",\"k2\":\"v2\"}"
+   "value": "{\"k2\":\"v2\",\"k1\":\"v1\"}"
   },
   {
    "key": "key_with_date_val",
-   "value": "\"November 7, 2023 at 5:00:02 PM GMT\""
+   "value": "\"2023-11-07T17:00:02.000Z\""
   },
   {
    "key": "key_with_dict_val_nested",
-   "value": "\"{\\n    k1 = v1;\\n    k2 = v2;\\n    k3 =     {\\n        nk1 = nv1;\\n        nk2 = \\\"2023-11-07 17:00:02 +0000\\\";\\n    };\\n}\""
+   "value": "{\"k3\":{\"nk1\":\"nv1\",\"nk2\":\"2023-11-07T17:00:02.000Z\"},\"k2\":\"v2\",\"k1\":\"v1\"}"
   },
   {
    "key": "key_with_num_val",
    "value": "1234"
   },
   {
-   "key": "key_with_str_val",
-   "value": "\"bar\""
+   "key": "key_with_arr_val",
+   "value": "[\"v1\",\"v2\",\"v3\"]"
   }
  ]
 }
diff --git a/Source/santad/testdata/protobuf/v5/exec.json b/Source/santad/testdata/protobuf/v5/exec.json
index b55e137ea..e6b6ba94f 100644
--- a/Source/santad/testdata/protobuf/v5/exec.json
+++ b/Source/santad/testdata/protobuf/v5/exec.json
@@ -200,16 +200,16 @@
  "quarantine_url": "google.com",
  "entitlements": [
   {
-   "key": "key_with_arr_val",
-   "value": "[\"v1\",\"v2\",\"v3\"]"
+   "key": "key_with_arr_val_multitype",
+   "value": "[\"v1\",\"v2\",\"v3\",123,\"2023-11-07T17:00:02.000Z\"]"
   },
   {
    "key": "key_with_data_val",
    "value": "\"SGVsbG8gV29ybGQ=\""
   },
   {
-   "key": "key_with_arr_val_multitype",
-   "value": "\"(\\n    v1,\\n    v2,\\n    v3,\\n    123,\\n    \\\"2023-11-07 17:00:02 +0000\\\"\\n)\""
+   "key": "key_with_str_val",
+   "value": "\"bar\""
   },
   {
    "key": "key_with_arr_val_nested",
@@ -217,23 +217,23 @@
   },
   {
    "key": "key_with_dict_val",
-   "value": "{\"k1\":\"v1\",\"k2\":\"v2\"}"
+   "value": "{\"k2\":\"v2\",\"k1\":\"v1\"}"
   },
   {
    "key": "key_with_date_val",
-   "value": "\"November 7, 2023 at 5:00:02 PM GMT\""
+   "value": "\"2023-11-07T17:00:02.000Z\""
   },
   {
    "key": "key_with_dict_val_nested",
-   "value": "\"{\\n    k1 = v1;\\n    k2 = v2;\\n    k3 =     {\\n        nk1 = nv1;\\n        nk2 = \\\"2023-11-07 17:00:02 +0000\\\";\\n    };\\n}\""
+   "value": "{\"k3\":{\"nk1\":\"nv1\",\"nk2\":\"2023-11-07T17:00:02.000Z\"},\"k2\":\"v2\",\"k1\":\"v1\"}"
   },
   {
    "key": "key_with_num_val",
    "value": "1234"
   },
   {
-   "key": "key_with_str_val",
-   "value": "\"bar\""
+   "key": "key_with_arr_val",
+   "value": "[\"v1\",\"v2\",\"v3\"]"
   }
  ]
 }
diff --git a/Source/santad/testdata/protobuf/v6/exec.json b/Source/santad/testdata/protobuf/v6/exec.json
index c55d46e86..4781ef27b 100644
--- a/Source/santad/testdata/protobuf/v6/exec.json
+++ b/Source/santad/testdata/protobuf/v6/exec.json
@@ -200,16 +200,16 @@
  "quarantine_url": "google.com",
  "entitlements": [
   {
-   "key": "key_with_arr_val",
-   "value": "[\"v1\",\"v2\",\"v3\"]"
+   "key": "key_with_arr_val_multitype",
+   "value": "[\"v1\",\"v2\",\"v3\",123,\"2023-11-07T17:00:02.000Z\"]"
   },
   {
    "key": "key_with_data_val",
    "value": "\"SGVsbG8gV29ybGQ=\""
   },
   {
-   "key": "key_with_arr_val_multitype",
-   "value": "\"(\\n    v1,\\n    v2,\\n    v3,\\n    123,\\n    \\\"2023-11-07 17:00:02 +0000\\\"\\n)\""
+   "key": "key_with_str_val",
+   "value": "\"bar\""
   },
   {
    "key": "key_with_arr_val_nested",
@@ -217,23 +217,23 @@
   },
   {
    "key": "key_with_dict_val",
-   "value": "{\"k1\":\"v1\",\"k2\":\"v2\"}"
+   "value": "{\"k2\":\"v2\",\"k1\":\"v1\"}"
   },
   {
    "key": "key_with_date_val",
-   "value": "\"November 7, 2023 at 5:00:02 PM GMT\""
+   "value": "\"2023-11-07T17:00:02.000Z\""
   },
   {
    "key": "key_with_dict_val_nested",
-   "value": "\"{\\n    k1 = v1;\\n    k2 = v2;\\n    k3 =     {\\n        nk1 = nv1;\\n        nk2 = \\\"2023-11-07 17:00:02 +0000\\\";\\n    };\\n}\""
+   "value": "{\"k3\":{\"nk1\":\"nv1\",\"nk2\":\"2023-11-07T17:00:02.000Z\"},\"k2\":\"v2\",\"k1\":\"v1\"}"
   },
   {
    "key": "key_with_num_val",
    "value": "1234"
   },
   {
-   "key": "key_with_str_val",
-   "value": "\"bar\""
+   "key": "key_with_arr_val",
+   "value": "[\"v1\",\"v2\",\"v3\"]"
   }
  ]
 }