diff --git a/lib/datadog/appsec/event.rb b/lib/datadog/appsec/event.rb
index 62a2247bda8..b598241979a 100644
--- a/lib/datadog/appsec/event.rb
+++ b/lib/datadog/appsec/event.rb
@@ -37,6 +37,9 @@ module Event
       ].map!(&:downcase).freeze
 
       MAX_ENCODED_SCHEMA_SIZE = 25000
+      # For more information about this number
+      # please check https://github.com/DataDog/dd-trace-rb/pull/3177#issuecomment-1747221082
+      MIN_SCHEMA_SIZE_FOR_COMPRESSION = 260
 
       # Record events for a trace
       #
@@ -75,7 +78,7 @@ def record_via_span(span, *events)
           end
         end
 
-        # rubocop: disable Metrics/MethodLength
+        # rubocop:disable Metrics/MethodLength
         def build_service_entry_tags(event_group)
           waf_events = []
           entry_tags = event_group.each_with_object({ '_dd.origin' => 'appsec' }) do |event, tags|
@@ -106,19 +109,21 @@ def build_service_entry_tags(event_group)
 
               parsed_value_size = parsed_value.size
 
-              compressed_data = compressed_and_base64_encoded(parsed_value)
-              compressed_data_size = compressed_data.size
+              schema_value = if parsed_value_size >= MIN_SCHEMA_SIZE_FOR_COMPRESSION
+                               compressed_and_base64_encoded(parsed_value)
+                             else
+                               parsed_value
+                             end
+              next unless schema_value
 
-              if compressed_data_size >= MAX_ENCODED_SCHEMA_SIZE && parsed_value_size >= MAX_ENCODED_SCHEMA_SIZE
+              if schema_value.size >= MAX_ENCODED_SCHEMA_SIZE
                 Datadog.logger.debug do
                   "Schema key: #{key} exceeds the max size value. It will not be included as part of the span tags"
                 end
                 next
               end
 
-              derivative_value = parsed_value_size > compressed_data_size ? compressed_data : parsed_value
-
-              tags[key] = derivative_value
+              tags[key] = schema_value
             end
 
             tags
@@ -128,25 +133,32 @@ def build_service_entry_tags(event_group)
           entry_tags['_dd.appsec.json'] = appsec_events if appsec_events
           entry_tags
         end
-        # rubocop: enable Metrics/MethodLength
+        # rubocop:enable Metrics/MethodLength
 
         private
 
         def compressed_and_base64_encoded(value)
           Base64.encode64(gzip(value))
-        rescue TypeError
+        rescue TypeError => e
+          Datadog.logger.debug do
+            "Failed to compress and encode value when populating AppSec::Event. Error: #{e.message}"
+          end
           nil
         end
 
         def json_parse(value)
           JSON.dump(value)
-        rescue ArgumentError
+        rescue ArgumentError => e
+          Datadog.logger.debug do
+            "Failed to parse value to JSON when populating AppSec::Event. Error: #{e.message}"
+          end
           nil
         end
 
         def gzip(value)
           sio = StringIO.new
-          gz = Zlib::GzipWriter.new(sio, Zlib::DEFAULT_COMPRESSION, Zlib::DEFAULT_STRATEGY)
+          # For an in depth comparison of Zlib options check https://github.com/DataDog/dd-trace-rb/pull/3177#issuecomment-1747215473
+          gz = Zlib::GzipWriter.new(sio, Zlib::BEST_SPEED, Zlib::DEFAULT_STRATEGY)
           gz.write(value)
           gz.close
           sio.string
diff --git a/sig/datadog/appsec/event.rbs b/sig/datadog/appsec/event.rbs
index 9f30df5d97a..36d75ca6e55 100644
--- a/sig/datadog/appsec/event.rbs
+++ b/sig/datadog/appsec/event.rbs
@@ -6,6 +6,7 @@ module Datadog
       ALLOWED_RESPONSE_HEADERS: untyped
 
       MAX_ENCODED_SCHEMA_SIZE: Numeric
+      MIN_SCHEMA_SIZE_FOR_COMPRESSION: Numeric
 
       def self.record: (Datadog::Tracing::SpanOperation, *untyped events) -> (nil | untyped)
 
diff --git a/spec/datadog/appsec/event_spec.rb b/spec/datadog/appsec/event_spec.rb
index 3ffd927a7a8..e79ecfbde1e 100644
--- a/spec/datadog/appsec/event_spec.rb
+++ b/spec/datadog/appsec/event_spec.rb
@@ -113,7 +113,8 @@
           end
 
           context 'JSON payload' do
-            it 'uses JSON string as is smaller than the compressed value' do
+            it 'uses JSON string when do not exceeds MIN_SCHEMA_SIZE_FOR_COMPRESSION' do
+              stub_const('Datadog::AppSec::Event::MIN_SCHEMA_SIZE_FOR_COMPRESSION', 3000)
               meta = top_level_span.meta
 
               expect(meta['_dd.appsec.s.req.headers']).to eq('[{"host":[8],"version":[8]}]')
@@ -121,8 +122,9 @@
           end
 
           context 'Compressed payload' do
-            it 'uses compressed value when is smaller than JSON string' do
+            it 'uses compressed value when JSON string is bigger than MIN_SCHEMA_SIZE_FOR_COMPRESSION' do
               result = "H4sIAOYoHGUAA4aphwAAAA=\n"
+              stub_const('Datadog::AppSec::Event::MIN_SCHEMA_SIZE_FOR_COMPRESSION', 1)
               expect(described_class).to receive(:compressed_and_base64_encoded).and_return(result)
 
               meta = top_level_span.meta