diff --git a/manifests/ruby.yml b/manifests/ruby.yml
index caa869e8143..ff685b1d55b 100644
--- a/manifests/ruby.yml
+++ b/manifests/ruby.yml
@@ -742,7 +742,11 @@ manifest:
   tests/appsec/test_service_activation_metric.py::TestServiceActivationRemoteConfigMetric: missing_feature
   tests/appsec/test_service_activation_metric.py::TestServiceActivationRemoteConfigurationConfigMetric: missing_feature
   tests/appsec/test_shell_execution.py::Test_ShellExecution: missing_feature
-  tests/appsec/test_span_tags_headers.py: bug (APPSEC-61286)
+  tests/appsec/test_span_tags_headers.py:
+    - weblog_declaration:
+        "*": v2.30.0-dev
+        graphql23: irrelevant
+        rails42: missing_feature  # Old Rack does not support to_ary for content-length computation
   tests/appsec/test_suspicious_attacker_blocking.py::Test_Suspicious_Attacker_Blocking: missing_feature
   tests/appsec/test_trace_tagging.py::Test_TraceTaggingRules: v2.22.0-dev
   tests/appsec/test_trace_tagging.py::Test_TraceTaggingRulesRcCapability: v2.22.0-dev
diff --git a/utils/build/docker/ruby/rack/config.ru b/utils/build/docker/ruby/rack/config.ru
index bf1be68db62..aa51e3d5417 100644
--- a/utils/build/docker/ruby/rack/config.ru
+++ b/utils/build/docker/ruby/rack/config.ru
@@ -470,6 +470,10 @@ class TraceSamplingMiddleware
 end
 
 use TraceSamplingMiddleware
+# NOTE: Most of the frameworks rely on Web Server to compute `Content-Length` header.
+#       But in this case to make it different from Rails and Sinatra we are going
+#       to provide it.
+use Rack::ContentLength
 
 # /flush
 module Flush