diff --git a/sentry-ruby/lib/sentry-ruby.rb b/sentry-ruby/lib/sentry-ruby.rb
index 52afec20e..12ed09d93 100644
--- a/sentry-ruby/lib/sentry-ruby.rb
+++ b/sentry-ruby/lib/sentry-ruby.rb
@@ -223,6 +223,16 @@ def set_context(*args)
       get_current_scope.set_context(*args)
     end
 
+    # Records a feature flag evaluation on the current scope and active span.
+    # Only boolean results are recorded.
+    # @param name [String, Symbol] the flag name
+    # @param result [Boolean] the evaluation result
+    # @return [void]
+    def add_feature_flag(name, result)
+      return unless initialized?
+      get_current_scope.add_feature_flag(name, result)
+    end
+
     # @!method set_attributes
     #   Updates the current scope's attributes by merging with the old value.
     #   @param attributes_hash [Hash]
diff --git a/sentry-ruby/lib/sentry/scope.rb b/sentry-ruby/lib/sentry/scope.rb
index bcf4328ad..c1fda4400 100644
--- a/sentry-ruby/lib/sentry/scope.rb
+++ b/sentry-ruby/lib/sentry/scope.rb
@@ -4,6 +4,7 @@
 require "sentry/breadcrumb_buffer"
 require "sentry/propagation_context"
 require "sentry/attachment"
+require "sentry/utils/ring_buffer"
 require "etc"
 
 module Sentry
@@ -27,9 +28,13 @@ class Scope
       :session,
       :attachments,
       :propagation_context,
-      :attributes
+      :attributes,
+      :flags
     ]
 
+    # Maximum number of feature flag evaluations kept on a scope.
+    MAX_FLAGS = 100
+
     attr_reader(*ATTRIBUTES)
 
     # @param max_breadcrumbs [Integer] the maximum number of breadcrumbs to be stored in the scope.
@@ -61,6 +66,7 @@ def apply_to_event(event, hint = nil)
         event.breadcrumbs = breadcrumbs
         event.rack_env = rack_env if rack_env
         event.attachments = attachments
+        apply_flags_to_event(event)
       end
 
       trace_context = get_trace_context
@@ -151,6 +157,7 @@ def dup
       copy.attachments = attachments.dup
       copy.event_processors = event_processors.dup
       copy.attributes = attributes.deep_dup
+      copy.flags = flags.dup
       copy
     end
 
@@ -170,6 +177,7 @@ def update_from_scope(scope)
       self.propagation_context = scope.propagation_context
       self.attachments = scope.attachments
       self.attributes = scope.attributes
+      self.flags = scope.flags.dup
     end
 
     # Updates the scope's data from the given options.
@@ -298,6 +306,22 @@ def remove_attribute(key)
       @attributes.delete(key.to_s)
     end
 
+    # Records a feature flag evaluation on the scope (and the active span, if any).
+    # Only boolean results are supported; other values are ignored.
+    # The scope keeps the most recent {MAX_FLAGS} distinct flags (oldest evicted first).
+    # @param name [String, Symbol] the flag name
+    # @param result [Boolean] the evaluation result
+    # @return [void]
+    def add_feature_flag(name, result)
+      return unless result == true || result == false
+
+      name = name.to_s
+      flags.set(name, result)
+
+      add_feature_flag_to_span(name, result)
+      nil
+    end
+
     # Sets the scope's level attribute.
     # @param level [String, Symbol]
     # @return [void]
@@ -389,6 +413,19 @@ def add_attachment(**opts)
 
     private
 
+    def add_feature_flag_to_span(name, result)
+      return unless span
+
+      span.set_flag(name, result)
+    end
+
+    def apply_flags_to_event(event)
+      return unless event.is_a?(ErrorEvent) && !flags.empty?
+
+      values = flags.values.map { |flag, result| { flag: flag, result: result } }
+      event.contexts[:flags] = { values: values }
+    end
+
     def set_default_value
       @contexts = { os: self.class.os_context, runtime: self.class.runtime_context }
       @extra = {}
@@ -404,6 +441,7 @@ def set_default_value
       @session = nil
       @attachments = []
       @attributes = {}
+      @flags = Utils::RingBuffer.new(MAX_FLAGS)
       generate_propagation_context
       set_new_breadcrumb_buffer
     end
diff --git a/sentry-ruby/lib/sentry/span.rb b/sentry-ruby/lib/sentry/span.rb
index b53554dc4..4942de161 100644
--- a/sentry-ruby/lib/sentry/span.rb
+++ b/sentry-ruby/lib/sentry/span.rb
@@ -70,6 +70,8 @@ module DataConventions
     }
 
     DEFAULT_SPAN_ORIGIN = "manual"
+    MAX_FLAGS = 10
+    SPAN_FLAG_ATTRIBUTE_PREFIX = "flag.evaluation."
 
     # An uuid that can be used to identify a trace.
     # @return [String]
@@ -104,6 +106,9 @@ module DataConventions
     # Span data
     # @return [Hash]
     attr_reader :data
+    # Feature flag data
+    # @return [Hash]
+    attr_reader :flags
     # Span origin that tracks what kind of instrumentation created a span
     # @return [String]
     attr_reader :origin
@@ -142,6 +147,7 @@ def initialize(
       @op = op
       @status = status
       @data = {}
+      @flags = {}
       @tags = {}
       @origin = origin || DEFAULT_SPAN_ORIGIN
     end
@@ -187,7 +193,7 @@ def to_h
         op: @op,
         status: @status,
         tags: @tags,
-        data: @data,
+        data: serialized_data,
         origin: @origin
       }
     end
@@ -203,7 +209,7 @@ def get_trace_context
         op: @op,
         status: @status,
         origin: @origin,
-        data: @data
+        data: serialized_data
       }
     end
 
@@ -293,6 +299,14 @@ def set_data(key, value)
       @data[key] = value
     end
 
+    # Sets a feature flag on the span.
+    # @param name [String] the flag name
+    # @param result [Boolean] the evaluation result
+    def set_flag(name, result)
+      flag = "#{SPAN_FLAG_ATTRIBUTE_PREFIX}#{name}"
+      @flags[flag] = result if @flags.size < MAX_FLAGS
+    end
+
     # Sets a tag to the span.
     # @param key [String, Symbol]
     # @param value [String]
@@ -305,5 +319,13 @@ def set_tag(key, value)
     def set_origin(origin)
       @origin = origin
     end
+
+    private
+
+    def serialized_data
+      return @data if @flags.empty?
+
+      @flags.merge(@data)
+    end
   end
 end
diff --git a/sentry-ruby/lib/sentry/utils/ring_buffer.rb b/sentry-ruby/lib/sentry/utils/ring_buffer.rb
new file mode 100644
index 000000000..1fe0ed391
--- /dev/null
+++ b/sentry-ruby/lib/sentry/utils/ring_buffer.rb
@@ -0,0 +1,38 @@
+# frozen_string_literal: true
+
+require "sentry/core_ext/object/deep_dup"
+
+module Sentry
+  module Utils
+    class RingBuffer
+      attr_reader :values
+
+      def initialize(capacity)
+        raise ArgumentError, "capacity must be positive" unless capacity.positive?
+
+        @capacity = capacity
+        @values = {}
+      end
+
+      def set(key, value)
+        @values.delete(key)
+        @values[key] = value
+        @values.shift if @values.size > @capacity
+      end
+
+      def clear
+        @values.clear
+      end
+
+      def empty?
+        @values.empty?
+      end
+
+      def dup
+        copy = self.class.new(@capacity)
+        copy.values.merge!(@values)
+        copy
+      end
+    end
+  end
+end
diff --git a/sentry-ruby/spec/sentry/scope/feature_flags_spec.rb b/sentry-ruby/spec/sentry/scope/feature_flags_spec.rb
new file mode 100644
index 000000000..0851f799e
--- /dev/null
+++ b/sentry-ruby/spec/sentry/scope/feature_flags_spec.rb
@@ -0,0 +1,94 @@
+# frozen_string_literal: true
+
+require "spec_helper"
+
+RSpec.describe Sentry::Scope do
+  subject(:scope) { described_class.new }
+
+  before do
+    perform_basic_setup { |config| config.traces_sample_rate = 1.0 }
+  end
+
+  describe "#add_feature_flag" do
+    it "adds flags to event contexts" do
+      scope.add_feature_flag("a", true)
+      scope.add_feature_flag(:b, false)
+
+      event = scope.apply_to_event(Sentry::ErrorEvent.new(configuration: Sentry.configuration))
+      expect(event.contexts[:flags]).to eq(values: [{ flag: "a", result: true }, { flag: "b", result: false }])
+    end
+
+    it "ignores non-boolean results" do
+      scope.add_feature_flag("a", "yes")
+      scope.add_feature_flag("b", nil)
+      expect(scope.flags.values).to be_empty
+    end
+
+    it "moves a re-evaluated flag to the end with its new result" do
+      scope.add_feature_flag("a", true)
+      scope.add_feature_flag("b", true)
+      scope.add_feature_flag("a", false)
+      expect(scope.flags.values).to eq("b" => true, "a" => false)
+    end
+
+    it "evicts the oldest flag beyond the limit" do
+      (Sentry::Scope::MAX_FLAGS + 1).times { |i| scope.add_feature_flag("f#{i}", true) }
+      expect(scope.flags.values.size).to eq(Sentry::Scope::MAX_FLAGS)
+      expect(scope.flags.values.first.first).to eq("f1")
+    end
+
+    it "does not add flags to transaction events" do
+      scope.add_feature_flag("a", true)
+      transaction = Sentry.start_transaction(name: "foo", op: "bar")
+      event = scope.apply_to_event(Sentry::TransactionEvent.new(configuration: Sentry.configuration, transaction: transaction))
+      expect(event.contexts).not_to have_key(:flags)
+    end
+
+    it "does not add flags to check-in events" do
+      scope.add_feature_flag("a", true)
+      event = Sentry::CheckInEvent.new(configuration: Sentry.configuration, slug: "foo", status: :ok)
+      scope.apply_to_event(event)
+      expect(event.contexts).not_to have_key(:flags)
+    end
+
+    it "is isolated in duplicated and updated scopes and cleared by #clear" do
+      scope.add_feature_flag("a", true)
+      copy = scope.dup
+      copy.add_feature_flag("b", true)
+      copy.add_feature_flag("a", false)
+      expect(scope.flags.values).to eq("a" => true)
+
+      updated = described_class.new
+      updated.update_from_scope(scope)
+      updated.add_feature_flag("b", true)
+      expect(scope.flags.values).to eq("a" => true)
+
+      scope.clear
+      expect(scope.flags.values).to be_empty
+    end
+
+    context "with an active span" do
+      let(:span) { Sentry::Span.new(transaction: nil) }
+      before { scope.set_span(span) }
+
+      it "records flag.evaluation.* span data, capped per span" do
+        scope.add_feature_flag("a", true)
+        expect(span.to_h[:data]["flag.evaluation.a"]).to eq(true)
+
+        12.times { |i| scope.add_feature_flag("g#{i}", true) }
+        keys = span.to_h[:data].keys.select { |k| k.start_with?("flag.evaluation.") }
+        expect(keys.size).to eq(Sentry::Span::MAX_FLAGS)
+
+        scope.add_feature_flag("a", false)
+        expect(span.to_h[:data]["flag.evaluation.a"]).to eq(true)
+      end
+    end
+  end
+
+  describe "Sentry.add_feature_flag" do
+    it "adds to the current scope" do
+      Sentry.add_feature_flag("x", true)
+      expect(Sentry.get_current_scope.flags.values).to eq("x" => true)
+    end
+  end
+end
diff --git a/sentry-ruby/spec/sentry/utils/ring_buffer_spec.rb b/sentry-ruby/spec/sentry/utils/ring_buffer_spec.rb
new file mode 100644
index 000000000..0bb9f947d
--- /dev/null
+++ b/sentry-ruby/spec/sentry/utils/ring_buffer_spec.rb
@@ -0,0 +1,27 @@
+# frozen_string_literal: true
+
+require "spec_helper"
+
+RSpec.describe Sentry::Utils::RingBuffer do
+  subject(:buffer) { described_class.new(2) }
+
+  it "keeps the most recent unique values" do
+    buffer.set("a", 1)
+    buffer.set("b", 2)
+    buffer.set("a", 3)
+    buffer.set("c", 4)
+
+    expect(buffer.values).to eq("a" => 3, "c" => 4)
+  end
+
+  it "copies and clears independently" do
+    buffer.set("a", 1)
+    copy = buffer.dup
+
+    copy.set("b", 2)
+    copy.clear
+
+    expect(buffer.values).to eq("a" => 1)
+    expect(copy).to be_empty
+  end
+end