diff --git a/Steepfile b/Steepfile
index 220e05b340b..6cf15ef45b0 100644
--- a/Steepfile
+++ b/Steepfile
@@ -19,10 +19,6 @@ target :datadog do
     # * `:information`, `:hint`: To see these, run `rake 'typecheck[--severity-level=information]'`
     #   or `rake 'typecheck[--severity-level=hint]'`
 
-    # These first checks are likely the easiest to fix, given they capture a mismatch
-    # between the already declared type in `.rbs` and the actual type inferred by Steep.
-    hash[Ruby::IncompatibleAssignment] = :information
-
     # These checks are a bit harder, because they represent the lack of sufficient type information.
     hash[Ruby::FallbackAny] = :information
     hash[Ruby::UnknownInstanceVariable] = :information
diff --git a/lib/datadog/appsec/context.rb b/lib/datadog/appsec/context.rb
index 0ff781fd4f6..48415b462c2 100644
--- a/lib/datadog/appsec/context.rb
+++ b/lib/datadog/appsec/context.rb
@@ -7,7 +7,8 @@ module AppSec
     # This class accumulates the context over the request life-cycle and exposes
     # interface sufficient for instrumentation to perform threat detection.
     class Context
-      ActiveContextError = Class.new(StandardError)
+      # Steep: https://github.com/soutaro/steep/issues/1880
+      ActiveContextError = Class.new(StandardError) # steep:ignore IncompatibleAssignment
 
       # TODO: add delegators for active trace span
       attr_reader :trace, :span, :events
diff --git a/lib/datadog/appsec/security_engine/result.rb b/lib/datadog/appsec/security_engine/result.rb
index e1a364a1dff..98913856c9f 100644
--- a/lib/datadog/appsec/security_engine/result.rb
+++ b/lib/datadog/appsec/security_engine/result.rb
@@ -70,7 +70,8 @@ class Error
 
           def initialize(duration_ext_ns:, input_truncated:)
             @events = []
-            @actions = @attributes = {}
+            @actions = {}
+            @attributes = {}
             @duration_ns = 0
             @duration_ext_ns = duration_ext_ns
             @input_truncated = !!input_truncated
diff --git a/lib/datadog/core/configuration/option_definition.rb b/lib/datadog/core/configuration/option_definition.rb
index 56c9575299b..e7be0c18ec9 100644
--- a/lib/datadog/core/configuration/option_definition.rb
+++ b/lib/datadog/core/configuration/option_definition.rb
@@ -42,7 +42,8 @@ def build(context)
         # Acts as DSL for building OptionDefinitions
         # @public_api
         class Builder
-          InvalidOptionError = Class.new(StandardError)
+          # Steep: https://github.com/soutaro/steep/issues/1880
+          InvalidOptionError = Class.new(StandardError) # steep:ignore IncompatibleAssignment
 
           attr_reader \
             :helpers
@@ -119,7 +120,8 @@ def apply_options!(options = {})
             env_parser(&options[:env_parser]) if options.key?(:env_parser)
             after_set(&options[:after_set]) if options.key?(:after_set)
             resetter(&options[:resetter]) if options.key?(:resetter)
-            setter(&options[:setter]) if options.key?(:setter)
+            # Steep: https://github.com/soutaro/steep/issues/477
+            setter(&options[:setter]) if options.key?(:setter) # steep:ignore BlockTypeMismatch
             type(options[:type], **(options[:type_options] || {})) if options.key?(:type)
           end
 
diff --git a/lib/datadog/core/configuration/options.rb b/lib/datadog/core/configuration/options.rb
index bafcef9aab2..87ef253cf6f 100644
--- a/lib/datadog/core/configuration/options.rb
+++ b/lib/datadog/core/configuration/options.rb
@@ -40,14 +40,16 @@ def option(name, meta = {}, &block)
 
           def default_helpers(name)
             option_name = name.to_sym
-            # @type var opt_getter: Configuration::OptionDefinition::helper_proc
-            opt_getter = proc do
+            # Steep: https://github.com/soutaro/steep/issues/335
+            # @type var opt_getter: Configuration::OptionDefinition::generic_proc
+            opt_getter = proc do # steep:ignore IncompatibleAssignment
               # These Procs uses `get/set_option`, but we only add them to the OptionDefinition helpers here.
               # Steep is right that these methods are not defined, but we only run these Procs in instance context.
               get_option(option_name) # steep:ignore NoMethod
             end
-            # @type var opt_setter: Configuration::OptionDefinition::helper_proc
-            opt_setter = proc do |value|
+            # Steep: https://github.com/soutaro/steep/issues/335
+            # @type var opt_setter: Configuration::OptionDefinition::generic_proc
+            opt_setter = proc do |value| # steep:ignore IncompatibleAssignment
               set_option(option_name, value) # steep:ignore NoMethod
             end
             {
@@ -127,7 +129,8 @@ def assert_valid_option!(name)
           end
         end
 
-        InvalidOptionError = Class.new(StandardError)
+        # Steep: https://github.com/soutaro/steep/issues/1880
+        InvalidOptionError = Class.new(StandardError) # steep:ignore IncompatibleAssignment
       end
     end
   end
diff --git a/lib/datadog/core/rate_limiter.rb b/lib/datadog/core/rate_limiter.rb
index 9c7e6da0bc2..2635f36c3e4 100644
--- a/lib/datadog/core/rate_limiter.rb
+++ b/lib/datadog/core/rate_limiter.rb
@@ -81,6 +81,10 @@ def effective_rate
 
         return current_window_rate if @prev_conforming_messages.nil? || @prev_total_messages.nil?
 
+        # Steep: Due to https://github.com/soutaro/steep/issues/477,
+        # the previous nil check does not narrow type to Integer
+        # The annotation fixes the typing error, but it takes effect in the method
+        # @type ivar @prev_total_messages: Integer
         (@conforming_messages.to_f + @prev_conforming_messages.to_f) / (@total_messages + @prev_total_messages)
       end
 
@@ -154,7 +158,11 @@ def update_rate_counts(allowed)
         if @current_window.nil?
           @current_window = now
         # If more than 1 second has past since last window, reset
-        elsif now - @current_window >= 1
+        #
+        # Steep: @current_window is a Float, but for some reason annotations does not work here
+        # Once a fix will be out for nil checks on instance variables, we can remove the steep:ignore
+        # https://github.com/soutaro/steep/issues/477
+        elsif now - @current_window >= 1 # steep:ignore UnresolvedOverloading
           @prev_conforming_messages = @conforming_messages
           @prev_total_messages = @total_messages
           @conforming_messages = 0
diff --git a/lib/datadog/core/utils/time.rb b/lib/datadog/core/utils/time.rb
index 63dc1b20419..c50d94bdf12 100644
--- a/lib/datadog/core/utils/time.rb
+++ b/lib/datadog/core/utils/time.rb
@@ -10,7 +10,7 @@ module Time
         # Current monotonic time
         #
         # @param unit [Symbol] unit for the resulting value, same as ::Process#clock_gettime, defaults to :float_second
-        # @return [Numeric] timestamp in the requested unit, since some unspecified starting point
+        # @return [Float|Integer] timestamp in the requested unit, since some unspecified starting point
         def get_time(unit = :float_second)
           Process.clock_gettime(Process::CLOCK_MONOTONIC, unit)
         end
diff --git a/lib/datadog/di/el/compiler.rb b/lib/datadog/di/el/compiler.rb
index e93d865cf60..9e0554483c4 100644
--- a/lib/datadog/di/el/compiler.rb
+++ b/lib/datadog/di/el/compiler.rb
@@ -22,7 +22,8 @@ def compile(ast)
 
         private
 
-        OPERATORS = {
+        # Steep: https://github.com/soutaro/steep/issues/363
+        OPERATORS = { # steep:ignore IncompatibleAssignment
           'eq' => '==',
           'ne' => '!=',
           'ge' => '>=',
@@ -31,16 +32,19 @@ def compile(ast)
           'lt' => '<',
         }.freeze
 
+        # Steep: https://github.com/soutaro/steep/issues/363
         SINGLE_ARG_METHODS = %w[
           len isEmpty isUndefined
-        ].freeze
+        ].freeze # steep:ignore IncompatibleAssignment
 
+        # Steep: https://github.com/soutaro/steep/issues/363
         TWO_ARG_METHODS = %w[
           startsWith endsWith contains matches
           getmember index instanceof
-        ].freeze
+        ].freeze # steep:ignore IncompatibleAssignment
 
-        MULTI_ARG_METHODS = {
+        # Steep: https://github.com/soutaro/steep/issues/363
+        MULTI_ARG_METHODS = { # steep:ignore IncompatibleAssignment
           'and' => '&&',
           'or' => '||',
         }.freeze
diff --git a/lib/datadog/di/probe_builder.rb b/lib/datadog/di/probe_builder.rb
index 98ee87056d8..6a4bea327dc 100644
--- a/lib/datadog/di/probe_builder.rb
+++ b/lib/datadog/di/probe_builder.rb
@@ -20,7 +20,8 @@ module DI
     #
     # @api private
     module ProbeBuilder
-      PROBE_TYPES = {
+      # Steep: https://github.com/soutaro/steep/issues/363
+      PROBE_TYPES = { # steep:ignore IncompatibleAssignment
         'LOG_PROBE' => :log,
       }.freeze
 
diff --git a/lib/datadog/di/probe_notification_builder.rb b/lib/datadog/di/probe_notification_builder.rb
index bd4bc623dd7..2f70fb24b92 100644
--- a/lib/datadog/di/probe_notification_builder.rb
+++ b/lib/datadog/di/probe_notification_builder.rb
@@ -46,7 +46,7 @@ def build_executed(context)
         build_snapshot(context)
       end
 
-      NANOSECONDS = 10**9
+      NANOSECONDS = 1_000_000_000
       MILLISECONDS = 1000
 
       def build_snapshot(context)
diff --git a/lib/datadog/profiling/collectors/code_provenance.rb b/lib/datadog/profiling/collectors/code_provenance.rb
index b9236620c44..4806cf30c2a 100644
--- a/lib/datadog/profiling/collectors/code_provenance.rb
+++ b/lib/datadog/profiling/collectors/code_provenance.rb
@@ -137,7 +137,8 @@ def initialize(kind:, name:, version:, path:, extra_paths:)
           end
 
           def to_json(arg = nil)
-            {kind: @kind, name: @name, version: @version, paths: @paths}.to_json(arg)
+            # Steep: https://github.com/ruby/rbs/pull/2691
+            {kind: @kind, name: @name, version: @version, paths: @paths}.to_json(arg) # steep:ignore ArgumentTypeMismatch
           end
 
           def path
diff --git a/lib/datadog/profiling/collectors/info.rb b/lib/datadog/profiling/collectors/info.rb
index e3ce7933b48..7719e0e78a4 100644
--- a/lib/datadog/profiling/collectors/info.rb
+++ b/lib/datadog/profiling/collectors/info.rb
@@ -16,7 +16,8 @@ module Collectors
       class Info
         def initialize(settings)
           @profiler_info = nil
-          @info = {
+          # Steep: https://github.com/soutaro/steep/issues/363
+          @info = { # steep:ignore IncompatibleAssignment
             platform: collect_platform_info,
             runtime: collect_runtime_info,
             application: collect_application_info(settings),
diff --git a/lib/datadog/profiling/http_transport.rb b/lib/datadog/profiling/http_transport.rb
index fe6d48c973a..d154c78a3f0 100644
--- a/lib/datadog/profiling/http_transport.rb
+++ b/lib/datadog/profiling/http_transport.rb
@@ -13,7 +13,10 @@ class HttpTransport
       def initialize(agent_settings:, site:, api_key:, upload_timeout_seconds:)
         @upload_timeout_milliseconds = (upload_timeout_seconds * 1_000).to_i
 
-        @exporter_configuration =
+        # Steep: multiple issues here
+        # first https://github.com/soutaro/steep/issues/363
+        # then https://github.com/soutaro/steep/issues/1603 (remove the .freeze to see it)
+        @exporter_configuration = # steep:ignore IncompatibleAssignment
           if agentless?(site, api_key)
             [:agentless, site, api_key].freeze
           else
diff --git a/lib/datadog/tracing/contrib/status_range_matcher.rb b/lib/datadog/tracing/contrib/status_range_matcher.rb
index d3cee9d4be2..75c26f60f6e 100644
--- a/lib/datadog/tracing/contrib/status_range_matcher.rb
+++ b/lib/datadog/tracing/contrib/status_range_matcher.rb
@@ -8,7 +8,8 @@ class StatusRangeMatcher
         attr_reader :ranges
 
         def initialize(ranges)
-          @ranges = Array(ranges)
+          # Steep: https://github.com/ruby/rbs/issues/1874
+          @ranges = Array(ranges) # steep:ignore IncompatibleAssignment
         end
 
         def +(other)
diff --git a/lib/datadog/tracing/contrib/utils/quantization/hash.rb b/lib/datadog/tracing/contrib/utils/quantization/hash.rb
index 521a1f18a2c..75b61fb8841 100644
--- a/lib/datadog/tracing/contrib/utils/quantization/hash.rb
+++ b/lib/datadog/tracing/contrib/utils/quantization/hash.rb
@@ -10,7 +10,9 @@ module Hash
             PLACEHOLDER = '?'
             EXCLUDE_KEYS = [].freeze
             SHOW_KEYS = [].freeze
-            DEFAULT_OPTIONS = {
+
+            # Steep: https://github.com/soutaro/steep/issues/363
+            DEFAULT_OPTIONS = { # steep:ignore IncompatibleAssignment
               exclude: EXCLUDE_KEYS,
               show: SHOW_KEYS,
               placeholder: PLACEHOLDER
diff --git a/lib/datadog/tracing/span_event.rb b/lib/datadog/tracing/span_event.rb
index b67e89a9905..9bf2974e68f 100644
--- a/lib/datadog/tracing/span_event.rb
+++ b/lib/datadog/tracing/span_event.rb
@@ -69,8 +69,8 @@ def to_native_format
 
       private
 
-      MIN_INT64_SIGNED = -2**63
-      MAX_INT64_SIGNED = 2 << 63 - 1
+      MIN_INT64_SIGNED = -2 << 62
+      MAX_INT64_SIGNED = (2 << 62) - 1
 
       # Checks the attributes hash to ensure it only contains serializable values.
       # Invalid values are removed from the hash.
diff --git a/lib/datadog/tracing/span_operation.rb b/lib/datadog/tracing/span_operation.rb
index 4dfae00ad6c..a9ada38896a 100644
--- a/lib/datadog/tracing/span_operation.rb
+++ b/lib/datadog/tracing/span_operation.rb
@@ -289,7 +289,8 @@ def finished?
       def duration
         return @duration_end - @duration_start if @duration_start && @duration_end
 
-        @end_time - @start_time if @start_time && @end_time
+        # Steep: https://github.com/soutaro/steep/issues/477
+        @end_time - @start_time if @start_time && @end_time # steep:ignore NoMethod
       end
 
       def set_error(e)
@@ -387,7 +388,8 @@ def pretty_print(q)
       class Events
         include Tracing::Events
 
-        DEFAULT_ON_ERROR = proc { |span_op, error| span_op&.set_error(error) }
+        # Steep: https://github.com/soutaro/steep/issues/335
+        DEFAULT_ON_ERROR = proc { |span_op, error| span_op&.set_error(error) } # steep:ignore IncompatibleAssignment
 
         attr_reader \
           :logger,
@@ -395,7 +397,7 @@ class Events
           :after_stop,
           :before_start
 
-        def initialize(logger: Datadog.logger, on_error: nil)
+        def initialize(logger: Datadog.logger)
           @logger = logger
           @after_finish = AfterFinish.new
           @after_stop = AfterStop.new
@@ -548,7 +550,10 @@ def duration_marker
       # Used for serialization
       # @return [Integer] in nanoseconds since Epoch
       def start_time_nano
-        @start_time.to_i * 1000000000 + @start_time.nsec
+        return 0 if @start_time.nil?
+
+        # Steep: https://github.com/soutaro/steep/issues/477
+        @start_time.to_i * 1000000000 + @start_time.nsec # steep:ignore NoMethod
       end
 
       # Used for serialization
diff --git a/sig/datadog/appsec/context.rbs b/sig/datadog/appsec/context.rbs
index 1aeb3370a9f..0da146469b8 100644
--- a/sig/datadog/appsec/context.rbs
+++ b/sig/datadog/appsec/context.rbs
@@ -15,7 +15,7 @@ module Datadog
 
       @interrupted: bool
 
-      ActiveContextError: ::StandardError
+      ActiveContextError: StandardError
 
       attr_reader trace: Tracing::TraceOperation
 
diff --git a/sig/datadog/appsec/metrics/collector.rbs b/sig/datadog/appsec/metrics/collector.rbs
index af7acb34745..9b3606d6ce4 100644
--- a/sig/datadog/appsec/metrics/collector.rbs
+++ b/sig/datadog/appsec/metrics/collector.rbs
@@ -17,7 +17,7 @@ module Datadog
 
           attr_accessor inputs_truncated: ::Integer
 
-          def self.new: (evals: ::Integer, matches: ::Integer, errors: ::Integer, timeouts: ::Integer, duration_ns: ::Integer, duration_ext_ns: ::Integer, inputs_truncated: ::Integer) -> void
+          def self.new: (evals: ::Integer, matches: ::Integer, errors: ::Integer, timeouts: ::Integer, duration_ns: ::Integer, duration_ext_ns: ::Integer, inputs_truncated: ::Integer) -> Store
         end
 
         @mutex: Mutex
diff --git a/sig/datadog/appsec/security_engine/engine.rbs b/sig/datadog/appsec/security_engine/engine.rbs
index 9958b76edfd..35b081515e3 100644
--- a/sig/datadog/appsec/security_engine/engine.rbs
+++ b/sig/datadog/appsec/security_engine/engine.rbs
@@ -8,7 +8,7 @@ module Datadog
 
         @ruleset_version: ::String
 
-        @reconfigured_ruleset_version: ::String?
+        @reconfigured_ruleset_version: ::String
 
         DEFAULT_RULES_CONFIG_PATH: ::String
         TELEMETRY_ACTIONS: ::Array[::String]
diff --git a/sig/datadog/core/configuration/option_definition.rbs b/sig/datadog/core/configuration/option_definition.rbs
index 85c58617683..ddf1b268f42 100644
--- a/sig/datadog/core/configuration/option_definition.rbs
+++ b/sig/datadog/core/configuration/option_definition.rbs
@@ -4,19 +4,31 @@ module Datadog
       class OptionDefinition
         type option_type = String | Integer | Float | Rational | Symbol | bool | Array[untyped] | Hash[untyped, untyped] | nil
 
-        type option_proc = (^(Options::GenericSettingsClass _settings) [self: Options::GenericSettingsClass] -> option_type)
+        type option_proc = (^(Options::GenericSettingsClass settings) [self: Options::GenericSettingsClass] -> option_type)
 
-        type helper_proc = (^(?) [self: Options::GenericSettingsClass] -> untyped)
+        type generic_proc = (^(?) [self: Options::GenericSettingsClass] -> untyped)
 
         type meta = {
-          default: (option_type | option_proc | Options::GenericSettingsClass)?,
-          default_proc: option_proc?,
-          env: String?,
-          env_parser: (^(String env_value) [self: Options::GenericSettingsClass] -> Option::env_value)?,
-          after_set: (^(option_type value, option_type old_value, Option::Precedence::Value precedence) [self: Options::GenericSettingsClass] -> void)?,
-          resetter: (^(option_type value) [self: Options::GenericSettingsClass] -> option_type)?,
-          setter: (^(option_type new_value, option_type old_value) [self: Options::GenericSettingsClass] -> option_type),
-          type: Symbol?,
+          ?default: (option_type | option_proc | Options::GenericSettingsClass)?,
+          ?default_proc: generic_proc?,
+          ?env: String?,
+          ?env_parser: (^(String env_value) [self: Options::GenericSettingsClass] -> Option::env_value)?,
+          ?after_set: (^(option_type value, option_type old_value, Option::Precedence::Value precedence) [self: Options::GenericSettingsClass] -> void)?,
+          ?resetter: (^(option_type value) [self: Options::GenericSettingsClass] -> option_type)?,
+          ?setter: (^(option_type new_value, option_type old_value) [self: Options::GenericSettingsClass] -> option_type)?,
+          ?type: Symbol?,
+          ?type_options: Hash[Symbol, untyped]
+        }
+
+        type meta_with_type_options = {
+          ?default: (option_type | option_proc | Options::GenericSettingsClass)?,
+          ?default_proc: generic_proc?,
+          ?env: String?,
+          ?env_parser: (^(String env_value) [self: Options::GenericSettingsClass] -> Option::env_value)?,
+          ?after_set: (^(option_type value, option_type old_value, Option::Precedence::Value precedence) [self: Options::GenericSettingsClass] -> void)?,
+          ?resetter: (^(option_type value) [self: Options::GenericSettingsClass] -> option_type)?,
+          ?setter: (^(option_type new_value, option_type old_value) [self: Options::GenericSettingsClass] -> option_type)?,
+          ?type: Symbol?,
           type_options: Hash[Symbol, untyped]
         }
 
@@ -24,7 +36,7 @@ module Datadog
 
         attr_reader default: option_type | option_proc | Options::GenericSettingsClass
 
-        attr_reader default_proc: option_proc?
+        attr_reader default_proc: generic_proc?
 
         attr_reader env: String?
 
@@ -42,7 +54,7 @@ module Datadog
 
         attr_reader type_options: Hash[Symbol, untyped]
 
-        def initialize: (String | Symbol name, meta meta) ?{ (option_type new_value, option_type old_value) [self: Options::GenericSettingsClass] -> option_type } -> void
+        def initialize: (String | Symbol name, meta_with_type_options meta) ?{ (option_type new_value, option_type old_value) [self: Options::GenericSettingsClass] -> option_type } -> void
 
         def build: (Options::GenericSettingsClass context) -> Option
 
@@ -50,13 +62,13 @@ module Datadog
           class InvalidOptionError < StandardError
           end
 
-          attr_reader helpers: Hash[Symbol, helper_proc]
+          attr_reader helpers: Hash[Symbol, generic_proc]
 
           @env: String?
           @env_parser: (^(String env_value) [self: Options::GenericSettingsClass] -> Option::env_value)?
           @default: option_type | option_proc | Options::GenericSettingsClass
-          @default_proc: option_proc?
-          @helpers: Hash[Symbol, helper_proc]
+          @default_proc: generic_proc?
+          @helpers: Hash[Symbol, generic_proc]
           @name: Symbol
           @after_set: (^(option_type value, option_type old_value, Option::Precedence::Value precedence) [self: Options::GenericSettingsClass] -> void)?
           @resetter: (^(option_type value) [self: Options::GenericSettingsClass] -> option_type)?
@@ -71,9 +83,9 @@ module Datadog
           def env_parser: () ?{ (String env_value) [self: Options::GenericSettingsClass] -> Option::env_value } -> void
 
           # can also be a class that includes Configuration::Base for new settings
-          def default: (?(option_type | option_proc | Options::GenericSettingsClass) value) ?{ () -> (option_type | option_proc | Options::GenericSettingsClass) } -> void
+          def default: (?(option_type | option_proc | Options::GenericSettingsClass) value) ?{ (Options::GenericSettingsClass settings) [self: Options::GenericSettingsClass] -> option_type } -> void
 
-          def default_proc: () ?{ (Options::GenericSettingsClass _settings) [self: Options::GenericSettingsClass] -> option_type } -> void
+          def default_proc: () ?{ (?) [self: Options::GenericSettingsClass] -> untyped } -> void
 
           def type: (Symbol? value, ?nilable: bool) -> void
 
diff --git a/sig/datadog/core/configuration/options.rbs b/sig/datadog/core/configuration/options.rbs
index b9f97931c7c..3f06a9b4822 100644
--- a/sig/datadog/core/configuration/options.rbs
+++ b/sig/datadog/core/configuration/options.rbs
@@ -41,9 +41,9 @@ module Datadog
 
           private
 
-          def default_helpers: (Symbol | String name) -> Hash[Symbol, OptionDefinition::helper_proc]
+          def default_helpers: (Symbol | String name) -> Hash[Symbol, OptionDefinition::generic_proc]
 
-          def define_helpers: (Hash[Symbol, OptionDefinition::helper_proc] helpers) -> void
+          def define_helpers: (Hash[Symbol, OptionDefinition::generic_proc] helpers) -> void
 
           # Fake methods to make it work with RBS. RBS cannot understand that this module is only used in a class context.
           def superclass: () -> singleton(Options)
diff --git a/sig/datadog/core/rate_limiter.rbs b/sig/datadog/core/rate_limiter.rbs
index 62c3d18dbb6..247de4d4f39 100644
--- a/sig/datadog/core/rate_limiter.rbs
+++ b/sig/datadog/core/rate_limiter.rbs
@@ -7,10 +7,7 @@ module Datadog
     end
 
     class TokenBucket < RateLimiter
-      # This should be `::Numeric`, but it's used with `*` method on another
-      # `Numeric` which makes steep fail with an error `Ruby::UnresolvedOverloading`
-      # "Cannot find compatible overloading of method"
-      @rate: ::Float
+      @rate: ::Float | ::Integer
 
       @max_tokens: ::Numeric
 
@@ -20,26 +17,19 @@ module Datadog
 
       @conforming_messages: ::Integer
 
-      # This should be `::Integer?` but steep can't see conditional branching
-      # which safe-guards us from errors like "undefined method for NilClass"
-      @prev_conforming_messages: ::Integer
+      @prev_conforming_messages: ::Integer?
 
-      # This should be `::Integer?` but steep can't see conditional branching
-      # which safe-guards us from errors like "undefined method for NilClass"
-      @prev_total_messages: ::Integer
+      @prev_total_messages: ::Integer?
 
-      # This should be `::Integer?`, but steep can't see conditional branching
-      # which safe-guards us from errors like "undefined method for NilClass"
-      @current_window: ::Numeric
+      @current_window: ::Float?
 
       @last_refill: ::Numeric
 
-      # This should be `::Numeric`, but has to follow `@rate` type definition
-      attr_reader rate: ::Float
+      attr_reader rate: ::Float | ::Integer
 
       attr_reader max_tokens: ::Numeric
 
-      def initialize: (::Numeric rate, ?::Numeric max_tokens) -> void
+      def initialize: (::Float | ::Integer rate, ?::Numeric max_tokens) -> void
 
       def allow?: (?::Integer size) -> bool
 
diff --git a/sig/datadog/core/telemetry/worker.rbs b/sig/datadog/core/telemetry/worker.rbs
index 4db805e7221..8a19e09899a 100644
--- a/sig/datadog/core/telemetry/worker.rbs
+++ b/sig/datadog/core/telemetry/worker.rbs
@@ -14,13 +14,13 @@ module Datadog
         @emitter: Emitter
         @metrics_manager: MetricsManager
         @sent_started_event: bool
-        @shutdown_timeout: Integer
+        @shutdown_timeout: Float | Integer
         @buffer_size: Integer
         @dependency_collection: bool
         @ticks_per_heartbeat: Integer
         @current_ticks: Integer
         @logger: ::Logger
-        
+
         attr_reader logger: ::Logger
         attr_reader initial_event: Telemetry::Event::Base
 	attr_reader initial_event_once: Datadog::Core::Utils::OnlyOnceSuccessful
@@ -38,7 +38,7 @@ module Datadog
         def enqueue: (Event::Base event) -> void
 
         def dequeue: () -> Array[Event::Base]
-	
+
 	def flush: () -> (true | false)
 
         private
diff --git a/sig/datadog/core/workers/polling.rbs b/sig/datadog/core/workers/polling.rbs
index 43c1360a92c..6b978e54cd0 100644
--- a/sig/datadog/core/workers/polling.rbs
+++ b/sig/datadog/core/workers/polling.rbs
@@ -10,7 +10,7 @@ module Datadog
           def perform: (*untyped args) -> untyped
         end
 
-        def stop: (?bool force_stop, ?::Integer timeout) -> untyped
+        def stop: (?bool force_stop, ?::Integer | ::Float timeout) -> untyped
 
         def enabled?: () -> bool
 
diff --git a/sig/datadog/di/instrumenter.rbs b/sig/datadog/di/instrumenter.rbs
index ad750db14b5..c6744e69001 100644
--- a/sig/datadog/di/instrumenter.rbs
+++ b/sig/datadog/di/instrumenter.rbs
@@ -3,34 +3,34 @@ module Datadog
     class Instrumenter
       class Location
         def initialize: (String path, Integer lineno, String? label) -> void
-        
+
         def path: () -> String
         def lineno: () -> Integer
         def label: () -> String?
       end
-      
+
       @settings: untyped
 
       @serializer: Serializer
 
-      @code_tracker: CodeTracker
-      
+      @code_tracker: CodeTracker?
+
       @logger: DI::Logger
-      
+
       @telemetry: Core::Telemetry::Component?
 
       @lock: Mutex
 
-      def initialize: (untyped settings, Serializer serializer, DI::Logger logger, ?code_tracker: CodeTracker?, ?telemetry: Core::Telemetry::Component) -> void
+      def initialize: (untyped settings, Serializer serializer, DI::Logger logger, ?code_tracker: CodeTracker?, ?telemetry: Core::Telemetry::Component?) -> void
 
       attr_reader settings: untyped
 
       attr_reader serializer: Serializer
 
-      attr_reader code_tracker: CodeTracker
-      
+      attr_reader code_tracker: CodeTracker?
+
       attr_reader logger: DI::Logger
-      
+
       attr_reader telemetry: Core::Telemetry::Component?
 
       def hook_method: (Probe probe, untyped responder) -> void
@@ -43,7 +43,7 @@ module Datadog
       def hook: (Probe probe, untyped responder) -> void
 
       def unhook: (Probe probe) -> void
-      
+
       def self.get_local_variables: (TracePoint trace_point) -> Hash[untyped, untyped]
       def self.get_instance_variables: (Object self) -> Hash[untyped, untyped]
 
diff --git a/sig/datadog/di/probe.rbs b/sig/datadog/di/probe.rbs
index 39a9f5e3f25..91137eeb789 100644
--- a/sig/datadog/di/probe.rbs
+++ b/sig/datadog/di/probe.rbs
@@ -15,8 +15,8 @@ module Datadog
 
       @method_name: String?
 
-      @template: String
-      @template_segments: Array[untyped]
+      @template: String?
+      @template_segments: Array[untyped]?
 
       @capture_snapshot: bool
 
@@ -26,7 +26,7 @@ module Datadog
 
       def initialize: (id: String, type: Symbol, ?file: String?, ?line_no: Integer?, ?type_name: String?, ?method_name: String?, ?template: String?, ?template_segments: Array[untyped]?, ?capture_snapshot: bool,
 	?condition: DI::EL::Expression?,
-	?max_capture_depth: Integer, ?max_capture_attribute_count: Integer?, ?rate_limit: Integer) -> void
+	?max_capture_depth: Integer?, ?max_capture_attribute_count: Integer?, ?rate_limit: Integer?) -> void
 
       attr_reader condition: DI::EL::Expression?
 
@@ -46,8 +46,8 @@ module Datadog
 
       attr_reader max_capture_attribute_count: Integer?
 
-      attr_reader template: String
-      attr_reader template_segments: Array[untyped]
+      attr_reader template: String?
+      attr_reader template_segments: Array[untyped]?
       attr_reader rate_limiter: Datadog::Core::RateLimiter
 
       def capture_snapshot?: () -> bool
diff --git a/sig/datadog/di/probe_notification_builder.rbs b/sig/datadog/di/probe_notification_builder.rbs
index 30ec3871bcd..32cc99a5a8c 100644
--- a/sig/datadog/di/probe_notification_builder.rbs
+++ b/sig/datadog/di/probe_notification_builder.rbs
@@ -3,7 +3,7 @@ module Datadog
     class ProbeNotificationBuilder
       NANOSECONDS: Integer
       MILLISECONDS: Integer
-      
+
       @serializer: Serializer
 
       def initialize: (untyped settings, Serializer serializer) -> void
@@ -35,12 +35,12 @@ module Datadog
       def timestamp_now: () -> Integer
 
       def get_local_variables: (TracePoint trace_point) -> Hash[Symbol,untyped]
-      
+
       def active_trace: () -> Datadog::Tracing::TraceSegment?
       def active_span: () -> Datadog::Tracing::SpanOperation?
 
       def tags: () -> untyped
-      
+
       def serialized_tags: () -> untyped
     end
   end
diff --git a/sig/datadog/di/serializer.rbs b/sig/datadog/di/serializer.rbs
index 1ff7f85effc..f08329a19e8 100644
--- a/sig/datadog/di/serializer.rbs
+++ b/sig/datadog/di/serializer.rbs
@@ -8,15 +8,15 @@ module Datadog
 
       @redactor: untyped
 
-      @telemetry: Core::Telemetry::Component
+      @telemetry: Core::Telemetry::Component?
 
-      def initialize: (untyped settings, untyped redactor, ?telemetry: Core::Telemetry::Component) -> void
+      def initialize: (untyped settings, untyped redactor, ?telemetry: Core::Telemetry::Component?) -> void
 
       attr_reader settings: Datadog::Core::Configuration::Settings
 
       attr_reader redactor: Datadog::DI::Redactor
 
-      attr_reader telemetry: Core::Telemetry::Component
+      attr_reader telemetry: Core::Telemetry::Component?
 
       def combine_args: (untyped args, untyped kwargs, untyped target_self) -> untyped
       def serialize_args: (untyped args, untyped kwargs, untyped instance_vars, ?depth: Integer, ?attribute_count: Integer?) -> untyped
@@ -24,7 +24,7 @@ module Datadog
       def serialize_value: (untyped value, ?name: String?, ?depth: Integer, ?attribute_count: Integer?, ?type: Class?) -> untyped
       def serialize_value_for_message: (untyped value, ?::Integer depth) -> untyped
 
-      def self.register: (?condition: Proc) {
+      def self.register: (?condition: Proc?) {
         (serializer: Serializer, value: untyped, name: Symbol, depth: Integer, ?attribute_count: Integer?) -> untyped } -> void
 
       private
diff --git a/sig/datadog/error_tracking/ext.rbs b/sig/datadog/error_tracking/ext.rbs
index 9d356f06ace..05745b5c3a9 100644
--- a/sig/datadog/error_tracking/ext.rbs
+++ b/sig/datadog/error_tracking/ext.rbs
@@ -11,7 +11,7 @@ module Datadog
 
       HANDLED_ERRORS_THIRD_PARTY: "third_party"
 
-      DEFAULT_HANDLED_ERRORS: ""
+      DEFAULT_HANDLED_ERRORS: nil
 
       VALID_HANDLED_ERRORS: ::Array[untyped]
 
diff --git a/sig/datadog/profiling/collectors/code_provenance.rbs b/sig/datadog/profiling/collectors/code_provenance.rbs
index 1bc6ce0ac05..3e52e1e10ea 100644
--- a/sig/datadog/profiling/collectors/code_provenance.rbs
+++ b/sig/datadog/profiling/collectors/code_provenance.rbs
@@ -3,7 +3,7 @@ module Datadog
     module Collectors
       class CodeProvenance
         def initialize: (?standard_library_path: String, ?ruby_native_filename: String?) -> void
-        def refresh: (?loaded_files: Array[String], ?loaded_specs: Array[Gem::Specification]) -> self
+        def refresh: (?loaded_files: Array[String], ?loaded_specs: Array[Gem::BasicSpecification]) -> self
         def generate_json: () -> ::String
 
         private
@@ -16,7 +16,7 @@ module Datadog
 
         def record_library: (Library) -> void
         def sort_libraries_by_longest_path_first: () -> void
-        def record_loaded_specs: (Array[Gem::Specification]) -> void
+        def record_loaded_specs: (Array[Gem::BasicSpecification]) -> void
         def record_loaded_files: (Array[String]) -> void
 
         class Library
@@ -32,7 +32,7 @@ module Datadog
           def version: -> String
           def path: -> String
 
-          def to_json: (?JSON::State state) -> String
+          def to_json: (?JSON::State? state) -> String
         end
       end
     end
diff --git a/sig/datadog/profiling/http_transport.rbs b/sig/datadog/profiling/http_transport.rbs
index 3e35adbc7ba..350faa55b38 100644
--- a/sig/datadog/profiling/http_transport.rbs
+++ b/sig/datadog/profiling/http_transport.rbs
@@ -1,7 +1,7 @@
 module Datadog
   module Profiling
     class HttpTransport
-      type exporter_configuration_array = [:agentless | :agent, untyped]
+      type exporter_configuration_array = [:agentless, String?, String?] | [:agent, String]
 
       attr_reader exporter_configuration: exporter_configuration_array
 
diff --git a/sig/datadog/tracing/contrib/graphql/unified_trace.rbs b/sig/datadog/tracing/contrib/graphql/unified_trace.rbs
index e23a949034b..9e94f54b1f2 100644
--- a/sig/datadog/tracing/contrib/graphql/unified_trace.rbs
+++ b/sig/datadog/tracing/contrib/graphql/unified_trace.rbs
@@ -91,7 +91,7 @@ module Datadog
 
           private
 
-          def trace: (Proc callable, String trace_key, (String | nil) resource, ?^(SpanOperation) -> void before, ?^(SpanOperation) -> void after, **untyped kwargs) ?{ (SpanOperation) -> void } -> untyped
+          def trace: (Proc callable, String trace_key, (String | nil) resource, ?(^(SpanOperation) -> void)? before, ?(^(SpanOperation) -> void)? after, **untyped kwargs) ?{ (SpanOperation) -> void } -> untyped
 
           def multiplex_resource: (GraphQL::Execution::Multiplex? multiplex) -> String?
 
diff --git a/sig/datadog/tracing/metadata/tagging.rbs b/sig/datadog/tracing/metadata/tagging.rbs
index c140a142c02..abec99635e6 100644
--- a/sig/datadog/tracing/metadata/tagging.rbs
+++ b/sig/datadog/tracing/metadata/tagging.rbs
@@ -3,7 +3,7 @@ module Datadog
     module Metadata
       module Tagging
         NUMERIC_TAG_SIZE_RANGE: ::Range[untyped]
-        ENSURE_AGENT_TAGS: ::Hash[untyped, true]
+        ENSURE_AGENT_TAGS: ::Hash[untyped, bool]
 
         def get_tag: (untyped key) -> untyped
         def set_tag: (untyped key, ?untyped? value) -> untyped
diff --git a/sig/datadog/tracing/span.rbs b/sig/datadog/tracing/span.rbs
index 9195c3a5e8f..0beb7727234 100644
--- a/sig/datadog/tracing/span.rbs
+++ b/sig/datadog/tracing/span.rbs
@@ -27,7 +27,7 @@ module Datadog
           ?id: (Integer | nil),
           ?meta: (Hash[String, String] | nil),
           ?metrics: (Hash[String, Float] | nil),
-          ?metastruct: Hash[String | Symbol, untyped],
+          ?metastruct: Hash[String | Symbol, untyped]?,
           ?parent_id: Integer,
           ?resource: String,
           ?service: (String | nil),
diff --git a/sig/datadog/tracing/span_event.rbs b/sig/datadog/tracing/span_event.rbs
index 643c3062fc1..97f0b6e7e38 100644
--- a/sig/datadog/tracing/span_event.rbs
+++ b/sig/datadog/tracing/span_event.rbs
@@ -16,7 +16,7 @@ module Datadog
       attr_reader attributes: attributes
       attr_reader time_unix_nano: untyped # TODO: Typing this also makes to_hash internal typecheck fail
 
-      def initialize: (String name, ?attributes: attributes, ?time_unix_nano: Integer) -> void
+      def initialize: (String name, ?attributes: attributes?, ?time_unix_nano: Integer?) -> void
 
       def to_hash: -> Hash[String, untyped]
       # TODO: Steep does not track Hash keys when they are added with `hash[:key] = val`.
@@ -44,4 +44,4 @@ module Datadog
       def validate_scalar_attribute!: (String key, attributeValue value)-> bool
     end
   end
-end
\ No newline at end of file
+end
diff --git a/sig/datadog/tracing/span_operation.rbs b/sig/datadog/tracing/span_operation.rbs
index e08c06112cf..011f8f8a315 100644
--- a/sig/datadog/tracing/span_operation.rbs
+++ b/sig/datadog/tracing/span_operation.rbs
@@ -14,7 +14,7 @@ module Datadog
 
       attr_reader span_events: untyped
 
-      attr_reader end_time: ::Time
+      attr_reader end_time: ::Time?
 
       attr_reader id: untyped
 
@@ -26,7 +26,7 @@ module Datadog
 
       attr_reader service: untyped
 
-      attr_reader start_time: ::Time
+      attr_reader start_time: ::Time?
 
       attr_reader trace_id: untyped
 
@@ -37,8 +37,8 @@ module Datadog
       def initialize: (
           String name,
           ?logger: Core::Logger,
-          ?events: Events,
-          ?on_error: on_error,
+          ?events: Events?,
+          ?on_error: on_error?,
           ?parent_id: Integer,
           ?resource: String,
           ?service: (String | nil),
@@ -106,7 +106,7 @@ module Datadog
 
         attr_reader before_start: untyped
 
-        def initialize: (?logger: Core::Logger, ?on_error: on_error) -> void
+        def initialize: (?logger: Core::Logger) -> void
 
         def on_error: () -> OnError
 
diff --git a/sig/datadog/version.rbs b/sig/datadog/version.rbs
index 430a1e00940..10a73e6a08f 100644
--- a/sig/datadog/version.rbs
+++ b/sig/datadog/version.rbs
@@ -1,18 +1,18 @@
 module Datadog
   module VERSION
-    MAJOR: 2
+    MAJOR: Integer
 
-    MINOR: 0
+    MINOR: Integer
 
-    PATCH: 0
+    PATCH: Integer
 
-    PRE: "dev"
+    PRE: String?
 
-    BUILD: nil
+    BUILD: String?
 
-    STRING: untyped
+    STRING: String
 
-    MINIMUM_RUBY_VERSION: "2.5.0"
-    MAXIMUM_RUBY_VERSION: "3.4"
+    MINIMUM_RUBY_VERSION: String
+    MAXIMUM_RUBY_VERSION: String
   end
 end