diff --git a/Gemfile b/Gemfile
index 38384131c01..d25788ece52 100644
--- a/Gemfile
+++ b/Gemfile
@@ -82,8 +82,8 @@ end
 
 group :check do
   if RUBY_VERSION >= '3.0.0' && RUBY_PLATFORM != 'java'
-    gem 'rbs', '~> 3.2.0', require: false
-    gem 'steep', '~> 1.6.0', require: false
+    gem 'rbs', '~> 3.5.0', require: false
+    gem 'steep', '~> 1.7.0', require: false
   end
   gem 'ruby_memcheck', '>= 3' if RUBY_VERSION >= '3.4.0' && RUBY_PLATFORM != 'java'
   gem 'standard', require: false
diff --git a/Steepfile b/Steepfile
index dfae78bba26..853aa813e01 100644
--- a/Steepfile
+++ b/Steepfile
@@ -5,6 +5,8 @@ target :datadog do
 
   ignore 'lib/datadog/appsec.rb'
   ignore 'lib/datadog/appsec/component.rb'
+  # Excluded due to https://github.com/soutaro/steep/issues/1232
+  ignore 'lib/datadog/appsec/configuration/settings.rb'
   ignore 'lib/datadog/appsec/contrib/'
   ignore 'lib/datadog/appsec/contrib/auto_instrument.rb'
   ignore 'lib/datadog/appsec/contrib/integration.rb'
@@ -69,6 +71,8 @@ target :datadog do
   ignore 'lib/datadog/core/metrics/options.rb'
   ignore 'lib/datadog/core/pin.rb'
   ignore 'lib/datadog/core/rate_limiter.rb'
+  # steep fails in this file due to https://github.com/soutaro/steep/issues/1231
+  ignore 'lib/datadog/core/remote/tie.rb'
   ignore 'lib/datadog/core/runtime/ext.rb'
   ignore 'lib/datadog/core/runtime/metrics.rb'
   ignore 'lib/datadog/core/transport/ext.rb'
diff --git a/lib/datadog/core/environment/execution.rb b/lib/datadog/core/environment/execution.rb
index 2049773a8d4..6d4a084ebec 100644
--- a/lib/datadog/core/environment/execution.rb
+++ b/lib/datadog/core/environment/execution.rb
@@ -25,9 +25,9 @@ def development?
           #   2. Checking if `Net::HTTP` is referring to the original one
           #   => ::Net::HTTP.equal?(::WebMock::HttpLibAdapters::NetHttpAdapter::OriginalNetHTTP)
           def webmock_enabled?
-            defined?(::WebMock::HttpLibAdapters::NetHttpAdapter) &&
+            !!(defined?(::WebMock::HttpLibAdapters::NetHttpAdapter) &&
               defined?(::Net::HTTP) &&
-              ::Net::HTTP.equal?(::WebMock::HttpLibAdapters::NetHttpAdapter.instance_variable_get(:@webMockNetHTTP))
+              ::Net::HTTP.equal?(::WebMock::HttpLibAdapters::NetHttpAdapter.instance_variable_get(:@webMockNetHTTP)))
           end
 
           private
@@ -68,7 +68,7 @@ def minitest?
 
           # Check if we are running from `bin/cucumber` or `cucumber/rake/task`.
           def cucumber?
-            defined?(::Cucumber::Cli)
+            !!defined?(::Cucumber::Cli)
           end
 
           # If this is a Rails application, use different heuristics to detect
@@ -80,7 +80,7 @@ def rails_development?
             # detecting its presence is enough to deduct if this is a development environment.
             #
             # @see https://github.com/rails/spring/blob/48b299348ace2188444489a0c216a6f3e9687281/README.md?plain=1#L204-L207
-            defined?(::Spring) || rails_env_development?
+            !!defined?(::Spring) || rails_env_development?
           end
 
           RAILS_ENV_DEVELOPMENT = Set['development', 'test'].freeze
@@ -94,7 +94,7 @@ def rails_development?
           # it's common to have a custom "staging" environment, and such environment normally want to run as close
           # to production as possible.
           def rails_env_development?
-            defined?(::Rails.env) && RAILS_ENV_DEVELOPMENT.include?(::Rails.env)
+            !!defined?(::Rails.env) && RAILS_ENV_DEVELOPMENT.include?(::Rails.env)
           end
         end
       end
diff --git a/lib/datadog/core/remote/tie.rb b/lib/datadog/core/remote/tie.rb
index f4279a471ba..ef0d331529a 100644
--- a/lib/datadog/core/remote/tie.rb
+++ b/lib/datadog/core/remote/tie.rb
@@ -19,6 +19,8 @@ def self.boot
             barrier = Datadog::Core::Remote.active_remote.barrier(:once)
           end
 
+          # steep does not permit the next line due to
+          # https://github.com/soutaro/steep/issues/1231
           Boot.new(barrier, t)
         end
       end
diff --git a/sig/datadog/core/remote/tie.rbs b/sig/datadog/core/remote/tie.rbs
index b4af9d4f2d4..793db6c802d 100644
--- a/sig/datadog/core/remote/tie.rbs
+++ b/sig/datadog/core/remote/tie.rbs
@@ -2,14 +2,14 @@ module Datadog
   module Core
     module Remote
       module Tie
-        class Boot < ::Struct[untyped]
+        class Boot < ::Struct[[Component::Barrier, Numeric]]
           def initialize: (Component::Barrier? barrier, Numeric? time) -> void
 
           attr_reader barrier: Component::Barrier
           attr_reader time: Numeric
         end
 
-        def self.boot: () -> (nil | Boot)
+        def self.boot: () -> Boot?
       end
     end
   end
diff --git a/sig/datadog/core/telemetry/event.rbs b/sig/datadog/core/telemetry/event.rbs
index 12fd27713c1..4818992176f 100644
--- a/sig/datadog/core/telemetry/event.rbs
+++ b/sig/datadog/core/telemetry/event.rbs
@@ -24,7 +24,7 @@ module Datadog
 
           def agent_transport: (untyped config) -> String
 
-          def conf_value: (String name, Object value, Integer seq_id, ?String origin) -> Hash[Symbol, untyped]
+          def conf_value: (String name, untyped value, Integer seq_id, ?String origin) -> Hash[Symbol, untyped]
 
           def to_value: (Object value) -> Object