diff --git a/CHANGELOG.md b/CHANGELOG.md
index fc9fa589b..7cb52ec0d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,7 +8,7 @@
   ```rb
   # takes an array of strings or regexps
   config.trace_propagation_targets = [/.*/]  # default is to all targets
-  config.trace_propagation_targets = [/example.com/, 'foobar.org']
+  config.trace_propagation_targets = [/example.com/, 'foobar.org/api/v2']
   ```
 
 ## 5.10.0
diff --git a/sentry-ruby/spec/sentry/configuration_spec.rb b/sentry-ruby/spec/sentry/configuration_spec.rb
index ac49db207..6cd571600 100644
--- a/sentry-ruby/spec/sentry/configuration_spec.rb
+++ b/sentry-ruby/spec/sentry/configuration_spec.rb
@@ -511,6 +511,17 @@ class SentryConfigurationSample < Sentry::Configuration
     end
   end
 
+  describe "#trace_propagation_targets" do
+    it "returns match all by default" do
+      expect(subject.trace_propagation_targets).to eq([/.*/])
+    end
+
+    it "accepts array of strings or regexps" do
+      subject.trace_propagation_targets = ["example.com", /foobar.org\/api\/v2/]
+      expect(subject.trace_propagation_targets).to eq(["example.com", /foobar.org\/api\/v2/])
+    end
+  end
+
   describe "#instrumenter" do
     it "returns :sentry by default" do
       expect(subject.instrumenter).to eq(:sentry)
diff --git a/sentry-ruby/spec/sentry/net/http_spec.rb b/sentry-ruby/spec/sentry/net/http_spec.rb
index 35279ad81..dc4605ffc 100644
--- a/sentry-ruby/spec/sentry/net/http_spec.rb
+++ b/sentry-ruby/spec/sentry/net/http_spec.rb
@@ -216,6 +216,76 @@
       end
     end
 
+    context "with custom trace_propagation_targets" do
+      before do
+        Sentry.configuration.trace_propagation_targets = ["example.com", /foobar.org\/api\/v2/]
+      end
+
+      it "doesn't add sentry headers to outgoing requests to different target" do
+        stub_normal_response
+
+        uri = URI("http://google.com/path")
+        http = Net::HTTP.new(uri.host, uri.port)
+        request = Net::HTTP::Get.new(uri.request_uri)
+
+        transaction = Sentry.start_transaction
+        Sentry.get_current_scope.set_span(transaction)
+
+        http.request(request)
+
+        expect(request.key?("sentry-trace")).to eq(false)
+        expect(request.key?("baggage")).to eq(false)
+      end
+
+      it "doesn't add sentry headers to outgoing requests to different target path" do
+        stub_normal_response
+
+        uri = URI("http://foobar.org/api/v1/path")
+        http = Net::HTTP.new(uri.host, uri.port)
+        request = Net::HTTP::Get.new(uri.request_uri)
+
+        transaction = Sentry.start_transaction
+        Sentry.get_current_scope.set_span(transaction)
+
+        http.request(request)
+
+        expect(request.key?("sentry-trace")).to eq(false)
+        expect(request.key?("baggage")).to eq(false)
+      end
+
+      it "adds sentry headers to outgoing requests matching string" do
+        stub_normal_response
+
+        uri = URI("http://example.com/path")
+        http = Net::HTTP.new(uri.host, uri.port)
+        request = Net::HTTP::Get.new(uri.request_uri)
+
+        transaction = Sentry.start_transaction
+        Sentry.get_current_scope.set_span(transaction)
+
+        http.request(request)
+
+        expect(request.key?("sentry-trace")).to eq(true)
+        expect(request.key?("baggage")).to eq(true)
+      end
+
+      it "adds sentry headers to outgoing requests matching regexp" do
+        stub_normal_response
+
+        uri = URI("http://foobar.org/api/v2/path")
+        http = Net::HTTP.new(uri.host, uri.port)
+        request = Net::HTTP::Get.new(uri.request_uri)
+
+        transaction = Sentry.start_transaction
+        Sentry.get_current_scope.set_span(transaction)
+
+        http.request(request)
+
+        expect(request.key?("sentry-trace")).to eq(true)
+        expect(request.key?("baggage")).to eq(true)
+      end
+    end
+
     it "doesn't record span for the SDK's request" do
       stub_sentry_response