From 9fa189010b9a8a541cf8c85507ae3fb0929ec25a Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Fri, 14 Feb 2025 14:45:02 +0000
Subject: [PATCH 1/7] Set up webmock for specs

---
 sentry-ruby/Gemfile             | 1 +
 sentry-ruby/spec/spec_helper.rb | 1 +
 2 files changed, 2 insertions(+)

diff --git a/sentry-ruby/Gemfile b/sentry-ruby/Gemfile
index 35cc658d2..592fe4858 100644
--- a/sentry-ruby/Gemfile
+++ b/sentry-ruby/Gemfile
@@ -33,3 +33,4 @@ gem "yard", github: "lsegal/yard"
 gem "webrick"
 gem "faraday"
 gem "excon"
+gem "webmock"
diff --git a/sentry-ruby/spec/spec_helper.rb b/sentry-ruby/spec/spec_helper.rb
index 00b3b310e..5cf761da2 100644
--- a/sentry-ruby/spec/spec_helper.rb
+++ b/sentry-ruby/spec/spec_helper.rb
@@ -25,6 +25,7 @@
 
 require "sentry-ruby"
 require "sentry/test_helper"
+require "webmock/rspec"
 
 require_relative "support/profiler"
 require_relative "support/stacktrace_test_fixture"

From 882b6fcd1ee2b08b10a046e0152ed19cbfa64d50 Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Fri, 14 Feb 2025 14:54:00 +0000
Subject: [PATCH 2/7] Replace faulty spec with something more useful

Not sure what the intention was but this spec
did not test any faraday error handling. What
actually happened was that HTTPTransport really
tried to hit the API and ended up with error.

We *do not* want to hit any APIs like that in specs,
this causes instability of the spec suite.

That's why I added webmock to ensure we're not sending
any HTTP requests in specs.
---
 sentry-ruby/lib/sentry/transport/http_transport.rb |  1 -
 sentry-ruby/spec/sentry/transport_spec.rb          | 11 +++++++----
 2 files changed, 7 insertions(+), 5 deletions(-)

diff --git a/sentry-ruby/lib/sentry/transport/http_transport.rb b/sentry-ruby/lib/sentry/transport/http_transport.rb
index e79bd0634..835867dac 100644
--- a/sentry-ruby/lib/sentry/transport/http_transport.rb
+++ b/sentry-ruby/lib/sentry/transport/http_transport.rb
@@ -23,7 +23,6 @@ class HTTPTransport < Transport
       Zlib::BufError, Errno::EHOSTUNREACH, Errno::ECONNREFUSED
     ].freeze
 
-
     def initialize(*args)
       super
       log_debug("Sentry HTTP Transport will connect to #{@dsn.server}") if @dsn
diff --git a/sentry-ruby/spec/sentry/transport_spec.rb b/sentry-ruby/spec/sentry/transport_spec.rb
index 059a8109b..621f45c30 100644
--- a/sentry-ruby/spec/sentry/transport_spec.rb
+++ b/sentry-ruby/spec/sentry/transport_spec.rb
@@ -531,11 +531,14 @@
         end
       end
 
-      context "with Faraday::Error" do
+      context "with an HTTP exception" do
+        before do
+          stub_request(:post, "http://sentry.localdomain:80/sentry/api/42/envelope/").
+          to_raise(Timeout::Error)
+        end
+
         it "raises the error" do
-          expect do
-            subject.send_event(event)
-          end.to raise_error(Sentry::ExternalError)
+          expect { subject.send_event(event) }.to raise_error(Sentry::ExternalError)
         end
       end
     end

From c9b6bd3e598e90dbaefd64fcf16ff1b5f6a0aca9 Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Fri, 14 Feb 2025 15:10:53 +0000
Subject: [PATCH 3/7] Stub requests in event sending spec

This spec was very flaky
---
 .../spec/sentry/client/event_sending_spec.rb  | 25 ++++++++++++++++---
 1 file changed, 21 insertions(+), 4 deletions(-)

diff --git a/sentry-ruby/spec/sentry/client/event_sending_spec.rb b/sentry-ruby/spec/sentry/client/event_sending_spec.rb
index 4950cb7c8..f87821ae9 100644
--- a/sentry-ruby/spec/sentry/client/event_sending_spec.rb
+++ b/sentry-ruby/spec/sentry/client/event_sending_spec.rb
@@ -10,6 +10,11 @@
       config.transport.transport_class = Sentry::DummyTransport
     end
   end
+
+  before do
+    stub_request(:post, Sentry::TestHelper::DUMMY_DSN)
+  end
+
   subject(:client) { Sentry::Client.new(configuration) }
 
   let(:hub) do
@@ -470,13 +475,16 @@
         before do
           configuration.background_worker_threads = 0
           Sentry.background_worker = Sentry::BackgroundWorker.new(configuration)
+
+          stub_request(:post, "http://sentry.localdomain/sentry/api/42/envelope/")
+            .to_raise(Timeout::Error)
         end
 
         it "swallows and logs Sentry::ExternalError (caused by transport's networking error)" do
           expect(client.capture_event(event, scope)).to be_nil
 
-          expect(string_io.string).to match(/Event sending failed: Failed to open TCP connection/)
-          expect(string_io.string).to match(/Event capturing failed: Failed to open TCP connection/)
+          expect(string_io.string).to match(/Event sending failed: Exception from WebMock/)
+          expect(string_io.string).to match(/Event capturing failed: Exception from WebMock/)
         end
 
         it "swallows and logs errors caused by the user (like in before_send)" do
@@ -502,13 +510,16 @@
       context "when sending events in background causes error", retry: 3 do
         before do
           Sentry.background_worker = Sentry::BackgroundWorker.new(configuration)
+
+          stub_request(:post, "http://sentry.localdomain/sentry/api/42/envelope/")
+            .to_raise(Timeout::Error)
         end
 
         it "swallows and logs Sentry::ExternalError (caused by transport's networking error)" do
           expect(client.capture_event(event, scope)).to be_a(Sentry::ErrorEvent)
           sleep(0.2)
 
-          expect(string_io.string).to match(/Event sending failed: Failed to open TCP connection/)
+          expect(string_io.string).to match(/Event sending failed: Exception from WebMock/)
         end
 
         it "swallows and logs errors caused by the user (like in before_send)" do
@@ -560,11 +571,14 @@
     describe "#send_event" do
       context "error happens when sending the event" do
         it "raises the error" do
+          stub_request(:post, "http://sentry.localdomain/sentry/api/42/envelope/")
+            .to_raise(Timeout::Error)
+
           expect do
             client.send_event(event)
           end.to raise_error(Sentry::ExternalError)
 
-          expect(string_io.string).to match(/Event sending failed: Failed to open TCP connection/)
+          expect(string_io.string).to match(/Event sending failed: Exception from WebMock/)
         end
       end
 
@@ -635,6 +649,9 @@
         end
 
         it "records lost span delta client reports" do
+          stub_request(:post, "http://sentry.localdomain/sentry/api/42/envelope/")
+            .to_raise(Timeout::Error)
+
           expect { client.send_event(transaction_event) }.to raise_error(Sentry::ExternalError)
           expect(client.transport).to have_recorded_lost_event(:before_send, 'span', num: 2)
         end

From fa20ea2177e8da342afad11a29071b7d2369cc4e Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Fri, 14 Feb 2025 15:18:26 +0000
Subject: [PATCH 4/7] Fix faraday spec even though it sends HTTP request

I'll figure it out eventually
---
 sentry-ruby/spec/sentry/faraday_spec.rb   | 6 ++++++
 sentry-ruby/spec/sentry/transport_spec.rb | 2 +-
 2 files changed, 7 insertions(+), 1 deletion(-)

diff --git a/sentry-ruby/spec/sentry/faraday_spec.rb b/sentry-ruby/spec/sentry/faraday_spec.rb
index 77e90db0a..170926927 100644
--- a/sentry-ruby/spec/sentry/faraday_spec.rb
+++ b/sentry-ruby/spec/sentry/faraday_spec.rb
@@ -271,6 +271,12 @@
 
     let(:url) { "http://example.com" }
 
+    around do |example|
+      WebMock.disable!
+      example.run
+      WebMock.enable!
+    end
+
     it "skips instrumentation" do
       transaction = Sentry.start_transaction
       Sentry.get_current_scope.set_span(transaction)
diff --git a/sentry-ruby/spec/sentry/transport_spec.rb b/sentry-ruby/spec/sentry/transport_spec.rb
index 621f45c30..bcef588fe 100644
--- a/sentry-ruby/spec/sentry/transport_spec.rb
+++ b/sentry-ruby/spec/sentry/transport_spec.rb
@@ -537,7 +537,7 @@
           to_raise(Timeout::Error)
         end
 
-        it "raises the error" do
+        it "raises Sentry::ExternalError" do
           expect { subject.send_event(event) }.to raise_error(Sentry::ExternalError)
         end
       end

From 3e7aebdb961d61a63a12e3f5f3351e091ff619df Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Fri, 14 Feb 2025 15:27:01 +0000
Subject: [PATCH 5/7] Use sentry request stubbing when needed

---
 .../spec/contexts/with_request_mock.rb        |  6 +--
 .../sentry/breadcrumb/http_logger_spec.rb     |  6 +++
 sentry-ruby/spec/sentry/net/http_spec.rb      |  6 +++
 .../http_transport_rate_limiting_spec.rb      |  8 +++-
 .../sentry/transport/http_transport_spec.rb   | 44 +++++++++++--------
 sentry-ruby/spec/sentry_spec.rb               |  8 +++-
 6 files changed, 54 insertions(+), 24 deletions(-)

diff --git a/sentry-ruby/spec/contexts/with_request_mock.rb b/sentry-ruby/spec/contexts/with_request_mock.rb
index e6c480256..d5c2fb3a6 100644
--- a/sentry-ruby/spec/contexts/with_request_mock.rb
+++ b/sentry-ruby/spec/contexts/with_request_mock.rb
@@ -12,7 +12,7 @@ def setsockopt(*args); end
     allow(TCPSocket).to receive(:open).and_return(FakeSocket.new)
   end
 
-  def stub_request(fake_response, &block)
+  def sentry_stub_request(fake_response, &block)
     allow_any_instance_of(Net::HTTP).to receive(:connect)
     allow_any_instance_of(Net::HTTP).to receive(:transport_request) do |http_obj, request|
       block.call(request, http_obj) if block
@@ -32,10 +32,10 @@ def build_fake_response(status, body: {}, headers: {})
 
   def stub_sentry_response
     # use bad request as an example is easier for verifying with error messages
-    stub_request(build_fake_response("400", body: { data: "bad sentry DSN public key" }))
+    sentry_stub_request(build_fake_response("400", body: { data: "bad sentry DSN public key" }))
   end
 
   def stub_normal_response(code: "200", &block)
-    stub_request(build_fake_response(code), &block)
+    sentry_stub_request(build_fake_response(code), &block)
   end
 end
diff --git a/sentry-ruby/spec/sentry/breadcrumb/http_logger_spec.rb b/sentry-ruby/spec/sentry/breadcrumb/http_logger_spec.rb
index a92c4c81a..3bd55966c 100644
--- a/sentry-ruby/spec/sentry/breadcrumb/http_logger_spec.rb
+++ b/sentry-ruby/spec/sentry/breadcrumb/http_logger_spec.rb
@@ -6,6 +6,12 @@
 RSpec.describe :http_logger do
   include_context "with request mock"
 
+  around do |example|
+    WebMock.disable!
+    example.run
+    WebMock.enable!
+  end
+
   let(:string_io) { StringIO.new }
   let(:logger) do
     ::Logger.new(string_io)
diff --git a/sentry-ruby/spec/sentry/net/http_spec.rb b/sentry-ruby/spec/sentry/net/http_spec.rb
index 9de0a6f76..1b5c00a1c 100644
--- a/sentry-ruby/spec/sentry/net/http_spec.rb
+++ b/sentry-ruby/spec/sentry/net/http_spec.rb
@@ -6,6 +6,12 @@
 RSpec.describe Sentry::Net::HTTP do
   include_context "with request mock"
 
+  around do |example|
+    WebMock.disable!
+    example.run
+    WebMock.enable!
+  end
+
   let(:string_io) { StringIO.new }
   let(:logger) do
     ::Logger.new(string_io)
diff --git a/sentry-ruby/spec/sentry/transport/http_transport_rate_limiting_spec.rb b/sentry-ruby/spec/sentry/transport/http_transport_rate_limiting_spec.rb
index 30dc42bbb..386d91e23 100644
--- a/sentry-ruby/spec/sentry/transport/http_transport_rate_limiting_spec.rb
+++ b/sentry-ruby/spec/sentry/transport/http_transport_rate_limiting_spec.rb
@@ -6,6 +6,12 @@
 RSpec.describe "rate limiting" do
   include_context "with request mock"
 
+  around do |example|
+    WebMock.disable!
+    example.run
+    WebMock.enable!
+  end
+
   before do
     perform_basic_setup do |config|
       config.logger = Logger.new(string_io)
@@ -107,7 +113,7 @@
 
   describe "rate limit header processing" do
     before do
-      stub_request(fake_response)
+      sentry_stub_request(fake_response)
     end
 
     shared_examples "rate limiting headers handling" do
diff --git a/sentry-ruby/spec/sentry/transport/http_transport_spec.rb b/sentry-ruby/spec/sentry/transport/http_transport_spec.rb
index a0973ef75..f04640c1e 100644
--- a/sentry-ruby/spec/sentry/transport/http_transport_spec.rb
+++ b/sentry-ruby/spec/sentry/transport/http_transport_spec.rb
@@ -6,6 +6,12 @@
 RSpec.describe Sentry::HTTPTransport do
   include_context "with request mock"
 
+  around do |example|
+    WebMock.disable!
+    example.run
+    WebMock.enable!
+  end
+
   let(:configuration) do
     Sentry::Configuration.new.tap do |config|
       config.dsn = Sentry::TestHelper::DUMMY_DSN
@@ -22,7 +28,7 @@
   subject { client.transport }
 
   it "logs a debug message only during initialization" do
-    stub_request(build_fake_response("200"))
+    sentry_stub_request(build_fake_response("200"))
     string_io = StringIO.new
     configuration.logger = Logger.new(string_io)
 
@@ -39,7 +45,7 @@
   end
 
   it "initializes new Net::HTTP instance for every request" do
-    stub_request(build_fake_response("200")) do |request|
+    sentry_stub_request(build_fake_response("200")) do |request|
       expect(request["User-Agent"]).to eq("sentry-ruby/#{Sentry::VERSION}")
     end
 
@@ -87,7 +93,7 @@
     let(:fake_response) { build_fake_response("200") }
 
     it 'sets default User-Agent' do
-      stub_request(fake_response) do |request|
+      sentry_stub_request(fake_response) do |request|
         expect(request["User-Agent"]).to eq("sentry-ruby/#{Sentry::VERSION}")
       end
 
@@ -97,7 +103,7 @@
     it "accepts custom proxy" do
       configuration.transport.proxy = { uri:  URI("https://example.com"), user: "stan", password: "foobar" }
 
-      stub_request(fake_response) do |_, http_obj|
+      sentry_stub_request(fake_response) do |_, http_obj|
         expect(http_obj.proxy_address).to eq("example.com")
         expect(http_obj.proxy_user).to eq("stan")
         expect(http_obj.proxy_pass).to eq("foobar")
@@ -109,7 +115,7 @@
     it "accepts a custom proxy string" do
       configuration.transport.proxy = "https://stan:foobar@example.com:8080"
 
-      stub_request(fake_response) do |_, http_obj|
+      sentry_stub_request(fake_response) do |_, http_obj|
         expect(http_obj.proxy_address).to eq("example.com")
         expect(http_obj.proxy_user).to eq("stan")
         expect(http_obj.proxy_pass).to eq("foobar")
@@ -122,7 +128,7 @@
     it "accepts a custom proxy URI" do
       configuration.transport.proxy = URI("https://stan:foobar@example.com:8080")
 
-      stub_request(fake_response) do |_, http_obj|
+      sentry_stub_request(fake_response) do |_, http_obj|
         expect(http_obj.proxy_address).to eq("example.com")
         expect(http_obj.proxy_user).to eq("stan")
         expect(http_obj.proxy_pass).to eq("foobar")
@@ -136,7 +142,7 @@
       begin
         ENV["http_proxy"] = "https://stan:foobar@example.com:8080"
 
-        stub_request(fake_response) do |_, http_obj|
+        sentry_stub_request(fake_response) do |_, http_obj|
           expect(http_obj.proxy_address).to eq("example.com")
           expect(http_obj.proxy_port).to eq(8080)
 
@@ -155,7 +161,7 @@
     it "accepts custom timeout" do
       configuration.transport.timeout = 10
 
-      stub_request(fake_response) do |_, http_obj|
+      sentry_stub_request(fake_response) do |_, http_obj|
         expect(http_obj.read_timeout).to eq(10)
 
         if Gem::Version.new(RUBY_VERSION) >= Gem::Version.new("2.6")
@@ -169,7 +175,7 @@
     it "accepts custom open_timeout" do
       configuration.transport.open_timeout = 10
 
-      stub_request(fake_response) do |_, http_obj|
+      sentry_stub_request(fake_response) do |_, http_obj|
         expect(http_obj.open_timeout).to eq(10)
       end
 
@@ -178,7 +184,7 @@
 
     describe "ssl configurations" do
       it "has the corrent default" do
-        stub_request(fake_response) do |_, http_obj|
+        sentry_stub_request(fake_response) do |_, http_obj|
           expect(http_obj.verify_mode).to eq(1)
           expect(http_obj.ca_file).to eq(nil)
         end
@@ -189,7 +195,7 @@
       it "accepts custom ssl_verification configuration" do
         configuration.transport.ssl_verification = false
 
-        stub_request(fake_response) do |_, http_obj|
+        sentry_stub_request(fake_response) do |_, http_obj|
           expect(http_obj.verify_mode).to eq(0)
           expect(http_obj.ca_file).to eq(nil)
         end
@@ -200,7 +206,7 @@
       it "accepts custom ssl_ca_file configuration" do
         configuration.transport.ssl_ca_file = "/tmp/foo"
 
-        stub_request(fake_response) do |_, http_obj|
+        sentry_stub_request(fake_response) do |_, http_obj|
           expect(http_obj.verify_mode).to eq(1)
           expect(http_obj.ca_file).to eq("/tmp/foo")
         end
@@ -211,7 +217,7 @@
       it "accepts custom ssl configuration" do
         configuration.transport.ssl  = { verify: false, ca_file: "/tmp/foo" }
 
-        stub_request(fake_response) do |_, http_obj|
+        sentry_stub_request(fake_response) do |_, http_obj|
           expect(http_obj.verify_mode).to eq(0)
           expect(http_obj.ca_file).to eq("/tmp/foo")
         end
@@ -225,7 +231,7 @@
     let(:fake_response) { build_fake_response("200") }
 
     it "compresses data by default" do
-      stub_request(fake_response) do |request|
+      sentry_stub_request(fake_response) do |request|
         expect(request["Content-Type"]).to eq("application/x-sentry-envelope")
         expect(request["Content-Encoding"]).to eq("gzip")
 
@@ -238,7 +244,7 @@
     end
 
     it "doesn't compress small event" do
-      stub_request(fake_response) do |request|
+      sentry_stub_request(fake_response) do |request|
         expect(request["Content-Type"]).to eq("application/x-sentry-envelope")
         expect(request["Content-Encoding"]).to eq("")
 
@@ -255,7 +261,7 @@
     it "doesn't compress data if the encoding is not gzip" do
       configuration.transport.encoding = "json"
 
-      stub_request(fake_response) do |request|
+      sentry_stub_request(fake_response) do |request|
         expect(request["Content-Type"]).to eq("application/x-sentry-envelope")
         expect(request["Content-Encoding"]).to eq("")
 
@@ -296,7 +302,7 @@
       let(:fake_response) { build_fake_response("404") }
 
       it "raises an error" do
-        stub_request(fake_response)
+        sentry_stub_request(fake_response)
 
         expect { subject.send_data(data) }.to raise_error(Sentry::ExternalError, /the server responded with status 404/)
       end
@@ -306,7 +312,7 @@
       let(:fake_response) { build_fake_response("500") }
 
       it "raises an error" do
-        stub_request(fake_response)
+        sentry_stub_request(fake_response)
 
         expect { subject.send_data(data) }.to raise_error(Sentry::ExternalError, /the server responded with status 500/)
       end
@@ -318,7 +324,7 @@
       end
 
       it "raises an error with header" do
-        stub_request(error_response)
+        sentry_stub_request(error_response)
 
         expect { subject.send_data(data) }.to raise_error(Sentry::ExternalError, /error_in_header/)
       end
diff --git a/sentry-ruby/spec/sentry_spec.rb b/sentry-ruby/spec/sentry_spec.rb
index 9a188e9f3..847829526 100644
--- a/sentry-ruby/spec/sentry_spec.rb
+++ b/sentry-ruby/spec/sentry_spec.rb
@@ -183,8 +183,14 @@
     context "with spotlight" do
       before { perform_basic_setup { |c| c.spotlight = true } }
 
+      around do |example|
+        WebMock.disable!
+        example.run
+        WebMock.enable!
+      end
+
       it "sends the event to spotlight too" do
-        stub_request(build_fake_response("200")) do |request, http_obj|
+        sentry_stub_request(build_fake_response("200")) do |request, http_obj|
           expect(request["Content-Type"]).to eq("application/x-sentry-envelope")
           expect(request["Content-Encoding"]).to eq("gzip")
           expect(http_obj.address).to eq("localhost")

From 6358f7ba3d10e9eff9cf19f261175562a3a507bf Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Mon, 17 Feb 2025 13:31:12 +0000
Subject: [PATCH 6/7] DRY up toggling webmock in specs

---
 sentry-ruby/spec/contexts/with_request_mock.rb            | 6 ++++++
 sentry-ruby/spec/sentry/breadcrumb/http_logger_spec.rb    | 6 ------
 sentry-ruby/spec/sentry/faraday_spec.rb                   | 8 +-------
 .../sentry/transport/http_transport_rate_limiting_spec.rb | 6 ------
 sentry-ruby/spec/sentry/transport/http_transport_spec.rb  | 6 ------
 sentry-ruby/spec/sentry_spec.rb                           | 8 +-------
 sentry-ruby/spec/spec_helper.rb                           | 6 ++++++
 7 files changed, 14 insertions(+), 32 deletions(-)

diff --git a/sentry-ruby/spec/contexts/with_request_mock.rb b/sentry-ruby/spec/contexts/with_request_mock.rb
index d5c2fb3a6..9a326376d 100644
--- a/sentry-ruby/spec/contexts/with_request_mock.rb
+++ b/sentry-ruby/spec/contexts/with_request_mock.rb
@@ -12,6 +12,12 @@ def setsockopt(*args); end
     allow(TCPSocket).to receive(:open).and_return(FakeSocket.new)
   end
 
+  around do |example|
+    WebMock.disable!
+    example.run
+    WebMock.enable!
+  end
+
   def sentry_stub_request(fake_response, &block)
     allow_any_instance_of(Net::HTTP).to receive(:connect)
     allow_any_instance_of(Net::HTTP).to receive(:transport_request) do |http_obj, request|
diff --git a/sentry-ruby/spec/sentry/breadcrumb/http_logger_spec.rb b/sentry-ruby/spec/sentry/breadcrumb/http_logger_spec.rb
index 3bd55966c..a92c4c81a 100644
--- a/sentry-ruby/spec/sentry/breadcrumb/http_logger_spec.rb
+++ b/sentry-ruby/spec/sentry/breadcrumb/http_logger_spec.rb
@@ -6,12 +6,6 @@
 RSpec.describe :http_logger do
   include_context "with request mock"
 
-  around do |example|
-    WebMock.disable!
-    example.run
-    WebMock.enable!
-  end
-
   let(:string_io) { StringIO.new }
   let(:logger) do
     ::Logger.new(string_io)
diff --git a/sentry-ruby/spec/sentry/faraday_spec.rb b/sentry-ruby/spec/sentry/faraday_spec.rb
index 170926927..d6b98d5a7 100644
--- a/sentry-ruby/spec/sentry/faraday_spec.rb
+++ b/sentry-ruby/spec/sentry/faraday_spec.rb
@@ -271,13 +271,7 @@
 
     let(:url) { "http://example.com" }
 
-    around do |example|
-      WebMock.disable!
-      example.run
-      WebMock.enable!
-    end
-
-    it "skips instrumentation" do
+    it "skips instrumentation", webmock: false do
       transaction = Sentry.start_transaction
       Sentry.get_current_scope.set_span(transaction)
 
diff --git a/sentry-ruby/spec/sentry/transport/http_transport_rate_limiting_spec.rb b/sentry-ruby/spec/sentry/transport/http_transport_rate_limiting_spec.rb
index 386d91e23..aff057345 100644
--- a/sentry-ruby/spec/sentry/transport/http_transport_rate_limiting_spec.rb
+++ b/sentry-ruby/spec/sentry/transport/http_transport_rate_limiting_spec.rb
@@ -6,12 +6,6 @@
 RSpec.describe "rate limiting" do
   include_context "with request mock"
 
-  around do |example|
-    WebMock.disable!
-    example.run
-    WebMock.enable!
-  end
-
   before do
     perform_basic_setup do |config|
       config.logger = Logger.new(string_io)
diff --git a/sentry-ruby/spec/sentry/transport/http_transport_spec.rb b/sentry-ruby/spec/sentry/transport/http_transport_spec.rb
index f04640c1e..b73c7dd93 100644
--- a/sentry-ruby/spec/sentry/transport/http_transport_spec.rb
+++ b/sentry-ruby/spec/sentry/transport/http_transport_spec.rb
@@ -6,12 +6,6 @@
 RSpec.describe Sentry::HTTPTransport do
   include_context "with request mock"
 
-  around do |example|
-    WebMock.disable!
-    example.run
-    WebMock.enable!
-  end
-
   let(:configuration) do
     Sentry::Configuration.new.tap do |config|
       config.dsn = Sentry::TestHelper::DUMMY_DSN
diff --git a/sentry-ruby/spec/sentry_spec.rb b/sentry-ruby/spec/sentry_spec.rb
index 847829526..856e37d52 100644
--- a/sentry-ruby/spec/sentry_spec.rb
+++ b/sentry-ruby/spec/sentry_spec.rb
@@ -183,13 +183,7 @@
     context "with spotlight" do
       before { perform_basic_setup { |c| c.spotlight = true } }
 
-      around do |example|
-        WebMock.disable!
-        example.run
-        WebMock.enable!
-      end
-
-      it "sends the event to spotlight too" do
+      it "sends the event to spotlight too", webmock: false do
         sentry_stub_request(build_fake_response("200")) do |request, http_obj|
           expect(request["Content-Type"]).to eq("application/x-sentry-envelope")
           expect(request["Content-Encoding"]).to eq("gzip")
diff --git a/sentry-ruby/spec/spec_helper.rb b/sentry-ruby/spec/spec_helper.rb
index 5cf761da2..4a72657ba 100644
--- a/sentry-ruby/spec/spec_helper.rb
+++ b/sentry-ruby/spec/spec_helper.rb
@@ -70,6 +70,12 @@
     skip("Skipping because one or more guards `#{guards.inspect}` returned false") if skip_examples
   end
 
+  config.around(:each, webmock: false) do |example|
+    WebMock.disable!
+    example.run
+    WebMock.enable!
+  end
+
   RSpec::Matchers.define :have_recorded_lost_event do |reason, data_category, num: 1|
     match do |transport|
       expect(transport.discarded_events[[reason, data_category]]).to eq(num)

From a744a558c21ef402bea8656a107cee036e8e16dc Mon Sep 17 00:00:00 2001
From: Peter Solnica <peter@solnica.online>
Date: Mon, 17 Feb 2025 13:31:45 +0000
Subject: [PATCH 7/7] Fix problematic spec

---
 sentry-ruby/spec/sentry/net/http_spec.rb      | 44 +++++++------------
 .../spec/sentry/rspec/matchers_spec.rb        |  1 +
 2 files changed, 17 insertions(+), 28 deletions(-)

diff --git a/sentry-ruby/spec/sentry/net/http_spec.rb b/sentry-ruby/spec/sentry/net/http_spec.rb
index 1b5c00a1c..3e50f9cbe 100644
--- a/sentry-ruby/spec/sentry/net/http_spec.rb
+++ b/sentry-ruby/spec/sentry/net/http_spec.rb
@@ -6,49 +6,37 @@
 RSpec.describe Sentry::Net::HTTP do
   include_context "with request mock"
 
-  around do |example|
-    WebMock.disable!
-    example.run
-    WebMock.enable!
-  end
-
   let(:string_io) { StringIO.new }
   let(:logger) do
     ::Logger.new(string_io)
   end
 
-  context "with IPv6 addresses" do
+  context "with tracing enabled" do
     before do
       perform_basic_setup do |config|
         config.traces_sample_rate = 1.0
+        config.transport.transport_class = Sentry::HTTPTransport
+        config.logger = logger
+        # the dsn needs to have a real host so we can make a real connection before sending a failed request
+        config.dsn = 'http://foobarbaz@o447951.ingest.sentry.io/5434472'
       end
     end
 
-    it "correctly parses the short-hand IPv6 addresses" do
-      stub_normal_response
-
-      transaction = Sentry.start_transaction
-      Sentry.get_current_scope.set_span(transaction)
+    context "with IPv6 addresses" do
+      it "correctly parses the short-hand IPv6 addresses" do
+        stub_normal_response
 
-      _ = Net::HTTP.get("::1", "/path", 8080)
+        transaction = Sentry.start_transaction
+        Sentry.get_current_scope.set_span(transaction)
 
-      expect(transaction.span_recorder.spans.count).to eq(2)
+        _ = Net::HTTP.get("::1", "/path", 8080)
 
-      request_span = transaction.span_recorder.spans.last
-      expect(request_span.data).to eq(
-        { "url" => "http://[::1]/path", "http.request.method" => "GET", "http.response.status_code" => 200 }
-      )
-    end
-  end
+        expect(transaction.span_recorder.spans.count).to eq(2)
 
-  context "with tracing enabled" do
-    before do
-      perform_basic_setup do |config|
-        config.traces_sample_rate = 1.0
-        config.transport.transport_class = Sentry::HTTPTransport
-        config.logger = logger
-        # the dsn needs to have a real host so we can make a real connection before sending a failed request
-        config.dsn = 'http://foobarbaz@o447951.ingest.sentry.io/5434472'
+        request_span = transaction.span_recorder.spans.last
+        expect(request_span.data).to eq(
+          { "url" => "http://[::1]/path", "http.request.method" => "GET", "http.response.status_code" => 200 }
+        )
       end
     end
 
diff --git a/sentry-ruby/spec/sentry/rspec/matchers_spec.rb b/sentry-ruby/spec/sentry/rspec/matchers_spec.rb
index 45e914f52..c20a7cfd3 100644
--- a/sentry-ruby/spec/sentry/rspec/matchers_spec.rb
+++ b/sentry-ruby/spec/sentry/rspec/matchers_spec.rb
@@ -12,6 +12,7 @@
       config.dsn = 'https://2fb45f003d054a7ea47feb45898f7649@o447951.ingest.sentry.io/5434472'
       config.enabled_environments = ["production"]
       config.environment = :test
+      config.transport.transport_class = Sentry::DummyTransport
     end
 
     setup_sentry_test