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/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/contexts/with_request_mock.rb b/sentry-ruby/spec/contexts/with_request_mock.rb
index e6c480256..9a326376d 100644
--- a/sentry-ruby/spec/contexts/with_request_mock.rb
+++ b/sentry-ruby/spec/contexts/with_request_mock.rb
@@ -12,7 +12,13 @@ def setsockopt(*args); end
     allow(TCPSocket).to receive(:open).and_return(FakeSocket.new)
   end
 
-  def stub_request(fake_response, &block)
+  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|
       block.call(request, http_obj) if block
@@ -32,10 +38,10 @@ 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/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
diff --git a/sentry-ruby/spec/sentry/faraday_spec.rb b/sentry-ruby/spec/sentry/faraday_spec.rb
index 77e90db0a..d6b98d5a7 100644
--- a/sentry-ruby/spec/sentry/faraday_spec.rb
+++ b/sentry-ruby/spec/sentry/faraday_spec.rb
@@ -271,7 +271,7 @@
 
     let(:url) { "http://example.com" }
 
-    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/net/http_spec.rb b/sentry-ruby/spec/sentry/net/http_spec.rb
index 9de0a6f76..3e50f9cbe 100644
--- a/sentry-ruby/spec/sentry/net/http_spec.rb
+++ b/sentry-ruby/spec/sentry/net/http_spec.rb
@@ -11,38 +11,32 @@
     ::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
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..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
@@ -107,7 +107,7 @@
 
   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..b73c7dd93 100644
--- a/sentry-ruby/spec/sentry/transport/http_transport_spec.rb
+++ b/sentry-ruby/spec/sentry/transport/http_transport_spec.rb
@@ -22,7 +22,7 @@
   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 +39,7 @@
   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 +87,7 @@
     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 +97,7 @@
     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 +109,7 @@
     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 +122,7 @@
     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 +136,7 @@
       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 +155,7 @@
     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 +169,7 @@
     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 +178,7 @@
 
     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 +189,7 @@
       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 +200,7 @@
       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 +211,7 @@
       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 +225,7 @@
     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 +238,7 @@
     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 +255,7 @@
     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 +296,7 @@
       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 +306,7 @@
       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 +318,7 @@
       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/transport_spec.rb b/sentry-ruby/spec/sentry/transport_spec.rb
index 059a8109b..bcef588fe 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
-        it "raises the error" do
-          expect do
-            subject.send_event(event)
-          end.to raise_error(Sentry::ExternalError)
+      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 Sentry::ExternalError" do
+          expect { subject.send_event(event) }.to raise_error(Sentry::ExternalError)
         end
       end
     end
diff --git a/sentry-ruby/spec/sentry_spec.rb b/sentry-ruby/spec/sentry_spec.rb
index 9a188e9f3..856e37d52 100644
--- a/sentry-ruby/spec/sentry_spec.rb
+++ b/sentry-ruby/spec/sentry_spec.rb
@@ -183,8 +183,8 @@
     context "with spotlight" do
       before { perform_basic_setup { |c| c.spotlight = true } }
 
-      it "sends the event to spotlight too" do
-        stub_request(build_fake_response("200")) do |request, http_obj|
+      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")
           expect(http_obj.address).to eq("localhost")
diff --git a/sentry-ruby/spec/spec_helper.rb b/sentry-ruby/spec/spec_helper.rb
index 00b3b310e..4a72657ba 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"
@@ -69,6 +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)