diff --git a/lib/raven/cli.rb b/lib/raven/cli.rb
index 7ccd45c28..585c0e511 100644
--- a/lib/raven/cli.rb
+++ b/lib/raven/cli.rb
@@ -18,7 +18,7 @@ def self.test(dsn = nil, silent = false, config = nil) # rubocop:disable all
 
       # wipe out env settings to ensure we send the event
       unless config.capture_allowed?
-        env_name = config.environments.pop || 'production'
+        env_name = config.environments.last || 'production'
         config.current_environment = env_name
       end
 
@@ -33,27 +33,16 @@ def self.test(dsn = nil, silent = false, config = nil) # rubocop:disable all
         evt = instance.capture_exception(e)
       end
 
-      if evt && !(evt.is_a? Thread)
-        if evt.is_a? Hash
-          instance.logger.debug "-> event ID: #{evt[:event_id]}"
-        else
-          instance.logger.debug "-> event ID: #{evt.id}"
-        end
-      elsif evt # async configuration
-        if evt.value.is_a? Hash
-          instance.logger.debug "-> event ID: #{evt.value[:event_id]}"
-        else
-          instance.logger.debug "-> event ID: #{evt.value.id}"
-        end
+      if evt
+        instance.logger.debug "-> event ID: #{evt.id}"
+        instance.logger.debug ""
+        instance.logger.debug "Done!"
+        evt
       else
         instance.logger.debug ""
         instance.logger.debug "An error occurred while attempting to send the event."
-        exit 1
+        false
       end
-
-      instance.logger.debug ""
-      instance.logger.debug "Done!"
-      evt
     end
   end
 end
diff --git a/spec/raven/cli_spec.rb b/spec/raven/cli_spec.rb
index 0bbb7aa20..9a8452e36 100644
--- a/spec/raven/cli_spec.rb
+++ b/spec/raven/cli_spec.rb
@@ -1,12 +1,69 @@
 require 'spec_helper'
 require 'raven/cli'
 
-RSpec.describe "CLI tests" do
-  it "posting an exception" do
-    event = Raven::CLI.test(Raven.configuration.server, true, Raven.configuration)
-    expect(event).to be_a(Raven::Event)
-    hash = event.to_hash
-    expect(hash[:exception][:values][0][:type]).to eq("ZeroDivisionError")
-    expect(hash[:exception][:values][0][:value]).to eq("divided by 0")
+RSpec.describe Raven::CLI do
+  # avoid unexpectedly mutating the shared configuration object
+  let(:config) { Raven.configuration.dup }
+
+  context "when there's no error" do
+    it "sends an event" do
+      event = described_class.test(config.server, true, config)
+
+      expect(event).to be_a(Raven::Event)
+      hash = event.to_hash
+      expect(hash[:exception][:values][0][:type]).to eq("ZeroDivisionError")
+      expect(hash[:exception][:values][0][:value]).to eq("divided by 0")
+    end
+
+    it "logs correct values" do
+      logger = spy
+      allow_any_instance_of(Raven::Instance).to receive(:logger).and_return(logger)
+
+      event = described_class.test(config.server, true, config)
+
+      expect(logger).to have_received(:debug).with("Sending a test event:")
+      expect(logger).to have_received(:debug).with("-> event ID: #{event.id}")
+      expect(logger).to have_received(:debug).with("Done!")
+    end
+  end
+
+  context "when there's an error" do
+    before do
+      # make Configuration#sample_allowed? fail
+      config.sample_rate = 2.0
+      allow(Random::DEFAULT).to receive(:rand).and_return(3.0)
+    end
+
+    it "returns false" do
+      event = described_class.test(config.server, true, config)
+
+      expect(event).to eq(false)
+    end
+
+    it "logs correct values" do
+      logger = spy
+      allow_any_instance_of(Raven::Instance).to receive(:logger).and_return(logger)
+
+      described_class.test(config.server, true, config)
+
+      expect(logger).to have_received(:debug).with("Sending a test event:")
+      expect(logger).to have_received(:debug).with("An error occurred while attempting to send the event.")
+      expect(logger).not_to have_received(:debug).with("Done!")
+    end
+  end
+
+  context "when with custom environments config" do
+    let(:config) { Raven.configuration.dup }
+
+    before do
+      config.environments = %w(production test)
+    end
+
+    it "still sends the test event" do
+      event = Raven::CLI.test(config.server, true, config)
+
+      expect(event).to be_a(Raven::Event)
+      expect(config.errors).to be_empty
+    end
   end
 end