diff --git a/lib/rubyshell/debugger.rb b/lib/rubyshell/debugger.rb
index 6313f74..b208499 100644
--- a/lib/rubyshell/debugger.rb
+++ b/lib/rubyshell/debugger.rb
@@ -5,27 +5,41 @@ module Debugger
     class << self
       def run_wrapper(command, debug: nil)
         if debug || RubyShell.debug?
-
           time_one = Process.clock_gettime(Process::CLOCK_MONOTONIC)
 
-          result = yield
+          begin
+            result = yield
+          rescue RubyShell::CommandError => e
+            time_two = Process.clock_gettime(Process::CLOCK_MONOTONIC)
+            log_command(command, time_two - time_one, e.status, e.stdout, e.stderr)
+            raise
+          end
 
           time_two = Process.clock_gettime(Process::CLOCK_MONOTONIC)
 
-          RubyShell.log(<<~TEXT
-            \nExecuted: #{command.to_shell.chomp}
-              Duration: #{format("%.6f", time_two - time_one)}s
-              Pid: #{result.metadata[:exit_status].pid}
-              Exit code: #{result.metadata[:exit_status].to_i}
-              Stdout: #{result.to_s.inspect}
-          TEXT
-                       )
+          log_command(command, time_two - time_one, result.metadata[:exit_status], result.to_s, "")
 
           result
         else
           yield
         end
       end
+
+      private
+
+      def log_command(command, duration, status, stdout, stderr)
+        pid = status.pid if status.respond_to?(:pid)
+
+        RubyShell.log(<<~TEXT
+          \nExecuted: #{command.to_shell.chomp}
+            Duration: #{format("%.6f", duration)}s
+            Pid: #{pid}
+            Exit code: #{status.respond_to?(:exitstatus) ? status.exitstatus : status.to_i}
+            Stdout: #{stdout.inspect}
+            Stderr: #{stderr.inspect}
+        TEXT
+                     )
+      end
     end
   end
-end
+end
\ No newline at end of file
diff --git a/lib/rubyshell/error.rb b/lib/rubyshell/error.rb
index 5f6120e..8b1c1e2 100644
--- a/lib/rubyshell/error.rb
+++ b/lib/rubyshell/error.rb
@@ -2,7 +2,7 @@
 
 module RubyShell
   class CommandError < StandardError
-    attr_reader :command, :status
+    attr_reader :command, :stdout, :stderr, :status
 
     def initialize(command:, stdout: "", stderr: "", status: "", message: nil)
       @command = command
diff --git a/spec/debugger_spec.rb b/spec/debugger_spec.rb
index 900f202..990eef6 100644
--- a/spec/debugger_spec.rb
+++ b/spec/debugger_spec.rb
@@ -41,6 +41,12 @@
 
       expect(log_output.join).to include("Stdout: \"#{expected_output}\"")
     end
+
+    it "logs the stderr" do
+      subject_method
+
+      expect(log_output.join).to include("Stderr: \"\"")
+    end
   end
 
   RSpec.shared_examples "a silent command" do
@@ -83,7 +89,73 @@ def subject_method
       def subject_method
         sh.echo("hello", _debug: true)
       end
+
+      def execute_failed_debug_command(stdout: nil, stderr: "bad")
+        script_parts = []
+        script_parts << "STDOUT.write(%q{#{stdout}})" if stdout
+        script_parts << "STDERR.write(%q{#{stderr}})" if stderr
+        script_parts << "exit 1"
+
+        sh.ruby("-e", "\"#{script_parts.join("; ")}\"", _debug: true)
+      end
+
       it_behaves_like "a logged command", "hello"
+
+      it "reraises failed commands" do
+        expect do
+          execute_failed_debug_command
+        end.to raise_error(RubyShell::CommandError)
+      end
+
+      context "when a failed debug command is rescued" do
+        before do
+          begin
+            execute_failed_debug_command
+          rescue RubyShell::CommandError
+            nil
+          end
+        end
+
+        it "logs failed command exit code before reraising" do
+          expect(log_output.join).to include("Exit code: 1")
+        end
+
+        it "logs failed command stdout before reraising" do
+          expect(log_output.join).to include("Stdout: \"\"")
+        end
+
+        it "logs failed command stderr before reraising" do
+          expect(log_output.join).to include("Stderr: \"bad\"")
+        end
+      end
+
+      context "when the caller rescues the command error" do
+        subject(:rescued_error) do
+          execute_failed_debug_command(stdout: "out", stderr: "bad")
+        rescue RubyShell::CommandError => e
+          e
+        end
+
+        it "keeps the rescued error type available" do
+          expect(rescued_error).to be_a(RubyShell::CommandError)
+        end
+
+        it "keeps the rescued error command available" do
+          expect(rescued_error.command.to_s).to include("STDOUT.write")
+        end
+
+        it "keeps the rescued error stdout available" do
+          expect(rescued_error.stdout).to eq("out")
+        end
+
+        it "keeps the rescued error stderr available" do
+          expect(rescued_error.stderr).to eq("bad")
+        end
+
+        it "keeps the rescued error status available" do
+          expect(rescued_error.status.exitstatus).to eq(1)
+        end
+      end
     end
 
     context "when debug mode is enabled globally" do