diff --git a/lib/bundler/gem_helper.rb b/lib/bundler/gem_helper.rb
index 8e1dd7c4f2..01101205e3 100644
--- a/lib/bundler/gem_helper.rb
+++ b/lib/bundler/gem_helper.rb
@@ -98,9 +98,9 @@ module Bundler
       built_gem_path ||= build_gem
       cmd = [*gem_command, "install", built_gem_path.to_s]
       cmd << "--local" if local
-      _, status = sh_with_status(cmd)
+      out, status = sh_with_status(cmd)
       unless status.success?
-        raise "Couldn't install gem, run `gem install #{built_gem_path}' for more detailed output"
+        raise("Running `#{cmd}` failed with the following output:\n\n#{out}\n")
       end
       Bundler.ui.confirm "#{name} (#{version}) installed."
     end
@@ -219,7 +219,7 @@ module Bundler
       out, status = sh_with_status(cmd, &block)
       unless status.success?
         cmd = cmd.shelljoin if cmd.respond_to?(:shelljoin)
-        raise(out.empty? ? "Running `#{cmd}` failed. Run this command directly for more detailed output." : out)
+        raise("Running `#{cmd}` failed with the following output:\n\n#{out}\n")
       end
       out
     end
diff --git a/spec/bundler/bundler/gem_helper_spec.rb b/spec/bundler/bundler/gem_helper_spec.rb
index 6c3ac3e035..2c43719aa1 100644
--- a/spec/bundler/bundler/gem_helper_spec.rb
+++ b/spec/bundler/bundler/gem_helper_spec.rb
@@ -219,7 +219,7 @@ RSpec.describe Bundler::GemHelper do
             FileUtils.touch app_gem_path
             app_gem_path
           end
-          expect { subject.install_gem }.to raise_error(/Couldn't install gem/)
+          expect { subject.install_gem }.to raise_error(/Running `#{gem_bin} install #{app_gem_path}` failed/)
         end
       end
     end