diff --git a/lib/rubygems/commands/exec_command.rb b/lib/rubygems/commands/exec_command.rb
index b46e843911..ac04efa578 100644
--- a/lib/rubygems/commands/exec_command.rb
+++ b/lib/rubygems/commands/exec_command.rb
@@ -34,6 +34,7 @@ class Gem::Commands::ExecCommand < Gem::Command
     "--version '#{Gem::Requirement.default}'"
   end
 
+  # TODO(segiddins): add a proper description!
   def description # :nodoc:
     <<-EOF
     EOF
@@ -76,7 +77,22 @@ class Gem::Commands::ExecCommand < Gem::Command
 
     options[:executable], gem_version = extract_gem_name_and_version(options[:args].shift)
     options[:gem_name] ||= options[:executable]
-    options[:version] = gem_version if gem_version
+
+    if gem_version
+      if options[:version].none?
+        options[:version] = Gem::Requirement.new(gem_version)
+      else
+        options[:version].concat [gem_version]
+      end
+    end
+
+    if options[:prerelease] && !options[:version].prerelease?
+      if options[:version].none?
+        options[:version] = Gem::Requirement.default_prerelease
+      else
+        options[:version].concat [Gem::Requirement.default_prerelease]
+      end
+    end
   end
 
   def check_executable
@@ -100,7 +116,7 @@ class Gem::Commands::ExecCommand < Gem::Command
   def install_if_needed
     activate!
   rescue Gem::MissingSpecError
-    verbose "#{dependency_to_s} not available locally"
+    verbose "#{Gem::Dependency.new(options[:gem_name], options[:version])} not available locally, installing from remote"
     install
     activate!
   end
@@ -133,6 +149,8 @@ class Gem::Commands::ExecCommand < Gem::Command
   def activate!
     gem(options[:gem_name], options[:version])
     Gem.finish_resolve
+
+    verbose "activated #{options[:gem_name]} (#{Gem.loaded_specs[options[:gem_name]].version})"
   end
 
   def load!
diff --git a/test/rubygems/test_gem_commands_exec_command.rb b/test/rubygems/test_gem_commands_exec_command.rb
new file mode 100644
index 0000000000..85cc786a02
--- /dev/null
+++ b/test/rubygems/test_gem_commands_exec_command.rb
@@ -0,0 +1,463 @@
+# frozen_string_literal: true
+require_relative "helper"
+require "rubygems/commands/exec_command"
+
+class TestGemCommandsExecCommand < Gem::TestCase
+  def setup
+    super
+    common_installer_setup
+
+    @cmd = Gem::Commands::ExecCommand.new
+
+    @orig_args = Gem::Command.build_args
+
+    common_installer_setup
+  end
+
+  def teardown
+    super
+
+    common_installer_teardown
+
+    Gem::Command.build_args = @orig_args
+  end
+
+  def test_error_with_no_arguments
+    e = assert_raise Gem::CommandLineError do
+      @cmd.invoke
+    end
+    assert_equal "Please specify an executable to run (e.g. gem exec COMMAND)",
+      e.message
+  end
+
+  def test_error_with_no_executable
+    e = assert_raise Gem::CommandLineError do
+      @cmd.invoke "--verbose", "--gem", "GEM", "--version", "< 10", "--conservative"
+    end
+    assert_equal "Please specify an executable to run (e.g. gem exec COMMAND)",
+      e.message
+  end
+
+  def test_full_option_parsing
+    @cmd.when_invoked do |options|
+      assert_equal options, {
+        args: ["install", "--no-color", "--help", "--verbose"],
+        executable: "pod",
+        :explicit_prerelease => false,
+        gem_name: "cocoapods",
+        prerelease: false,
+        :version => Gem::Requirement.new(["> 1", "< 1.3"]),
+        build_args: nil,
+      }
+    end
+    @cmd.invoke "--gem", "cocoapods", "-v", "> 1", "--version", "< 1.3", "--verbose", "--", "pod", "install", "--no-color", "--help", "--verbose"
+ end
+
+  def test_single_arg_parsing
+    @cmd.when_invoked do |options|
+      assert_equal options, {
+        args: [],
+        executable: "rails",
+        gem_name: "rails",
+        :version => Gem::Requirement.new([">= 0"]),
+        build_args: nil,
+      }
+    end
+    @cmd.invoke "rails"
+  end
+
+  def test_single_arg_parsing_with_version
+    @cmd.when_invoked do |options|
+      assert_equal options, {
+        args: [],
+        executable: "rails",
+        gem_name: "rails",
+        :version => Gem::Requirement.new(["= 7.1"]),
+        build_args: nil,
+      }
+    end
+    @cmd.invoke "rails:7.1"
+  end
+
+  def test_gem_without_executable
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 2
+    end
+
+    util_clear_gems
+
+    use_ui @ui do
+      e = assert_raise Gem::MockGemUi::TermError, @ui.error do
+        @cmd.invoke "a:2"
+      end
+      assert_equal 1, e.exit_code
+      assert_equal "ERROR:  Failed to load executable `a`, are you sure the gem `a` contains it?\n", @ui.error
+    end
+  end
+
+  def test_gem_with_executable
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 2 do |s|
+        s.executables = %w[a]
+        s.files = %w[bin/a lib/a.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin a]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump}"
+        end
+      end
+    end
+
+    util_clear_gems
+
+    use_ui @ui do
+      @cmd.invoke "a:2"
+      assert_equal "a-2\n", @ui.output
+    end
+  end
+
+  def test_gem_with_other_executable_name
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 2 do |s|
+        s.executables = %w[foo]
+        s.files = %w[bin/foo lib/a.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin foo]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump}"
+        end
+      end
+    end
+
+    util_clear_gems
+
+    use_ui @ui do
+      @cmd.invoke "a:2"
+      assert_equal "a-2\n", @ui.output
+    end
+  end
+
+  def test_gem_with_executable_error
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 2 do |s|
+        s.executables = %w[foo]
+        s.files = %w[bin/foo lib/a.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin foo]) do |f|
+          f << "raise #{s.original_name.dump}"
+        end
+      end
+    end
+
+    util_clear_gems
+
+    use_ui @ui do
+      e = assert_raise RuntimeError do
+        @cmd.invoke "a:2"
+      end
+      assert_equal "a-2", e.message
+      assert_empty @ui.error
+    end
+  end
+
+  def test_gem_with_multiple_executables_one_match
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 2 do |s|
+        s.executables = %w[foo a]
+        s.files = %w[bin/foo bin/a lib/a.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin foo]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+
+        write_file File.join(*%W[gems #{s.original_name}      bin a]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+      end
+    end
+
+    util_clear_gems
+
+    use_ui @ui do
+      @cmd.invoke "a:2"
+      assert_equal "a-2 a\n", @ui.output
+    end
+  end
+
+  def test_gem_with_multiple_executables_no_match
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 2 do |s|
+        s.executables = %w[foo bar]
+        s.files = %w[bin/foo bin/bar lib/a.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin foo]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+
+        write_file File.join(*%W[gems #{s.original_name}      bin bar]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+      end
+    end
+
+    util_clear_gems
+
+    use_ui @ui do
+      @cmd.invoke "a:2"
+      assert_equal "a-2 foo\n", @ui.output
+    end
+  end
+
+  def test_gem_dependency_contains_executable
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 2 do |s|
+        s.executables = %w[]
+        s.files = %w[lib/a.rb]
+
+        s.add_dependency "b"
+      end
+
+      fetcher.gem "b", 2 do |s|
+        s.executables = %w[a]
+        s.files = %w[bin/a lib/b.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin a]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+      end
+    end
+
+    util_clear_gems
+
+    use_ui @ui do
+      @cmd.invoke "a:2"
+      assert_equal "b-2 a\n", @ui.output
+    end
+  end
+
+  def test_gem_dependency_contains_other_executable
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 2 do |s|
+        s.executables = %w[]
+        s.files = %w[lib/a.rb]
+
+        s.add_dependency "b"
+      end
+
+      fetcher.gem "b", 2 do |s|
+        s.executables = %w[foo]
+        s.files = %w[bin/foo lib/b.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin foo]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+      end
+    end
+
+    util_clear_gems
+
+    use_ui @ui do
+      e = assert_raise Gem::MockGemUi::TermError do
+        @cmd.invoke "a:2"
+      end
+      assert_equal 1, e.exit_code
+      assert_equal <<~ERR, @ui.error
+        ERROR:  Failed to load executable `a`, are you sure the gem `a` contains it?
+      ERR
+    end
+  end
+
+  def test_other_gem_contains_executable
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 2 do |s|
+        s.executables = %w[]
+        s.files = %w[lib/a.rb]
+      end
+
+      fetcher.gem "b", 2 do |s|
+        s.executables = %w[a]
+        s.files = %w[bin/a lib/b.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin foo]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+      end
+    end
+
+    util_clear_gems
+
+    use_ui @ui do
+      e = assert_raise Gem::MockGemUi::TermError do
+        @cmd.invoke "a:2"
+      end
+      assert_equal 1, e.exit_code
+      assert_equal <<~ERR, @ui.error
+        ERROR:  Failed to load executable `a`, are you sure the gem `a` contains it?
+      ERR
+    end
+  end
+
+  def test_missing_gem
+    spec_fetcher do |fetcher|
+    end
+
+    use_ui @ui do
+      e = assert_raise Gem::MockGemUi::TermError do
+        @cmd.invoke "a"
+      end
+      assert_equal 2, e.exit_code
+      assert_equal <<~ERR, @ui.error
+        ERROR:  Could not find a valid gem 'a' (>= 0) in any repository
+      ERR
+    end
+  end
+
+  def test_version_mismatch
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 1
+    end
+
+    util_clear_gems
+
+    use_ui @ui do
+      e = assert_raise Gem::MockGemUi::TermError do
+        @cmd.invoke "a:2"
+      end
+      assert_equal 2, e.exit_code
+      assert_equal <<~ERR, @ui.error
+        ERROR:  Could not find a valid gem 'a' (= 2) in any repository
+        ERROR:  Possible alternatives: a
+      ERR
+    end
+  end
+
+  def test_pre_argument
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 1 do |s|
+        s.executables = %w[foo]
+        s.files = %w[bin/foo lib/a.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin foo]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+      end
+      fetcher.gem "a", "1.1.a" do |s|
+        s.executables = %w[foo ]
+        s.files = %w[bin/foo lib/a.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin foo]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+      end
+    end
+
+    util_clear_gems
+
+    use_ui @ui do
+      @cmd.invoke "--pre", "a"
+      assert_equal "a-1.1.a foo\n", @ui.output
+    end
+  end
+
+  def test_pre_version_option
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 1 do |s|
+        s.executables = %w[foo]
+        s.files = %w[bin/foo lib/a.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin foo]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+      end
+      fetcher.gem "a", "1.1.a" do |s|
+        s.executables = %w[foo ]
+        s.files = %w[bin/foo lib/a.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin foo]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+      end
+    end
+
+    util_clear_gems
+
+    use_ui @ui do
+      @cmd.invoke "-v", ">= 0.a", "a"
+      assert_equal "a-1.1.a foo\n", @ui.output
+    end
+  end
+
+  def test_conservative_missing_gem
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 1 do |s|
+        s.executables = %w[foo]
+        s.files = %w[bin/foo lib/a.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin foo]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+      end
+    end
+
+    util_clear_gems
+
+    use_ui @ui do
+      e = assert_raise Gem::MockGemUi::TermError do
+        @cmd.invoke "--verbose", "--conservative", "a:2"
+      end
+      assert_equal 2, e.exit_code
+      assert_include @ui.output, "a (= 2) not available locally"
+      assert_equal <<~ERROR, @ui.error
+        ERROR:  Could not find a valid gem 'a' (= 2) in any repository
+        ERROR:  Possible alternatives: a
+      ERROR
+    end
+  end
+
+  def test_conservative
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 1 do |s|
+        s.executables = %w[foo]
+        s.files = %w[bin/foo lib/a.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin foo]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+      end
+    end
+
+    util_clear_gems
+
+    use_ui @ui do
+      @cmd.invoke "--verbose", "--conservative", "a"
+      assert_include @ui.output, "a (>= 0) not available locally"
+      assert_include @ui.output, "a-1 foo"
+    end
+
+    @ui.outs.truncate(0)
+
+    spec_fetcher do |fetcher|
+      fetcher.gem "a", 1 do |s|
+        s.executables = %w[foo]
+        s.files = %w[bin/foo lib/a.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin foo]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+      end
+
+      fetcher.gem "a", 2 do |s|
+        s.executables = %w[foo]
+        s.files = %w[bin/foo lib/a.rb]
+
+        write_file File.join(*%W[gems #{s.original_name}      bin foo]) do |f|
+          f << "Gem.ui.say #{s.original_name.dump} + ' ' + File.basename(__FILE__)"
+        end
+      end
+    end
+
+    use_ui @ui do
+      @cmd.invoke "--verbose", "--conservative", "a"
+      assert_not_include @ui.output, "a (>= 0) not available locally"
+      assert_include @ui.output, "a-1 foo"
+    end
+  end
+end