diff --git a/lib/irb.rb b/lib/irb.rb
index 6ac0c49f5..9e11c874d 100644
--- a/lib/irb.rb
+++ b/lib/irb.rb
@@ -1036,6 +1036,9 @@ def eval_input
           rescue Interrupt, Exception => exc
             handle_exception(exc)
             @context.workspace.local_variable_set(:_, exc)
+            if statement.warning
+              warn statement.warning
+            end
           end
         end
       end
@@ -1119,22 +1122,28 @@ def each_top_level_statement
 
     def build_statement(code)
       code.force_encoding(@context.io.encoding) unless code.frozen?
-      command_match = COMMAND_REGEXP.match(code.strip)
-
-      if command_match
-        command_or_alias = command_match[:cmd_name]
-        arg = [command_match[:cmd_arg], command_match[:cmd_flag]].compact.join(' ')
-        # Transform a non-identifier alias (@, $) or keywords (next, break)
-        command_name = @context.command_aliases[command_or_alias.to_sym]
-        command = command_name || command_or_alias
-        command_class = ExtendCommandBundle.load_command(command)
-      end
 
-      if command_class
-        Statement::Command.new(code, command, arg, command_class)
+      possible_command_or_alias = code.split.first
+
+      possible_command_name = @context.command_aliases[possible_command_or_alias.to_sym]
+      possible_command_name = possible_command_name || possible_command_or_alias
+      command_class = ExtendCommandBundle.load_command(possible_command_name)
+
+      command_syntax_match = COMMAND_REGEXP.match(code.strip)
+
+      if command_class && command_syntax_match
+        arg = [command_syntax_match[:cmd_arg], command_syntax_match[:cmd_flag]].compact.join(' ')
+        Statement::Command.new(code, possible_command_name, arg, command_class)
       else
+        if command_class
+          warning_msg = <<~MSG
+            The input `#{code.strip}` was recognised as a Ruby expression, but it matched the name of the `#{possible_command_name}` command.
+            If you intended to run it as a command, please check if the syntax is correct.
+          MSG
+        end
+
         is_assignment_expression = @scanner.assignment_expression?(code, local_variables: @context.local_variables)
-        Statement::Expression.new(code, is_assignment_expression)
+        Statement::Expression.new(code, is_assignment_expression, warning: warning_msg)
       end
     end
 
diff --git a/lib/irb/statement.rb b/lib/irb/statement.rb
index b12110600..4a7f4a7dc 100644
--- a/lib/irb/statement.rb
+++ b/lib/irb/statement.rb
@@ -2,7 +2,7 @@
 
 module IRB
   class Statement
-    attr_reader :code
+    attr_reader :code, :warning
 
     def is_assignment?
       raise NotImplementedError
@@ -21,9 +21,10 @@ def evaluable_code
     end
 
     class Expression < Statement
-      def initialize(code, is_assignment)
+      def initialize(code, is_assignment, warning: nil)
         @code = code
         @is_assignment = is_assignment
+        @warning = warning
       end
 
       def suppresses_echo?
@@ -66,6 +67,9 @@ def should_be_handled_by_debugger?
       end
 
       def evaluable_code
+        # Because measure command is used as a method, we need to treat it differently
+        return @code if @command == "measure"
+
         # Hook command-specific transformation to return valid Ruby code
         if @command_class.respond_to?(:transform_args)
           arg = @command_class.transform_args(@arg)
diff --git a/test/irb/test_irb.rb b/test/irb/test_irb.rb
index 499889067..d0e73036b 100644
--- a/test/irb/test_irb.rb
+++ b/test/irb/test_irb.rb
@@ -58,6 +58,51 @@ def test_symbol_aliases_dont_affect_ruby_syntax
       assert_include output, "=> \"It's a foo\""
       assert_include output, "=> \"It's a bar\""
     end
+
+    def test_errored_input_that_match_a_command_raises_a_syntax_check_reminder
+      write_ruby <<~'RUBY'
+        class Foo
+        end
+        binding.irb
+      RUBY
+
+      errored_output = run_ruby_file do
+        type "show_source Foo bar"
+        type "exit!"
+      end
+
+      # The input should cause an error as it's evaluated as Ruby code
+      assert_include errored_output, 'undefined local variable or method `bar\''
+
+      # Because it starts with the name of a command, it should also raise a warning
+      assert_include errored_output,
+        'The input `show_source Foo bar` was recognised as a Ruby expression, but it matched the name of the `show_source` command.'
+      assert_include errored_output,
+        'If you intended to run it as a command, please check if the syntax is correct.'
+
+      output = run_ruby_file do
+        type "show_source Foo"
+        type "exit!"
+      end
+
+      # The input should work as a command
+      assert_include output, "From: #{@ruby_file.path}:1"
+      # Therefore, it should not raise a warning
+      assert_not_include output,
+        'If you intended to run it as a command, please check if the syntax is correct.'
+
+      output = run_ruby_file do
+        type "show_source = 'foo'"
+        type "show_source + 'bar'"
+        type "exit!"
+      end
+
+      # The input should work as Ruby code
+      assert_include(output, '=> "foobar"')
+      # Therefore, it should not raise a warning either
+      assert_not_include output,
+        'If you intended to run it as a command, please check if the syntax is correct.'
+    end
   end
 
   class IrbIOConfigurationTest < TestCase