diff --git a/src/main/java/picocli/CommandLine.java b/src/main/java/picocli/CommandLine.java
index 88d7fe1bd..d5f048a85 100644
--- a/src/main/java/picocli/CommandLine.java
+++ b/src/main/java/picocli/CommandLine.java
@@ -15334,9 +15334,29 @@ static class AutoHelpMixin {
     @Command(name = "help", header = "Display help information about the specified command.",
             synopsisHeading = "%nUsage: ", helpCommand = true,
             description = {"%nWhen no COMMAND is given, the usage help for the main command is displayed.",
-                    "If a COMMAND is specified, the help for that command is shown.%n"})
+                    "If a COMMAND is specified, the help for that command is shown.%n"},
+            preprocessor = HelpCommand.HelpPreprocessor.class)
     public static final class HelpCommand implements IHelpCommandInitializable, IHelpCommandInitializable2, Runnable {
 
+        /** Custom {@link IParameterPreprocessor} to greedily consume the {@link #commands} parameter
+         * when it matches a command, before repeatable subcommand processing consumes it instead.
+         */
+        private static class HelpPreprocessor implements IParameterPreprocessor {
+            @Override
+            public boolean preprocess(Stack<String> args, CommandSpec commandSpec, ArgSpec argSpec, Map<String, Object> info) {
+                if (!args.isEmpty()) {
+                    final String arg = args.peek();
+                    if (commandSpec.parent().subcommands().get(arg) != null) {
+                        final HelpCommand help = (HelpCommand) commandSpec.userObject();
+                        help.commands = arg;
+                        args.pop();
+                        return true;
+                    }
+                }
+                return false;
+            }
+        }
+
         @Option(names = {"-h", "--help"}, usageHelp = true, descriptionKey = "helpCommand.help",
                 description = "Show usage help for the help command and exit.")
         private boolean helpRequested;
diff --git a/src/test/java/picocli/Issue2123RepeatableVsHelpTest.java b/src/test/java/picocli/Issue2123RepeatableVsHelpTest.java
new file mode 100644
index 000000000..f18cd04a1
--- /dev/null
+++ b/src/test/java/picocli/Issue2123RepeatableVsHelpTest.java
@@ -0,0 +1,79 @@
+package picocli;
+
+import org.junit.Test;
+import picocli.CommandLine.Command;
+import picocli.CommandLine.HelpCommand;
+
+import java.io.PrintWriter;
+import java.io.StringWriter;
+
+import static org.hamcrest.CoreMatchers.containsString;
+import static org.hamcrest.CoreMatchers.equalTo;
+import static org.hamcrest.MatcherAssert.assertThat;
+import static org.hamcrest.object.HasToString.hasToString;
+import static picocli.CommandLine.ExitCode.OK;
+
+public class Issue2123RepeatableVsHelpTest {
+
+    @Command(name = "tool", mixinStandardHelpOptions = true, subcommandsRepeatable = true)
+    static class Tool {
+    }
+
+    @Command(name = "sub", mixinStandardHelpOptions = true)
+    static class Subcommand implements Runnable {
+        @Override
+        public void run() {
+        }
+    }
+
+    private final StringWriter out = new StringWriter();
+
+    private final CommandLine commandLine = new CommandLine(new Tool())
+            .addSubcommand(new Subcommand())
+            .addSubcommand(new HelpCommand())
+            .setOut(new PrintWriter(out))
+            .setErr(new PrintWriter(out));
+
+    @Test
+    public void testToolHelpShowsToolUsage() {
+        final int result = commandLine.execute("help");
+
+        assertThat(out, hasToString(containsString("Usage: tool [-hV]")));
+        assertThat(result, equalTo(OK));
+    }
+
+    @Test
+    public void testToolHelpSubShowsToolSubUsage() {
+        final int result = commandLine.execute("help", "sub");
+
+        assertThat(out, hasToString(containsString("Usage: tool sub")));
+        assertThat(result, equalTo(OK));
+    }
+
+    @Test
+    public void testToolDashHSubShowsToolSubUsage() {
+        final int result = commandLine.execute("-h", "sub");
+
+        assertThat(out, hasToString(containsString("Usage: tool [-hV]")));
+        assertThat(result, equalTo(OK));
+    }
+
+    @Test
+    public void testToolSubHelpShowsToolSubUsage() {
+        final int result = commandLine.execute("sub", "help");
+
+        // With subcommandsRepeatable = false, "help" wasn't allowed so returns USAGE showing usage for "sub"
+        // With subcommandsRepeatable = true, "help" is processed alone so returns OK showing usage for "tool"
+        // It would be helpful to note that "sub" is the latest command in use so return OK showing usage for "sub"
+        assertThat(out, hasToString(containsString("Usage: tool [-hV]")));
+        assertThat(result, equalTo(OK));
+    }
+
+    @Test
+    public void testToolSubDashHShowsToolSubUsage() {
+        final int result = commandLine.execute("sub", "-h");
+
+        assertThat(out, hasToString(containsString("Usage: tool sub")));
+        assertThat(result, equalTo(OK));
+    }
+}