diff --git a/spring-shell-core/src/main/java/org/springframework/shell/core/command/CommandHelpRenderer.java b/spring-shell-core/src/main/java/org/springframework/shell/core/command/CommandHelpRenderer.java
index 641eecd99..1fef73a06 100644
--- a/spring-shell-core/src/main/java/org/springframework/shell/core/command/CommandHelpRenderer.java
+++ b/spring-shell-core/src/main/java/org/springframework/shell/core/command/CommandHelpRenderer.java
@@ -82,7 +82,7 @@ private static void appendSynopsis(Command command, StringBuilder helpMessageBui
 		if (!options.isEmpty()) {
 			for (CommandOption option : options) {
 				helpMessageBuilder.append(" ");
-				if (isRequired(option)) {
+				if (!isRequired(option)) {
 					helpMessageBuilder.append("[");
 				}
 				if (option.longName() != null) {
@@ -92,7 +92,7 @@ private static void appendSynopsis(Command command, StringBuilder helpMessageBui
 					helpMessageBuilder.append("-").append(option.shortName());
 				}
 				helpMessageBuilder.append(" ").append(option.type().getSimpleName());
-				if (isRequired(option)) {
+				if (!isRequired(option)) {
 					helpMessageBuilder.append("]");
 				}
 			}
diff --git a/spring-shell-core/src/test/java/org/springframework/shell/core/command/CommandHelpRendererTests.java b/spring-shell-core/src/test/java/org/springframework/shell/core/command/CommandHelpRendererTests.java
index dc2d252b8..6c2f52adb 100644
--- a/spring-shell-core/src/test/java/org/springframework/shell/core/command/CommandHelpRendererTests.java
+++ b/spring-shell-core/src/test/java/org/springframework/shell/core/command/CommandHelpRendererTests.java
@@ -127,7 +127,7 @@ void testRenderHelpWithRequiredAndOptionalOptions() {
 					This command says hi to the user.
 
 				SYNOPSIS
-					hi [--name String] --times int --help
+					hi --name String [--times int] --help
 
 				OPTIONS
 					--name or -n String
@@ -173,7 +173,7 @@ void testRenderHelpWithOptionalOptionMissingDefaultValueUsesPrimitiveDefault() {
 					hi - Say hi
 
 				SYNOPSIS
-					hi --times int --help
+					hi [--times int] --help
 
 				OPTIONS
 					--times or -t int
diff --git a/spring-shell-core/src/test/java/org/springframework/shell/core/command/HelpTests.java b/spring-shell-core/src/test/java/org/springframework/shell/core/command/HelpTests.java
index 04faad565..9e722e69b 100644
--- a/spring-shell-core/src/test/java/org/springframework/shell/core/command/HelpTests.java
+++ b/spring-shell-core/src/test/java/org/springframework/shell/core/command/HelpTests.java
@@ -108,7 +108,7 @@ void testHelpMessageForCommand() throws Exception {
 					This command says hi to the user.
 
 				SYNOPSIS
-					hi [--name String] --times int --help
+					hi --name String [--times int] --help
 
 				OPTIONS
 					--name or -n String
@@ -185,7 +185,7 @@ void testHelpMessageForCommandWithArgs() throws Exception {
 					This command says hi to the user.
 
 				SYNOPSIS
-					hi --times int [(String)] [(String)] --help
+					hi [--times int] [(String)] [(String)] --help
 
 				OPTIONS
 					--times or -t int
@@ -259,7 +259,7 @@ void testHelpMessageForCommandWithVariadicArgs() throws Exception {
 					This command says hi to the user.
 
 				SYNOPSIS
-					hi --name String (Integer...) --help
+					hi [--name String] (Integer...) --help
 
 				OPTIONS
 					--name String
@@ -339,7 +339,7 @@ void testSynopsisSpaceBetweenNonRequiredOptions() throws Exception {
 					This command says hi to the user.
 
 				SYNOPSIS
-					hi [--name String] --times int --suffix String --help
+					hi --name String [--times int] [--suffix String] --help
 
 				OPTIONS
 					--name or -n String
@@ -416,7 +416,7 @@ void testHelpMessageForCommandAlias() throws Exception {
 					This command says hi to the user.
 
 				SYNOPSIS
-					hi [--name String] --times int --help
+					hi --name String [--times int] --help
 
 				OPTIONS
 					--name or -n String
@@ -478,7 +478,7 @@ void testHelpMessageForCommandWithoutHelpText() throws Exception {
 					hi - Say hi
 
 				SYNOPSIS
-					hi [--name String] --help
+					hi --name String --help
 
 				OPTIONS
 					--name or -n String