diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/Cli/CliScraperTraversalTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/Cli/CliScraperTraversalTests.cs
index bdaef2fccce..1d20f00d562 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/Cli/CliScraperTraversalTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/Cli/CliScraperTraversalTests.cs
@@ -1,3 +1,4 @@
+using Microsoft.Extensions.Logging;
 using Microsoft.Extensions.Logging.Abstractions;
 using ModularPipelines.Attributes;
 using ModularPipelines.OptionsGenerator.Models;
@@ -90,7 +91,8 @@ fake sibling [flags]
                   --value string   Supply a value
                 """,
         });
-        var scraper = new TestCobraScraper(executor);
+        var logger = new RecordingLogger();
+        var scraper = new TestCobraScraper(executor, logger);
 
         await Assert.That(scraper.DeclaresCommandGroup(emptyGroupHelp)).IsTrue();
         await Assert.That(scraper.GetSubcommands(emptyGroupHelp)).IsEmpty();
@@ -101,6 +103,25 @@ await Assert.That(commands.Select(command => command.FullCommand))
             .IsEquivalentTo(["fake sibling"]);
         await Assert.That(executor.Arguments)
             .IsEquivalentTo(["--help", "parent --help", "sibling --help"]);
+        await Assert.That(logger.Warnings).Contains(warning =>
+            warning.Exception is InvalidOperationException
+            && warning.Message.Contains("Failed to validate subcommand discovery: fake parent"));
+    }
+
+    [Test]
+    public async Task SharedTraversal_Detects_Command_On_Second_Usage_Line()
+    {
+        const string helpText = """
+            Usage:
+              fake [flags]
+              fake <command> [flags]
+
+            Available Commands:
+            """;
+        var scraper = new TestCobraScraper(new StubExecutor(
+            new Dictionary<string, string>(StringComparer.OrdinalIgnoreCase)));
+
+        await Assert.That(scraper.DeclaresCommandGroup(helpText)).IsTrue();
     }
 
     [Test]
@@ -409,11 +430,11 @@ private static async Task<IReadOnlyList<CliCommandDefinition>> ScrapeAsync(ICliS
 
     private sealed class TestCobraScraper : CobraCliScraper
     {
-        public TestCobraScraper(ICliCommandExecutor executor)
+        public TestCobraScraper(ICliCommandExecutor executor, ILogger? logger = null)
             : base(
                 executor,
                 new HelpTextCache(NullLogger<HelpTextCache>.Instance),
-                NullLogger<TestCobraScraper>.Instance)
+                logger ?? NullLogger<TestCobraScraper>.Instance)
         {
         }
 
@@ -438,6 +459,29 @@ public TestCobraScraper(ICliCommandExecutor executor)
         public IReadOnlyList<string> GetSubcommands(string helpText) => ExtractSubcommands(helpText).ToList();
     }
 
+    private sealed class RecordingLogger : ILogger
+    {
+        public List<(string Message, Exception? Exception)> Warnings { get; } = [];
+
+        public IDisposable? BeginScope<TState>(TState state)
+            where TState : notnull => null;
+
+        public bool IsEnabled(LogLevel logLevel) => true;
+
+        public void Log<TState>(
+            LogLevel logLevel,
+            EventId eventId,
+            TState state,
+            Exception? exception,
+            Func<TState, Exception?, string> formatter)
+        {
+            if (logLevel == LogLevel.Warning)
+            {
+                Warnings.Add((formatter(state, exception), exception));
+            }
+        }
+    }
+
     private sealed class TestPodmanCliScraper(ICliCommandExecutor executor)
         : PodmanCliScraper(
             executor,
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/CosignCliScraperTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/CosignCliScraperTests.cs
index 03b964c17a3..8a63d64d782 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/CosignCliScraperTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/CosignCliScraperTests.cs
@@ -33,6 +33,54 @@ await Assert.That(subcommands).IsEquivalentTo(
             ["attest", "sign", "verify", "verify-blob-attestation"]);
     }
 
+    [Test]
+    public async Task Extracts_Cosign_V3_All_Word_Command_Table()
+    {
+        const string helpText = """
+            Tools for interacting with a Sigstore protobuf bundle
+
+            Usage:
+            cosign bundle [command]
+
+            Available Commands:
+            create      Create a Sigstore protobuf bundle
+            inspect     Inspect a Sigstore protobuf bundle
+            upgrade     Upgrade a Sigstore protobuf bundle
+
+            Flags:
+                -h, --help=false:
+            """;
+
+        var subcommands = new TestCosignCliScraper().Extract(helpText);
+
+        await Assert.That(subcommands).IsEquivalentTo(["create", "inspect", "upgrade"]);
+    }
+
+    [Test]
+    [Arguments("signing-config", "signing config")]
+    [Arguments("trusted-root", "trusted root")]
+    public async Task Extracts_Cosign_V3_Single_Row_All_Word_Command_Tables(
+        string commandGroup,
+        string description)
+    {
+        var helpText = $"""
+            Tools for interacting with a Sigstore protobuf {description}
+
+            Usage:
+            cosign {commandGroup} [command]
+
+            Available Commands:
+            create      Create a Sigstore protobuf {description}
+
+            Flags:
+                -h, --help=false:
+            """;
+
+        var subcommands = new TestCosignCliScraper().Extract(helpText);
+
+        await Assert.That(subcommands).IsEquivalentTo(["create"]);
+    }
+
     [Test]
     public async Task Parses_Cosign_V3_Default_Value_Flag_Format()
     {
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/PulumiCliScraperTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/PulumiCliScraperTests.cs
index c1c5b5798ed..9b9ba843d9f 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/PulumiCliScraperTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/PulumiCliScraperTests.cs
@@ -7,6 +7,22 @@ namespace ModularPipelines.OptionsGenerator.Tests.Scrapers;
 
 public class PulumiCliScraperTests
 {
+    [Test]
+    public async Task Env_Run_Command_Operand_Is_Not_A_Command_Group()
+    {
+        const string helpText = """
+            Run a command within an environment.
+
+            Usage:
+              pulumi env run <environment-name> -- <command> [args]
+
+            Run a command
+              The command receives the environment variables.
+            """;
+
+        await Assert.That(new TestPulumiCliScraper().DeclaresCommandGroup(helpText)).IsFalse();
+    }
+
     [Test]
     public async Task Env_Get_Preserves_Required_Environment_And_Optional_Path()
     {
@@ -91,5 +107,7 @@ public TestPulumiCliScraper()
             var usage = ParseUsageSynopsis(commandPath, helpText);
             return ParseCommandAsync(commandPath, helpText, usage, CancellationToken.None);
         }
+
+        public bool DeclaresCommandGroup(string helpText) => HelpDeclaresCommandGroup(helpText);
     }
 }
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/SnykCliScraperTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/SnykCliScraperTests.cs
index 7aa16bba2c6..16a62cda80a 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/SnykCliScraperTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/SnykCliScraperTests.cs
@@ -56,18 +56,26 @@ public async Task Sbom_Help_Exposes_Test_Subcommand()
     }
 
     [Test]
-    public async Task Command_Help_Does_Not_Treat_Examples_As_Subcommands()
+    public async Task Command_Help_Does_Not_Treat_Examples_As_A_Command_Group()
     {
         const string helpText = """
-            Test a project for vulnerabilities.
-
+            Test
             Usage
               snyk test [<OPTIONS>]
 
-            See code test, container test, and iac test for related commands.
+            Options for build tools
+              The format is snyk <command> -- [<context-specific_options>]
+
+            Examples for the snyk test command
+              $ snyk test
             """;
 
-        await Assert.That(new TestSnykCliScraper().Extract(helpText)).IsEmpty();
+        var scraper = new TestSnykCliScraper();
+        using (Assert.Multiple())
+        {
+            await Assert.That(scraper.Extract(helpText)).IsEmpty();
+            await Assert.That(scraper.DeclaresCommandGroup(helpText)).IsFalse();
+        }
     }
 
     [Test]
@@ -396,6 +404,8 @@ public TestSnykCliScraper()
 
         public IReadOnlyList<string> Extract(string helpText) => ExtractSubcommands(helpText).ToList();
 
+        public bool DeclaresCommandGroup(string helpText) => HelpDeclaresCommandGroup(helpText);
+
         public bool CanGenerate(string helpText) => HasOptions(helpText);
 
         public Task<CliCommandDefinition?> Parse(string[] commandPath, string helpText) =>
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
index c0e7f8171d1..cee253687e7 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
@@ -997,11 +997,11 @@ private static void ValidateArgumentGroups(CliCommandDefinition command)
     protected static partial Regex OptionLinePattern();
 
     [GeneratedRegex(
-        @"^[ \t]*(?:Usage:?[ \t]*(?:\r?\n[ \t]*)?)?[^\r\n]*(?:<command>|\[command\])[^\r\n]*\r?$",
+        @"^[ \t]*Usage:?[ \t]*(?:[^\r\n]*\r?\n[ \t]*){0,2}[^\r\n]*(?:<command>|\[command\])[^\r\n]*\r?$",
         RegexOptions.IgnoreCase | RegexOptions.Multiline)]
     private static partial Regex CommandGroupUsagePattern();
 
-    [GeneratedRegex(@"^[ \t]*[A-Z][A-Z0-9 _/-]*COMMANDS?:?[ \t]*\r?$", RegexOptions.IgnoreCase | RegexOptions.Multiline)]
+    [GeneratedRegex(@"^[ \t]*[A-Z][A-Z0-9 _/-]*COMMANDS:?[ \t]*\r?$", RegexOptions.IgnoreCase | RegexOptions.Multiline)]
     private static partial Regex CommandSectionHeadingPattern();
 
     [GeneratedRegex(
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CobraCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CobraCliScraper.cs
index 0038d2cc372..cb083b249fb 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CobraCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CobraCliScraper.cs
@@ -945,7 +945,7 @@ private static string DetermineCSharpType(
     /// Matches section headers like "Flags:", "Usage:", etc.
     /// </summary>
     [GeneratedRegex(
-        @"^(?:[A-Z][\w\s]*:|[A-Z][\w ]*(?:Commands|Flags|Options|Usage|Examples))\s*$",
+        @"^(?:[A-Z][\w \t]*:|[A-Z][\w ]*(?:Commands|Flags|Options|Usage|Examples))\s*$",
         RegexOptions.IgnoreCase | RegexOptions.Multiline)]
     private static partial Regex SectionHeaderPattern();