From 6871f717f88bdb96067672b3fbda4ae46d9e5f4d Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Sun, 23 Aug 2026 19:51:46 +0100
Subject: [PATCH 01/15] fix(generator): model repeatable options

Derive collection shapes from shared repeatability markers across Terraform, Pip, Packer, and Snyk adapters.

Fixes #3988
---
 .../Scrapers/RepeatableOptionAdapterTests.cs  | 133 ++++++++++++++++++
 .../Scrapers/Cli/PackerCliScraper.cs          |   5 +-
 .../Scrapers/Cli/PipCliScraper.cs             |   5 +-
 .../Scrapers/Cli/SnykCliScraper.cs            |  10 +-
 .../Scrapers/Cli/TerraformCliScraper.cs       |   6 +-
 5 files changed, 152 insertions(+), 7 deletions(-)
 create mode 100644 tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs

diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
new file mode 100644
index 00000000000..8af52d0a98f
--- /dev/null
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
@@ -0,0 +1,133 @@
+using Microsoft.Extensions.Logging.Abstractions;
+using ModularPipelines.OptionsGenerator.Models;
+using ModularPipelines.OptionsGenerator.Scrapers.Cli;
+using ModularPipelines.OptionsGenerator.TypeDetection;
+
+namespace ModularPipelines.OptionsGenerator.Tests.Scrapers;
+
+public class RepeatableOptionAdapterTests
+{
+    private static ICliCommandExecutor Executor { get; } =
+        new ProcessCliCommandExecutor(NullLogger<ProcessCliCommandExecutor>.Instance);
+
+    private static IHelpTextCache Cache { get; } =
+        new HelpTextCache(NullLogger<HelpTextCache>.Instance);
+
+    [Test]
+    public async Task Terraform_Recognizes_Multiple_Times_Prose()
+    {
+        const string helpText = """
+            Usage: terraform apply [options]
+
+            Options:
+              -var-file=path  Set variables from a file. This flag can be used multiple times.
+            """;
+        var command = await new TestTerraformCliScraper().Parse(["terraform", "apply"], helpText);
+
+        await AssertRepeatable(command, "-var-file");
+    }
+
+    [Test]
+    public async Task Pip_Recognizes_Multiline_Multiple_Times_Prose()
+    {
+        const string helpText = """
+            Usage: pip freeze [options]
+
+            General Options:
+              -r, --requirement <file>  Install from the given requirements file.
+                                        This option can be used multiple times.
+            """;
+        var command = await new TestPipCliScraper().Parse(["pip", "freeze"], helpText);
+
+        await AssertRepeatable(command, "--requirement");
+    }
+
+    [Test]
+    public async Task Packer_Recognizes_Repeatable_Prose()
+    {
+        const string helpText = """
+            Usage: packer build [options]
+
+            Options:
+              -var-file=path  Set a variable file; repeatable for additional files.
+            """;
+        var command = await new TestPackerCliScraper().Parse(["packer", "build"], helpText);
+
+        await AssertRepeatable(command, "--var-file");
+    }
+
+    [Test]
+    public async Task Snyk_Recognizes_Repeated_Prose()
+    {
+        const string helpText = """
+            Usage: snyk monitor [<OPTIONS>]
+
+            Options
+              --project-environment=<ENVIRONMENT>
+                  Set the project environment. Can be repeated.
+            """;
+        var command = await new TestSnykCliScraper().Parse(["snyk", "monitor"], helpText);
+
+        await AssertRepeatable(command, "--project-environment");
+    }
+
+    private static async Task AssertRepeatable(
+        CliCommandDefinition? command,
+        string switchName)
+    {
+        var option = command!.Options.Single(item => item.SwitchName == switchName);
+        using (Assert.Multiple())
+        {
+            await Assert.That(option.AcceptsMultipleValues).IsTrue();
+            await Assert.That(option.CSharpType).IsEqualTo("IEnumerable<string>?");
+        }
+    }
+
+    private sealed class TestTerraformCliScraper()
+        : TerraformCliScraper(
+            RepeatableOptionAdapterTests.Executor,
+            RepeatableOptionAdapterTests.Cache,
+            NullLogger<TerraformCliScraper>.Instance)
+    {
+        public Task<CliCommandDefinition?> Parse(string[] commandPath, string helpText) =>
+            ParseCommandAsync(
+                commandPath,
+                helpText,
+                ParseUsageSynopsis(commandPath, helpText),
+                CancellationToken.None);
+    }
+
+    private sealed class TestPipCliScraper()
+        : PipCliScraper(
+            RepeatableOptionAdapterTests.Executor,
+            RepeatableOptionAdapterTests.Cache,
+            NullLogger<PipCliScraper>.Instance)
+    {
+        public Task<CliCommandDefinition?> Parse(string[] commandPath, string helpText) =>
+            ParseCommandAsync(commandPath, helpText, CancellationToken.None);
+    }
+
+    private sealed class TestPackerCliScraper()
+        : PackerCliScraper(
+            RepeatableOptionAdapterTests.Executor,
+            RepeatableOptionAdapterTests.Cache,
+            NullLogger<PackerCliScraper>.Instance)
+    {
+        public Task<CliCommandDefinition?> Parse(string[] commandPath, string helpText) =>
+            ParseCommandAsync(
+                commandPath,
+                helpText,
+                ParseUsageSynopsis(commandPath, helpText),
+                CancellationToken.None);
+    }
+
+    private sealed class TestSnykCliScraper()
+        : SnykCliScraper(
+            RepeatableOptionAdapterTests.Executor,
+            RepeatableOptionAdapterTests.Cache,
+            NullLogger<SnykCliScraper>.Instance)
+    {
+        public Task<CliCommandDefinition?> Parse(string[] commandPath, string helpText) =>
+            ParseCommandAsync(commandPath, helpText, CancellationToken.None);
+    }
+}
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
index a9e9d488032..fa5ed43111b 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
@@ -212,7 +212,8 @@ private List<CliOptionDefinition> ParseOptions(string helpText)
             }
 
             var isFlag = string.IsNullOrEmpty(valueHint) || valueHint.Contains("true") || valueHint.Contains("false");
-            var csharpType = isFlag ? "bool?" : "string?";
+            var acceptsMultipleValues = !isFlag && DescriptionDeclaresRepeatableOption(description);
+            var csharpType = acceptsMultipleValues ? "IEnumerable<string>?" : isFlag ? "bool?" : "string?";
 
             options.Add(new CliOptionDefinition
             {
@@ -223,7 +224,7 @@ private List<CliOptionDefinition> ParseOptions(string helpText)
                 Description = description,
                 IsFlag = isFlag,
                 IsRequired = false,
-                AcceptsMultipleValues = false,
+                AcceptsMultipleValues = acceptsMultipleValues,
                 IsKeyValue = false,
                 IsNumeric = false,
                 ValueSeparator = "=",
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PipCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PipCliScraper.cs
index b5b1e7432ed..a62537fc38b 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PipCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PipCliScraper.cs
@@ -274,7 +274,8 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
                 }
 
                 var isFlag = string.IsNullOrEmpty(valueHint) && IsBooleanOption(longForm, description);
-                var csharpType = isFlag ? "bool?" : "string?";
+                var acceptsMultipleValues = !isFlag && DescriptionDeclaresRepeatableOption(description);
+                var csharpType = acceptsMultipleValues ? "IEnumerable<string>?" : isFlag ? "bool?" : "string?";
 
                 options.Add(new CliOptionDefinition
                 {
@@ -285,7 +286,7 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
                     Description = description,
                     IsFlag = isFlag,
                     IsRequired = false,
-                    AcceptsMultipleValues = false,
+                    AcceptsMultipleValues = acceptsMultipleValues,
                     IsKeyValue = false,
                     IsNumeric = false,
                     ValueSeparator = isFlag ? " " : " ",
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/SnykCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/SnykCliScraper.cs
index 0b0a7ceded0..111db4c5747 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/SnykCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/SnykCliScraper.cs
@@ -321,6 +321,9 @@ private void ParseOptionLines(
                     && !isNumeric
                     && !ValueOptionsWithoutHelpPlaceholders.Contains(longForm);
                 var isBoolean = IsBooleanValueHint(valueHint);
+                var acceptsMultipleValues = !isFlag
+                    && !isBoolean
+                    && DescriptionDeclaresRepeatableOption(description ?? string.Empty);
                 var csharpType = isFlag || isBoolean ? "bool?" : isNumeric ? "int?" : "string?";
 
                 CliEnumDefinition? enumDef = null;
@@ -345,6 +348,11 @@ private void ParseOptionLines(
                     }
                 }
 
+                if (acceptsMultipleValues)
+                {
+                    csharpType = $"IEnumerable<{csharpType.TrimEnd('?')}>?";
+                }
+
                 options.Add(new CliOptionDefinition
                 {
                     SwitchName = longForm,
@@ -354,7 +362,7 @@ private void ParseOptionLines(
                     Description = description,
                     IsFlag = isFlag,
                     IsRequired = description?.Contains("Required.", StringComparison.OrdinalIgnoreCase) == true,
-                    AcceptsMultipleValues = false,
+                    AcceptsMultipleValues = acceptsMultipleValues,
                     IsKeyValue = false,
                     IsNumeric = isNumeric,
                     ValueSeparator = isFlag ? " " : "=",
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
index c1d34c35bd8..b97e677ed86 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
@@ -315,7 +315,9 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
                 isFlag = true;
             }
 
-            var csharpType = isFlag ? "bool?" : (isInteger ? "int?" : "string?");
+            var acceptsMultipleValues = !isFlag && DescriptionDeclaresRepeatableOption(description);
+            var scalarType = isFlag ? "bool" : isInteger ? "int" : "string";
+            var csharpType = acceptsMultipleValues ? $"IEnumerable<{scalarType}>?" : $"{scalarType}?";
 
             options.Add(new CliOptionDefinition
             {
@@ -326,7 +328,7 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
                 Description = description,
                 IsFlag = isFlag,
                 IsRequired = false,
-                AcceptsMultipleValues = false,
+                AcceptsMultipleValues = acceptsMultipleValues,
                 IsKeyValue = false,
                 IsNumeric = isInteger,
                 ValueSeparator = isFlag ? " " : "=",

From 00987e91a1edc316c98fb7a5f5bf0a97b52df748 Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Sun, 23 Aug 2026 19:55:04 +0100
Subject: [PATCH 02/15] refactor(generator): reduce parser complexity

---
 .../Scrapers/Cli/TerraformCliScraper.cs                      | 5 ++++-
 1 file changed, 4 insertions(+), 1 deletion(-)

diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
index b97e677ed86..9dc51d73d00 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
@@ -315,7 +315,7 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
                 isFlag = true;
             }
 
-            var acceptsMultipleValues = !isFlag && DescriptionDeclaresRepeatableOption(description);
+            var acceptsMultipleValues = IsRepeatableValueOption(isFlag, description);
             var scalarType = isFlag ? "bool" : isInteger ? "int" : "string";
             var csharpType = acceptsMultipleValues ? $"IEnumerable<{scalarType}>?" : $"{scalarType}?";
 
@@ -340,6 +340,9 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
         return options;
     }
 
+    private static bool IsRepeatableValueOption(bool isFlag, string description) =>
+        !isFlag && DescriptionDeclaresRepeatableOption(description);
+
     /// <summary>
     /// Checks if a value hint indicates a numeric type.
     /// </summary>

From 7c8c234c9810dd3f4955fb8409b4604fc58275ae Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Sun, 23 Aug 2026 19:59:36 +0100
Subject: [PATCH 03/15] test(options): cover repeatable typed values

Refs #4006
---
 .../Scrapers/RepeatableOptionAdapterTests.cs  | 38 ++++++++++++++++++-
 1 file changed, 36 insertions(+), 2 deletions(-)

diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
index 8af52d0a98f..4d73bdd21bf 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
@@ -71,15 +71,49 @@ Set the project environment. Can be repeated.
         await AssertRepeatable(command, "--project-environment");
     }
 
+    [Test]
+    public async Task Snyk_Preserves_Numeric_Element_Type_For_Repeatable_Options()
+    {
+        const string helpText = """
+            Usage: snyk test [<OPTIONS>]
+
+            Options
+              --max-depth=<DEPTH>
+                  Set the maximum dependency depth. Can be repeated.
+            """;
+        var command = await new TestSnykCliScraper().Parse(["snyk", "test"], helpText);
+
+        await AssertRepeatable(command, "--max-depth", "IEnumerable<int>?");
+    }
+
+    [Test]
+    public async Task Snyk_Preserves_Enum_Element_Type_For_Repeatable_Options()
+    {
+        const string helpText = """
+            Usage: snyk test [<OPTIONS>]
+
+            Options
+              --severity-threshold=<low|medium|high|critical>
+                  Report only vulnerabilities at the selected threshold. Can be repeated.
+            """;
+        var command = await new TestSnykCliScraper().Parse(["snyk", "test"], helpText);
+
+        await AssertRepeatable(
+            command,
+            "--severity-threshold",
+            "IEnumerable<SnykSeverityThreshold>?");
+    }
+
     private static async Task AssertRepeatable(
         CliCommandDefinition? command,
-        string switchName)
+        string switchName,
+        string expectedType = "IEnumerable<string>?")
     {
         var option = command!.Options.Single(item => item.SwitchName == switchName);
         using (Assert.Multiple())
         {
             await Assert.That(option.AcceptsMultipleValues).IsTrue();
-            await Assert.That(option.CSharpType).IsEqualTo("IEnumerable<string>?");
+            await Assert.That(option.CSharpType).IsEqualTo(expectedType);
         }
     }
 

From 09fbe4719f0f05c8f750479d920e99501249e698 Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Sun, 23 Aug 2026 20:02:50 +0100
Subject: [PATCH 04/15] refactor(generator): extract terraform type shape

---
 .../Scrapers/Cli/TerraformCliScraper.cs                  | 9 +++++++--
 1 file changed, 7 insertions(+), 2 deletions(-)

diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
index 9dc51d73d00..31a4fa74a6f 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
@@ -316,8 +316,7 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
             }
 
             var acceptsMultipleValues = IsRepeatableValueOption(isFlag, description);
-            var scalarType = isFlag ? "bool" : isInteger ? "int" : "string";
-            var csharpType = acceptsMultipleValues ? $"IEnumerable<{scalarType}>?" : $"{scalarType}?";
+            var csharpType = GetCSharpType(isFlag, isInteger, acceptsMultipleValues);
 
             options.Add(new CliOptionDefinition
             {
@@ -343,6 +342,12 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
     private static bool IsRepeatableValueOption(bool isFlag, string description) =>
         !isFlag && DescriptionDeclaresRepeatableOption(description);
 
+    private static string GetCSharpType(bool isFlag, bool isInteger, bool acceptsMultipleValues)
+    {
+        var scalarType = isFlag ? "bool" : isInteger ? "int" : "string";
+        return acceptsMultipleValues ? $"IEnumerable<{scalarType}>?" : $"{scalarType}?";
+    }
+
     /// <summary>
     /// Checks if a value hint indicates a numeric type.
     /// </summary>

From ea76cb3386f9af62db1a3b9692387c476370e4e6 Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Sun, 23 Aug 2026 20:43:06 +0100
Subject: [PATCH 05/15] fix(generator): narrow repeatability prose

Require explicit option-repeatability language so operational retry descriptions remain scalar.
---
 .../Scrapers/RepeatableOptionAdapterTests.cs  | 19 +++++++++++++++++++
 .../Scrapers/Cli/CliScraperBase.cs            | 16 ++++++++++++++--
 2 files changed, 33 insertions(+), 2 deletions(-)

diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
index 4d73bdd21bf..8ac5a615924 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
@@ -56,6 +56,25 @@ public async Task Packer_Recognizes_Repeatable_Prose()
         await AssertRepeatable(command, "--var-file");
     }
 
+    [Test]
+    public async Task Packer_Does_Not_Treat_Operational_Repetition_As_Repeatable()
+    {
+        const string helpText = """
+            Usage: packer build [options]
+
+            Options:
+              -retry-count=count  Retry the operation multiple times before failing.
+            """;
+        var command = await new TestPackerCliScraper().Parse(["packer", "build"], helpText);
+        var option = command!.Options.Single(item => item.SwitchName == "--retry-count");
+
+        using (Assert.Multiple())
+        {
+            await Assert.That(option.AcceptsMultipleValues).IsFalse();
+            await Assert.That(option.CSharpType).IsEqualTo("string?");
+        }
+    }
+
     [Test]
     public async Task Snyk_Recognizes_Repeated_Prose()
     {
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 2061ee64935..f6ba5e326f9 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
@@ -1051,8 +1051,20 @@ private static void ValidateArgumentGroups(CliCommandDefinition command)
     private static partial Regex ExplicitBooleanValuePattern();
 
     [GeneratedRegex(
-        @"\b(?:one\s+or\s+more|zero\s+or\s+more|multiple\s+(?:times|values)|more\s+than\s+once|repeat(?:able|ed|edly)?)\b",
-        RegexOptions.IgnoreCase)]
+        """
+        \b(?:
+            repeatable
+            |(?:can|may)\s+be\s+repeated
+            |(?:can|may)\s+be\s+
+                (?:specified|supplied|provided|used|passed|set|given)\s+
+                (?:multiple\s+times|more\s+than\s+once)
+            |(?:specify|supply|provide|use|pass|set|give)\s+
+                (?:multiple\s+times|more\s+than\s+once)
+            |(?:one|zero)\s+or\s+more\s+values?
+            |multiple\s+values
+        )\b
+        """,
+        RegexOptions.IgnoreCase | RegexOptions.IgnorePatternWhitespace)]
     private static partial Regex RepeatableValuePattern();
 
     [GeneratedRegex(@"\x1B(?:\][^\x07\x1B]*(?:\x07|\x1B\\)|\[[0-?]*[ -/]*[@-~])")]

From 6a1df555d8e9ebddfa1eef18d2c967fd50170248 Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Sun, 23 Aug 2026 21:11:32 +0100
Subject: [PATCH 06/15] fix(generator): qualify repeatability prose

---
 .../Scrapers/RepeatableOptionAdapterTests.cs  | 21 +++++++++++++++++
 .../Scrapers/Cli/CliScraperBase.cs            | 23 +++++++++++++++----
 .../Scrapers/Cli/PackerCliScraper.cs          |  2 +-
 .../Scrapers/Cli/PipCliScraper.cs             |  2 +-
 .../Scrapers/Cli/SnykCliScraper.cs            |  7 +++---
 .../Scrapers/Cli/TerraformCliScraper.cs       |  5 +---
 .../Scrapers/Cli/WinGetCliScraper.cs          |  2 +-
 7 files changed, 47 insertions(+), 15 deletions(-)

diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
index 8ac5a615924..687160d9855 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
@@ -75,6 +75,27 @@ public async Task Packer_Does_Not_Treat_Operational_Repetition_As_Repeatable()
         }
     }
 
+    [Test]
+    [Arguments("This argument must be repeated for each entry.", true)]
+    [Arguments("The value is repeated across runs.", true)]
+    [Arguments("Provide one or more paths to scan.", true)]
+    [Arguments("Validates multiple values against a schema.", false)]
+    public async Task Packer_Classifies_Explicit_Repeatability_Prose(
+        string description,
+        bool expected)
+    {
+        var helpText = $"""
+            Usage: packer build [options]
+
+            Options:
+              -var-file=path  {description}
+            """;
+        var command = await new TestPackerCliScraper().Parse(["packer", "build"], helpText);
+        var option = command!.Options.Single(item => item.SwitchName == "--var-file");
+
+        await Assert.That(option.AcceptsMultipleValues).IsEqualTo(expected);
+    }
+
     [Test]
     public async Task Snyk_Recognizes_Repeated_Prose()
     {
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 f6ba5e326f9..d764940420c 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
@@ -971,6 +971,15 @@ protected static bool HelpDeclaresRepeatableOption(
     protected static bool DescriptionDeclaresRepeatableOption(string description) =>
         RepeatableValuePattern().IsMatch(description);
 
+    /// <summary>
+    /// Returns whether a value-taking, non-Boolean option is described as repeatable.
+    /// </summary>
+    protected static bool IsRepeatableValueOption(
+        string description,
+        bool isFlag,
+        bool isBoolean = false) =>
+        !isFlag && !isBoolean && DescriptionDeclaresRepeatableOption(description);
+
     /// <summary>
     /// Parses indentation-based argument declarations into a reusable nested group model.
     /// The adapter only recognizes one tool-specific declaration line; traversal,
@@ -1054,14 +1063,18 @@ private static void ValidateArgumentGroups(CliCommandDefinition command)
         """
         \b(?:
             repeatable
-            |(?:can|may)\s+be\s+repeated
-            |(?:can|may)\s+be\s+
+            |(?:can|may|must|should)\s+be\s+repeated
+            |(?:is|are)\s+repeated
+            |(?:can|may|must|should)\s+be\s+
                 (?:specified|supplied|provided|used|passed|set|given)\s+
                 (?:multiple\s+times|more\s+than\s+once)
             |(?:specify|supply|provide|use|pass|set|give)\s+
-                (?:multiple\s+times|more\s+than\s+once)
-            |(?:one|zero)\s+or\s+more\s+values?
-            |multiple\s+values
+                (?:
+                    multiple\s+times
+                    |more\s+than\s+once
+                    |(?:one|zero)\s+or\s+more\s+[\w-]+
+                    |multiple\s+[\w-]+
+                )
         )\b
         """,
         RegexOptions.IgnoreCase | RegexOptions.IgnorePatternWhitespace)]
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
index fa5ed43111b..41a07c0cdc4 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
@@ -212,7 +212,7 @@ private List<CliOptionDefinition> ParseOptions(string helpText)
             }
 
             var isFlag = string.IsNullOrEmpty(valueHint) || valueHint.Contains("true") || valueHint.Contains("false");
-            var acceptsMultipleValues = !isFlag && DescriptionDeclaresRepeatableOption(description);
+            var acceptsMultipleValues = IsRepeatableValueOption(description, isFlag);
             var csharpType = acceptsMultipleValues ? "IEnumerable<string>?" : isFlag ? "bool?" : "string?";
 
             options.Add(new CliOptionDefinition
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PipCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PipCliScraper.cs
index a62537fc38b..5a8f01750f2 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PipCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PipCliScraper.cs
@@ -274,7 +274,7 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
                 }
 
                 var isFlag = string.IsNullOrEmpty(valueHint) && IsBooleanOption(longForm, description);
-                var acceptsMultipleValues = !isFlag && DescriptionDeclaresRepeatableOption(description);
+                var acceptsMultipleValues = IsRepeatableValueOption(description, isFlag);
                 var csharpType = acceptsMultipleValues ? "IEnumerable<string>?" : isFlag ? "bool?" : "string?";
 
                 options.Add(new CliOptionDefinition
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/SnykCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/SnykCliScraper.cs
index 111db4c5747..91c5b26f776 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/SnykCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/SnykCliScraper.cs
@@ -321,9 +321,10 @@ private void ParseOptionLines(
                     && !isNumeric
                     && !ValueOptionsWithoutHelpPlaceholders.Contains(longForm);
                 var isBoolean = IsBooleanValueHint(valueHint);
-                var acceptsMultipleValues = !isFlag
-                    && !isBoolean
-                    && DescriptionDeclaresRepeatableOption(description ?? string.Empty);
+                var acceptsMultipleValues = IsRepeatableValueOption(
+                    description ?? string.Empty,
+                    isFlag,
+                    isBoolean);
                 var csharpType = isFlag || isBoolean ? "bool?" : isNumeric ? "int?" : "string?";
 
                 CliEnumDefinition? enumDef = null;
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
index 31a4fa74a6f..afb88b6bdb4 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
@@ -315,7 +315,7 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
                 isFlag = true;
             }
 
-            var acceptsMultipleValues = IsRepeatableValueOption(isFlag, description);
+            var acceptsMultipleValues = IsRepeatableValueOption(description, isFlag, isBoolean);
             var csharpType = GetCSharpType(isFlag, isInteger, acceptsMultipleValues);
 
             options.Add(new CliOptionDefinition
@@ -339,9 +339,6 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
         return options;
     }
 
-    private static bool IsRepeatableValueOption(bool isFlag, string description) =>
-        !isFlag && DescriptionDeclaresRepeatableOption(description);
-
     private static string GetCSharpType(bool isFlag, bool isInteger, bool acceptsMultipleValues)
     {
         var scalarType = isFlag ? "bool" : isInteger ? "int" : "string";
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/WinGetCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/WinGetCliScraper.cs
index 36d4dae8e7d..adc644b213a 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/WinGetCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/WinGetCliScraper.cs
@@ -437,7 +437,7 @@ private List<CliOptionDefinition> ParseArguments(string helpText, HashSet<string
         // WinGet options are generally strings or booleans
         // Boolean flags typically have descriptions like "Enable...", "Disable...", etc.
         var isFlag = IsKnownBooleanOption(className, longForm) || IsBooleanDescription(description);
-        var acceptsMultipleValues = !isFlag && DescriptionDeclaresRepeatableOption(description);
+        var acceptsMultipleValues = IsRepeatableValueOption(description, isFlag);
         var csharpType = isFlag
             ? "bool?"
             : acceptsMultipleValues

From 92d3e5cd91a0e43aae2ee1410571c787f899ac06 Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Sun, 23 Aug 2026 21:31:57 +0100
Subject: [PATCH 07/15] fix(generator): preserve repeatable phrases

---
 .../Scrapers/Cli/CliScraperTraversalTests.cs  | 24 +++++++++++++++++++
 .../Scrapers/Cli/CliScraperBase.cs            |  3 ++-
 2 files changed, 26 insertions(+), 1 deletion(-)

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 406f8ab0b71..afae3b0b358 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
@@ -620,6 +620,30 @@ fake execute [flags]
         await Assert.That(tag.CSharpType).IsEqualTo("IEnumerable<string>?");
     }
 
+    [Test]
+    [Arguments("Accepts multiple values")]
+    [Arguments("One or more label selectors")]
+    public async Task SharedShapeInference_Preserves_Common_Repeatability_Phrases(string description)
+    {
+        var helpText = $"""
+            Execute a command.
+
+            Usage:
+              fake execute [flags]
+
+            Flags:
+              --tag string   {description}
+            """;
+        var scraper = new TestCobraScraper(new StubExecutor(
+            new Dictionary<string, string>(StringComparer.OrdinalIgnoreCase)));
+
+        var command = await scraper.Parse(["fake", "execute"], helpText);
+        var tag = command!.Options.Single();
+
+        await Assert.That(tag.AcceptsMultipleValues).IsTrue();
+        await Assert.That(tag.CSharpType).IsEqualTo("IEnumerable<string>?");
+    }
+
     [Test]
     public async Task SharedShapeInference_Models_Optional_Cobra_Option_Values()
     {
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 d764940420c..b332ecd7b04 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
@@ -1065,10 +1065,11 @@ private static void ValidateArgumentGroups(CliCommandDefinition command)
             repeatable
             |(?:can|may|must|should)\s+be\s+repeated
             |(?:is|are)\s+repeated
+            |(?:one|zero)\s+or\s+more\s+[\w-]+
             |(?:can|may|must|should)\s+be\s+
                 (?:specified|supplied|provided|used|passed|set|given)\s+
                 (?:multiple\s+times|more\s+than\s+once)
-            |(?:specify|supply|provide|use|pass|set|give)\s+
+            |(?:accepts?|specify|supply|provide|use|pass|set|give)\s+
                 (?:
                     multiple\s+times
                     |more\s+than\s+once

From 7d8365fbc5255c4e4b5d043977aacb12331fdbaf Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Sun, 23 Aug 2026 21:47:44 +0100
Subject: [PATCH 08/15] fix(generator): reject operational counts

---
 .../Scrapers/RepeatableOptionAdapterTests.cs                    | 2 ++
 .../Scrapers/Cli/CliScraperBase.cs                              | 2 +-
 2 files changed, 3 insertions(+), 1 deletion(-)

diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
index 687160d9855..00e1d3329bb 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
@@ -80,6 +80,8 @@ public async Task Packer_Does_Not_Treat_Operational_Repetition_As_Repeatable()
     [Arguments("The value is repeated across runs.", true)]
     [Arguments("Provide one or more paths to scan.", true)]
     [Arguments("Validates multiple values against a schema.", false)]
+    [Arguments("Retry the operation one or more times before failing.", false)]
+    [Arguments("This operation runs one or more attempts depending on configuration.", false)]
     public async Task Packer_Classifies_Explicit_Repeatability_Prose(
         string description,
         bool expected)
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 b332ecd7b04..6b53fbb1c92 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
@@ -1065,7 +1065,7 @@ private static void ValidateArgumentGroups(CliCommandDefinition command)
             repeatable
             |(?:can|may|must|should)\s+be\s+repeated
             |(?:is|are)\s+repeated
-            |(?:one|zero)\s+or\s+more\s+[\w-]+
+            |\A(?:one|zero)\s+or\s+more\s+[\w-]+
             |(?:can|may|must|should)\s+be\s+
                 (?:specified|supplied|provided|used|passed|set|given)\s+
                 (?:multiple\s+times|more\s+than\s+once)

From e37254888fa4865cd41801db28d788b385f89901 Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Sun, 23 Aug 2026 22:03:06 +0100
Subject: [PATCH 09/15] fix(generator): harden repeatable detection

---
 .../Scrapers/RepeatableOptionAdapterTests.cs  | 18 +++++++++
 .../Scrapers/WinGetCliScraperTests.cs         | 25 +++++++++++++
 .../Scrapers/Cli/CliScraperBase.cs            |  3 +-
 .../Scrapers/Cli/PackerCliScraper.cs          | 37 ++++++++++++++++++-
 .../Scrapers/Cli/WinGetCliScraper.cs          |  4 +-
 5 files changed, 84 insertions(+), 3 deletions(-)

diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
index 00e1d3329bb..ec607ace53d 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
@@ -56,6 +56,21 @@ public async Task Packer_Recognizes_Repeatable_Prose()
         await AssertRepeatable(command, "--var-file");
     }
 
+    [Test]
+    public async Task Packer_Recognizes_Multiline_Repeatable_Prose()
+    {
+        const string helpText = """
+            Usage: packer build [options]
+
+            Options:
+              -var-file=path  Set a variable file.
+                              Can be repeated for additional files.
+            """;
+        var command = await new TestPackerCliScraper().Parse(["packer", "build"], helpText);
+
+        await AssertRepeatable(command, "--var-file");
+    }
+
     [Test]
     public async Task Packer_Does_Not_Treat_Operational_Repetition_As_Repeatable()
     {
@@ -82,6 +97,9 @@ public async Task Packer_Does_Not_Treat_Operational_Repetition_As_Repeatable()
     [Arguments("Validates multiple values against a schema.", false)]
     [Arguments("Retry the operation one or more times before failing.", false)]
     [Arguments("This operation runs one or more attempts depending on configuration.", false)]
+    [Arguments("One or more attempts are made before failure.", false)]
+    [Arguments("One or more times may be required.", false)]
+    [Arguments("One or more retries may be attempted.", false)]
     public async Task Packer_Classifies_Explicit_Repeatability_Prose(
         string description,
         bool expected)
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/WinGetCliScraperTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/WinGetCliScraperTests.cs
index bfc90695c52..1f613a87f8e 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/WinGetCliScraperTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/WinGetCliScraperTests.cs
@@ -49,6 +49,31 @@ List installed packages.
         }
     }
 
+    [Test]
+    public async Task Explicit_Repeatability_Takes_Precedence_Over_Boolean_Heuristics()
+    {
+        const string helpText = """
+            List installed packages.
+
+            usage: winget list [<options>]
+
+            The following options are available:
+              --source   Accepts multiple values
+            """;
+
+        var command = await new TestWinGetCliScraper().Parse(
+            ["winget", "list"],
+            helpText);
+        var source = command!.Options.Single(option => option.SwitchName == "--source");
+
+        using (Assert.Multiple())
+        {
+            await Assert.That(source.IsFlag).IsFalse();
+            await Assert.That(source.AcceptsMultipleValues).IsTrue();
+            await Assert.That(source.CSharpType).IsEqualTo("IEnumerable<string>?");
+        }
+    }
+
     [Test]
     public async Task Does_Not_Mark_Boolean_Flags_As_Repeatable_Values()
     {
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 6b53fbb1c92..77700d0137c 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
@@ -1065,7 +1065,8 @@ private static void ValidateArgumentGroups(CliCommandDefinition command)
             repeatable
             |(?:can|may|must|should)\s+be\s+repeated
             |(?:is|are)\s+repeated
-            |\A(?:one|zero)\s+or\s+more\s+[\w-]+
+            |\A(?:one|zero)\s+or\s+more\s+
+                (?!(?:attempts?|times?|retries?)\b)[\w-]+
             |(?:can|may|must|should)\s+be\s+
                 (?:specified|supplied|provided|used|passed|set|given)\s+
                 (?:multiple\s+times|more\s+than\s+once)
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
index 41a07c0cdc4..acae8f7d88f 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
@@ -179,8 +179,9 @@ private List<CliOptionDefinition> ParseOptions(string helpText)
 
         var lines = section.Split('\n');
 
-        foreach (var line in lines)
+        for (var i = 0; i < lines.Length; i++)
         {
+            var line = lines[i];
             var match = PackerOptionPattern().Match(line);
             if (!match.Success)
             {
@@ -205,6 +206,8 @@ private List<CliOptionDefinition> ParseOptions(string helpText)
 
             seenOptions.Add(longForm);
 
+            i = AccumulateMultiLineDescription(lines, i, ref description);
+
             var propertyName = NormalizePropertyName(longForm);
             if (propertyName is null)
             {
@@ -236,6 +239,38 @@ private List<CliOptionDefinition> ParseOptions(string helpText)
         return options;
     }
 
+    private static int AccumulateMultiLineDescription(
+        string[] lines,
+        int currentIndex,
+        ref string description)
+    {
+        var descriptionParts = new List<string>();
+        if (!string.IsNullOrEmpty(description))
+        {
+            descriptionParts.Add(description);
+        }
+
+        var optionIndent = lines[currentIndex].Length - lines[currentIndex].TrimStart().Length;
+        var nextIndex = currentIndex + 1;
+        while (nextIndex < lines.Length)
+        {
+            var nextLine = lines[nextIndex];
+            var trimmedNext = nextLine.Trim();
+            if (string.IsNullOrWhiteSpace(trimmedNext)
+                || trimmedNext.StartsWith('-')
+                || nextLine.Length - nextLine.TrimStart().Length <= optionIndent)
+            {
+                break;
+            }
+
+            descriptionParts.Add(trimmedNext);
+            nextIndex++;
+        }
+
+        description = string.Join(" ", descriptionParts);
+        return nextIndex - 1;
+    }
+
     /// <summary>
     /// Checks if help text indicates the command has options.
     /// </summary>
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/WinGetCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/WinGetCliScraper.cs
index adc644b213a..68fb1c55923 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/WinGetCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/WinGetCliScraper.cs
@@ -436,7 +436,9 @@ private List<CliOptionDefinition> ParseArguments(string helpText, HashSet<string
 
         // WinGet options are generally strings or booleans
         // Boolean flags typically have descriptions like "Enable...", "Disable...", etc.
-        var isFlag = IsKnownBooleanOption(className, longForm) || IsBooleanDescription(description);
+        var declaresRepeatability = DescriptionDeclaresRepeatableOption(description);
+        var isFlag = IsKnownBooleanOption(className, longForm)
+                     || (!declaresRepeatability && IsBooleanDescription(description));
         var acceptsMultipleValues = IsRepeatableValueOption(description, isFlag);
         var csharpType = isFlag
             ? "bool?"

From 01060a1d2b7c333d1c167a22448985baffe3d30e Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Mon, 24 Aug 2026 06:00:00 +0100
Subject: [PATCH 10/15] fix(generator): harden repeatable prose

Refs #4006
---
 .../Scrapers/RepeatableOptionAdapterTests.cs  |  6 +++
 .../Scrapers/Cli/CliScraperBase.cs            | 47 ++++++++++---------
 .../Scrapers/Cli/PackerCliScraper.cs          |  3 +-
 .../Scrapers/Cli/PipCliScraper.cs             |  3 +-
 .../Scrapers/Cli/SnykCliScraper.cs            |  5 +-
 .../Scrapers/Cli/TerraformCliScraper.cs       |  4 +-
 .../Scrapers/Cli/WinGetCliScraper.cs          |  9 ++--
 7 files changed, 42 insertions(+), 35 deletions(-)

diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
index ec607ace53d..b3473a0498e 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
@@ -100,6 +100,12 @@ public async Task Packer_Does_Not_Treat_Operational_Repetition_As_Repeatable()
     [Arguments("One or more attempts are made before failure.", false)]
     [Arguments("One or more times may be required.", false)]
     [Arguments("One or more retries may be attempted.", false)]
+    [Arguments("Provide one or more attempts before failing.", false)]
+    [Arguments("Accepts one or more retries.", false)]
+    [Arguments("Give one or more times to retry.", false)]
+    [Arguments("Supports multiple values.", true)]
+    [Arguments("Takes multiple values.", true)]
+    [Arguments("Value can contain multiple values.", true)]
     public async Task Packer_Classifies_Explicit_Repeatability_Prose(
         string description,
         bool expected)
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 77700d0137c..67a4f9575cf 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
@@ -980,6 +980,14 @@ protected static bool IsRepeatableValueOption(
         bool isBoolean = false) =>
         !isFlag && !isBoolean && DescriptionDeclaresRepeatableOption(description);
 
+    /// <summary>
+    /// Converts a scalar C# type into its repeatable collection representation when needed.
+    /// </summary>
+    protected static string AsCSharpType(string scalarType, bool acceptsMultipleValues) =>
+        acceptsMultipleValues
+            ? $"IEnumerable<{scalarType.TrimEnd('?')}>?"
+            : scalarType;
+
     /// <summary>
     /// Parses indentation-based argument declarations into a reusable nested group model.
     /// The adapter only recognizes one tool-specific declaration line; traversal,
@@ -1059,27 +1067,24 @@ private static void ValidateArgumentGroups(CliCommandDefinition command)
         RegexOptions.IgnoreCase)]
     private static partial Regex ExplicitBooleanValuePattern();
 
-    [GeneratedRegex(
-        """
-        \b(?:
-            repeatable
-            |(?:can|may|must|should)\s+be\s+repeated
-            |(?:is|are)\s+repeated
-            |\A(?:one|zero)\s+or\s+more\s+
-                (?!(?:attempts?|times?|retries?)\b)[\w-]+
-            |(?:can|may|must|should)\s+be\s+
-                (?:specified|supplied|provided|used|passed|set|given)\s+
-                (?:multiple\s+times|more\s+than\s+once)
-            |(?:accepts?|specify|supply|provide|use|pass|set|give)\s+
-                (?:
-                    multiple\s+times
-                    |more\s+than\s+once
-                    |(?:one|zero)\s+or\s+more\s+[\w-]+
-                    |multiple\s+[\w-]+
-                )
-        )\b
-        """,
-        RegexOptions.IgnoreCase | RegexOptions.IgnorePatternWhitespace)]
+    private const string RepeatableItemCountPattern =
+        @"(?:one|zero)\s+or\s+more\s+(?!(?:attempts?|times?|retries?)\b)[\w-]+";
+
+    private const string RepeatableValueRegex =
+        @"\b(?:"
+        + @"repeatable"
+        + @"|(?:can|may|must|should)\s+be\s+repeated"
+        + @"|(?:is|are)\s+repeated"
+        + @"|\A" + RepeatableItemCountPattern
+        + @"|(?:can|may|must|should)\s+be\s+"
+        + @"(?:specified|supplied|provided|used|passed|set|given)\s+"
+        + @"(?:multiple\s+times|more\s+than\s+once)"
+        + @"|(?:accepts?|specify|supply|provide|use|pass|set|give|supports?|takes?|contains?)\s+"
+        + @"(?:multiple\s+times|more\s+than\s+once|"
+        + RepeatableItemCountPattern
+        + @"|multiple\s+[\w-]+))\b";
+
+    [GeneratedRegex(RepeatableValueRegex, RegexOptions.IgnoreCase | RegexOptions.IgnorePatternWhitespace)]
     private static partial Regex RepeatableValuePattern();
 
     [GeneratedRegex(@"\x1B(?:\][^\x07\x1B]*(?:\x07|\x1B\\)|\[[0-?]*[ -/]*[@-~])")]
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
index acae8f7d88f..40bc1f1a32b 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
@@ -216,7 +216,8 @@ private List<CliOptionDefinition> ParseOptions(string helpText)
 
             var isFlag = string.IsNullOrEmpty(valueHint) || valueHint.Contains("true") || valueHint.Contains("false");
             var acceptsMultipleValues = IsRepeatableValueOption(description, isFlag);
-            var csharpType = acceptsMultipleValues ? "IEnumerable<string>?" : isFlag ? "bool?" : "string?";
+            var scalarType = isFlag ? "bool?" : "string?";
+            var csharpType = AsCSharpType(scalarType, acceptsMultipleValues);
 
             options.Add(new CliOptionDefinition
             {
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PipCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PipCliScraper.cs
index 5a8f01750f2..0987ad4c5f1 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PipCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PipCliScraper.cs
@@ -275,7 +275,8 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
 
                 var isFlag = string.IsNullOrEmpty(valueHint) && IsBooleanOption(longForm, description);
                 var acceptsMultipleValues = IsRepeatableValueOption(description, isFlag);
-                var csharpType = acceptsMultipleValues ? "IEnumerable<string>?" : isFlag ? "bool?" : "string?";
+                var scalarType = isFlag ? "bool?" : "string?";
+                var csharpType = AsCSharpType(scalarType, acceptsMultipleValues);
 
                 options.Add(new CliOptionDefinition
                 {
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/SnykCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/SnykCliScraper.cs
index 91c5b26f776..281fa516162 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/SnykCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/SnykCliScraper.cs
@@ -349,10 +349,7 @@ private void ParseOptionLines(
                     }
                 }
 
-                if (acceptsMultipleValues)
-                {
-                    csharpType = $"IEnumerable<{csharpType.TrimEnd('?')}>?";
-                }
+                csharpType = AsCSharpType(csharpType, acceptsMultipleValues);
 
                 options.Add(new CliOptionDefinition
                 {
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
index afb88b6bdb4..6fe23534b9e 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/TerraformCliScraper.cs
@@ -341,8 +341,8 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
 
     private static string GetCSharpType(bool isFlag, bool isInteger, bool acceptsMultipleValues)
     {
-        var scalarType = isFlag ? "bool" : isInteger ? "int" : "string";
-        return acceptsMultipleValues ? $"IEnumerable<{scalarType}>?" : $"{scalarType}?";
+        var scalarType = isFlag ? "bool?" : isInteger ? "int?" : "string?";
+        return AsCSharpType(scalarType, acceptsMultipleValues);
     }
 
     /// <summary>
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/WinGetCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/WinGetCliScraper.cs
index 68fb1c55923..0977c25928a 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/WinGetCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/WinGetCliScraper.cs
@@ -439,12 +439,9 @@ private List<CliOptionDefinition> ParseArguments(string helpText, HashSet<string
         var declaresRepeatability = DescriptionDeclaresRepeatableOption(description);
         var isFlag = IsKnownBooleanOption(className, longForm)
                      || (!declaresRepeatability && IsBooleanDescription(description));
-        var acceptsMultipleValues = IsRepeatableValueOption(description, isFlag);
-        var csharpType = isFlag
-            ? "bool?"
-            : acceptsMultipleValues
-                ? "IEnumerable<string>?"
-                : "string?";
+        var acceptsMultipleValues = !isFlag && declaresRepeatability;
+        var scalarType = isFlag ? "bool?" : "string?";
+        var csharpType = AsCSharpType(scalarType, acceptsMultipleValues);
 
         return new CliOptionDefinition
         {

From c446a513c6c7cfcf400f1d8c72879b6d13986d22 Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Mon, 24 Aug 2026 06:12:33 +0100
Subject: [PATCH 11/15] fix(packer): parse quoted option values

---
 .../Scrapers/RepeatableOptionAdapterTests.cs       | 14 ++++++++++++++
 .../Scrapers/Cli/PackerCliScraper.cs               |  6 ++++--
 2 files changed, 18 insertions(+), 2 deletions(-)

diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
index b3473a0498e..98436986b85 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
@@ -56,6 +56,20 @@ public async Task Packer_Recognizes_Repeatable_Prose()
         await AssertRepeatable(command, "--var-file");
     }
 
+    [Test]
+    public async Task Packer_Recognizes_Quoted_Repeatable_Value()
+    {
+        const string helpText = """
+            Usage: packer build [options]
+
+            Options:
+              -var 'key=value'  Set a variable. Can be repeated.
+            """;
+        var command = await new TestPackerCliScraper().Parse(["packer", "build"], helpText);
+
+        await AssertRepeatable(command, "--var");
+    }
+
     [Test]
     public async Task Packer_Recognizes_Multiline_Repeatable_Prose()
     {
diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
index 40bc1f1a32b..a7880b7983f 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/PackerCliScraper.cs
@@ -214,7 +214,9 @@ private List<CliOptionDefinition> ParseOptions(string helpText)
                 continue;
             }
 
-            var isFlag = string.IsNullOrEmpty(valueHint) || valueHint.Contains("true") || valueHint.Contains("false");
+            var isFlag = string.IsNullOrEmpty(valueHint)
+                         || valueHint.Equals("true", StringComparison.OrdinalIgnoreCase)
+                         || valueHint.Equals("false", StringComparison.OrdinalIgnoreCase);
             var acceptsMultipleValues = IsRepeatableValueOption(description, isFlag);
             var scalarType = isFlag ? "bool?" : "string?";
             var csharpType = AsCSharpType(scalarType, acceptsMultipleValues);
@@ -306,7 +308,7 @@ protected override bool HasOptions(string helpText)
     ///   -debug             Debug mode enabled
     ///   -var 'key=value'   Variable for templates
     /// </summary>
-    [GeneratedRegex(@"^\s+(?<flag>-[\w-]+)(?:=(?<value>\S+)|\s+'[^']+')?\s{2,}(?<desc>.*)$", RegexOptions.Multiline)]
+    [GeneratedRegex(@"^\s+(?<flag>-[\w-]+)(?:=(?<value>\S+)|\s+'(?<value>[^']+)')?\s{2,}(?<desc>.*)$", RegexOptions.Multiline)]
     private static partial Regex PackerOptionPattern();
 
     #endregion

From 9a78e979d4b548f054727d9cf27026bf43707a55 Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Mon, 24 Aug 2026 06:18:51 +0100
Subject: [PATCH 12/15] fix(generator): reject qualified retry counts

---
 .../Scrapers/RepeatableOptionAdapterTests.cs                 | 4 ++++
 .../Scrapers/Cli/CliScraperBase.cs                           | 5 ++++-
 2 files changed, 8 insertions(+), 1 deletion(-)

diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
index 98436986b85..a5986e27e79 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
@@ -117,6 +117,10 @@ public async Task Packer_Does_Not_Treat_Operational_Repetition_As_Repeatable()
     [Arguments("Provide one or more attempts before failing.", false)]
     [Arguments("Accepts one or more retries.", false)]
     [Arguments("Give one or more times to retry.", false)]
+    [Arguments("One or more retry attempts before failing.", false)]
+    [Arguments("Zero or more retry attempts may be made.", false)]
+    [Arguments("One or more connection retries before giving up.", false)]
+    [Arguments("One or more polling attempts before timing out.", false)]
     [Arguments("Supports multiple values.", true)]
     [Arguments("Takes multiple values.", true)]
     [Arguments("Value can contain multiple values.", true)]
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 67a4f9575cf..89db2818c23 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
@@ -1067,8 +1067,11 @@ private static void ValidateArgumentGroups(CliCommandDefinition command)
         RegexOptions.IgnoreCase)]
     private static partial Regex ExplicitBooleanValuePattern();
 
+    private const string OperationalCountPhrasePattern =
+        @"(?:[\w-]+\s+){0,2}(?:attempts?|times?|retries?)\b";
+
     private const string RepeatableItemCountPattern =
-        @"(?:one|zero)\s+or\s+more\s+(?!(?:attempts?|times?|retries?)\b)[\w-]+";
+        @"(?:one|zero)\s+or\s+more\s+(?!" + OperationalCountPhrasePattern + @")[\w-]+";
 
     private const string RepeatableValueRegex =
         @"\b(?:"

From 48d1b15c45ff5c8963507335197ee474c3fd00d9 Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Mon, 24 Aug 2026 07:30:40 +0100
Subject: [PATCH 13/15] fix(generator): align repeatable parser tests

---
 .../Scrapers/RepeatableOptionAdapterTests.cs         | 12 ++++++++++--
 1 file changed, 10 insertions(+), 2 deletions(-)

diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
index a5986e27e79..c0de5687276 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
@@ -222,7 +222,11 @@ private sealed class TestPipCliScraper()
             NullLogger<PipCliScraper>.Instance)
     {
         public Task<CliCommandDefinition?> Parse(string[] commandPath, string helpText) =>
-            ParseCommandAsync(commandPath, helpText, CancellationToken.None);
+            ParseCommandAsync(
+                commandPath,
+                helpText,
+                ParseUsageSynopsis(commandPath, helpText),
+                CancellationToken.None);
     }
 
     private sealed class TestPackerCliScraper()
@@ -246,6 +250,10 @@ private sealed class TestSnykCliScraper()
             NullLogger<SnykCliScraper>.Instance)
     {
         public Task<CliCommandDefinition?> Parse(string[] commandPath, string helpText) =>
-            ParseCommandAsync(commandPath, helpText, CancellationToken.None);
+            ParseCommandAsync(
+                commandPath,
+                helpText,
+                ParseUsageSynopsis(commandPath, helpText),
+                CancellationToken.None);
     }
 }

From 3f5db575110282eba817a92fdf0f36d7e79ddf8d Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Mon, 24 Aug 2026 07:51:28 +0100
Subject: [PATCH 14/15] fix(generator): retain boolean value options

---
 .../Scrapers/Cli/CliScraperTraversalTests.cs  | 44 ++++++++++++++++---
 .../Scrapers/Cli/CliScraperBase.cs            |  2 +
 2 files changed, 40 insertions(+), 6 deletions(-)

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 afae3b0b358..9c1be2661fb 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
@@ -687,13 +687,42 @@ fake [flags]
         {
             ["--help"] = helpText,
         });
-        var scraper = new ShapeMismatchScraper(executor);
+        var scraper = new OptionShapeScraper(executor);
 
         var commands = await ScrapeAsync(scraper);
 
         await Assert.That(commands).IsEmpty();
     }
 
+    [Test]
+    public async Task SharedTraversal_Preserves_Boolean_Value_Options_With_Repeatability_Prose()
+    {
+        const string helpText = """
+            Execute a command.
+
+            Usage:
+              fake [flags]
+
+            Flags:
+              --tag=<true|false>   May be specified multiple times
+            """;
+        var executor = new StubExecutor(new Dictionary<string, string>(StringComparer.OrdinalIgnoreCase)
+        {
+            ["--help"] = helpText,
+        });
+        var scraper = new OptionShapeScraper(executor, "bool?");
+
+        var command = (await ScrapeAsync(scraper)).Single();
+        var option = command.Options.Single();
+
+        using (Assert.Multiple())
+        {
+            await Assert.That(option.CSharpType).IsEqualTo("bool?");
+            await Assert.That(option.IsFlag).IsFalse();
+            await Assert.That(option.AcceptsMultipleValues).IsFalse();
+        }
+    }
+
     [Test]
     public async Task SharedTraversal_Propagates_Invalid_Operand_Coverage()
     {
@@ -718,7 +747,7 @@ await Assert.That(Scrape)
     [Test]
     public async Task Shared_Skip_Filter_Preserves_Uppercase_Subcommands()
     {
-        var scraper = new ShapeMismatchScraper(new StubExecutor(
+        var scraper = new OptionShapeScraper(new StubExecutor(
             new Dictionary<string, string>(StringComparer.OrdinalIgnoreCase)));
 
         await Assert.That(scraper.Skips("SSH")).IsFalse();
@@ -899,14 +928,17 @@ public Task<bool> IsAvailableAsync(
             Task.FromResult(true);
     }
 
-    private sealed class ShapeMismatchScraper : CliScraperBase
+    private sealed class OptionShapeScraper : CliScraperBase
     {
-        public ShapeMismatchScraper(ICliCommandExecutor executor)
+        private readonly string _csharpType;
+
+        public OptionShapeScraper(ICliCommandExecutor executor, string csharpType = "string?")
             : base(
                 executor,
                 new HelpTextCache(NullLogger<HelpTextCache>.Instance),
-                NullLogger<ShapeMismatchScraper>.Instance)
+                NullLogger<OptionShapeScraper>.Instance)
         {
+            _csharpType = csharpType;
         }
 
         public override string ToolName => "fake";
@@ -938,7 +970,7 @@ public ShapeMismatchScraper(ICliCommandExecutor executor)
                     {
                         SwitchName = "--tag",
                         PropertyName = "Tag",
-                        CSharpType = "string?",
+                        CSharpType = _csharpType,
                         Description = "May be specified multiple times",
                     },
                 ],
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 89db2818c23..36e1c99872e 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
@@ -1003,6 +1003,7 @@ private static void ValidateOptionShapes(CliCommandDefinition command, string he
         foreach (var option in command.Options)
         {
             var description = option.Description ?? string.Empty;
+            var isBoolean = option.CSharpType is "bool" or "bool?";
             if (HelpDeclaresExplicitBooleanValue(description) && option.IsFlag)
             {
                 throw new InvalidOperationException(
@@ -1011,6 +1012,7 @@ private static void ValidateOptionShapes(CliCommandDefinition command, string he
             }
 
             if (!option.IsFlag
+                && !isBoolean
                 && HelpDeclaresRepeatableOption(helpText, option.SwitchName, description)
                 && !option.AcceptsMultipleValues)
             {

From 6ff7908fd8bb573478361f810100a92e57f253b9 Mon Sep 17 00:00:00 2001
From: Tom Longhurst <30480171+thomhurst@users.noreply.github.com>
Date: Mon, 24 Aug 2026 08:56:08 +0100
Subject: [PATCH 15/15] fix(generator): retain passive repeatability

---
 .../Scrapers/RepeatableOptionAdapterTests.cs                   | 3 +++
 .../Scrapers/Cli/CliScraperBase.cs                             | 2 +-
 2 files changed, 4 insertions(+), 1 deletion(-)

diff --git a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
index c0de5687276..aeaec591051 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
@@ -121,6 +121,9 @@ public async Task Packer_Does_Not_Treat_Operational_Repetition_As_Repeatable()
     [Arguments("Zero or more retry attempts may be made.", false)]
     [Arguments("One or more connection retries before giving up.", false)]
     [Arguments("One or more polling attempts before timing out.", false)]
+    [Arguments("This option can be specified one or more times.", true)]
+    [Arguments("May be provided zero or more times.", true)]
+    [Arguments("This option should be used more than once.", true)]
     [Arguments("Supports multiple values.", true)]
     [Arguments("Takes multiple values.", true)]
     [Arguments("Value can contain multiple values.", true)]
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 36e1c99872e..57ae62a37a6 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/CliScraperBase.cs
@@ -1083,7 +1083,7 @@ private static void ValidateArgumentGroups(CliCommandDefinition command)
         + @"|\A" + RepeatableItemCountPattern
         + @"|(?:can|may|must|should)\s+be\s+"
         + @"(?:specified|supplied|provided|used|passed|set|given)\s+"
-        + @"(?:multiple\s+times|more\s+than\s+once)"
+        + @"(?:(?:one|zero)\s+or\s+more\s+times|multiple\s+times|more\s+than\s+once)"
         + @"|(?:accepts?|specify|supply|provide|use|pass|set|give|supports?|takes?|contains?)\s+"
         + @"(?:multiple\s+times|more\s+than\s+once|"
         + RepeatableItemCountPattern