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..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
@@ -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()
     {
@@ -663,13 +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()
     {
@@ -694,7 +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();
@@ -875,14 +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";
@@ -914,7 +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.Tests/Scrapers/RepeatableOptionAdapterTests.cs b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
new file mode 100644
index 00000000000..aeaec591051
--- /dev/null
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator.Tests/Scrapers/RepeatableOptionAdapterTests.cs
@@ -0,0 +1,262 @@
+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 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()
+    {
+        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()
+    {
+        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]
+    [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)]
+    [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)]
+    [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("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)]
+    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()
+    {
+        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");
+    }
+
+    [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 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(expectedType);
+        }
+    }
+
+    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,
+                ParseUsageSynopsis(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,
+                ParseUsageSynopsis(commandPath, helpText),
+                CancellationToken.None);
+    }
+}
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 2061ee64935..57ae62a37a6 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 +971,23 @@ 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>
+    /// 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,
@@ -986,6 +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(
@@ -994,6 +1012,7 @@ private static void ValidateOptionShapes(CliCommandDefinition command, string he
             }
 
             if (!option.IsFlag
+                && !isBoolean
                 && HelpDeclaresRepeatableOption(helpText, option.SwitchName, description)
                 && !option.AcceptsMultipleValues)
             {
@@ -1050,9 +1069,27 @@ private static void ValidateArgumentGroups(CliCommandDefinition command)
         RegexOptions.IgnoreCase)]
     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)]
+    private const string OperationalCountPhrasePattern =
+        @"(?:[\w-]+\s+){0,2}(?:attempts?|times?|retries?)\b";
+
+    private const string RepeatableItemCountPattern =
+        @"(?:one|zero)\s+or\s+more\s+(?!" + OperationalCountPhrasePattern + @")[\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+"
+        + @"(?:(?: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
+        + @"|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 a9e9d488032..a7880b7983f 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)
             {
@@ -205,14 +206,20 @@ private List<CliOptionDefinition> ParseOptions(string helpText)
 
             seenOptions.Add(longForm);
 
+            i = AccumulateMultiLineDescription(lines, i, ref description);
+
             var propertyName = NormalizePropertyName(longForm);
             if (propertyName is null)
             {
                 continue;
             }
 
-            var isFlag = string.IsNullOrEmpty(valueHint) || valueHint.Contains("true") || valueHint.Contains("false");
-            var csharpType = isFlag ? "bool?" : "string?";
+            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);
 
             options.Add(new CliOptionDefinition
             {
@@ -223,7 +230,7 @@ private List<CliOptionDefinition> ParseOptions(string helpText)
                 Description = description,
                 IsFlag = isFlag,
                 IsRequired = false,
-                AcceptsMultipleValues = false,
+                AcceptsMultipleValues = acceptsMultipleValues,
                 IsKeyValue = false,
                 IsNumeric = false,
                 ValueSeparator = "=",
@@ -235,6 +242,38 @@ 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>
@@ -269,7 +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
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..0987ad4c5f1 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 +274,9 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
                 }
 
                 var isFlag = string.IsNullOrEmpty(valueHint) && IsBooleanOption(longForm, description);
-                var csharpType = isFlag ? "bool?" : "string?";
+                var acceptsMultipleValues = IsRepeatableValueOption(description, isFlag);
+                var scalarType = isFlag ? "bool?" : "string?";
+                var csharpType = AsCSharpType(scalarType, acceptsMultipleValues);
 
                 options.Add(new CliOptionDefinition
                 {
@@ -285,7 +287,7 @@ 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..281fa516162 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 +321,10 @@ private void ParseOptionLines(
                     && !isNumeric
                     && !ValueOptionsWithoutHelpPlaceholders.Contains(longForm);
                 var isBoolean = IsBooleanValueHint(valueHint);
+                var acceptsMultipleValues = IsRepeatableValueOption(
+                    description ?? string.Empty,
+                    isFlag,
+                    isBoolean);
                 var csharpType = isFlag || isBoolean ? "bool?" : isNumeric ? "int?" : "string?";
 
                 CliEnumDefinition? enumDef = null;
@@ -345,6 +349,8 @@ private void ParseOptionLines(
                     }
                 }
 
+                csharpType = AsCSharpType(csharpType, acceptsMultipleValues);
+
                 options.Add(new CliOptionDefinition
                 {
                     SwitchName = longForm,
@@ -354,7 +360,7 @@ 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..6fe23534b9e 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 +315,8 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
                 isFlag = true;
             }
 
-            var csharpType = isFlag ? "bool?" : (isInteger ? "int?" : "string?");
+            var acceptsMultipleValues = IsRepeatableValueOption(description, isFlag, isBoolean);
+            var csharpType = GetCSharpType(isFlag, isInteger, acceptsMultipleValues);
 
             options.Add(new CliOptionDefinition
             {
@@ -326,7 +327,7 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
                 Description = description,
                 IsFlag = isFlag,
                 IsRequired = false,
-                AcceptsMultipleValues = false,
+                AcceptsMultipleValues = acceptsMultipleValues,
                 IsKeyValue = false,
                 IsNumeric = isInteger,
                 ValueSeparator = isFlag ? " " : "=",
@@ -338,6 +339,12 @@ private List<CliOptionDefinition> ParseOptions(string helpText, string[] command
         return options;
     }
 
+    private static string GetCSharpType(bool isFlag, bool isInteger, bool acceptsMultipleValues)
+    {
+        var scalarType = isFlag ? "bool?" : isInteger ? "int?" : "string?";
+        return AsCSharpType(scalarType, acceptsMultipleValues);
+    }
+
     /// <summary>
     /// Checks if a value hint indicates a numeric type.
     /// </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 36d4dae8e7d..0977c25928a 100644
--- a/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/WinGetCliScraper.cs
+++ b/tools/ModularPipelines.OptionsGenerator/src/ModularPipelines.OptionsGenerator/Scrapers/Cli/WinGetCliScraper.cs
@@ -436,13 +436,12 @@ 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 csharpType = isFlag
-            ? "bool?"
-            : acceptsMultipleValues
-                ? "IEnumerable<string>?"
-                : "string?";
+        var declaresRepeatability = DescriptionDeclaresRepeatableOption(description);
+        var isFlag = IsKnownBooleanOption(className, longForm)
+                     || (!declaresRepeatability && IsBooleanDescription(description));
+        var acceptsMultipleValues = !isFlag && declaresRepeatability;
+        var scalarType = isFlag ? "bool?" : "string?";
+        var csharpType = AsCSharpType(scalarType, acceptsMultipleValues);
 
         return new CliOptionDefinition
         {