diff --git a/tools/ComplianceRunner/src/Shared/Compliance.Shared/FileFilter.cs b/tools/ComplianceRunner/src/Shared/Compliance.Shared/FileFilter.cs
index 8df6ee2..3043935 100644
--- a/tools/ComplianceRunner/src/Shared/Compliance.Shared/FileFilter.cs
+++ b/tools/ComplianceRunner/src/Shared/Compliance.Shared/FileFilter.cs
@@ -30,14 +30,55 @@ public static bool IsRelevantFile(string file, string checkType)
 
     /// <summary>
     /// Returns true for .json files whose path contains "datasets" (case-insensitive),
-    /// matching BHoMBot's DatasetCompliance filter exactly:
-    ///   x.ToLower().Contains("datasets") &amp;&amp; x.EndsWith(".json")
+    /// except versioning upgrade maps, which are never Dataset documents.
     /// </summary>
+    /// <remarks>
+    /// The path test is BHoMBot's DatasetCompliance filter,
+    /// <c>x.ToLower().Contains("datasets") &amp;&amp; x.EndsWith(".json")</c>. The upgrade-map
+    /// exclusion is a deliberate divergence from it, so the two no longer agree.
+    /// </remarks>
     public static bool IsDatasetFile(string file)
     {
         if (!file.EndsWith(".json", StringComparison.OrdinalIgnoreCase))
             return false;
 
-        return file.Contains("datasets", StringComparison.OrdinalIgnoreCase);
+        if (!file.Contains("datasets", StringComparison.OrdinalIgnoreCase))
+            return false;
+
+        return !IsVersioningUpgradeMap(file);
+    }
+
+    /// <summary>
+    /// True for a versioning upgrade map, named Versioning_&lt;digits&gt;.json.
+    /// </summary>
+    /// <remarks>
+    /// These hold <c>{"Dataset":{"ToNew":..,"ToOld":..}}</c>, carry no <c>_t</c>, and can never
+    /// deserialise into a BH.oM.Data.Library.Dataset. They are caught by the path test above
+    /// only when some directory supplies the "datasets" substring, which in practice is a
+    /// project directory named *_Datasets. The rule lives here rather than in a per-repository
+    /// pathspec because a repository carrying no pathspec must still get the right answer.
+    ///
+    /// Anchored on the file name, not the path, so a directory named Versioning_93 does not
+    /// take every file under it out of scope.
+    ///
+    /// The digit is what separates a generated upgrade map from a hand-authored dataset that
+    /// happens to start with the same word: Versioning_Rules.json stays in scope. Discriminating
+    /// on content instead, by requiring a top-level _t, was rejected: it would also skip a real
+    /// Dataset document that had lost its _t, which is a defect this check exists to catch.
+    /// </remarks>
+    public static bool IsVersioningUpgradeMap(string file)
+    {
+        // Both separators are split by hand rather than through Path.GetFileName, which treats
+        // '\' as one only on Windows. Paths arrive from git with '/' and from a caller on
+        // Windows with '\', and the answer must not depend on which platform is asking.
+        var normalized = file.Replace("\\", "/");
+        int lastSlash = normalized.LastIndexOf('/');
+        var name = lastSlash >= 0 ? normalized[(lastSlash + 1)..] : normalized;
+
+        const string prefix = "Versioning_";
+        if (!name.StartsWith(prefix, StringComparison.OrdinalIgnoreCase))
+            return false;
+
+        return name.Length > prefix.Length && char.IsAsciiDigit(name[prefix.Length]);
     }
 }
diff --git a/tools/ComplianceRunner/tests/Compliance.Tests/Integration/DatasetComplianceRunnerE2ETests.cs b/tools/ComplianceRunner/tests/Compliance.Tests/Integration/DatasetComplianceRunnerE2ETests.cs
index 9646503..dfacac7 100644
--- a/tools/ComplianceRunner/tests/Compliance.Tests/Integration/DatasetComplianceRunnerE2ETests.cs
+++ b/tools/ComplianceRunner/tests/Compliance.Tests/Integration/DatasetComplianceRunnerE2ETests.cs
@@ -49,6 +49,40 @@ public void NonJsonFile_ExitsWithCode0()
         Assert.That(exitCode, Is.EqualTo(0));
     }
 
+    [Test]
+    [Description("A versioning upgrade map under a *_Datasets project directory is filtered before BHoM is called, and counts as not relevant rather than as an examined file.")]
+    public void VersioningUpgradeMap_UnderADatasetsDirectory_IsNotExamined()
+    {
+        // The shape that fails today: the file name is the only signal, and the "datasets"
+        // substring comes from the project directory rather than from a data directory.
+        var (exitCode, stdout) = RunnerFixture.Run("DatasetComplianceRunner",
+            "--output", "json", "BHoM_Datasets/Versioning_93.json");
+
+        var root = JsonDocument.Parse(stdout).RootElement;
+        Assert.Multiple(() =>
+        {
+            Assert.That(exitCode, Is.EqualTo(0));
+            Assert.That(root.GetProperty("status").GetString(),         Is.EqualTo("Pass"));
+            Assert.That(root.GetProperty("annotationCount").GetInt32(), Is.EqualTo(0));
+        });
+    }
+
+    [Test]
+    [Description("The digit gate holds end to end: Versioning_Rules.json is still selected, so it reaches the BHoM call and is reported as missing on disk rather than filtered.")]
+    public void VersioningRulesJson_IsStillInScope()
+    {
+        // Distinguishes "filtered out" from "examined": a filtered file never reaches the
+        // File.Exists branch, so the [SKIP] line is what proves this one was not filtered.
+        var (exitCode, stdout) = RunnerFixture.Run("DatasetComplianceRunner",
+            "--output", "json", "BHoM_Datasets/Versioning_Rules.json");
+
+        Assert.Multiple(() =>
+        {
+            Assert.That(exitCode, Is.EqualTo(0));
+            Assert.That(stdout, Does.Contain("[SKIP] File not found"));
+        });
+    }
+
     // ── JSON output structure ─────────────────────────────────────────────────
 
     [Test]
diff --git a/tools/ComplianceRunner/tests/Compliance.Unit.Tests/Unit/FileFilterTests.cs b/tools/ComplianceRunner/tests/Compliance.Unit.Tests/Unit/FileFilterTests.cs
index 69ab273..9e47289 100644
--- a/tools/ComplianceRunner/tests/Compliance.Unit.Tests/Unit/FileFilterTests.cs
+++ b/tools/ComplianceRunner/tests/Compliance.Unit.Tests/Unit/FileFilterTests.cs
@@ -40,7 +40,48 @@ public class IsDatasetFileTests
         [TestCase("datasets/foo.json",        ExpectedResult = true)]  // root-level
         [TestCase("DataSets/foo.json",        ExpectedResult = true)]  // root-level, mixed case
         [TestCase("DataSets/LCA/deep/x.json", ExpectedResult = true)]  // root-level, nested
+
+        // Versioning upgrade maps. The live case is a project directory supplying the
+        // "datasets" substring, which is how BuroHappold_Datasets/Versioning_93.json and
+        // BHoM_Datasets/Versioning_100.json get selected at all.
+        [TestCase("BHoM_Datasets/Versioning_93.json",        ExpectedResult = false)]
+        [TestCase("BHoM_Datasets/Versioning_100.json",       ExpectedResult = false)]
+        [TestCase(@"BHoM_Datasets\Versioning_93.json",       ExpectedResult = false)] // backslash separators
+        [TestCase("Datasets/Versioning_9.json",              ExpectedResult = false)] // single digit
+        [TestCase("a/Datasets/deep/Versioning_93.json",      ExpectedResult = false)] // at depth
+        [TestCase("BHoM_Datasets/versioning_93.json",        ExpectedResult = false)] // name case-insensitive
+        [TestCase("BHoM_Datasets/Versioning_93.JSON",        ExpectedResult = false)] // extension case-insensitive
+
+        // The digit gate. A hand-authored dataset starting with the same word stays in scope,
+        // which is the whole reason the rule is not a bare Versioning_* match.
+        [TestCase("Datasets/Versioning_Rules.json",          ExpectedResult = true)]
+        [TestCase("BHoM_Datasets/Versioning_.json",          ExpectedResult = true)]
+        [TestCase("BHoM_Datasets/Versioning.json",           ExpectedResult = true)]
+
+        // Anchored on the file name, so a directory named for a version does not take the real
+        // datasets under it out of scope.
+        [TestCase("Datasets/Versioning_93/RealDataset.json", ExpectedResult = true)]
+
+        // The prefix has to start the name. A dataset merely containing the word is unaffected.
+        [TestCase("Datasets/MyVersioning_93.json",           ExpectedResult = true)]
+
+        // Pins the anchoring itself rather than the digit test. The name is contrived on
+        // purpose: the prefix has to appear at an offset AND a digit has to sit at the index
+        // the digit test reads, which is the only way the two can disagree. Without it, a
+        // relaxed prefix match still passes every realistic fixture above, because reading a
+        // fixed index lands inside the prefix whenever the prefix is not at the start.
+        [TestCase("Datasets/012345678901Versioning_5.json",  ExpectedResult = true)]
         public bool IsDatasetFile(string file)
             => FileFilter.IsDatasetFile(file);
+
+        // The upgrade-map rule on its own, so a failure says which of the two predicates moved.
+        // These paths carry no "datasets" substring, so IsDatasetFile rejects them anyway and
+        // could not distinguish the two.
+        [TestCase("Tagging_oM/Versioning_93.json",  ExpectedResult = true)]
+        [TestCase("Tagging_oM/Versioning_Rules.json", ExpectedResult = false)]
+        [TestCase("Versioning_93.json",             ExpectedResult = true)]  // no directory at all
+        [TestCase("Structure_oM/Versioning_93.txt", ExpectedResult = true)]  // extension is IsDatasetFile's job
+        public bool IsVersioningUpgradeMap(string file)
+            => FileFilter.IsVersioningUpgradeMap(file);
     }
 }