diff --git a/pkgs/sdk/server/src/Integrations/TestData.cs b/pkgs/sdk/server/src/Integrations/TestData.cs
index b16c4e50..ca999809 100644
--- a/pkgs/sdk/server/src/Integrations/TestData.cs
+++ b/pkgs/sdk/server/src/Integrations/TestData.cs
@@ -807,7 +807,7 @@ internal ItemDescriptor CreateFlag(int version)
                     null,
                     $"rule{index}",
                     r._clauses.Select(c => new Internal.Model.Clause(
-                        null,
+                        c._contextKind,
                         c._attribute,
                         Operator.ForName(c._operator),
                         c._values.ToArray(),
@@ -985,7 +985,9 @@ public FlagRuleBuilder AndNotMatch(string attribute, params LdValue[] values) =>
 
             private FlagRuleBuilder AddClause(ContextKind contextKind, AttributeRef attr, string op, LdValue[] values, bool negate)
             {
-                _clauses.Add(new Clause(attr, op, values, negate));
+                // Convert ContextKind.Default to null for consistency
+                ContextKind? storedContextKind = contextKind == ContextKind.Default ? (ContextKind?)null : contextKind;
+                _clauses.Add(new Clause(storedContextKind, attr, op, values, negate));
                 return this;
             }
 
@@ -1046,13 +1048,15 @@ public FlagMigrationBuilder CheckRatio(long? checkRatio)
 
         internal class Clause
         {
+            internal readonly ContextKind? _contextKind;
             internal readonly AttributeRef _attribute;
             internal readonly string _operator;
             internal readonly LdValue[] _values;
             internal readonly bool _negate;
 
-            internal Clause(AttributeRef attribute, string op, LdValue[] values, bool negate)
+            internal Clause(ContextKind? contextKind, AttributeRef attribute, string op, LdValue[] values, bool negate)
             {
+                _contextKind = contextKind;
                 _attribute = attribute;
                 _operator = op;
                 _values = values;
diff --git a/pkgs/sdk/server/test/Integrations/TestDataTest.cs b/pkgs/sdk/server/test/Integrations/TestDataTest.cs
index 478e779d..653dca15 100644
--- a/pkgs/sdk/server/test/Integrations/TestDataTest.cs
+++ b/pkgs/sdk/server/test/Integrations/TestDataTest.cs
@@ -301,6 +301,112 @@ public void FlagRules()
                 );
         }
 
+        [Fact]
+        public void IfMatchContext_WithSpecificContextKind_CreatesClauseWithContextKind()
+        {
+            var companyKind = ContextKind.Of("company");
+
+            VerifyFlag(
+                f => f.IfMatchContext(companyKind, "name", LdValue.Of("Acme")).ThenReturn(true),
+                fb => ExpectedBooleanFlag(fb).Rules(new RuleBuilder().Id("rule0").Variation(0).Clauses(
+                    new ClauseBuilder().ContextKind(companyKind).Attribute("name").Op("in").Values("Acme").Build()
+                ).Build())
+            );
+        }
+
+        [Fact]
+        public void IfNotMatchContext_WithSpecificContextKind_CreatesNegatedClauseWithContextKind()
+        {
+            var companyKind = ContextKind.Of("company");
+
+            VerifyFlag(
+                f => f.IfNotMatchContext(companyKind, "name", LdValue.Of("Acme")).ThenReturn(true),
+                fb => ExpectedBooleanFlag(fb).Rules(new RuleBuilder().Id("rule0").Variation(0).Clauses(
+                    new ClauseBuilder().ContextKind(companyKind).Attribute("name").Op("in").Values("Acme").Negate(true).Build()
+                ).Build())
+            );
+        }
+
+        [Fact]
+        public void AndMatchContext_WithMultipleContextKinds_CreatesClausesWithDifferentContextKinds()
+        {
+            var companyKind = ContextKind.Of("company");
+            var orgKind = ContextKind.Of("org");
+
+            VerifyFlag(
+                f => f.IfMatchContext(companyKind, "name", LdValue.Of("Acme"))
+                    .AndMatchContext(orgKind, "key", LdValue.Of("org-123"))
+                    .ThenReturn(true),
+                fb => ExpectedBooleanFlag(fb).Rules(new RuleBuilder().Id("rule0").Variation(0).Clauses(
+                    new ClauseBuilder().ContextKind(companyKind).Attribute("name").Op("in").Values("Acme").Build(),
+                    new ClauseBuilder().ContextKind(orgKind).Attribute("key").Op("in").Values("org-123").Build()
+                ).Build())
+            );
+        }
+
+        [Fact]
+        public void AndNotMatchContext_WithContextKind_CreatesNegatedClauseWithContextKind()
+        {
+            var companyKind = ContextKind.Of("company");
+
+            VerifyFlag(
+                f => f.IfMatchContext(companyKind, "name", LdValue.Of("Acme"))
+                    .AndNotMatchContext(companyKind, "status", LdValue.Of("inactive"))
+                    .ThenReturn(true),
+                fb => ExpectedBooleanFlag(fb).Rules(new RuleBuilder().Id("rule0").Variation(0).Clauses(
+                    new ClauseBuilder().ContextKind(companyKind).Attribute("name").Op("in").Values("Acme").Build(),
+                    new ClauseBuilder().ContextKind(companyKind).Attribute("status").Op("in").Values("inactive").Negate(true).Build()
+                ).Build())
+            );
+        }
+
+        [Fact]
+        public void IfMatch_WithDefaultUser_CreatesClauseWithNullContextKind()
+        {
+            VerifyFlag(
+                f => f.IfMatch("name", LdValue.Of("Lucy")).ThenReturn(true),
+                fb => ExpectedBooleanFlag(fb).Rules(new RuleBuilder().Id("rule0").Variation(0).Clauses(
+                    new ClauseBuilder().Attribute("name").Op("in").Values("Lucy").Build()
+                ).Build())
+            );
+        }
+
+        [Fact]
+        public void IfMatch_AndMatchContext_MixesDefaultUserAndSpecificContextKind()
+        {
+            var companyKind = ContextKind.Of("company");
+
+            VerifyFlag(
+                f => f.IfMatch("name", LdValue.Of("Lucy"))
+                    .AndMatchContext(companyKind, "name", LdValue.Of("Acme"))
+                    .ThenReturn(true),
+                fb => ExpectedBooleanFlag(fb).Rules(new RuleBuilder().Id("rule0").Variation(0).Clauses(
+                    new ClauseBuilder().Attribute("name").Op("in").Values("Lucy").Build(),
+                    new ClauseBuilder().ContextKind(companyKind).Attribute("name").Op("in").Values("Acme").Build()
+                ).Build())
+            );
+        }
+
+        [Fact]
+        public void AndMatchContext_TwoCustomContextKindsOnSameAttribute_StoresCorrectContextKinds()
+        {
+            var contextA = ContextKind.Of("context_a");
+            var contextB = ContextKind.Of("context_b");
+
+            VerifyFlag(
+                f => f.IfMatchContext(contextA, "key", LdValue.Of("A1"))
+                    .AndMatchContext(contextB, "key", LdValue.Of("B2"))
+                    .ThenReturn(true),
+                fb => ExpectedBooleanFlag(fb).Rules(new RuleBuilder().Id("rule0").Variation(0).Clauses(
+                    new ClauseBuilder().ContextKind(contextA).Attribute("key").Op("in").Values("A1").Build(),
+                    new ClauseBuilder().ContextKind(contextB).Attribute("key").Op("in").Values("B2").Build()
+                ).Build())
+            );
+        }
+
+        private static Func<FeatureFlagBuilder, FeatureFlagBuilder> ExpectedBooleanFlag =>
+            fb => fb.Variations(true, false).On(true).OffVariation(1).FallthroughVariation(0);
+
         [Fact]
         public void ItCanSetTheSamplingRatio()
         {
diff --git a/pkgs/sdk/server/test/Integrations/TestDataWithClientTest.cs b/pkgs/sdk/server/test/Integrations/TestDataWithClientTest.cs
index cc54fe28..19362e51 100644
--- a/pkgs/sdk/server/test/Integrations/TestDataWithClientTest.cs
+++ b/pkgs/sdk/server/test/Integrations/TestDataWithClientTest.cs
@@ -132,5 +132,242 @@ public void DataSourcePropagatesToMultipleClients()
                 }
             }
         }
+
+        [Fact]
+        public void IfMatchContext_MatchingContextKind_EvaluatesToTrue()
+        {
+            var companyKind = ContextKind.Of("company");
+
+            _td.Update(_td.Flag("company-flag")
+                .BooleanFlag()
+                .FallthroughVariation(false)
+                .IfMatchContext(companyKind, "name", LdValue.Of("Acme"))
+                .ThenReturn(true));
+
+            using (var client = new LdClient(_config))
+            {
+                var matchingCompany = Context.Builder("company-123")
+                    .Kind(companyKind)
+                    .Set("name", "Acme")
+                    .Build();
+
+                Assert.True(client.BoolVariation("company-flag", matchingCompany, false));
+            }
+        }
+
+        [Fact]
+        public void IfMatchContext_NonMatchingAttributeValue_EvaluatesToFalse()
+        {
+            var companyKind = ContextKind.Of("company");
+
+            _td.Update(_td.Flag("company-flag")
+                .BooleanFlag()
+                .FallthroughVariation(false)
+                .IfMatchContext(companyKind, "name", LdValue.Of("Acme"))
+                .ThenReturn(true));
+
+            using (var client = new LdClient(_config))
+            {
+                var nonMatchingCompany = Context.Builder("company-456")
+                    .Kind(companyKind)
+                    .Set("name", "OtherCorp")
+                    .Build();
+
+                Assert.False(client.BoolVariation("company-flag", nonMatchingCompany, false));
+            }
+        }
+
+        [Fact]
+        public void IfMatchContext_WrongContextKind_EvaluatesToFalse()
+        {
+            var companyKind = ContextKind.Of("company");
+
+            _td.Update(_td.Flag("company-flag")
+                .BooleanFlag()
+                .FallthroughVariation(false)
+                .IfMatchContext(companyKind, "name", LdValue.Of("Acme"))
+                .ThenReturn(true));
+
+            using (var client = new LdClient(_config))
+            {
+                // User context with same attribute value should not match (wrong context kind)
+                var userContext = Context.Builder("user-123")
+                    .Set("name", "Acme")
+                    .Build();
+
+                Assert.False(client.BoolVariation("company-flag", userContext, false));
+            }
+        }
+
+        [Fact]
+        public void IfMatchContext_MultiContextWithMatchingKind_EvaluatesToTrue()
+        {
+            var companyKind = ContextKind.Of("company");
+
+            _td.Update(_td.Flag("company-flag")
+                .BooleanFlag()
+                .FallthroughVariation(false)
+                .IfMatchContext(companyKind, "name", LdValue.Of("Acme"))
+                .ThenReturn(true));
+
+            using (var client = new LdClient(_config))
+            {
+                // Multi-context with matching company should return true
+                var multiContext = Context.NewMulti(
+                    Context.New("user-123"),
+                    Context.Builder("company-123").Kind(companyKind).Set("name", "Acme").Build()
+                );
+
+                Assert.True(client.BoolVariation("company-flag", multiContext, false));
+            }
+        }
+
+        [Fact]
+        public void AndMatchContext_BothConditionsMatch_EvaluatesToTrue()
+        {
+            var companyKind = ContextKind.Of("company");
+            var orgKind = ContextKind.Of("org");
+
+            _td.Update(_td.Flag("multi-kind-flag")
+                .BooleanFlag()
+                .FallthroughVariation(false)
+                .IfMatchContext(companyKind, "name", LdValue.Of("Acme"))
+                .AndMatchContext(orgKind, "tier", LdValue.Of("premium"))
+                .ThenReturn(true));
+
+            using (var client = new LdClient(_config))
+            {
+                var matchingMulti = Context.NewMulti(
+                    Context.Builder("company-123").Kind(companyKind).Set("name", "Acme").Build(),
+                    Context.Builder("org-456").Kind(orgKind).Set("tier", "premium").Build()
+                );
+
+                Assert.True(client.BoolVariation("multi-kind-flag", matchingMulti, false));
+            }
+        }
+
+        [Fact]
+        public void AndMatchContext_OnlyFirstConditionMatches_EvaluatesToFalse()
+        {
+            var companyKind = ContextKind.Of("company");
+            var orgKind = ContextKind.Of("org");
+
+            _td.Update(_td.Flag("multi-kind-flag")
+                .BooleanFlag()
+                .FallthroughVariation(false)
+                .IfMatchContext(companyKind, "name", LdValue.Of("Acme"))
+                .AndMatchContext(orgKind, "tier", LdValue.Of("premium"))
+                .ThenReturn(true));
+
+            using (var client = new LdClient(_config))
+            {
+                var onlyCompanyMatches = Context.NewMulti(
+                    Context.Builder("company-123").Kind(companyKind).Set("name", "Acme").Build(),
+                    Context.Builder("org-456").Kind(orgKind).Set("tier", "standard").Build()
+                );
+
+                Assert.False(client.BoolVariation("multi-kind-flag", onlyCompanyMatches, false));
+            }
+        }
+
+        [Fact]
+        public void AndMatchContext_OnlySecondConditionMatches_EvaluatesToFalse()
+        {
+            var companyKind = ContextKind.Of("company");
+            var orgKind = ContextKind.Of("org");
+
+            _td.Update(_td.Flag("multi-kind-flag")
+                .BooleanFlag()
+                .FallthroughVariation(false)
+                .IfMatchContext(companyKind, "name", LdValue.Of("Acme"))
+                .AndMatchContext(orgKind, "tier", LdValue.Of("premium"))
+                .ThenReturn(true));
+
+            using (var client = new LdClient(_config))
+            {
+                var onlyOrgMatches = Context.NewMulti(
+                    Context.Builder("company-123").Kind(companyKind).Set("name", "OtherCorp").Build(),
+                    Context.Builder("org-456").Kind(orgKind).Set("tier", "premium").Build()
+                );
+
+                Assert.False(client.BoolVariation("multi-kind-flag", onlyOrgMatches, false));
+            }
+        }
+
+        [Fact]
+        public void AndMatchContext_NeitherConditionMatches_EvaluatesToFalse()
+        {
+            var companyKind = ContextKind.Of("company");
+            var orgKind = ContextKind.Of("org");
+
+            _td.Update(_td.Flag("multi-kind-flag")
+                .BooleanFlag()
+                .FallthroughVariation(false)
+                .IfMatchContext(companyKind, "name", LdValue.Of("Acme"))
+                .AndMatchContext(orgKind, "tier", LdValue.Of("premium"))
+                .ThenReturn(true));
+
+            using (var client = new LdClient(_config))
+            {
+                var neitherMatches = Context.NewMulti(
+                    Context.Builder("company-123").Kind(companyKind).Set("name", "OtherCorp").Build(),
+                    Context.Builder("org-456").Kind(orgKind).Set("tier", "standard").Build()
+                );
+
+                Assert.False(client.BoolVariation("multi-kind-flag", neitherMatches, false));
+            }
+        }
+
+        [Fact]
+        public void AndMatchContext_TwoCustomContextKindsOnSameAttribute_EvaluatesCorrectly()
+        {
+            var contextA = ContextKind.Of("context_a");
+            var contextB = ContextKind.Of("context_b");
+
+            _td.Update(_td.Flag("flag_A")
+                .BooleanFlag()
+                .FallthroughVariation(false)
+                .IfMatchContext(contextA, "key", LdValue.Of("A1"))
+                .AndMatchContext(contextB, "key", LdValue.Of("B2"))
+                .ThenReturn(true));
+
+            using (var client = new LdClient(_config))
+            {
+                // Both contexts match - should return true
+                var bothMatch = Context.NewMulti(
+                    Context.Builder("A1").Kind(contextA).Build(),
+                    Context.Builder("B2").Kind(contextB).Build()
+                );
+                Assert.True(client.BoolVariation("flag_A", bothMatch, false));
+
+                // Only context_a matches - should return false
+                var onlyAMatches = Context.NewMulti(
+                    Context.Builder("A1").Kind(contextA).Build(),
+                    Context.Builder("wrong").Kind(contextB).Build()
+                );
+                Assert.False(client.BoolVariation("flag_A", onlyAMatches, false));
+
+                // Only context_b matches - should return false
+                var onlyBMatches = Context.NewMulti(
+                    Context.Builder("wrong").Kind(contextA).Build(),
+                    Context.Builder("B2").Kind(contextB).Build()
+                );
+                Assert.False(client.BoolVariation("flag_A", onlyBMatches, false));
+
+                // Neither matches - should return false
+                var neitherMatches = Context.NewMulti(
+                    Context.Builder("wrong1").Kind(contextA).Build(),
+                    Context.Builder("wrong2").Kind(contextB).Build()
+                );
+                Assert.False(client.BoolVariation("flag_A", neitherMatches, false));
+
+                // Wrong context kinds - should return false
+                var wrongKinds = Context.NewMulti(
+                    Context.Builder("A1").Build(), // user context, not context_a
+                    Context.Builder("B2").Build()  // user context, not context_b
+                );
+                Assert.False(client.BoolVariation("flag_A", wrongKinds, false));
+            }
+        }
     }
 }