diff --git a/src/main/java/io/getunleash/strategy/constraints/StringConstraintOperator.java b/src/main/java/io/getunleash/strategy/constraints/StringConstraintOperator.java
index 5a300b420..3106d1c8b 100644
--- a/src/main/java/io/getunleash/strategy/constraints/StringConstraintOperator.java
+++ b/src/main/java/io/getunleash/strategy/constraints/StringConstraintOperator.java
@@ -58,17 +58,18 @@ private boolean startsWith(
             List<String> values, Optional<String> contextValue, boolean caseInsensitive) {
         return contextValue
                 .map(
-                        c ->
+                        actualContextValue ->
                                 values.stream()
                                         .anyMatch(
-                                                v -> {
+                                                value -> {
                                                     if (caseInsensitive) {
-                                                        return v.toLowerCase(comparisonLocale)
+                                                        return actualContextValue
+                                                                .toLowerCase(comparisonLocale)
                                                                 .startsWith(
-                                                                        c.toLowerCase(
+                                                                        value.toLowerCase(
                                                                                 comparisonLocale));
                                                     } else {
-                                                        return c.startsWith(v);
+                                                        return actualContextValue.startsWith(value);
                                                     }
                                                 }))
                 .orElse(false);
diff --git a/src/test/java/io/getunleash/strategy/constraints/StringConstraintOperatorTest.java b/src/test/java/io/getunleash/strategy/constraints/StringConstraintOperatorTest.java
index 34234ee85..1ed3f76dd 100644
--- a/src/test/java/io/getunleash/strategy/constraints/StringConstraintOperatorTest.java
+++ b/src/test/java/io/getunleash/strategy/constraints/StringConstraintOperatorTest.java
@@ -211,4 +211,56 @@ public void shouldSupportInvertingStringContains() {
                         .build();
         assertThat(strategy.isEnabled(parameters, ctx, constraintList)).isFalse();
     }
+
+    @Test
+    public void startsWithShouldMatchCorrectlyWhenCaseSensitive() {
+        Strategy strategy = new DefaultStrategy();
+        List<Constraint> constraintList =
+                Collections.singletonList(
+                        new Constraint(
+                                "email",
+                                Operator.STR_STARTS_WITH,
+                                Collections.singletonList("testuser"),
+                                false,
+                                false));
+        Map<String, String> parameters = new HashMap<>();
+        UnleashContext ctx =
+                UnleashContext.builder()
+                        .environment("dev")
+                        .addProperty("email", "TESTUSER@getunleash.io")
+                        .build();
+        assertThat(strategy.isEnabled(parameters, ctx, constraintList)).isFalse();
+        UnleashContext ctx2 =
+                UnleashContext.builder()
+                        .environment("dev")
+                        .addProperty("email", "testuser@getunleash.io")
+                        .build();
+        assertThat(strategy.isEnabled(parameters, ctx2, constraintList)).isTrue();
+    }
+
+    @Test
+    public void startsWithShouldMatchCorrectlyWhenCaseInsensitive() {
+        Strategy strategy = new DefaultStrategy();
+        List<Constraint> constraintList =
+                Collections.singletonList(
+                        new Constraint(
+                                "email",
+                                Operator.STR_STARTS_WITH,
+                                Collections.singletonList("testuser"),
+                                false,
+                                true));
+        Map<String, String> parameters = new HashMap<>();
+        UnleashContext ctx =
+                UnleashContext.builder()
+                        .environment("dev")
+                        .addProperty("email", "TESTUSER@getunleash.io")
+                        .build();
+        assertThat(strategy.isEnabled(parameters, ctx, constraintList)).isTrue();
+        UnleashContext ctx2 =
+                UnleashContext.builder()
+                        .environment("dev")
+                        .addProperty("email", "testuser@getunleash.io")
+                        .build();
+        assertThat(strategy.isEnabled(parameters, ctx2, constraintList)).isTrue();
+    }
 }