diff --git a/app/proprietary/src/test/java/stirling/software/proprietary/security/database/H2SQLConditionTest.java b/app/proprietary/src/test/java/stirling/software/proprietary/security/database/H2SQLConditionTest.java
new file mode 100644
index 000000000..0f4642bbd
--- /dev/null
+++ b/app/proprietary/src/test/java/stirling/software/proprietary/security/database/H2SQLConditionTest.java
@@ -0,0 +1,63 @@
+package stirling.software.proprietary.security.database;
+
+import static org.junit.jupiter.api.Assertions.*;
+import static org.mockito.Mockito.*;
+
+import org.junit.jupiter.api.Test;
+import org.springframework.context.annotation.ConditionContext;
+import org.springframework.core.type.AnnotatedTypeMetadata;
+import org.springframework.mock.env.MockEnvironment;
+
+class H2SQLConditionTest {
+
+    private final H2SQLCondition condition = new H2SQLCondition();
+
+    private boolean eval(MockEnvironment env) {
+        ConditionContext ctx = mock(ConditionContext.class);
+        when(ctx.getEnvironment()).thenReturn(env);
+        AnnotatedTypeMetadata md = mock(AnnotatedTypeMetadata.class);
+        return condition.matches(ctx, md);
+    }
+
+    @Test
+    void returnsFalse_whenEnableCustomDatabase_missing_or_false() {
+        // missing -> parseBoolean(null) = false
+        assertFalse(eval(new MockEnvironment()), "Missing flag should be treated as false");
+
+        // explicitly false (even if type=h2)
+        MockEnvironment envFalse =
+                new MockEnvironment()
+                        .withProperty("system.datasource.enableCustomDatabase", "false")
+                        .withProperty("system.datasource.type", "h2");
+        assertFalse(eval(envFalse), "Flag=false must short-circuit to false even if type=h2");
+    }
+
+    @Test
+    void returnsTrue_whenEnabled_and_type_is_h2_caseInsensitive() {
+        MockEnvironment env =
+                new MockEnvironment()
+                        .withProperty("system.datasource.enableCustomDatabase", "true")
+                        .withProperty("system.datasource.type", "h2");
+        assertTrue(eval(env));
+
+        MockEnvironment envUpper =
+                new MockEnvironment()
+                        .withProperty("system.datasource.enableCustomDatabase", "true")
+                        .withProperty("system.datasource.type", "H2");
+        assertTrue(eval(envUpper));
+    }
+
+    @Test
+    void returnsFalse_whenEnabled_but_type_not_h2_or_missing() {
+        MockEnvironment envNotH2 =
+                new MockEnvironment()
+                        .withProperty("system.datasource.enableCustomDatabase", "true")
+                        .withProperty("system.datasource.type", "postgresql");
+        assertFalse(eval(envNotH2));
+
+        MockEnvironment envMissingType =
+                new MockEnvironment()
+                        .withProperty("system.datasource.enableCustomDatabase", "true");
+        assertFalse(eval(envMissingType));
+    }
+}